Flashcards
med chem 2
Flashcards do conjunto (147)
- 1—beta-D-Digitoxose
sugar moiety of cardiac glycoside - 2—beta-D-Glucose
sugar moiety of cardiac glycoside - 3—beta-L-Rhamnose
sugar moiety of cardiac glycoside - 4—beta-D-Cymarose
sugar moiety of cardiac glycoside - 5—digitoxigenin
non sugar aglycone moiety of cardiac glycoside
steroid structure
cyclopentanoperhydrophenanthrene
cardenolide (5 membered lactone ring)
planr source - 6—digoxigenin
non sugar aglycone moiety of cardiac glycoside
steroid structure
cyclopentanoperhydrophenanthrene
more polar - 7—strophanthidin
non sugar aglycone moiety of cardiac glycoside
steroid structure
cyclopentanoperhydrophenanthrene - 8—gitoxigenin
non sugar aglycone moiety of cardiac glycoside
steroid structure
cyclopentanoperhydrophenanthrene - 9—ouabagenin
non sugar aglycone moiety of cardiac glycoside
steroid structure
cyclopentanoperhydrophenanthrene - 10—bufadienolide
non sugar aglycone moiety of cardiac glycoside
steroid structure
cyclopentanoperhydrophenanthrene
6 membered lactone ring
animal source
- 11—lanatoside A
cardiac glycoside
digitalis lanata
digitoxigenin+glucose-3-acetyl(digitoxose)3 - 12—digitoxin
cardiac glycoside - 13—digoxin
cardiac glycoside - 14—ouabain
cardiac glycoside
very polar
not clinically used - 15—inamrinone
positive inotropic agents
phosphodiesterase enzyme inhibitor
thrombocytopenia
metabolized in liver - 16—milrinone
positive inotropic agents
phosphodiesterase enzyme inhibitor
more potent
less toxic
unchanged excretion - 17—dobutamine
positive inotropic agents
beta 1-adrenoceptor agonists
inactive orally and given IV - 18—nitric-nitrate
nitrovasodilator
organic nitrate - 19—nitrous-nitrite
nitrovasodilator
organ nitrite - 20—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 - 21—glyceryl trinitrate (nitroglycerin)
antianginal agent
nitrovasodilator
prodrug
explosive in dynamite
colorless oil
volatile
skin absorption - 22—erythrityl tetranitrate
antianginal agent
nitrovasodilator
prodrug
solid
slightly water soluble
more soluble in organic solvents
slower onset/long duration of action
low volatility - 23—pentaerythritol tetranitrate
antianginal agent
nitrovasodilator
prodrug
crystalline
weakly insoluble in alcohol
readily soluble in acetone
powerful explosive - 24—isosorbide dinitrate
antianginal agent
nitrovasodilator
prodrug
solid
water soluble
give active metabolite (100% bioavailable) - 25—nifedipine
antianginal
calcium channel blocker
DHP
orally active/ metabolized
decrease afterload
reflex tachycardia - 26—amlodipine
antianginal
calcium channel blocker
DHP
orally active/ metabolized
decrease afterload
reflex tachycardia
bioavailability: 60-90%
DOA: 24h - 27—nicardipine
antianginal
calcium channel blocker
DHP
orally active/ metabolized
decrease afterload
reflex tachycardia - 28—verapamil
antianginal
calcium channel blocker
non DHP/ phenylalkylamine
orally active/ metabolized by CYP3A4 and CYP2D6
decrease HR
- inotropic, chronotropic, dromotropic - 29—bepiridil
antiangina
calcium channel blocker
non DHP/ diarylaminopropylaminoether
rarely used - 30—diltiazem
antianginal
calcium channel blocker
non DHP/ benzothiazepine
orally active/ metabolized by hydrolysis
decrease HR
- inotropic, chronotropic, dromotropic - 31—noverapamil
metabolite of verapamil
by N-demethylation
30-50% active as parent drug - 32—desacetyldiltiazem
metabolite of diltiazem
by hydrolysis of ester
30-50% active as parent drug - 33—dipyridamole
antianginal
coronary vasodilator
antiplatelet activity
non selective so rarely used - 34—papaverine
antianginal
coronary vasodilator
orally active
antispasmotic
non selective so rarely used - 35—cyclandelate
antianginal
coronary vasodilator
non selective so rarely used - 36—MPPP (designer heroin)
active opioid agonist
reversed ester of meperidine
phenylpiperidine synthetic analgesics - 37—nisentil (alpha-prodine)
phenylpiperidine synthetic analgesics - 38—demerol (meperidine)
active opioid agonist
phenylpiperidine synthetic analgesics - 39—MPTP
N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
byproduct of MPPP
metabolized orally/IV/inhalation by MAO-B
lead to parkinsonism - 40—MPP+
1-methyl-4-phenylpyridinium
toxic
irreversible damage of DA neurons
metabolite of MPTP - 41—benztropine mesylate
anticholinergic (antimuscarinic) agent
synthetic
centrally acting
limited use
given with dopaminergic therapy
severe central and peripheral side effects - 42—trihexyphenidyl hydrochloride
anticholinergic (antimuscarinic) agent
synthetic
centrally acting
limited use
given with dopaminergic therapy
severe central and peripheral side effects
salt/pH dependent - 43—procyclidine hydrochloride
anticholinergic (antimuscarinic) agent
synthetic
centrally acting
limited use
given with dopaminergic therapy
severe central and peripheral side effects
salt/pH dependent - 44—biperiden hydrochloride
anticholinergic agent
synthetic
salt
pH dependent - 45—diphenhydramine hydrochloride
antihistamine - 46—orphenadrine hydrochloride
antihistamine
centrally acting
limited use
given with dopaminergic therapy
severe central and peripheral side effects - 47—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% - 48—dopamine
3,4-dihydroxyphenylethylamine
highly basic (doesn't cross the brain)
rapidly metabolized - 49—3-methoxy-4-hydroxy phenylalanine
metabolite of L-DOPA by COMT - 50—3,4-dihydroxyphenylacetic acid
metabolite of dopamine by MAO - 51—vanillylmandelic acid (VMA)
final metabolite of L-DOPA - 52—carbidopa
decarboxylase inhibitor
delivers more L-DOPA to brain
acts peripherally
doesn't cross the BBB - 53—selegiline
first generation irreversible MAO-B inhibitor
orally metabolized
gives metamphetamine
side effect: vasoconstriction, hallucination - 54—rasagiline
second generation irreversible MAO-B inhibitor
orally metabolized to 1-aminoindan
no side effects - 55—tolcapone
reversible non specific COMT inhibitor
long acting (8-12h)
centrally and peripherally acting
nausea, hallucination
hepatic failure - 56—entacapone
reversible non specific COMT inhibitor
short acting (2h)
mostly peripherally
nausea,hallucination - 57—amphetamine
metabolite of metamphetamine (metabolite of selegiline)
causes side effects of selegiline
- 58—metamphetamine
metabolite of selegiline
- 59—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
- 60—Memantine
admantane derivative
dopamine releasing agent
inhibit dopamine reuptake
- 61—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 - 62—o-demethylquinidine
metabolite of quinidine
active
by partial hepatic metabolism - 63—oxydihydroquinidine
metabolite of quinidine
active
by partial hepatic metabolism - 64—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%) - 65—n-acetylprocainamide
metabolite of procainamide
active - 66—p-aminobenzoic acid
metabolite of procainamide - 67—metabolite of procainamide
- 68—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 - 69—lidocaine
antiarrhythmic
class 1B
local anesthetic
first pass metabolism (n-dealkylation)
SE: emesis, convulsion - 70—monoethylxylidine
metabolite of lidocaine
give glycine xylidide
active
CNS effect - 71—metabolite of lidocaine
- 72—metabolite of lidocaine
- 73—tocainide
antiarrhythmic
class 1B
orally active/ absorbed (bcz of alpha methyl)
slow metabolism
for emergency ventricular arrhythmias
SE: GI disturbance, CNS effects - 74—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) - 75—phenytoin
antiarrhythmia
class 1B
anticonvulsant
orally active
IV use
p-hydroxylation (inactive)
for atrial and ventricular arrhythmias - 76—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 - 77—propafenone
antiarrhythmic
class 1C
local anesthetic
orally, IV
GI absorption
hepatic metabolism by CYP2D6 - 78—moricizine
antiarrhythmia
class 1C
phenothiazine
orally
short half-life
but effect lasts hours (active metabolite) - 79—encainide
antiarrhythmia
class 1C
not used - 80—ibutilide
antiarrhythmic
class 3
methanesulfonanilide derivative
no beta adrenergic blocking activity
only by IV infusion - 81—bretylium tosylate
antiarrhythmic
class 3
adrenergic neuronal blocking agent
antihypertensive
given IV
for life threatening cases of ventricular arrhythmia - 82—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 - 83—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%) - 84—Sotalol
antiarrhythmic
class 3
methanesulfonanilide derivative
non selective beta blocker
- 85—verapamil
antiarrhythmic
class 4
slows phase 4
slow SA node firing and conduction to AV node - 86—diltiazem
antiarrhythmic
class 4
slows phase 4
slow SA node firing and conduction to AV node - 87—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 - 88—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 - 89—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 - 90—perindopril
RAS inhibitor
ACEI
prodrug
active
renal excretion
DOA= 24h
SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure - 91—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 - 92—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 - 93—quinapril
RAS inhibitor
ACEI
prodrug
active
renal excretion
DOA= 24h
SE: hypotension, hyperkalemia,dry cough, taste disturbance, headache, nausea, diarrhea, angioedema, acute renal failure - 94—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 - 95—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 - 96—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 - 97—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 - 98—disulfide dimer
metabolite of captopril
inactive - 99—captopril cysteine disulfide
metabolite of captopril
inactive - 100—glucuronide conjugate
metabolite of benazepril - 101—diketopiperazine metabolite
metabolite of ramapril
inactive - 102—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 - 103—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 - 104—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 - 105—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 - 106—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 - 107—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 - 108—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 - 109—EXP-3174
metabolite of losartan by CYP3A4
active
non competitive antagonist
tetrazol derivative - 110—mannitol
osmotic diuretics
very polar
given IV
if orally--> osmotic diarrhea - 111—sorbitol
osmotic diuretics
very polar
given IV
if orally--> osmotic diarrhea - 112—isosorbide
osmotic diuretics
given orally - 113—urea
osmotic diuretics
given IV
unpleasant taste
- 114—acetazolamide
diuretics
carbonic anhydrase inhibitors
arylsulfonamide
for glaucoma
cause hypokalemia and metabolic acidosis - 115—methazolamide
diuretics
carbonic anhydrase inhibitors
arylsulfonamide
for glaucoma
cause hypokalemia and metabolic acidosis - 116—ethoxzolamide
diuretics
carbonic anhydrase inhibitors
arylsulfonamide
for glaucoma
cause hypokalemia and metabolic acidosis - 117—dichlorphenamide
diuretics
carbonic anhydrase inhibitors
arylsulfonamide
for glaucoma
cause hypokalemia and metabolic acidosis - 118—benzene-1,3-disulfonamide
aryl sulfonamide derivative - 119—aminochlorphenamine
diuretics
benzothiadiazine (thiazide) - 120—6-chloro-1,2,4-benzothiadiazine-7-sulfonamide-1,1-dioxide
diuretics
benzothiadiazine (thiazide) - 121—quinethazone
diuretics
thiazide-like
quinazolinone derivative
orally active
long DOA (18-24h) - 122—metolazone
diuretics
thiazide-like
quinazolinone derivative
orally active
long DOA
more potent - 123—chlorthalidone
diuretics
thiazide-like
phthalamidine derivative
orally active
long DOA (48-72h) - 124—indapamide
diuretics
thiazide-like
indoline derivative
orally active
long DOA (24-36h)
potent - 125—furosemide
diuretic
loop diuretic
orally active
quick onset of action (30min)
short DOA (6h)
SE: electrolyte and fluid imbalance, hypokalemia, hyperurecemia, ototoxicity, hypersensitivity - 126—5-sulfamoyl-anthranilic acid
diuretic
loop diuretic
orthoaminobenzoic acid - 127—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 - 128—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 - 129—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 - 130—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...) - 131—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...) - 132—canrenoic acid
metabolite of canrenone
inactive - 133—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...) - 134—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 - 135—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 - 136—antodyne

- 137—apomorphine
- 138—baclofen
- 139—bromocriptine(parlodel)
- 140—carisoprodol(rela soma)

- 141—dantrolene sodium (dantrium)
- 142—diazepam

- 143—mephenesin
- 144—meprobamate (equanil)

- 145—pergolide (permax)
- 146—ropinirol (requip)
- 147—S-Pramipexole (mixapex)
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- FlashCards sobre med chem 2, criado por lola_smily em 11-02-2015.
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