Medchem Exam 2

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Acetylcholine (Muscarinic Agonist)
An ester formed by acetyl and choline, which contains an ethanol and quat N compound for local use. Will be metabolized by esterases, so short living. Used locally as eye drops for increasing contractions to prevent increases in intraocular pressure for glaucoma.
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Methacholine Chloride (Muscarinic Agonist)
Eyedrops for glaucoma. It will not get into the systemic circulation and only has local effects due to the quat N. Unionized species wanted so that it doesn’t absorb.
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Carbachol (Muscarinic Agonist) Instead of a straight ester that will be metabolized quickly by esterases, we have a carbamate (half ester, half amide) that will last a little longer in our system. Used as eyedrops for glaucoma.
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Bethanochol/Urecholine (Muscarinic Agonists)

Used in combination with other drugs. Oral and subq injection. Also contains a carbamate like carbachol, but also a methyl like methacholine. NOT USED IN THE EYE. Used for urinary retention and for paralytic ileus to increase contraction. Quat N for local use.  

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Cevimeline/Evoxac (Muscarinic Agonist)

Contains an oxathiole and a spiro. The sulfur group adds lipophilicity and it has a tertiary amine, so it can get into the CNS and be used for Alzheimer’s. Will not be uses for glaucoma because it’s systemically spread. 

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Varenicline/Chantix (Nicotinic Partial Agonist)

High affinity to the receptor with very little intrinsic activity. Must be tapered. Has nothing to do with acetylcholine and is used for smoking cessation.

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Physostigmine/Eserine (Reversible Competitive Cholinesterase Inhibitor)

Quaternary ammonium, so it can go into the CNS for Alzheimer’s. It has a basic aliphatic N on the outermost ring. Can also be used for glaucoma  as eyedrops. It’s a carbamated enzyme and stable, so it will take a long time to lose the carbamate group instead of an acetylated group. 

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Pyridostigmine/Mestinon (Reversible Competitive Cholinesterase Inhibitor)

Pyridine structure. Unlike Neostigmine, the N is inside the ring and has a permanent + charge. Can have a chloride. Quat N tho…but used for glaucoma or myesthinia gravis IV??

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Neostigmine/Prostigmin (Reversible Competitive Cholinesterase Inhibitor)

Has chloride. Carbamated enzyme. Quaternary N, so it cannot be used for Alzheimer’s. It can only be used for myesthnia gravis by injection and eyedrops for glaucoma.

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Rivastigmine/Exelon (Reversible Competitive Cholinesterase Inhibitor)

Carbamated enzyme. Tertiary enzyme, so it will go into the brain for Alzheimer’s. Used orally. 

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Diisopropyl Flurophosphate/DFP (Irreversible Competitive Cholinesterase Inhibitor)

Has a phosphate PO4 that will strongly bind to the serine and not let go. Used as long acting eye drops for glaucoma. 

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Echothiophate/Phospholine (Irreversible Competitive Cholinesterase Inhibitor)

Has a phosphate PO4 group that strongly binds to serine and won’t let go. Phosphoric acid, not acetic acid. You’ll geta phosphorylated enzyme that’s irreversible. It also contains a quaternary enzyme, so used locally for long acting eyedrops for glaucoma.

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2-PAM (Irreversible Cholinesterase Inhibitor Antidote)

Contains an oxine group that contains a hydroxy, which loves the enzyme harder than phosphate. It’ll bitch-slap the phosphate off the enzyme to free it.

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Tacrine/Cognex (Reversible Noncompetitive Cholinesterase Inhibitor)

Binds to a different area than the active site and changes the shape for acetylcholine to have a harder time from binding to the enzyme and being acetylated like a little bitch. ALLOSTERIC FUCKAS. Does not look like Ach, and has both nicotininc and muscarinic activity. Selectively used to treat Alzheimer’s cuz it goes in the brain. 

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Hexamethonium Bromide (Depolarizing Competitive Ganglionic Blocker)

When HTN is out of control, the drug cuts the signal from the ganglia so there’s no Ach in ANS and PNS. Used for surgery, pernicious HTN, and smoking cessation. Will have bromide and quaternary N and we do want it to spread, so used for emergency HTN by injection.

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Mecamylamine/Inversine (Noncompetitive Ganglionic Blocker) 

When HTN is out of control, used to cut signal off from ganglia so there is no Ach in ANS and PNS. Used for surgery and smoking cessation too. Used orally. Allosteric.

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Pancuronium/Pavulon (Neuromuscular Junction Blocker)

Nicotinic activity only. Steroid type. Blocks skeletal muscle movement during surgery. Quaternary and used by injection. Long acting and will stop breathing, so be careful not to die.

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Rocuronium/Zemuron/Esmeron (Neuromuscular Junction Blocker)

Nicotinic activity only. Steroid type. Blocks skeletal muscle movement during surgery. Quaternary and used by injection. Long acting and will stop breathing, so be careful not to die.

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Demecarium Bromide (Neuromuscular Junction Blocker)

Nicotinic activity only. Isoquinoline-type. Blocks skeletal muscle movement during surgery. Quaternary and used by injection. Long acting and will stop breathing, so be careful not to die.

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Atropine (Anticholinergic)

Lipophilic, spacer, 3/4 N. Used as a salt as a tertiary amine. Always used as sulfate. Can be used for anything that requires blocking the contraction of smooth muscle. Aromatic ring causes high affinity to receptor and prevents Ach from binding to receptor. Ester means it’ll be short living, so cannot be used in the brain. Contains a tropane group and a chiral carbon. 

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Benzatropine/Cogentin (Anticholinergic)

Has an ether instead of an ester, so it’s longer acting. It will also be more lipophilic and used as the drug of choice for Parkinson’s disease. 

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Scopolamine/Hyoscine (Anticholinergic)

Used for motion sickness as ear patches. Contains an epoxide and will make it more lipophilic to get into the brain slowly. 

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Homatropine Methylbromide (Anticholinergic)

Contains lipophilic area and tertiary amine, but becomes a quaternary amine for local effects. Does not have a CH2 with the OH like atropine. Used for midriasis. 

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Ipratropium Bromide/Atrovent (Anticholinergic)

Used in the lungs as inhalation with other drugs for asthma. Quaternary N, so cannot be used orally. We replaced the H on N with an isopropyl, so now it’s a quaternary salt but used carefully for local asthma.

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Diphenoxylate/Lomotil (Anticholinergic)

Lipophilic due to two phenyl groups. Not a quaternary ammonium because you want it to act locally in the GIT for diarrhea. Because it is an ester, it would break apart easily and become an unabsorbable amphoteric molecule. O will be a bioisostere of CH2. The ester is hydrolyzed into an ester (unstable), is always ionized, and never gets absorbed.

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Tolterodine/Detrol (Anticholinergic)

Lipophilic group, spacer, tertiary amine. Used for bladder incontinence.

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Oxybutynin/Ditropan (Anticholinergic)

Lipophilic, spacer, tertiary amine. Used for bladder incontinence.

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Metaraminol/Aramine (a1 Selective Agonist)

Used by injection for shock and for nose shit. Powerful vasoconstrictor, nasal drops. Anaphylactic shock through IV. Has a phenolic hydroxy at position 3, but no Oh on position 4. On the META position.  Generally poor absorption due to polar groups like NE.

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Phenylephrine (a1 Selective Agonist)

Used by injection for shock and for nose shit. Powerful vasoconstrictor, nasal drops. Anaphylactic shock through IV. Has a phenolic hydroxy at position 3, but no Oh on position 4. On the META position.  Generally poor absorption due to polar groups like NE.

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Methoxamine Hcl/Vasoxyl (a1 Selective Agonist)

Used by injection for shock and for nose shit. Powerful vasoconstrictor, nasal drops. Anaphylactic shock through IV. Has a phenolic hydroxy at position 3, but no Oh on position 4. On the META position. Generally poor absorption due to polar groups like NE.

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Metazoline/Otrivin (a1 Selective Agonist)

Unrelated to NE backbone.

On its own, imidazoline is nonselective. With a methylene group, it’ll become a1 selective only through d- electron donating through phenyl and methyl interaction. Contains a phenyl group. Used as nasal decongestant nasal drops or eye drops for conjunctivitis. Also for shock, but very lipophilic, so not used often.

 

 

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Oxymetazoline/Afrin (a1 Selective Agonist)

Unrelated to NE backbone.

On its own, imidazoline is nonselective. With a methylene group, it’ll become a1 selective only through d- electron donating through phenyl and methyl interaction. Contains a phenyl group. Used as nasal decongestant nasal drops or eye drops for conjunctivitis. Also for shock, but very lipophilic, so not used often.

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Naphazoline/Naphcon-A (a1 Selective Agonist)

Unrelated to NE backbone.

On its own, imidazoline is nonselective. With a methylene group, it’ll become a1 selective only through d- electron donating through phenyl and methyl interaction. Contains a naphthalene group. Used as nasal decongestant nasal drops or eye drops for conjunctivitis. Also for shock, but very lipophilic, so not used often.

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Tetrahydrozoline/Visine (a1 Selective Agonist)

Unrelated to NE backbone.

On its own, imidazoline is nonselective. With a methylene group, it’ll become a1 selective only through d- electron donating through phenyl and methyl interaction. Contains a naphthalene group. Used as nasal decongestant nasal drops or eye drops for conjunctivitis. Also for shock, but very lipophilic, so not used often.

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Clonidine/Catapres (a2 Selective Agonist)

Constricts blood vessels peripherally but used for HTN, and causes “inhibition of sympathetic outflow” centrally. Only used orally because you don’t want to make your HTN worse. Used as HCl salts, they’re amines. They don’t look like NE. Halogens interact with the phenyl and creates a d+ for electron withdrawing for high bond with receptor. High oral absorption through lipophilic aromatic ring. The imidazoline is a pharmacophere (like).

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Guanfacine/Estulic (a2 Selective Agonist)

Constricts blood vessels peripherally but used for HTN, and causes “inhibition of sympathetic outflow” centrally. Only used orally because you don’t want to make your HTN worse. Used as HCl salts, they’re amines. They don’t look like NE. Halogens interact with the phenyl and creates a d+ for electron withdrawing for high bond with receptor. High oral absorption through lipophilic aromatic ring. The imidazoline is a pharmacophere (like).

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Guanabenz/Wytensin (a2 Selective Agonist)

Constricts blood vessels peripherally but used for HTN, and causes “inhibition of sympathetic outflow” centrally. Only used orally because you don’t want to make your HTN worse. Used as HCl salts, they’re amines. They don’t look like NE. Halogens interact with the phenyl and creates a d+ for electron withdrawing for high bond with receptor. High oral absorption through lipophilic aromatic ring. The imidazoline is a pharmacophere (like). Contains guanido group.

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Isoproterenol/Isoprenaline (Nonselective b1/2 Agonist)

Increases FOC and bronchodilation by inhalation/injection/oral. Isopropyl group for nonselective b selectivity. Has an epinephrine structure and added lipophilic groups for liking b receptor.

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Dobutamine (b1 Selective Agonist)

Sympathomimetic. Removing the OH makes the drug go exclusively to the heart for FOC CHF. Used by injection. Has epinephrine structure with added methyls for lipophilicity to go to the b receptor.

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Metaproterenol/Orciprenaline (b2 Selective Agonist)

Used as a bronchodilator for asthma. Used by inj/inh/oral. Has epinephrine-like structure except with meta (1,3) OH’s, separated by 3 carbons. Lipophilic area is the isopropyl. Eliminated by phase 2.

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Terbutaline/Bronclyn (b2 Selective Agonist)

Used as a bronchodilator for asthma. Used by inj/inh/oral. Has epinephrine-like structure except with meta (1,3) OH’s, separated by 3 carbons. Has a t-butyl. Eliminated by phase 2.

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Fenoterol (b2 Selective Agonist)

Used as a bronchodilator for asthma. Used orally. Has epinephrine-like structure except with meta (1,3) OH’s, separated by 3 carbons. Has a phenol. Eliminated by phase 2.

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Albuterol/Proair (b2 Selective Agonist)

NOT a catechol!! Aliphatic saturated carbons, and more lipophilic. Polarity is still the same, with four strong polar groups. Metabolism is not affected – it’ll go to phase 2 conjugation. 

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Salmeterol/Serevent (b2 Selective Agonist)

4 strong polar groups and lipophilic. Goes directly to phase 2. Localized in the lungs for asthma and has a 16 carbon chain. If given orally, it’ll have poor absorption and so it’s used for inhalation, but will be toxic systemically.

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Amphetamine/Adderall (Indirect Acting Sympathomimetic)

Drugs that block reabsorption of NE, so there will be more floating around. Has a plain phenyl. Used for weight loss (Fen-Fen), causing respiration, ADHD, and are addictive. There are NO OH’s. Phenylethylamine backbone.

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Methamphetamine/Desoxyn (Indirect Acting Sympathomimetic)

Drugs that block reabsorption of NE, so there will be more floating around. Has a plain phenyl. Used for weight loss (Fen-Fen), causing respiration, ADHD, and are addictive. There are NO OH’s. Added an extra methyl onto amphetamine. Phenylethylamine backbone.

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Methylphenidate/Ritalin (Indirect Acting Sympathomimetic)

Drugs that block reabsorption of NE, so there will be more floating around. Has a plain phenyl. Used for weight loss (Fen-Fen), causing respiration, ADHD, and are addictive. There are NO OH’s. Phenylethylamine backbone. 

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Labetolol (Nonselective a1/b1/2 Adrenergic Antagonist)

Used for HTN and antiarrhythmic. Used oral and by injection as a HCl salt (see the basic amine?). Similar to feneterol. Contains phenylethylamine and only one hydroxy to signify antagonism here I guess. Amide. Metabolized through phase 2 for the OH.

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Tolazoline (Nonselective a1/2 Antagonist)

Imidazoline backbone with a toluene group. This is the only time you’ll see a drug with less lipophilicity and affinity for the receptor than the agonist, though it does have more than NE. Not used for regular HTN – used for newborns with pulmonary HTN. Given IV as a HCl salt.

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Phentolamine/Regitine (Nonselective a1/2 Antagonist)

Contains a phenol and a toluene group. As usual, more lipophilic and higher affinity for the receptor than the agonist. Powerful antiHTN drug and the DOC for pheochromocytoma, caused by chromafine tumors releasing too much norepinephrine/adrenaline.

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Trimazosin (Selective a1 Antagonist)

AntiHTN, but NOT arrhythmic, because a1 is not on the heart. Has a benzyoprimidine/quinazoline backbone with a piperazine and goes to phase 2 directly, so used for multiple doses. Has a O-C-OH. No difference in activity with other drugs.

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Prazosin/Minipress (Selective a1 Antagonist)

AntiHTN, but not arrhythmic, no a1 on the heart. Has a benzopyrimidine/quinazoline backbone with a piperazine structure. Contains a furan. Used once a day orally. No difference in activity with the others. Metabolized by o-demethylation.

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Terazosin/Hytrin (Selective a1 Antagonist)

AntiHTN, but not arrhythmic, no a1 on the heart. Has a benzopyrimidine/quinazoline backbone with a piperazine structure. Contains THF. Used once a day orally. No difference in activity with the others. Metabolized by o-demethylation.

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Doxazosin/Cardura (Selective a1 Antagonist)

AntiHTN, but not arrhythmic, no a1 on the heart. Has a benzopyrimidine/quinazoline backbone with a piperazine structure. Contains a benzodioxane. Used once a day orally. No difference in activity with the others. Metabolized by o-demethylation.

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 Alfuzosin (Selective a1 Antagonist)

 Very specific affinity to a1 and goes to the prostate for BPH due to excessive NE and testosterone. No piperazine, an aliphatic chain instead. Selective specically to a1A. 

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Tamsulosin/Flomax (Selective a1 Antagonist)

Phenylethylamine backbone. Sulfonamide makes the drug and liver hate each other, so it’ll go straight to the kidney and urinary tract. This is great because you want it to work in the prostate anyway. Oral tablet once a day. Selective to a1A. 

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Yohimbine (Selective a2 Blocker)

Sexual impetus. 

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Propranolol/Inderal (Nonselective b1/2 Antagonist)

AntiHTN, arrhythmia, angina. Has phenylethylamine backbone, but with an O-CH2 instead to block the activity at b receptors. Isopropyl. Aromatic hydroxylation phase 1 in the liver. Contraindicated in asthmatics. Orally/injection.

Pindolol (Nonselective b1/2 Antagonist)

AntiHTN, arrhythmia, angina. Has phenylethylamine backbone, but with an O-CH2 instead to block the activity at b receptors. Metabolized in liver. Very lipophilic. Contraindicated in asthmatics. Orally/injection.

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Nadolol/Corgard (Nonselective b1/2 Antagonist)

Not a fucking catechol. Used for antiHTN, arrythmia, angina. Phase 2 metabolism due to the polar OH. Given in multiple doses and goes straight to the kidney. Short acting. Contraindicated in kidney dysfunction. Orally/injection. 

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Acebutolol/Sectral (Selective b1 Antagonist)

AntiHTN, angina, and arrhythmia, but no worry about lungs (b2). Contains an N-acetyl group.

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Atenolol/Tenormin (Selective b1 Antagonist)

AntiHTN, angina, and arrhythmia, but no worry about lungs (b2). Contains an amide, and metabolized by amidases. 

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Metoprolol/Lopressor (Selective b1 Antagonist)

AntiHTN, angina, and arrhythmia, but no worry about lungs (b2). Contains an ether, but will have fast metabolism by o-demethylation.

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Bisoprolol/Zebeta (Selective b1 Antagonist)

AntiHTN, angina, and arrhythmia, but no worry about lungs (b2). Contains an isopropyl to slow down metabolism. Longer acting. 

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Betaxolol/Kerlone (Selective b1 Antagonist)

AntiHTN, angina, and arrhythmia, but no worry about lungs (b2). Contains a cyclopropol group that gives steric hindrance for slower metabolism. Equivalent in DOA to bisoprolol.

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Esmolol/Brevibloc (Selective b1 Antagonist)

AntiHTN, angina, and arrhythmia, but no worry about lungs (b2). Contains an ester. Quick metabolism everywhere by esterases. Ineffective orally, and can only be used by injection for emergencies to decrease HTN. Afterwards, cut them off immediately. No kidney danger.

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Norepinephrine 

Adrenergic. Loves a;b. Makes constriction in blood vessels.

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Epinephrine

Adrenergic. Loves b;a and will have more lipophilic carbons.

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