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Aspirin

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1

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

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2

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

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3

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

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4

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

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5

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

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6

Randitine

(Zantac) Histamine H2 Receptor antagonist

Prevents receptor promoting excess HCl production

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7

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

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8

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

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9

Zanamivir

Inhibits neuraminidase enzyme needed so virus can be released from host cell. Amide, carboxamide, alkenyl and ether.

Also has hydroxyl, ether

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10

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

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