Aspirin
Mild analgesic prevents enzymes synthesizing substances that release pain. Intercepts pain at source, also ANTICOAGULANT
Made w/ salicylic acid and acylating agent to form ester which is then purified by recrystallisation (min. amount hot solvent, crystals)
MP determines purity - lower, vague MP is impure.
3 OH signals - 1 both, 1 acid and 1 water
2 carbonyl - 1 both, 1 aspirin
Low solubility, react w/ strong base to make bioavailable salt
Penicillin
Antibiotic previously from fungi now synthesised. Prevents cell wall cross linking, ruptures when water absorbed
Strained beta lactam ring opens and covalently bonds to enzyme active site blocking cell wall production
Penicillinase hydrolyses ring before it reaches target - modify R. Can also increase safety, stability and solubility
MRSA resistance due to over prescription - not completing full course, resistant bacteria return as symptoms go before disease
Codeine
Strong opioid analgesic which works by temporarily binding to opioid receptors in the brain, preventing pain impulses transmission without CNS suppression.
Ether side group. Make by reacting CH3I w/ morphine in KOH
More BBB permeable than morphine but less than diamorphine
Morphine
Strong opioid analgesic which works by temporarily binding to opioid receptors in the brain, preventing pain impulses transmission without CNS suppression.
Makes heroin/codeine. Least permeable as hydroxyl H bonds to H2O
Diamorphine
Strong opioid analgesic which works by temporarily binding to opioid receptors in the brain, preventing pain impulses transmission without CNS suppression.
Ester side group and made w/ CH3COOH and morphine. H2O made
Ester group won’t H bond so highly permeable and rapid onset relief
Randitine
(Zantac) Histamine H2 Receptor antagonist
Prevents receptor promoting excess HCl production
Omeprazole
(Prilosec) inhibits proton pumps so H+ ions can’t physically move into the stomach. Drug converted into active metabolite in acidic medium of the cells
Oseltamivir
Inhibits neuraminidase enzyme needed so virus can be released from host cell. Amide, carboxamide, alkenyl and ether.
Ester group.
Petrochemical synthesis problematic. Synthesis from shikimic acid in star anise better but limited production, now made by GMO bacteria glucose fermentation
Zanamivir
Inhibits neuraminidase enzyme needed so virus can be released from host cell. Amide, carboxamide, alkenyl and ether.
Also has hydroxyl, ether
Taxol
(Paclitaxel) Optically active anti cancer drug used in chemo for breast cancer. Prevents cell division.
Originally used pacific yew tree bark but killed trees so now needles
Chiral auxiliary used for asymmetric organic synthesis of required enantiomer. Chiral intermediate formed w/ rest of molecular means reagent only approaches from desired side for product. Auxiliary then removed, recycled