med chem 2

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Fichas sobre med chem 2, creado por lola_smily el 11/02/2015.
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beta-D-Digitoxose sugar moiety of cardiac glycoside
beta-D-Glucose sugar moiety of cardiac glycoside
beta-L-Rhamnose sugar moiety of cardiac glycoside
beta-D-Cymarose sugar moiety of cardiac glycoside
digitoxigenin non sugar aglycone moiety of cardiac glycoside steroid structure cyclopentanoperhydrophenanthrene cardenolide (5 membered lactone ring) planr source
digoxigenin non sugar aglycone moiety of cardiac glycoside steroid structure cyclopentanoperhydrophenanthrene more polar
strophanthidin non sugar aglycone moiety of cardiac glycoside steroid structure cyclopentanoperhydrophenanthrene
gitoxigenin non sugar aglycone moiety of cardiac glycoside steroid structure cyclopentanoperhydrophenanthrene
ouabagenin non sugar aglycone moiety of cardiac glycoside steroid structure cyclopentanoperhydrophenanthrene
bufadienolide non sugar aglycone moiety of cardiac glycoside steroid structure cyclopentanoperhydrophenanthrene 6 membered lactone ring animal source
lanatoside A cardiac glycoside digitalis lanata digitoxigenin+glucose-3-acetyl(digitoxose)3
digitoxin cardiac glycoside
digoxin cardiac glycoside
ouabain cardiac glycoside very polar not clinically used
inamrinone positive inotropic agents phosphodiesterase enzyme inhibitor thrombocytopenia metabolized in liver
milrinone positive inotropic agents phosphodiesterase enzyme inhibitor more potent less toxic unchanged excretion
dobutamine positive inotropic agents beta 1-adrenoceptor agonists inactive orally and given IV
nitric-nitrate nitrovasodilator organic nitrate
nitrous-nitrite nitrovasodilator organ nitrite
amyl nitrite antianginal agent nitrovasodilator prodrug isopentyl nitrite give inactive metabolite volatile at RT most rapid onset/short duration of action insoluble in water/miscible with organic solvents
glyceryl trinitrate (nitroglycerin) antianginal agent nitrovasodilator prodrug explosive in dynamite colorless oil volatile skin absorption
erythrityl tetranitrate antianginal agent nitrovasodilator prodrug solid slightly water soluble more soluble in organic solvents slower onset/long duration of action low volatility
pentaerythritol tetranitrate antianginal agent nitrovasodilator prodrug crystalline weakly insoluble in alcohol readily soluble in acetone powerful explosive
isosorbide dinitrate antianginal agent nitrovasodilator prodrug solid water soluble give active metabolite (100% bioavailable)
nifedipine antianginal calcium channel blocker DHP orally active/ metabolized decrease afterload reflex tachycardia
amlodipine antianginal calcium channel blocker DHP orally active/ metabolized decrease afterload reflex tachycardia bioavailability: 60-90% DOA: 24h
nicardipine antianginal calcium channel blocker DHP orally active/ metabolized decrease afterload reflex tachycardia
verapamil antianginal calcium channel blocker non DHP/ phenylalkylamine orally active/ metabolized by CYP3A4 and CYP2D6 decrease HR - inotropic, chronotropic, dromotropic
bepiridil antiangina calcium channel blocker non DHP/ diarylaminopropylaminoether rarely used
diltiazem antianginal calcium channel blocker non DHP/ benzothiazepine orally active/ metabolized by hydrolysis decrease HR - inotropic, chronotropic, dromotropic
noverapamil metabolite of verapamil by N-demethylation 30-50% active as parent drug
desacetyldiltiazem metabolite of diltiazem by hydrolysis of ester 30-50% active as parent drug
dipyridamole antianginal coronary vasodilator antiplatelet activity non selective so rarely used
papaverine antianginal coronary vasodilator orally active antispasmotic non selective so rarely used
cyclandelate antianginal coronary vasodilator non selective so rarely used
MPPP (designer heroin) active opioid agonist reversed ester of meperidine phenylpiperidine synthetic analgesics
nisentil (alpha-prodine) phenylpiperidine synthetic analgesics
demerol (meperidine) active opioid agonist phenylpiperidine synthetic analgesics
MPTP N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine byproduct of MPPP metabolized orally/IV/inhalation by MAO-B lead to parkinsonism
MPP+ 1-methyl-4-phenylpyridinium toxic irreversible damage of DA neurons metabolite of MPTP
benztropine mesylate anticholinergic (antimuscarinic) agent synthetic centrally acting limited use given with dopaminergic therapy severe central and peripheral side effects
trihexyphenidyl hydrochloride anticholinergic (antimuscarinic) agent synthetic centrally acting limited use given with dopaminergic therapy severe central and peripheral side effects salt/pH dependent
procyclidine hydrochloride anticholinergic (antimuscarinic) agent synthetic centrally acting limited use given with dopaminergic therapy severe central and peripheral side effects salt/pH dependent
biperiden hydrochloride anticholinergic agent synthetic salt pH dependent
diphenhydramine hydrochloride antihistamine
orphenadrine hydrochloride antihistamine centrally acting limited use given with dopaminergic therapy severe central and peripheral side effects
L-DOPA levo dihydroxyphenylalanine precursor of dopamine absorbed in GI and enters brain by active transport less basic given orally alone 1-3% to brain with carbidopa 10%
dopamine 3,4-dihydroxyphenylethylamine highly basic (doesn't cross the brain) rapidly metabolized
3-methoxy-4-hydroxy phenylalanine metabolite of L-DOPA by COMT
3,4-dihydroxyphenylacetic acid metabolite of dopamine by MAO
vanillylmandelic acid (VMA) final metabolite of L-DOPA
carbidopa decarboxylase inhibitor delivers more L-DOPA to brain acts peripherally doesn't cross the BBB
selegiline first generation irreversible MAO-B inhibitor orally metabolized gives metamphetamine side effect: vasoconstriction, hallucination
rasagiline second generation irreversible MAO-B inhibitor orally metabolized to 1-aminoindan no side effects
tolcapone reversible non specific COMT inhibitor long acting (8-12h) centrally and peripherally acting nausea, hallucination hepatic failure
entacapone reversible non specific COMT inhibitor short acting (2h) mostly peripherally nausea,hallucination
amphetamine metabolite of metamphetamine (metabolite of selegiline) causes side effects of selegiline
metamphetamine metabolite of selegiline
amantadine primary amine admantane derivative dopamine releasing agent inhibit dopamine reuptake protonated/lipophilic less potent short lived benefits (few weeks) reversible side effects: insomnia hallucination, depression, confusion, agitation
Memantine admantane derivative dopamine releasing agent inhibit dopamine reuptake
quinidine antiarrhythmic class 1A alkaloid (cinchona bark) basic hepatic metabolism/unchanged renal excrection for supraventricular tachycardia inhibit renal excretion of digoxin - inotropic/anticholinergic act/peripheral alpha adrenergic SE: GI disturbances
o-demethylquinidine metabolite of quinidine active by partial hepatic metabolism
oxydihydroquinidine metabolite of quinidine active by partial hepatic metabolism
procainamide antiarrhythmic class 1A from procaine gd GI absorbance (70-80% biovailability) liver metabolism unchanged renal excretion for ventricular tachycardia SE: lupus syndrome (20-30%)
n-acetylprocainamide metabolite of procainamide active
p-aminobenzoic acid metabolite of procainamide
metabolite of procainamide
disopyramide antiarrhythmic class 1A phosphate salt rapid and highly GI absorbance liver metabolism (50%)-> active(n-deacetylation) renal excretion (50%) for ventricular and atrial arrhythmias SE: anticholinergic effects
lidocaine antiarrhythmic class 1B local anesthetic first pass metabolism (n-dealkylation) SE: emesis, convulsion
monoethylxylidine metabolite of lidocaine give glycine xylidide active CNS effect
metabolite of lidocaine
metabolite of lidocaine
tocainide antiarrhythmic class 1B orally active/ absorbed (bcz of alpha methyl) slow metabolism for emergency ventricular arrhythmias SE: GI disturbance, CNS effects
mexiletine antiarrhythmia class 1B xylyloxy and ethylamine derivative hydrolysis --> ether given orally and IV renal, hepatic elimination like lidocaine and tocainamide p-hydroxylation and hydroxymethylation (inactive)
phenytoin antiarrhythmia class 1B anticonvulsant orally active IV use p-hydroxylation (inactive) for atrial and ventricular arrhythmias
flecainide antiarrhythmia class 1C fluorinated benzamide derivative acetate form oral absorption liver metabolism (50%)--> m-O-dealkylation (active) SE: aggravation of arrhythmias, blurred vision, headache, nausea, GI disturbance
propafenone antiarrhythmic class 1C local anesthetic orally, IV GI absorption hepatic metabolism by CYP2D6
moricizine antiarrhythmia class 1C phenothiazine orally short half-life but effect lasts hours (active metabolite)
encainide antiarrhythmia class 1C not used
ibutilide antiarrhythmic class 3 methanesulfonanilide derivative no beta adrenergic blocking activity only by IV infusion
bretylium tosylate antiarrhythmic class 3 adrenergic neuronal blocking agent antihypertensive given IV for life threatening cases of ventricular arrhythmia
amiodarone antiarrhythmia class 3 coronary vasodilator iodine containing agent--> affect thyroid hormone activity (hypo and hyperthyroidism) t1/2 = 25d (very long) for life threatening ventricular arrhythmia
dofetilide antiarrhythmic class 3 bis-methanesulfonanilide derivative more potent GI absorbtion (96-100% bioavailability) protein binding 60-70% metabolized by CYP3A4 (dealkylation, n-oxydation)--> inactive unchanged excretion (80%)
Sotalol antiarrhythmic class 3 methanesulfonanilide derivative non selective beta blocker
verapamil antiarrhythmic class 4 slows phase 4 slow SA node firing and conduction to AV node
diltiazem antiarrhythmic class 4 slows phase 4 slow SA node firing and conduction to AV node
benazepril RAS inhibitor ACEI prodrug active undergoes glucuronidation DOA= 24h renal excretion SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure
moexipril RAS inhibitor ACEI prodrug active renal, fecal excretion DOA= 24h SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure
captopril RAS inhibitor ACEI active renal excretion DOA= 6-12h gd lipid solubility acidic gives dimer SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure
perindopril RAS inhibitor ACEI prodrug active renal excretion DOA= 24h SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure
enalapril RAS inhibitor ACEI prodrug active hepatic metabolism renal excretion DOA= 24h SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure
enalaprilat RAS inhibitor ACEI active given IV gd lipid solubility renal excretion DOA= 6h SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure
quinapril RAS inhibitor ACEI prodrug active renal excretion DOA= 24h SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure
fosinopril sodium RAS inhibitor ACEI prodrug active acidic renal, hepatic excretion DOA= 24h SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure
ramipril RAS inhibitor ACEI prodrug active do glucuronidation, cyclization-> inactive renal excretion DOA= 24h SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure
lisinopril RAS inhibitor ACEI active gd lipophilicity renal excretion DOA= 24h SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure
trandolapril RAS inhibitor ACEI prodrug active renal,fecal excretion DOA= 24h SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure
disulfide dimer metabolite of captopril inactive
captopril cysteine disulfide metabolite of captopril inactive
glucuronide conjugate metabolite of benazepril
diketopiperazine metabolite metabolite of ramapril inactive
valsartan RAS inhibitor angiotensin 2 receptor blocker (ARB) competitive antagonist tetrazol derivative orally active renal elimination SE: same as ACEI but no dry cough, taste disturbances, angioedema
irbesartan RAS inhibitor angiotensin 2 receptor blocker (ARB) competitive antagonist tetrazol derivative orally active fecal, renal elimination SE: same as ACEI but no dry cough, taste disturbances, angioedema
telmisartan RAS inhibitor angiotensin 2 receptor blocker (ARB) competitive antagonist orally active fecal elimination SE: same as ACEI but no dry cough, taste disturbances, angioedema
losartan RAS inhibitor angiotensin 2 receptor blocker (ARB) competitive antagonist tetrazol derivative orally active metabolized into active fecal, renal elimination SE: same as ACEI but no dry cough, taste disturbances, angioedema
candesartan cilexetil RAS inhibitor angiotensin 2 receptor blocker (ARB) competitive antagonist tetrazol derivative prodrug metabolized into active fecal, renal elimination SE: same as ACEI but no dry cough, taste disturbances, angioedema
olmesartan medoxomil RAS inhibitor angiotensin 2 receptor blocker (ARB) competitive antagonist tetrazol derivative prodrug metabolized into active fecal, renal elimination SE: same as ACEI but no dry cough, taste disturbances, angioedema
eprosartan RAS inhibitor angiotensin 2 receptor blocker (ARB) competitive antagonist orally active fecal, renal elimination SE: same as ACEI but no dry cough, taste disturbances, angioedema
EXP-3174 metabolite of losartan by CYP3A4 active non competitive antagonist tetrazol derivative
mannitol osmotic diuretics very polar given IV if orally--> osmotic diarrhea
sorbitol osmotic diuretics very polar given IV if orally--> osmotic diarrhea
isosorbide osmotic diuretics given orally
urea osmotic diuretics given IV unpleasant taste
acetazolamide diuretics carbonic anhydrase inhibitors arylsulfonamide for glaucoma cause hypokalemia and metabolic acidosis
methazolamide diuretics carbonic anhydrase inhibitors arylsulfonamide for glaucoma cause hypokalemia and metabolic acidosis
ethoxzolamide diuretics carbonic anhydrase inhibitors arylsulfonamide for glaucoma cause hypokalemia and metabolic acidosis
dichlorphenamide diuretics carbonic anhydrase inhibitors arylsulfonamide for glaucoma cause hypokalemia and metabolic acidosis
benzene-1,3-disulfonamide aryl sulfonamide derivative
aminochlorphenamine diuretics benzothiadiazine (thiazide)
6-chloro-1,2,4-benzothiadiazine-7-sulfonamide-1,1-dioxide diuretics benzothiadiazine (thiazide)
quinethazone diuretics thiazide-like quinazolinone derivative orally active long DOA (18-24h)
metolazone diuretics thiazide-like quinazolinone derivative orally active long DOA more potent
chlorthalidone diuretics thiazide-like phthalamidine derivative orally active long DOA (48-72h)
indapamide diuretics thiazide-like indoline derivative orally active long DOA (24-36h) potent
furosemide diuretic loop diuretic orally active quick onset of action (30min) short DOA (6h) SE: electrolyte and fluid imbalance, hypokalemia, hyperurecemia, ototoxicity, hypersensitivity
5-sulfamoyl-anthranilic acid diuretic loop diuretic orthoaminobenzoic acid
bumetanidediuretic loop diuretic 5-sulfamoyl-3-aminobenzoic acid derivative more potent (50X) orally active quick onset of action (30min) short DOA (6h) SE: electrolyte and fluid imbalance, hypokalemia, hyperurecemia, ototoxicity, hypersensitivity
torsemide diuretic loop diuretic 4-amino-3-pyridine-sulfonylurea derivative orally active quick onset of action (30min) short DOA (6h) SE: electrolyte and fluid imbalance, hypokalemia, hyperurecemia, less ototoxicity, hypersensitivity
ethacrynic acid diuretic loop diuretic phenoxyacetic acid derivative orally active quick onset of action (30min) short DOA (6h) SE: electrolyte and fluid imbalance, hypokalemia, hyperurecemia, greater ototoxicity, hypersensitivity, GI disturbances
spironolactone diuretic potassium sparing agent aldosterone receptor antagonist steroid moiety orally active extensive first pass metabolism t 1/2= 1.4h short onset (17-72h)/long DOA(2-3d) SE: hyperkalemia, GI disturbances, steroid related (gynecomastia, breast tenderness...)
canrenone diuretic potassium sparing agent aldosterone receptor antagonist steroid moiety orally active metabolite of spironolactone t 1/2=16.5 h SE: hyperkalemia, GI disturbances, steroid related (gynecomastia, breast tenderness...)
canrenoic acid metabolite of canrenone inactive
elprenone diuretic potassium sparing agent aldosterone receptor antagonist steroid moiety orally active extensive first pass metabolism t 1/2= 5h short onset (17-72h)/long DOA(2-3d) SE: hyperkalemia, GI disturbances, steroid related (gynecomastia, breast tenderness...)
triamterene diuretic potassium sparing agent non-aldosterone receptor antagonist 2,4,7-triamino-6-phenylpteridine active incomplete absorbtion extensive metabolism into active (20% excreted unchanged, 80% metabolised t 1/2= 4h SE: hyperkalemia, renal stones
amiloride diuretic potassium sparing agent non-aldosterone receptor antagonist aminopyrazine or pyrazinoly guanidine active mostly charged incomplete absorbtion renal excretion unchanged t 1/2= 21h SE: hyperkalemia
antodyne
apomorphine
baclofen
bromocriptine(parlodel)
carisoprodol(rela soma)
dantrolene sodium (dantrium)
diazepam
mephenesin
meprobamate (equanil)
pergolide (permax)
ropinirol (requip)
S-Pramipexole (mixapex)
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