Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
MODULE 1: GENERAL CHEMISTRY & INORGANIC
PHARMACEUTICAL CHEMISTRY
Chemistry
- Physical science
- Study of the composition, structure, properties, and behavior of
matter
- “The Central Science”
- The ABC of Pharmacy Practice”
Matter
- Anything that has mass and volume
- Made up of particles
- Exist in 4 fundamental states
o Solid
o Liquid
o Gas
o Plasma
- Mass – amount of matter present in the material
- Weight = mass x pull of gravity
- Units of Measurement:
o Length – Meter (m)
o Mass – Kilogram (kg)
o Time – Seconds (sec)
o Temperature – Kelvin (K)
- Plasma
o Colorless fluid part of blood, lymph, or milk, in which
corpuscles or fat globules are suspended
o Serum
§ Amber-colored protein-rich liquid that separates
out when blood coagulates
§ Used to provide immunity
§ Diagnostic agent
Classifications of Matter
- Element
o Simplest form of matter
o 1 kind of material or atom
- Compound
o Substances composed of two or more elements united
chemically in definite proportion
-
Mixture
o Composed of 2 or more substances
chemically combined
States of Matter
Solid
Liquid
Shape
Definite
Indefinite
Volume
Definite
Definite
IFA Strength
Strongest
Strong
Molecular Motion
Vibration
Gliding
that are not
Gas
Indefinite
Indefinite
Weakest
Constant
Random Motion
Changes that <atter undergoes
- Physical Change – change in phase
-
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Chemical Change – change in both intrinsic and extrinsic
properties
o Evidences of Chemical Change
§ Evolution of gas
§ Formation of precipitate
§ Emission of light
§ Generation of Electricity
§ Production of Mechanical Energy
§ Absorption/Liberation of Heat
o Processes Involved in Chemical Change
§ Oxidation
• (+O)
§ Reduction
• (-O or +H)
§ Neutralization
• acid + base à salt + water
§ Hydrolysis
• water + salt à acid + base
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Reviewer by: camila kim vertucio
Saponification
• alkali + fats à soap + glycerol
§ Fermentation
• Organic substances + microbes à
alcohol
Nuclear Change – △ in structure, properties, composition of the
nucleus à in the transmutation of the element
o Nuclear Fission – splitting of a heavy atom
o Nuclear Fusion – union of 2 light atoms to form a bigger
molecule
§
-
Atom
- Basic unit of matter
- Greek – “atomos” – indivisible
o Proton – (+) charge
o Neutron – no charge
o Electron – (-) charge
Element
- Pure chemical substance
- Contains only 1 type of atom
- Currently, there are 118 elements
-
Atomic number = # of protons = # of electrons
Mass number = # of protons + # of neutrons
Isotope – same number of protons (so same element), but
different number of neutrons
- Isotone – same number of neutrons
- Isobar – same mass number
- Ion – charged atom
- 3 Most Abundant Elements
o Oxygen
o Silicon
o Aluminum
- 1st produced artificially
o Technetium
- Rarest Element
o Astatine
- Liquid at Room Temperature
o Mercury
o Bromine
Allotropism
- Allotrope – atoms of different elements can link together in
different ways to form substances with different properties
- Allotropes of Ca:
o Diamond, Graphite
- Allotropes of O:
o [O] nascent, O2 molecular, O3 ozone
- Orbitals – region in space where the probability of finding an
election is greatest
Mixtures
- Composed of two or more elements or substances which are not
chemically combined
- Heterogenous – two or more distinct phases
- Homogenous – only one phase or single phase
Solutions
o Uniform mixture
o Composed of solute and solvent
o Atoms, molecules, or ions of the substance become
dispersed
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Suspension
o Homogenous dispersion insoluble in a liquid
o Coarse mixture
o Finely divided solid materials distributed in a liquid
Colloids
o Contain particles bigger than those in solutions but
smaller than those in suspension
o Particle of solute are not broken down to the size of the
molecules but are small dispersed throughout the
medium
o Exhibit the light scattering effect
o Dividing line between solution and homogeneous mixture
o 4 Properties of Colloids: (always remember T-BAC)
Tyndall effect
§ Light scattering effect
Brownian movement
§ Zigzag movement of colloidal particles
Adsorption
Charged electrically
§ Electrophoresis – gel electrophoresis à SHSPAGE (used to separate protein and nucleic
acids)
§ Cathode (-) – reduction takes place
§ Anode (+) – oxidation takes place
- Homogeneous mixture
o True Solution
o Colloid
Metals vs Non-Metals
- Metallic Property – capability of an element to lose an electron
Metals
Non-Metals
Good conductors of heat and
Poor conductors
electricity
Form BASIC oxides
From ACIDIC oxides
Lustrous, Ductile, Malleable
Dull & Brittle if Solid
High Density
Low Density
High Melting point
Low Melting point
Tends to lose electron
Tends to accept electron
-
How to remember Metalloids?
Mnemonic: “SIGE PO, SABI NI ATE BABY”
o Silicon, Germanium, Polonium, Antimony, Arsenic,
Telurium, Boron
Properties of Elements
- Electronegativity – ability of an element to attract electrons to
itself
- Electron Affinity – energy gained by an atom when an electron is
added to it
- Ionization Energy/Ionization Potential – amount of energy
required to remove an electron from a neutral atom
Properties Used to Identify Substances
Intensive/Intrinsic vs Extensive/Extrinsic
- Intensive/Intrinsic – independent of mass or amount
- Extensive/Extrinsic – dependent on mass
- Physical Properties – observed or measured without changing
the identity of matter
o Example: MP, BP, Solubility, p, malleability, ductility
- Chemical Properties – describe the change or the reaction a
substance undergoes
o Flammability, Reactivity, Inertness
Laws of Stoichiometry
- Law of Definite Proportions (Proust’s Law)
Elements (sameàratio) Same Compound
- Law of Multiple Proportions
Elements (diffàratio) Different Compound
Note: Ratio must be a whole number
Chemical Reactions
- Direct Union/Synthesis/Composition
Simple Subs à Complex Subs
MgO + H2O à Hg(OH)2
- Decomposition/Analysis
Complex Subs △à Simple Subs
H2CO3 △à H2O + CO2
- Single Replacement Reaction
A + BC à B + AC
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Electrochemistry
- Separation of particles based on e- charge
Making it simpler
-
Double Displacement Reaction/Metathesis
AB + CD à AD + BC
Example: Neutralization Reaction
Reduction-Oxidation Reaction (REDOX)
o GEROA – gain electron reduction oxidizing agent
§ In this process of reduction, there is/are gain of
electron/s, and the one responsible for this is the
oxidizing agent
o LEORA – loss electron oxidation reducing agent
§ In this process of oxidation there is/are loss of
electron/s and the one responsible for this is the
reducing agent
Atomic Structure
- Democritus – Atomos
- Dalton – Billiard Ball Model
- Thomson – Raisin Bread Model / Electron
- Rutherford – Gold Foil Experiment / Proton in the Nucleus
- James Chadwick – Neutron
- Bohr – Planetary Model
- Schrodinger – Quantum Mechanic Model / 3D Model
Quantum Numbers
- Principal Quantum Number (n)
o Describes the Main Electron Shell and the Size of the
electron cloud
§ Value: 1, 2, 3, 4…
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-
Angular/Azimuthal Quantum Number (l)
o Describes the subshell and the shape of the electron
cloud
§ Value 0 up to n-1
- Magnetic Quantum Number (Ml)
o Describes the orbital or orientation in space
§ Values: -l, 0, l
- Spin (Ms or s)
o Values: +1/2 or -1/2
Rules/Principles
- Pauli’s Exclusion Principle
o No 2 e- can have the same set of quantum numbers
- Aufbau’s Principle
o Building up Principle
o Electrons are placed first on the subshell with lowest
energy level
- Hund’s Rule
o Electrons are spread singly before pairing up
Periodic Table of Elements
- There are 118 Elements, 18 Groups/Families, 7 periods/series
- Lavoisier – 1st to set up the table (33 elements)
- Dobereiner – Triads
- Newland – law of octaves
o 8 elements are grouped before another set of 8 elements
- Meyer & Mendeleev – 1st Periodic Law
o Properties are periodic functions of atomic weight
- Moseley – First modern Periodic Table
- Family A
o Representative elements
o Occupies
§ S block – IA & IIA
§ P block – IIIA & VIIIA
- Family B
o Transition elements
o Occupies
§ D block – transition metals
§ F block – Lanthanide or Lanthanoid series – Rare
Periodic Trends
-
Atomic Radius
o ½ the distance between 2 nuclei
o Right to Left increases
o Top to Bottom increases
- Electronegativity
o Ability to attract electrons
o Left to Right increases
o Going up increases
- Ionization Energy or Potential
o Ability to remove an electron from a positively charged
atom
o Left to Right increases
o Going up increases
- Electron Affinity
o Property to accept an electron
o Right to Left increases
o Top to Bottom Increases
Chemical Bonding
- Forces that hold atoms together
- All elements try to achieve the configuration of the Noble Gases
- Octet Rule – atoms become stable when the valence electron
will complement fully the valence shell
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Types of Chemical Bonding
- Complete Electron Transfer (Ionic Bond)
o Bond formed by a metal and a non-metal
o Electrostatic Bond
- Sharing of Electrons (Covalent Bond)
o 2 nonpolar (similar atoms) à equal electron sharing
o 2 polar (dissimilar atoms) à unequal electron sharing
VSEPR theory
- Valence Shell Electron Pair Repulsion
- model used to predict 3D molecular geometry based on the
number of valence shell electron bond pairs among the atoms in
a molecule
IMF (Intermolecular Forces of Attraction)
- Dipole-Dipole (Keesom Forces)
- Dipole-Induced Dipole (Debye Forces)
- London Forces (Dispersion/Van der Waals)
- Hydrogen Bonds (hydrogen attached to a highly electronegative
atom)
STP (Standard Temperature and Pressure)
- Conditions:
o 1 atm / 760 mmHg (torr)
o 0oC / 273 K (Kelvin)
- Note: At STP – 1 mole of a substance occupies 22.4 L
Physical Properties of Systems
- Additive Property – depends on sum
o Molecular weight
- Constitutive property – type and arrangement
o Optical rotation, refractive index
- Colligative Property – number of solute
o VPL, BPE, FPD, OP
- Density = mass per unit volume (m/v)
- Specific Gravity = # of sample/ # of standard
- Specific volume = reciprocal of spgr
Colligative Properties
Vapor Pressure Lowering
- Addition of a non-volatile solute lowers the VP of a liquid
- A liquid in a closed container will establish an equilibrium with its
vapor
- When equilibrium is reached, vapor exerts a pressure (vapor
pressure)
- Volatile – exhibits VP
- Nonvolatile – no measurable VP
- Raoult’s Law – lowering of a vapor pressure of a solvent is equal
to the product of the mole fraction of the solute and vapor
pressure of the solvent
- Formula:
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Boiling Point Elevation
- BP – temp at which liquid pressure is equal to atmospheric
pressure (1 atm = 760 mmHg)
- The boiling point of a solution containing a non-volatile solute
would be higher than the pure solvent because the solute
would lower the vapor pressure of the solvent
- Formula:
- Kb = ebullioscopic/molal BPE constant (0.52oC/m)
- M = molality
- w1 = weight of solvent
- w2 = weight of solute
- MW2 = molecular wt of solute
Freezing Point Depression
- FP – temp at which the solid and liquid phases are in equilibrium
under an external pressure
- In general, solutions have a lower freezing point than the pure
solvent
- Applications:
o Salt is spread on roads to melt ice
o Ethylene glycol as “anti-freeze”
- Formula:
-
Also defined as the pressure required to prevent osmosis in
solutions.
Hypertonic – causes crenation
Hypotonic – causes swelling/lysis
Isotonic – 0.9% (w/v) NaCl
Formula:
- π = osmotic pressure in atm
- V = volume in L
- n = no. of moles of solute
- R = gas constant (0.08205 L·atm/mol·K)
- T = absolute temperature
Gas Laws
- Boyle’s Law – volume is inversely proportional to pressure
o Formula: P1V1 = P2V2
- Charles’ Law – volume is directly proportional to temperature
(Kelvin)
o Formula: V1/T1 = V2/T2
- Avogadro’s Law – volume is directly proportional to moles
o Formula: V1/n1 = V2/n2
- Dalton’s Law of Partial Pressure – the pressure exerted by a
mixture of gases is the sum of the partial pressures that each
gas in the mixture exert individually
o Formula
-
- Kf = cryoscopic/FPD constant (Kf = 1.86oC/m)
Osmotic Pressure
- Osmosis – movement of water across a semipermeable
membrane from low to high concentration
- This is the pressure required to offset the movement of solvent
thru a s. membrane
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Ideal Gas Law
o Formula: PV=nRT
Graham’s Law – rate of the effusion of two gases (and diffusion)
are inversely proportional to the square roots of their densities
providing the temperature and pressure are the same for the two
gases
o Formula:
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o
o
Diffusion – gradual mixing of molecules of one gas with
the molecules of another gas by virtue of their kinetic
properties
Effusion – passage of a gas under pressure through a
small opening
Solutions
- Solute + Solvent
- Factors affecting solubility:
o Nature of Solute and Solvent
o Temperature: ⬆ Temp = ⬆ Solubility (Most of the time)
o Pressure: ⬆ Pressure = ⬆ Solubility of gas in liquid
(Henry’s Law)
- Exceptions:
o Exothermic - ⬆ Temp = ⬇ Solubility
o Solution of gas in liquid: ⬆ Temp = ⬇ Solubility
Chemical Thermodynamics
- Thermodynamic System – part of the universe isolated from the
rest by a boundary
- Surrounding = everything outside
Type of System
Allows Exchange of
Open (Non-conservative)
Matter and Energy
Closed (Conservative)
Energy ONLY
Isolated (Adiabatic)
No Matter, No Energy
Law of Thermodynamics
- 1st Law of Thermodynamics - Heat and work are forms of energy
transfer. Energy is invariably conserved, however the internal
energy of a closed system may change as heat is transferred
into or out of the system or work is done on or by the system
o Remember: Conservation of Energy & Energy of the
Universe if Constant
- 2nd Law of Thermodynamics - An isolated system, if not already
in its state of thermodynamic equilibrium, spontaneously evolves
towards it. Thermodynamic equilibrium has the greatest entropy
among the states accessible to the system.
o Remember: Entropy, Gibbs Free Energy, GFE –
expendable amount of energy
o
△G(-) = Spontaneous, △G(+) = Non-Spontaneous, △G(0)
= Equilibrium
3rd Law of Thermodynamics - The entropy of a system
approaches a constant value as the temperature approaches
zero. The entropy of a system at absolute zero is typically zero,
and in all cases is determined only by the number of different
ground states it has. Specifically, the entropy of a pure crystalline
substance at absolute zero temperature is zero
Chemical Equilibrium
- State at which the amount of reactant and products present are
constant
- Le Chatelier’s Principle
o If a system is subjected to stress, the system will adjust
to relieve the stress
o Stress:
§ Concentration
§ Pressure and Volume
§ Temperature
§ Catalyst – causes NO SHIFT in Equilibrium
Ionic Equilibrium
- Electrolytes dissociates into ions
- Acids and Bases
Acids
Bases
Sour taste
Bitter taste
Litmus: blue to red
Litmus: red to blue
+ metals à H gas
Feel slippery
+ carbonate & bicarbonate à
Phenolphthalein: pink to violet
CO2
Phenolphthalein: colorless
Methyl orange: yellow
Methyl orange: pink/red
NaOH, KOH, Ca(OH)2
HCl, HClO3, HClO4, HBr, HI,
HNO3, H2SO4, H3PO4
- Electrolytes – conductors
o Weak
§ incomplete dissolution
o Strong
§ strong acids and bases, complete dissolution
-
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-
Non-Electrolytes – will not dissociate, will not conduct electricity
Acid-base Theories
Theory
Acid
Base
Arrhenius
H+ in H2O
OH- in H2O
Bronsted-Lowry
H+ donor
Accepts H+
Lewis
Accepts e pair
e- pair donor
Neutralization
- Acid + Base à Salt and Water
- Titration – progressive addition of a solution of known
concentration to a substance of unknown concentration
- Indicator – Substance that changes color at the end point
- Neutralization
point
(Stoichiometric
point/Equivalence
Point/Theoretical Point) – point when equal amounts of acid and
base have reacted; non-observable
- Endpoint – Experimental approximate of neutralization point;
observable
- pH – the negative logarithm of the H+ concentration
Basic Principles of Analysis
pH
- number of grams equivalent of H per liter of solution
- pH = -log[H+]
- pOH = -log[OH-]
- pH + pOH = 14
- (–) value of pH is possible
- >14 value is also possible
- Protolysis – process whereby a proton is transferred from one
molecule to another
- Autoprotolysis – process whereby there is a transfer of proton
from one molecule to another identical molecule
- Amphoteric – property where a substance can act either as acid
or base
- Isohydric – a solution having the same pH as the standard
solution
Salts
- Neutral Salt = SA + SB
- Acidic Salt = SA + WB
- Basic Salt = WA + SB
-
Strong Acid – ionizing more completely
o H-CBNIPS
§ HCl, HBr, HNO3, HI, HClO4, H2SO4
Strong Base – releasing more hydrogen ions
o Hydroxides of Group IA/IIA
Ka – acid dissociation constant
Kb – base dissociation constant
Ksp – solubility product constant
pH7 – neutral
pH<7 – acidic
pH>7 – basic
pH Calculations
Buffers
- Solutions that have the property of resisting changes in pH when
acids or bases are added to them
- This property results from the presence of a buffer pair which
consists of either:
o Weak acid and some salt of a weak acid or its conjugate
base
o Weak base and some salt of a weak base or its conjugate
acid
- Henderson-Hasselbach Equation
o Weak acids
o
-
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Weak bases
Buffer Capacity
o Ability of a buffer solution to resist changes in pH
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Depends on the amount of the acid and the base from
which the buffer can neutralize before pH begins to
change to an appreciable degree
o Van Slyke
§ Was responsible for a quantitative expression
§ Amount of g/l of strong acid or strong base
required to be added to a solution to change its
pH by 1 unit
§ Higher buffer capacity, lower change in pH
o Pearson’s HSAB Principle
§ Hard acids are electron acceptor with high
positive charges and relatively small sizes while
soft acids have low positive charges and relatively
large sizes
Nuclear Chemistry
- Radioactivity – decomposition process of unstable nuclei to more
stable ones
- Radiation – energy and particles released during the
decomposition process
3 Types of Natural Radioactivity
- ɑ-radiation - ɑ-particle
o Mass number decrease
by 4 and atomic
number by 2
- β-radiation – e- (neutron à
proton)
o mass number stays the same but the atomic number
increases by 1
o
-
γ-radiation – γ-rays are high energy photons
o no change in mass number and atomic number
Units of Radioactivity
- Non-SI – Curie (Ci) – 1Ci = 3.7 x 1010 decays/sec
- SI: Bequerel (Bq) – 1Bq = 1 decay/sex
- Unit of Radiation Damage – R.E.M.
- Unit of amount of exposure to Radiation – rad or gray
MODULE 1: INORGANIC MEDICINAL & PHARMACEUTICAL
CHEMISTRY
Alkali Metals
- Group IA: Alkali Metals
- Most Reactive Metals
- Valence = 1
Hydrogen (H)
- Inflammable air
- Lightest element
- Isotopes:
o Protium – most abundant
o Deuterium – heavy hydrogen
o Tritium – radioactive
Lithium (Li)
- Earth
- Lightest Metal
- Pharmacologic Action:
o Depressant
o Diuretic
- Non-Pharmacologic Action
o Heat exchanger in aircon
- Important Compounds
o Lithium Bromide – LiBr
§ Depressant
o Lithium Carbonate – Li2CO3
§ DOC for Mania
§ BN: Lithase
Sodium (Na)
- Natrium
- Extracellular fluid
- Pharmacologic Action:
o Fluid Retention
- Important Compounds:
o Sodium Acetate (C2H3NaO2)
§ Diuretic
§ Urinary and systemic alkalizer
§ Antacid
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o
o
o
o
o
o
o
o
o
Sodium Bicarbonate (NaHCO3)
§ Baking Soda
§ Systemic Antacid
§ Carbonating Agent
§ Side Effects:
• Systemic alkalosis
• Rebound hyperacidity
Na Dihydrogen Phosphate (NaH2PO4)
§ Feet enema
§ Cathartic
Sodium Metabisulfite (Na2S2O5)
§ Water soluble antioxidant
Sodium Carbonate (Na2CO3)
§ Antacid
§ Carbonating agent
Sodium Chloride (NaCl)
§ Rock salt, table salt, soler salt
§ Electrolyte replenisher
§ Tonicity adjusting agent
§ Condiments
§ Preservative
Sodium Citrate (Na3C6H5O7)
§ Alkalizer
§ Buffer
§ Diuretic
§ Expectorant
§ Shorten the Coagulation time
Sodium Fluoride (NaF)
§ Anticariogenic (2% solution)
Sodium Hydroxide (NaOH)
§ Caustic soda
§ Sosa
§ Lye
§ Saponifying agent
Sodium Phosphite (Na2HPO3)
§ Reducing agent
o
o
o
o
o
o
o
o
Sodium Hypochlorite (NaClO)
§ Dakin’s solution, chlorox
§ Oxidizing agent
§ Disinfectant
§ Bleaching agent
Sodium Iodide (NaI)
§ Expectorant
§ Antifungal
§ Iodine Solubilizer
Sodium Lactate (NaC3H5O3)
§ Antacid
§ Diuretic
Sodium Nitrate (NaNO3)
§ Chile Salt Peter
§ Vasodilator
§ Meat preservation
§ Treatment in Cyanide Poisoning
Sodium Sulfate (Na2SO4)
§ Glauber’s salt
§ Cathartic
Sodium Tartrate (C4H4Na2O6)
§ Primary standard of KFR for water content
determination
Sodium Thiocyanate (NaSCN)
§ Hypotensive agent
Sodium Thiosulfate (Na2S2O3)
§ Hypochlor, Photographer’s hypo
§ Treatment of cyanide poisoning with sodium
nitrate
§ VS in iodometry and permanganometry
Potassium (K)
- Kalium
- Most abundant and predominant intracellular cation
- Deficiency: Hypokalemia
- Pharmacologic Action:
o Diuretic
o Important in Muscle Contraction
- Important Compounds
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o
o
o
o
o
o
o
o
o
o
o
Potassium Acetate (CH3CO2K)
§ Antacid
§ Diuretic
§ Urinary and systemic alkalizer
Potassium Bicarbonate (KHCO3)
§ Systemic antacid
§ Carbonating agent
§ Source of bicarbonate ion
Potassium Bitartrate (KC4H5O6)
§ Cream of tartar, creamor
§ Laxative
Potassium Bromide (KBr)
§ Antidepressant
Potassium Carbonate (K2CO3)
§ Potash, salt of peter, perlash
§ Antacid
§ Carbonating agent
§ Carbonate source
Potassium Chlorate (KClO3)
§ Oxidizing agent
§ Component in:
• Toothpaste, gargle and mouthwash
Potassium Chloride (KCl)
§ Electrolyte replenisher
§ Take note: SLOW push
Potassium Citrate (C6H5K3O7)
§ Diuretic
§ Expectorant
§ Diaphoretic
Potassium Hydroxide (KOH)
§ Caustic potash, lye potash
§ Saponifying agent (SOFT soap)
Potassium Iodide (KI)
§ Expectorant
§ Antifungal
§ Iodine solubilizer
Potassium Nitrate (KNO3)
§ Salt peter, salitre, salt prunella
§ Diuretic
§ Meat preservative
o Potassium Permanganate (KMnO4)
§ Mineral chameleon
§ Oxidizing agent
§ VS in permanganometry
o Potassium Dihydrogen Phosphate (KH2PO4)
§ Cathartic
o Potassium Sodium Tartrate (KNaC4H4O6·4H2O)
§ Rochelle Salt, Sal Signette
§ Cathartic
§ Sequestering agent
o Potassium Thiocyanate (KSCN)
§ Hypotensive agent
o K2Sx·K2S2O3
§ Sulfurated potash, liver of sulfur
Ammonium (NH4)
- Hypothetical alkali metal
- Pharmacologic Action
o Diuretic
o Buffer
o Expectorant (like iodide)
o Anti-Cariogenic (like fluoride)
- Important Compounds
o NH4Br
§ Depressant
§ Sedative
o (NH4)2CO3
§ Sal volatile, hartshorn
§ Expectorant (ammonium)
§ Antacid (carbonate)
§ Respiratory stimulant
o NH4Cl
§ Muriate of hartshorn
§ Expectorant
§ Diuretic
§ Urinary acidifier
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HgNH2Cl
§ White precipitate
§ Topical anti-infective
o NH4I
§ Source of iodide
§ Expectorant
§ Antifungal
o NH4CH3COO
§ Spirit of Mendererus
§ Styptic
Coinage Metals
- Can occur in free metal state
- Complexes/chelates
Copper (Cu)
- Cuprum
- Only reddish metal
- Component of hemocyanin and cytochrome oxidase
- Important Alloys:
o Brass – Cu + Zn
o Bronze – Cu + Sn
- Pharmacologic Actions
o Protein precipitant
o Enhances physiological utilization of iron
o Toxicity: Wilson’s Disease
§ Antidote: Penicillamine
- Important Compounds
o CUSO4·5H2O
§ Blue vitriol, blue stone
§ Component of Benedict’s, Barfoed’s
Fehling’s Ingredient
§ Antidote for Phosphorus poisoning
§ Ingredient of Bordeaux mixture
o [Cu3(AsO3)2·Cu(C2H3O2)2]
§ Paris green
§ Insecticide
o (Cu)3(C6H5O7)3
§ Astringent in 8% concentration
Silver (Ag)
- Argentum, shining, bright
- Pharmacologic Action:
o Oligodynamic Property (germicidal action)
- Toxicity: Argyria
- Antidote: Normal Saline Solution (NSS)
- Important Compounds
Soluble Compounds
o AgNO3
§ Lapiz infernulariz, lunar caustic, indelible ink,
caustic pencil
§ Treatment of warts
§ Eye antiseptic for newborn babies of mother with
gonorrhea
o Ag(NH3)2NO3
§ Howe’s solution
§ Dental protective
§ Desensitizing agent
Insoluble Compounds
o AgI
§ Poisonous
§ Disinfectant
o Ag Proteinate
§ Mild Ag Proteinate
• Argyrol
• Antiseptic for the eye
o
§
and
§
Strong Ag Proteinate
• Protargol
• Stronger germicide for ear and throat
Colloidal Ag Proteinate
• Collargol
• General germicide
Gold (Au)
- Aurum, shining dawn, king of all metals
- Most malleable and ductile
- Best conductor of electricity
13
Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
-
Dissolved by:
o Aqua Regia (3 part HCl + 1 part HNO3)
o Selenic Acid
- Important Compounds
o Aurothioglucose (IM)
§ Treatment of gout and RA
o Gold Na Thiomalate (IM)
§ Treatment of gout and RA
o Auranofin (PO)
§ Treatment of gout and RA
Alkaline Earth Metals
Beryllium (Be)
- Never employed in medicine because it is the most toxic metal
- Fluorescent lamp
Magnesium (Mg)
- Lightest of all structurally important metal
- Chlorophyll component
- Compound of Gringnard’s reagent
- Natural Sources:
o As Silicates (talc, asbestos)
o As CO3 (magnesite, dolomite)
o As SO4 (keisrite)
- Pharmacologic Action
o Laxative
o Depressant
o Natural Calcium Channel Blocker
- Antidote: Ca Gluconate
- Important Compounds
o MgCO3
§ Magnesia
§ Antacid
§ Laxative
o Mg(OH)2
§ Milk of magnesia, magnesia magma
§ Antacid
§ Laxative
o MgO
§ Calcined Magnesia
o
o
o
o
§ Laxative
§ Antacid
§ Component of Universal Antidote
2MgO·3SiO2·nH2O
§ Antacid
§ Advantage:
• Prolonged antacid action
MgSO4
§ Epsom Salt
§ Cathartic (PO)
§ Anticonvulsant (IM)
§ Antidote for Ba toxicity
Hydrated Mg Silicate
§ Talc, soapstone, French chalk
§ Softest mineral
§ Filtering agent
§ Clarifying agent
§ Dusting powder
Mg3(C6H5O7)2
§ Magnesium Citrate
§ Lemonade purgante, purgative lemon
Calcium (Ca)
- 2nd most abundant cat ion in extracellular fluid
- Vitamin D is needed for its maximum absorption
- Pharmacologic Action
o Blood coagulation factor
o Important muscle contraction
o Important release of neurotransmitter
o Primary element of bones and teeth
- Deficiency state
o Osteoporosis
o Osteomalacia (adults)
o Rickets (immature mamals)
o Hypocalcemia
- Important Compounds
o CaBr2
§ Sedative
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Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
o
o
o
o
o
o
o
o
o
o
§ Depressant
CaCO3
§ Precipitated chalk, prepared chalk
§ Antacid
§ Ingredient of toothpaste, dentifrices
CaCl2
§ Muriate of lime
§ Ca replenisher
Ca Gluconate
§ Ca supplement and replenisher
Ca(OH)2
-solid-liquid
§ Slaked lime, milk of lime, calcium hydrate
§ Antacid
§ Saponifying agent
Ca(C3H5O3)2
§ Ca supplement
CaHPO4·2H2O
§ Source of Ca and PO4
CaO
§ Lime, quicklime, calx
§ Component of Bordeaux mixture
§ Insecticide
Ca3(PO4)2
§ Bone ash
§ Antacid
CaClO or CaOCl
§ Chlorinated lime, chloride of lime
§ Disinfectant bleaching agent
CaSO4·½ H2O or 2H2O W
§ GPlaster of paris, gypsum, terra alba
§ Rodenticide
§ Prep of surgical casts and dental impressions
Strontium (Sr)
- Manufacture of flares
- Important Compound
o SrCl2
§ Temperature de sensitizing agent (Sensodyne)
Barium (Ba)
- Heavy
- Toxicity: Baritosis
- Antidote: Epsom Salt
- Important Compounds
o BaSO4
§ Radiopaque substance used for GIT imaging
o BA(OH)2
§ CO2 absorbent
Radium (Ra)
- Marie Curie
- Radioactive element used for:
o Cancer radiotherapy
o Diagnostic purpose
Volatile Metals
Zinc
- Present in insulin
- Pharmacologic Action
o Astringent
o Antiseptic
o Antiperspirant
o Protectant
- Container of batteries
- Protective coating of galvanized iron
- Deficiency: Parakeratosis
- Antidote: NaHCO3
- Important Compounds
o ZnCl2
§ Burnett’s disinfectant fluid
§ Disinfectant/antiseptic
§ Dentin desensitizer
§ Corrosive
o ZnO
§ Zinc white, Lassar’s paste
§ Antiseptic
§ Astringent
§ Topical protectant
15
Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
o
o
o
o
o
ZnO2
§ Antiseptic
ZnS
§ White lotion, while sulfide
§ Parasiticide, topical protectant, antiseptic
ZnSO4·7H2O
§ White vitriol
§ Emetic
§ Astringent
§ Prep of white lotion
Hydrated Zinc Silicate
§ Natural calamine
§ Topical protectant
Zinc-Eugenol Cement
§ Dental protective
Cadmium (Cd)
- Pharmacologic Action
o Astringent
- Manufacture of stink bomb
- Poisoning – Itai-itai (ouch-ouch)
- Antidote – BAL (British Anti-Lewesite) or Dimercaprol
- Important Compound
o CdCl2
§ Emetic
§ Treatment of Tinea infection
o CdS
§ Yellow sulfide
§ Anti-seborrheic
o CdSO4
§ Ophthalmic antiseptic
Mercury (Hg)
- Quicksilver, messenger of Gods
- Diuretic
- Antiseptic
- Treatment of Syphilis
- Cathartic
- Parasiticidal/Fungicidal
-
Industrial Use:
o Thermometer
o Amalgams (dental cement)
- Disease: Minamata
- Antidote: EDTA
- Important Compounds
o Hg2Cl2
§ Calomel
§ Cathartic
§ Local antiseptic
o HgCl2
§ Corrosive sublimate
§ Disinfectant
o HgI
§ Treatment of syphilis
o HgI2
§ Stimulant of indolent ulcers
o K2HgI4
§ Antiseptic
§ Component of Mayer’s reagent
o HgNH2Cl
§ White precipitate
§ Topical antiseptic
o HgO
§ Yellow precipitate
§ Ophthalmic anti-infective
Boron (B)
- Industrial use:
o Vulcanizing rubber
- Important Compounds
o H3BO3
§ Sal sativum
§ Toxicity: lobster appearance
§ Buffer (ophthalmic solution 2%)
§ Antiseptic
§ Tonicity adjusting agent
o Na2B4O7·10H2O
§ Borax
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Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
§
§
§
§
§
Aluminum (Al)
- Most abundant metal
- 3rd most abundant element
- Pharmacological Uses:
o Astringent
o Aluminum foils used for burn patients
- Important Compounds
o AlCL3·6H2O
§ Astringent
§ Antiseptic
§ Antiperspirant/deodorant
o
o
o
o
o
o
•
Na Tetraborate
Dobelle’s solution
Antiseptic
Eye wash
Wet dressing for wounds
Alum
§ [AlNH4(SO4)2·12H2O] – NH4 salt
§ [AlK(SO4)2·12H2O] – K salt
§ Astringent
Al(OH)3
§ Amphojel, Cremalin Gel
§ Antacid
§ Protectant
§ Disadvantage: constipation
AlPO4
§ Phosphagel
§ Antacid
§ Astringent
§ Demulcent
Al2(CO3)3
§ Treatment of phosphatic calculci
Al2O3
§ Alumina
§ Treatment of silicosis
Aluminum Silicate
§ Kaolin
§
§
China clay, native hydrated aluminum
silicate
• Adsorbent in diarrhea
Bentonite
• Soap clay, mineral soap, native colloidal
hydrated magnesium silicate
• Suspending agent
Pumice
• Volcanic origin and used as dental
abrasive
Gallium (Ga)
- Substitute for mercury in manufacture of arc lamps
Carbon Group
Carbon (C)
- Manifestation
o Crystalline – graphite, diamond
o Amorphous – coal, anthracite
- Important Compounds
o CO2
§ Treatment of acne, warts, corns, calluses,
eczema
o CO3-2
§ Antacid
§ For effervescent tablets
o CO
§ 210x greater affinity to hemoglobin than oxygen
leading to asphyxia then death
§ Treatment:
• 100% O2
• Artificial air (He 80%, O2 20%)
• Hyperbaric O2
Silicon (Si)
- 2nd most abundant element
- Important Compounds
o SiO2
§ Toxicity: Silicosis
17
Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
o
o
o
o
o
o
o
Glass
§ Na2CO3 + pure silica
Kaolin
§ Adsorbent
Purified Siliceous Earth
§ Absorbent
Bentonite
§ Suspending agent
Talc
§ Clarifying agent
§ Dusting agent
Attapulgite
§ Polymagma, diatabs, quintess
§ Adsorbent
Simethicone
§ Polymeric Dimethyl Siloxane
§ Antiflatulent
Tin (Sn)
- Stannum
- Preparation of tin cans
- Important Compounds
o SnF2
§ Anticariogenic
o SnO2
§ Germicide
Lead (Pb)
- Plumbum
- Astringent
- Protein precipitant
- Poisoning: Plumbism
- Antidote: EDTA
- Sources of Poisoning
o Lead pipes
o Paints
o Batteries
- Important Compounds
o Pb(CH3COO)2
§ Sugar of lead
§ Astringent
Pb2(CH3COO)
§ Goulard’s extract
§ Astringent
§ Antiseptic
o PbO
§ Litharge
Titanium/Zirconium
Titanium (Ti)
- Titan, sons of the earth
- Powerful reducing agent
- Important Compound
o TiO2
§ Opacifying agent
• Ocusert
§ UV Ray Protectant
• TiO2 reflects UV
Zirconium (Zr)
- Use: same with aluminum but banned due to granuloma
formation
- Former Official Compounds
o Oxide
o CO3
§ Both used as antiperspirant and for athlete’s foot
Nitrogen Group
Nitrogen (N)
- Mephitic air, azote, without life
- Most abundant gas in air: 71% N2, 29% O2
- Important Compounds
o N2 – very stable
§ Used as INERT atmosphere for readily oxidizable
substance
§ Liquid N2
• Used as refrigerant
• Container: Black
o N2O
§ Laughing gas
o
18
Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
§
§
§
o
o
NO2
§
§
NO3§
Inhalation anesthetic
S/E: Diffusion hypoxia
Container: Blue
Vasodilator
For cyanide poisoning
Preservative
Aromatic Ammonia spirit
§ Spirit of Hartshorn, spirit of sal volatile
§ Respiratory stimulant
Phosphorus (P)
- Light carrier, St. Elmo’s fire
- 2 forms:
o White – poisonous
o Red – non-poisonous
- Important Compound
o PO4
§ Antacid
§ Cathartic
Arsenic (As)
- Lewisite metal
- Insecticide
o Copper aceto arsenate (Paris green)
- Antidote: BAL
- Important Compounds
o As2O3
§ Insecticide
§ Anti-leukemic
o AsI3
§ Primary standard in the preparation of ceric
sulfate
Antimony (Sb)
- Pharmacologic use:
o Expectorant
o Emetic
o
o Anti-helminthic
Important Compound
o SbKOC4H4O6
§ Tartar emetic, brown mixture
§ Emetic
§ Tx of schistosomiasis
Bismuth (Bi)
- Beautiful meadow
- Pharmacologic Action
o Astringent
o Antiseptic
o Internal Protective for ulcer
- Causes
o Dark stool & Blue-black gums
- Antidote: BAL/ Dimercaprol
Tantalum (Ta)
- Not affected by any body fluid, therefore inert in our body
- Sheet form use in repair of bones, nerve, and tissue
Chalcogens
Oxygen (O)
- Empyreal air, dephlogisticated air, “yne”
- Most abundant element
- Treatment of hypoxia/asphyxia
- Container: Green
Sulfur (S)
- Brimstone, shubari, enemy of copper
- Used in preparation of scabicidal and keratolytic ointment or
lotion
- Stimulant cathartic
- Depilatory agent
- Anti-dandruff
Selenium (Se)
- Selena, moon
- Essential trace element
- Promotes absorption of Vitamin E
- Antioxidant
-
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Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
-
Important Compound
o SeS2 (Selsun blue)
§ Anti-dandruff
Chromium, Molybdenum, Uranium
Chromium
- Essential trace element
- Glucose tolerance factor
- Deficiency: Hyperglycemia
- Important Compound
o K2Cr2O7
§ Oxidizing agent
Molybdenum (Mo)
- Essential trace element
- Co-factor enzyme
- Important compound
o Molybdenum Oxide + FeSO4
§ Hematinic
§ BN: Mol-Iron
Uranium (U)
- Discovered by Becquerel
- Radioactive element used for manufacture of atomic bombs
- No pharmaceutical use
Halogens
Fluorine
- Strongest oxidizing agent
- Poisoning: Fluorosis
- Principal Manifestation:
o Motted Enamel
o Abnormal bone growth
- Important Compounds
o NaF
§ Anticariogenic at 2% solution
o SnF2
§ Anticariogenic at 8% solution
Chlorine (Cl)
- Dephlogisticated muriatic acid
- Most Abundant Extracellular anion
- Used as Water disinfectant
-
Important Compounds
o Hypochlorite (Na, K)
§ Bleaching agent
o HCl
§ Tx of achlorhydria
Bromine (Br)
- Dark reddish brown fuming liquid with suffocating odor
- Pharmacologic Action
o Sedative
o Depressant
- Poisoning: Bromism
- Principal Manifestation
o Skin Eruption
o Psychosis
o Weakness
o Headache
- Antidote: NaCl and NH4Cl
Iodine (I)
- Expectorant
- Anti-fungal
- Deficiency: Goiter
- Elemental Iodine preparation
o Strong Iodine Solution – Lugol’s soln
o Iodine Tincture – disinfectant
o Povidone-Iodine – Betadine
Astatine (At)
- Only metallic
- Only synthetic halogen
- Only radioactive halogen
Manganese/Technecium
Manganese (Mn)
- Co-factor in:
o Protein synthesis
o Phosphorylation
o Fatty acid and cholesterol synthesis
- Poisoning: Parkinson-like
- Important Compound
20
Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
KMnO4
§ Mineral chameleon
§ Oxidizing agent
§ Antiseptic
Technecium (Tc)
- 1st element produced artificially
- Used in preparation of radiopharmaceuticals
Noble Gases
Helium (He)
- 2nd lightest gas
- Toxicity (Inhalation) – Donald duck-like sound
- Container: Brown
Neon (Ne)
- For advertising
Argon (Ar)
- Most abundant noble gas
- Substitute for N2 in providing inert atmosphere
Krypton (Kr)
- Least abundant of all noble gases
- Have inhalational anesthetic activity
Xenon (Xe)
- Investigational with inhalational anesthetic activity
Radon (Rn)
- Niton
- Synthetic noble gas
- Used for treatment of Cervical CA
Iron (Fe)
- Present in proteins:
o Hemogloin
o Transferrin
o Ferritin
o Cytochrome oxidase
- Enhance absorption of:
o Vitamin C
o Copper
- Hematinic
o
-
Toxicity:
o GIT Distress
o Cardiac Collapse
- Antidote: Deferoxamine
- Important Compounds
o FeSO4
§ Green vitriol
§ Hematinic
§ S/E: constipation
o Ferrous Gluconate
§ BN: Fergon
§ Adv: less irritating
o Ferrous Fumarate
§ BN: Toleron
o FeCO3
§ Chalybeate pills, Ferrunginous pills
§ Hematinic
o FeCl3
§ Astringent
§ Styptic
§ Detection of tannins
o Fe4[Fe(CN)6]3
§ Ferric ferrocyanide
§ Prussian blue
o Fe3[Fe(CN)6]2
§ Ferrous ferricyanide
§ Turnbull’s blue
Other Metals
Cobalt (Co)
- Essential in development of erythrocyte and hemoglobin
- Component of Vitamin B12
- Deficiency: Megaloblastic Anemia
- Important Compound
o CoCl2
§ Lover’s ink, sympathetic ink
§ Desiccator indicator
21
Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
Nickel (Ni)
- Old Nick’s copper
- Fossil fuel
Osmium (Os)
- Heaviest
- Densest metal
- Important Compounds
o Osmic acid
o Osmium tetroxide
§ Both used in staining microorganism for
microscopic study specially in electron
microscopy
Platinum (Pt) & Palladium (Pd)
- Catalyst in finely divided steel
Flame Test
Metals
Non-luminous flame
Under cobalt gas
Sodium
Persistent Golden Yellow
Nil
Potassium
Violet
Crimson
Lithium
Carmine Red
Purple
Calcium
Brick Red
Light Green
Strontium
Crimson
Purple
Barium
Yellowish Green
Bluish-Green
Borate, Cu,
Green
Tl, P
Pb, As, Sb,
Blue
Yellow
Bi, Cu
Ammonium
colorless
MODULE 1: ORGANIC CHEMISTRY &
ORGANIC MEDICINAL CHEMISTRY
Organic Chemistry
- Branch of chemistry that deals with carbon-containing
compounds with:
o H, O, P, N, S, X
- Isomerism
o Existence of two or more compounds having the same
molecular formula, but different structure
-
Isomer
o Compounds having the same molecular formula, but
different structure
Stereochemistry
o Branch of organic chemistry that is solely dedicated to
the study of isomers
Carbon
- Contains 4 binding sites for other atoms to attach to it
- These four binding sites, when bonded with
atoms/molecules form a tetrahedron
- Group 4, Period 2
- Atomic No. 6
o 1s2 2s2 2p2
22
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Reviewer by: camila kim vertucio
o Needs 4 more electrons to complete its octet
o Valence: 4
o Can only share: covalence
Hydrocarbon
- Contains C, H
- Hydrocarbon Derivatives – hydrocarbons that bear other carbon
& hydrogen atoms & other elements such as Oxygen, Nitrogen,
Sulfur, Halogen, Phosphorus, etc
Aliphatic
- Single chain, no ring/s
- Saturated – single bonds only
o Alkane (parafins)
o CnH2n+2
- Unsaturated – has multiple bonds
o Alkenes – double bond
§ CnH2n
o Alkynes – triple bonds
§ CnH2n-2
Aromatic
- Presence of ring/s, specifically benzene ring & its derivatives
- Examples
Alicyclic or Carbocyclic
- Chains that form a ring and behave like aliphatic (single bonds)
- Examples
o Cyclopropane
o Cyclobutene
o Cyclopropane
o Cyclobutene
- Cycloalkanes:
o CnH2n
Oxygen-Containing
- Aldehydes (RCHO)
o Ketones (RCOR)
- Ethers (ROR)
o Formed during dehydration of alcohol
o CnH2n+20
- Alcohols (Phenol)
-
Carboxylic Acid
o Carboxyl, -COOH
o Organic acid (RCOOH)
Carboxylic Acid Derivatives
o Acid acyl
o Anhydrides
o Ester (RCOOR)
o Amides
Nitrogen Containing
- Amines (amino group, –NH)
o Primary Amines: RNH2
o Secondary Amines: R2NH
o Tertiary Amines: R3N
- Heterocyclic
- Nitrogen-compounds
Halogen-containing
- Alkyl halides
- Aryl halides
Phosphorus-containing
- Phosphate groups
- Organophosphate
-
-
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Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
Sulfur-containing
- Thiols (–SH)
o Sulfur analogue of alcohols
o Sulfhydryls
- Thioethers (R-S-R)
Systems of Nomenclature
- Common
o Uses the name given when it was discovered
o Formic acid – ants
o Butyric acid – butter
o Prefixes: n-, iso-, neo- Derived
o Derived from parent compound
- IUPAC
o Most SYSTEMATIC
Based on
§ Longest continuous C chain or parent chain
§ Use of numbers
§ Use of C # prefixes
o QSAR – Quantitative Structure & Activity Relationship
IUPAC Rules:
o Name by considering the longest carbon chain
o Number C atoms consecutively from one end so that the
branches or substituents are given the lowest position
numbers
o Modify the Suffix based on the type of formula or the
functional group
§ ROH (-ol)
§ RCHO (-al)
§ RCOR (-one)
§ RCOOH (-oic acid)
o Identify the substituents & indicate the positions by using
numbers
§ CH3 (methyl)
§ R (alkyl)
§ OCH3 (methoxy)
§ OR (Alkoxy)
o
↑
§ Cl (Chloro)
§ Br (Bromo)
§ NH2 (Amino)
o If there is more than one of the same substituent/ alkyl
group on the chain, indicate the number of groups by
using prefixes; di- two; tri-three; tetra-four; & so on.
Saturated Hydrocarbons
- Alkanes: CnH2n+2 (-ane)
# of C
Prefix
+ -ane
Molecular Formula
atoms
1
MethMethane
CH4
2
EthEthane
C2H6
3
PropPropane
C3H8
4
ButButane
C4H10
5
PentPentane
C5H12
6
HexHexane
C6H14
7
HeptHeptane
C7H16
8
OctOctane
C8H18
9
NonNonane
C9H20
10
DecDecane
C10H22
(separate pdf for examples)
- Alkyl groups
o Can participate in Van der Waals interaction and
hydrophobic bonding
o Metabolism: Oxidation
o Aryl Groups (Ar) – aromatic (benzene ring) with a
hydrogen atom removed
- Reactions to Consider
o Combustion – chemical reaction in which HC burns (rapid
oxidation) & produces CO2 and H2O
- Cycloalkanes – alkanes that exist in the shape of a ring
o Cyclopropane/Trimethylene
o Cyclobutane
o Cyclopentane
Unsaturated Hydrocarbons – have multiple bonds in their molecules
- Alkenes: CnH2n (-ene)
o Double bond
24
Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
Ex: Propene: CH3-CH=CH2
Reactive site occur in C=C – double bond (e- rich)
o Electrophile (E!) – e- poor/ e- loving reagents (+)
o Nucleophile (N !) – e- rich reagent (-)
o Electrophilic Addition – alkene react with electrophiles
- Alkynes: CnH2n-2 (-yne)
o Triple bond (one or more)
- Aromatics – contain benzene ring that have multiple double
bonds
o Benzene: C6H6 (subject to substitution electrophilic)
o Toluene – methyl derivative of benzene
o Xylene – dimethyl benzene
Aromaticity (Criteria)
o Cyclic
o Flat/Planar – (sp2C = double bond)
o Conjugated double bonds – having alternating double
bonds
o Huckel’s Rule – 4n+2 rule
Stereochemistry (Reasons)
Order of Bonding
- Structurally isomer
- Chain – branching
o Exhibited by alkanes
o Differ in the arrangement of C atoms
o C4H10 (butane/isobutane)
o
o
-
-
C5H12 (pentane/ isopentane/ neopentane)
Position – position of multiple bond or differ in the position of
substituent or functional group
o Differ in position of the substituent or unsaturated bonds
o
C4H8 – alkene with 1 double bond
o
C3H7Br
o
Prefixes that designate positions in the benzene:
§ Ortho – indicate substances on the benzene ring
in positions next to each other
§
Meta – substituents on the benzene ring
separated by one carbon atom
§
Para – substituents separated by two carbon
atoms
Functional Isomer – functional group
o Differ in their functional groups
Spatial Orientation
- Arrangement of atom in space
- Stereoisomer
o Geometric Isomers – double bond (alkene), cyclic – CisTrans
25
Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
§
§
o
Cis (means on the same side)
Trans (means across or on opposite sides)
Cyclobutane
Planar – not a stable
conformation, all are eclipsing
Conformational Isomers
§ Open chain/acyclic – can be obtained in rotation
along a single bond
§ Cyclic-ring flipping
Ethane
Saw horse projection
Butterfly conformation – more
Stable
Cyclopentane
Planar – not stable
Perspective formula
(dash – back, wedge – front)
Envelope conformation
Cyclohexane
Chair – most stable
Newman projection
eclipse conformation &
staggered conformation (more
stable)
Planar – not stable
Boat conformation – more
stable
26
Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
Optical Activity
- Ability of a compound to rotate a polarized light either to right or
to the left
- Can only be determined by POLARIMETER
- Dextrorotatory = d/(+)
- Levorotatory = l/(-)
Chiral Center/Chiral Carbon/Asymmetric Chiral Carbon
- Stereocenter
- Carbon to which four different atoms or group of atoms are
attached
No symmetry element
- Enantiomers – mirror images but not superimposable
o Optical Isomer since they rotate light in the opposite
direction
- Diastereomers – non-mirror images, not superimposable
- Mesocompounds – mirror images, superimposable
o Same compounds
- Epimer – special type of diastereomers
o Identical in all except in one chiral center
o Differ only in configuration at one asymmetry carbon
atom
§ D-glucose/D-mannose – epimers at 2
§ D-glucose/D-galactose – epimers at 4
- Anomer – differ only in configuration at Carbon 1 (carbonyl C or
anomeric C)
o
Fischer Projection Formula
-
-
-
Tartaric Acid
= # stereoisomers = 2n (n = chiral center)
= 22
=4
27
I-II - mirror images
o Superimposable
§ Meso
compounds
(compounds
with
stereocenters but are chiral)
§ Optically inactive
II-III – non mirror images
o Non Superimposable
§ Diastereomers
III-IV – mirror images
o Non Superimposable
§ Enantiomers
Meso Compounds – compounds with stereocenters but are
chiral
o Characterized by the presence of a plane of symmetry
and are superimposable
Racemic Mixtures (racemates)
o Produced with mixtures of equimolar concentrations of
dextro & levo isomers
o Contain equal amounts of
§ D & L isomers
§ R & S isomers – determine by Cahn-IngoldPrelog
o Example: Thalidomide
§ exist 2 chiral center
§ r-thalidomide – sedative/ hypnotic
§ s-thalidomide – teratogenic
§ Thalidomide syndrome – because of the
presence of s-thalidomide
• Phocomelia (short limb)
• Amelia (no limb)
Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
Haworth Projection
- Presents a cyclic sugar structure
- Bioisostere - substituents or groups w/ similar physical or
chemical properties that in impart similar biological properties to
a chemical compounds
Purpose:
o Enhance the desired biological or physical properties of
a compound without making significant changes in
chemical structure
o Increase Potency
o Decrease Side effects
o Increase duration of action by altering metabolism
o Isosteric analogs may act antagnonistically w/ the parent
molecule
Example of Bioisosteric replacements:
o Fluorine vs Hydrogen
o Hydroxyl vs Amino Acids
o Hydroxyl vs Thiol Groups
o Methyl, Methoxyl, Hydroxyl, Amino groups vs Hydrogen
o Fluoro, Chloro, and Bromo, thiol vs Methyl and other
small alkyl groups
Types of Organic Reactions:
o Addition
o Substitution
o Elimination
o Re-arrangement
o Propagation, Initiation, Termination
o Oxidation
o Reduction
Organic Medicinal Chemistry
- Deals with the physicochemical properties of drugs that affect
its biological action
- Practice of medicinal chemistry is devoted to the discovery and
development of new drugs
Anti-Infective Agents
- Joseph Lister – introduced phenol (carbolic acid)
- Paul Ehrlich – Salvarsan (compound 606), selective toxicity
-
Atoxyl (sodium arsanilate and arsphenamine) – for sleeping
sickness
- Germicides – anti-infective agents that are used locally
- Antisepsis – apply to living tissue
- Decontamination – destruction or marked reduction in the
number or activity of microorganisms
- Disinfection – on inanimate objects
- Sanitation – reduction to a level acceptable for public health
- Sterilization – kills all types including spores
- Pasteurization – nonsporulating microorganisms (65o-100oC)
Local Anti-Infectives or Germicides
Alcohols and Related Compounds
- activity ↑with MW until C8 (octanol), Branching ↓ antibacterial
potency
- As primary alcohol chain ↑, Van der Waals interactions ↑,
ability to penetrate microbial membranes ↑
- As water solubility ↓, potency ↓ with MW
Alcohol, USP (Spiritus vini rectificatus, wine spirit, Grain alcohol)
- Fermentation product from grain and many other carbs, or
sulfuric-acid-catalyzed hydration of ethylene
- Most widely abused of all recreational drugs
- Commercial: 95% ethanol (forms an azeotrope in water that
distills at 78.2:C)
- Antidote: disulfiram blocks aldehyde dehydrogenase à
acetaldehyde (nausea, vomiting, flushing)
- Denatured - Completely denatured alcohol contains added
methanol (wood alcohol) and benzene
- Rubbing (70%) - Astringent, rubefacient, refrigerant, mild local
anesthetic
- Dehydrated/Absolute - nlt 99% ethanol; obtained by azeotropic
distillation
- Isopropyl - Rapidly bactericidal (50% to 95%), 40% equal
antiseptic power to a 60% ethanol
Ethylene Oxide
- Used to sterilize temp-sensitive medical equipment and those
that could not be autoclaved
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Pharmacy Board Exam Reviewer
Reviewer by: camila kim vertucio
-
Carboxide – 10% ethylene oxide + 90% CO2 (to prevent
explosion)
- MOA: alkylation of functional groups in nucleic acids and
proteins
Formaldehyde Solution (Formalin)
- nlt 37% of formaldehyde + methanol (retard polymerization to
formic acid and paraformaldehyde)
- MOA: direct, nonspecific alkylation of nucleophilic functional
groups
Glutarol/Glutaraldehyde (Cidex)
- components: glutaraldehyde and buffer
Phenols and their Derivatives
- standard for germicides
- phenol coefficient – ratio of a dilution of a given test disinfectant
to the solution of phenol that is required to kill a strain of S.typhi
under carefully controlled time and temperature
- straight-chain and substitution with alkyl, aryl, and halogen ↑
bactericidal activity
- low concentrations: denature bacterial proteins, high
concentrations: lysis of cell membranes
Phenol (Carbolic Acid)
- Introduced as surgical antiseptic by Joseph Lister; its use is now
obsolete
- Exhibits germicidal activity (general protoplasmic poison),
caustic, local anesthetic
- Liquefied Phenol – Phenol with 10% water
- p-Chlorophenol – used in combination with camphor in liquid
petrolatum
- p-Chloro-m-xylenol – 2% (shampoo), for athlete’s foot and jock
itch
- Hexachlorophene – easily adsorbed onto skin and enters
sebaceous glands (neurotoxicity)
Cresol
- mixture of three isomeric methylphenols; obtained from coal tar
or petroleum
- Chlorocresol – preservative
Thymol
- m-cresol; from Thymus vulgaris; mild fungicidal (tinea)
Eugenol
- from clove oil; applied on cotton to relieve toothaches, ingredient
in mouthwashes
Resorcinol
- weak antiseptic, keratolytic
- Hexylresorcinol - produces numbness when applied to tongue;
ingred in lozenges
Oxidizing Agents
- MOA: Oxidation (peroxides) and protein denaturation
(permanganates)
- Poor penetrability to infected tissues and organic matter
- Hydrogen Peroxide - active against anaerobic bacteria, wound
cleansing
- Carbamide Peroxide (urea + H2O2) - releases hydrogen
peroxide when mixed with water
- Hydrous Benzoyl Peroxide (2.5%, 5%, 10%) - most effective
topical OTC agent for the control of acne
Halogen-Containing Compounds
Iodine (oldest known germicide)
- Iodine tincture (2% solution of iodine in 50% alcohol with NaI)
- Lugol’s sol’n/Strong Iodine Sol’n (5% iodine in water with KI)
- Iodine Solution (2% iodine in water with KI)
Iodophors (Iodine + nonionic surfactants)
- Povidone-Iodine (Betadine)— complex with the nonionic
surfactant polymer, polyvinylpyrrolidone
Chlorine-Containing Compounds
- Disinfection of water supplies
- Forms Hypochlorous acid (HClO) when dissolved in water
- Halazone - disinfects drinking water
- Chloroazodin - a glyceryltriacetate solution is used as wound
dressing
- Oxychlorosene Sodium - complex of sodium salt of
dodecylbenzesulfonic acid and hypochlorous acid
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