Epinephrine (+) is 20 times more potent than its (-) enantiomer.

Levorphanol (L) has potent narcotic, analgesic and anti-tussive effect. Whereas its mirror
image dextrorphanol (D) has only anti-tussive action.
D-propoxyphene is analgesic, while (L) is anti-tussive.
Pseudoephedrine has lower CNS toxicity and vasopressor activity than ephedrine.
Epimerization is important in drug degradation and inactivation.
Cis-diethylstilbestrol has only 7% estrogenic activity of trans-diethylstilbestrol.
Cis-retinoic acid – isotretinoin used orally and trans-retinoic acid – tretinoin used topically in
the treatment of acne.
Trans conformation of acetylcholine binds to muscarinic receptors while gauche
conformation binds to nicotinic receptors.
Bioisosters are molecules containing groups that are spatially and electrochemically
equivalent. E.g. amide bond and ester bond in procainamide and procaine respectively.
Amino acids have zweitter ion structure (has both positive and negative electrical charge)
which accounts for their high melting points and lower water solubility.
The pH at which zweitter ion exists is called isoelectric point.
The pH at which cation exists is below isoelectric point.
The pH at which anion exists is above isoelectric point.
Α-methyl dopa is zweitter ion, being water insoluble, it is formulated as ethyl ester
hydrochloride for aqueous injection.

Conversion of amino acids

Glycine Purine Base

Glutathione Contain three amino acids
- ɣ - glutamyl
- cysteinyl
- glycine
Creatine Phosphorylated by creatine
Also known as phosphokinase to creatine
-Methyl guanidinoacetate phosphate
Synthesized from
- glycine Creatine lose water and
- arginine form creatinine which is
- methionine rapidly removed from
blood and excreted by
kidney.
 Haem Combine with globin =
Glycine + succinylcholine = haemoglobin
Haem

Phenylalanine Through phenylalanine Converted into tyrosine

hydroxylase and
dihydrobiopterin (DHB)
reductase enzymes

Deficiency of this enzymes Cause phenylketonuria

- accumulation of
phenylalanine

Tyrosine precursor of - dopamine

catecholamines - norepinephrine
- epinephrine
Epinephrine - structure active relationship
Meta -OH group Essential for activity
Removal of para -OH group Only has Selectivity for α-receptor
Addition of methyl group on α – carbon Improve oral activity
Larger N-substitution than methyl on α-carbon Has selectivity for β-receptor, e.g.
- dobutamine
- terbutaline

Tyrosine (…continue) Many tyrosine residues Thyroid hormones

iodinated to form - Thyroglobulin as a
thyroglobulin precursor
Melanin Tyrosine to dopa to melanin

Tryptophan Precursor of serotonin and melatonin

nicotinic acid (niacin)
indole and skatole

Glutamic acid Glutamate CNS neurotransmitter

Glutathione synthesis
Folic acid synthesis
Synthesis of GABA from
glutamic acid
Dihydrofolic acid
A mixture of
- Pteridine base
- PABA
- Glutamic acid
By L-glutamic acid
decarboxylase enzyme

Arginine Urea Arginine and citrulline

involve in urea cycle in liver
Creatine
 Nitric oxide (NO) Arginine by NO synthase =
NO + citrulline

Aspartate - Precursor of Purine & pyrimidine

(also act as excitatory synthesis
neurotransmitter)
Asparagine A part of oxytocin
Urea cycle

Carbohydrates
- Polyhydroxy aldehydes or ketones

Monosaccharides Polyhydroxy aldehydes Glucose

Polyhydroxy ketones
Aldehyde monosaccharides Reducing agents
Tes-tape test Glucose
-reagent strips with - glucose oxidase
enzymes + orthotolidine dye - peroxidase
Fructose
Used previously with
Benedict’s solution
Glucuronic acid + H2O2
Convert orthotolidine dye to
intense blue color

Oligosaccharides Short chain of Only hydrolysed by acid not

monosaccharides by base
Sucrose Glucose + fructose
Maltose 2 – glucose
Lactose Glucose + galactose
Lactulose A synthetic disaccharide
Lactulose Broken by bacteria in colon So, drop in pH and thus
- also can act as an into Acetic acid + lactic acid Conversion of toxic NH3
osmotic laxative into non-toxic and non-
absorbable NH4+ ion
Reduction in NH3 level Favouring more diffusion of
cause concentration NH3 from blood and so on,
gradient in colon So used in treatment of
hepatic encephalopathy due
to hyperammonemia

Polysaccharides Also called glycans Classified as homo- and

hetero- polysaccharides
Homopolysaccharides Starch Insoluble in water due to
- contain one type of highly branched chain
monomeric units
Glycogen Main storage of
polysaccharides
 Dextran
Heteropolysaccharides Heparin
- two or more type of Used to treat blood clot
monomeric units
Hyaluronic acid
Present in vitreous and
synovial fluid
Fatty acids
Saturated or unsaturated long chain carboxylic acids
Oxidation of double bond Of unsaturated FA
FA + glycerol = ester Called triacylglycerol
Examples of FA
Formic acid One carbon
Acetic acid Two carbon
Stearic acid 18 carbons
Oleic acid 18 carbons & unsaturated
Ricinoleic acid 16 carbons & -OH group sub
Castor oil (ricinolein) Ester of ricinoleic acid with
glycerol
White wax Ester of high MW
(molecular weight) of
alcohol and acids
Carnauba wax Higher MW than white wax
gives it hardness
Cetyl palmitate Ester of palmitic acid and
Cetyl alcohol
Mineral oils A mixture of liquid
- specific gravity is less hydrocarbons, obtained
than 1 – lighter than from petroleum
water.
Petroleum Mixture of liquid aliphatic
hydrocarbons with solid
hydrocarbons
10 ppm vit. E (tocopherol), Added to unsaturated
an antioxidant mineral oil
Prostaglandins & Synthesised from
leukotrienes arachidonic acid
Arachidonic acid Derived from phospholipid
Used as plasma expanders
in patient who experienced
loss of blood
acid mucopolysaccharide
(sulphate of N-acetyl
glucosamine and iduronate)
Consists of altering units of
N-acetyl glucosamine and
N-acetyl muramic acid
Is fatty acid
Called rancidity
Stored in fatty tissues and
used as energy store
Actually, not a FA
Cis form
Presence of -OH, make it
polar & miscible with
alcohol, immiscible with
mineral oils
Not a FA
Derived by bleaching
beeswax (yellow wax)
So, used in polishing
mixture of coated tablet
Obtained from the head of
sperm whale
Being non-polar,
Immiscible with water,
alcohol and castor oil.
Non-polar
immiscible with alcohol
To prevent oxidation,
So prevent from undesirable
odour and taste
The main precursor in
humans
 membrane by
phospholipase A2
Cyclooxygenase enzymes Prostaglandins
COX 1 & COX 2
5-lipooxygenase enzyme Leukotrienes

Saponification: - the reaction of fat (triglycerides) or oil with an inorganic alkali (KOH) to
prepare soap and glycerol.
e.g. sodium stearate, potassium stearate
zinc stearate – water repellent powder
- used as a tablet lubricant
- but cause pulmonary inflammation

Opioids: - prototype is morphine.

Morphine has 5 asymmetric centres and naturally occurs as L(-) enantiomers.

Morphine analogue Chemical name

Codeine Methylmorphine
Heroin Diacetyl morphine
Numorphan Oxymorphone
Dilaudid Hydromorphone
Dionin Ethylmorphine

Pentazocine Mixed opioid agonist – antagonist

- used for analgesia
Naloxone An opioid antagonist
Pentazocine + naloxone To reduce potential abuse effect of
pentazocine &
to decrease its respiratory depressive effect