Medicinal Chemistry

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Adrenergic Agonists/Catecholamine pharmacophore

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Primary or secondary amine 2 carbons away from substituted benzene ring.

Ethylamine chain essential to adrenergic activity

Ex: epinephrine, norepinephrine

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Norepinephrine (sympathomimetics, nonselective adrenergic agonist)

Catechol group prone to oxidation

Alertness, increase heart rate and blood pressure, reduces blood flow to gastrointestinal system , releases glucose from energy stores

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Epinephrine (sympathomimetics, nonselective adrenergic agonist)

Used to treat cardiac arrest and hypotensive crisis. Vasoconstrictor, ionotropic (increase contractility)/chronotropic (increase heart rate)

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Phenylephrine (sympathomimetics, selective α-adrenergic agonist)

Removal of para hydroxyl group increases α-receptor activity

Nasal decongestant. Maintain systemic blood pressure in hypotensive conditions

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Oxymetazoline (sympathomimetics, selective α-adrenergic agonist)

Bulky para or meta substitution on benzene ring increases α activity

Nasal decongestant; vasoconstrictor in nasal mucosa

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Pseudoephedrine (indirect sympathomimetics, α-agonist)

Removal of hydroxyls from catechol ring and addition of α-methyl group reduced direct receptor activity and increase indirect activity.

Norepinephrine releasing

Nasal decongestant

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Amphetamine (indirect sympathomimetics) Removal of hydroxyls from catechol ring and addition of α-methyl group reduced direct receptor activity and increase indirect activity.

Enhance catecholamine release in CNS. Used to treat ADHD

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Dobutamine (sympathomimetics, selective β-adrenergic agonist)

Bulky N-substitution increases β-receptor selectivity

Used in acute heart failure. Ionotropic via β1 receptors - open calcium channels (enhanced contractility)

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Albuterol (sympathomimetics, selective β-adrenergic agonist)

Bulky N-substitution increases β-receptor selectivity

Alteration of meta hydroxyl group increases β2 selectivity over β1

Bronchodilator (activate β2 receptors)

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Bethanecol

Selective muscarinic agonist used to treat postoperative urinary retention and abdominal distention

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Neostigmine

Reversible acetylcholine esterase inhibitor used to treat abdominal distention, urinary retention, and myasthenia gravis

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Ampicillin

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Benzothiazide

Thiazide diuretics

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Succinylcholine chloride

Nicotine antagonist used as depolarizing neuromuscular blocking agent

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Cephalexin (cephalosporin antibiotic)

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Antiepileptic agents

Ex- phenytoin (X=NH)

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Propranolol

Nonselective β2 adrenergic antagonist

Used to treat hypertension and arrhymias

(Substitution para to phenoxy position increase β1 selectivity)

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Warfarin

Oral anticoagulant

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Fluvastatin

Statin used to treat hypercholesterolemia

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Chlorpropamide

Used to treat diabetes

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Lidocaine

Local anesthetic

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Barbiturates

Sedative hypnotics, antiepileptics, anesthetics

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Pioglitazone

Glitazone antidiabetic agent

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1,4-Benzodiazepines

Anxiolytics, antiepileptics, muscle relaxants

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Imipramine

Antidepressant

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Chlorpromazine

Antipsychotic agent

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Doxycycline

Antimicrobial agent

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Amprenavir

Antiviral and HIV protease inhibitor

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Phenylisopropylamines

CNS stimulants (ex- amphetamine)

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Morphine

Opioid receptor agonist

Nearly all opioids and opiates have the morphine pharmacophore (above)

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Naltrexone

Opioid receptor antagonist

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Hydrocortisone

Adrenocorticoid

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Celecoxib

Selective COX-2 inhibitor

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Digoxin

Cardiac glycoside

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Diphenhydramine

1st gen ethanolamine ether antihistamine

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Promethazine

1st gen tricyclic antihistamine, H1 antagonist

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Miconazole

Imidazole antifungal

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Cetirizine

2nd gen nonsedating H1 antihistamine

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Nifedipine

Calcium channel blocker used to treat angina pectoris and hypertension

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Famotidine

H2 receptor antagonist used to treat peptic ulcers

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Ciprofloxacin

Quinolone antimicrobial

Fluoroquinolones structure above:

- c7 substituent: heterocyclic for gram neg activity. N for oral activity

-x8 : N increases bioavailability; methoxy group increases stability to uv light

-R1 and R2 groups affect gram pos potency

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Sulfamethoxazole

Sulfonamide antimicrobial

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Omeprazole

H+/K+ ATPase proton pump inhibitor used to treat peptic ulcers

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Sulfonamides with antimicrobial activity

Acidity of sulfonamide group key to activity. Electron withdrawing R' group (ie- heteroaromatic ring) improves activity by enhancing acidity

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Sulfonamides with antidiabetic activity

X= O, S, or N

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Sulfonamides with diuretic activity

(Thiazide diuretics)

Ex- hydrochlorothiazide

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Sulfonamides with diuretic activity (high ceiling diuretics)

Ex-furosemide