Flashcards
med chem 2 exam 2
Cards in this deck (240)
- 1—histidine
- 2—histamine
- 3—khellin
antihistaminic
inhibit histamine release
chromone moiety
from ammi visnaga
bronchodilatory effect (don't reverse bronchoconstriction)
- 4—cromolyn sodium
antihistaminic
inhibit histamine and SRS-A release (locally)
bis-chromone
no bronchodilatory and antihistaminic effects
strictly prophylactic
low oral bioavailability (poor absorption)
by inhalation (for allergic rhinitis)
topically: eye drops (for allergic conjunctivitis)
5-30 min before attack
if chronic use: tolerance
- 5—nedocromil sodium
antihistaminic
inhibit histamine release
chromone derivative
by inhalation: aerosol (for prophylaxis of asthma)
ophthalmic solution (for seasonal, perennial allergic conjunctivitis)
- 6—lodoxamide
antihistaminic
mast cell stabilizer (inhibit immediate hypersensitivity reaction)
topically: eye (for conjunctivitis)
- 7—pemirolast potassium
antihistaminic
inhibit histamine release
pyrimidone
- 8—phenbenzamine
H1 antihistaminic
ethylenediamine
SE: sedation, drowsiness, impair mental activity
- 9—Tripelennamine
H1 antihistaminic
ethylenediamine
SE: sedation, drowsiness, impair mental activity
- 10—pyrilamine
H1 antihistaminic
ethylenediamine
local anesthetic effect (tongue numbness)
SE: sedation, drowsiness, impair mental activity
- 11—thonzylamine
H1 antihistaminic
ethylenediamine
SE: sedation, drowsiness, impair mental activity
- 12—methapyrilene
H1 antihistaminic
ethylenediamine
SE: sedation, drowsiness, impair mental activity
- 13—antazoline
H1 antihistaminic
ethylenediamine
SE: sedation, drowsiness, impair mental activity
- 14—Diphenhydramine
H1 antihistamine
ethanolamine ether
antihistaminic, antiemetic, antitussive, marked sedation, anticholinergic, antidyskinetic
SE: sedation, drowsiness
- 15—bromodiphenhydramine
H1 antihistamine
ethanolamine ether
more lipid soluble, more potent
antihistaminic, antiemetic, antitussive, marked sedation, anticholinergic, antidyskinetic
SE: sedation, drowsiness
- 16—chlorodiphenhydramine
H1 antihistamine
ethanolamine ether
more lipid soluble, more potent
antihistaminic, antiemetic, antitussive, marked sedation, anticholinergic, antidyskinetic
SE: sedation, drowsiness
- 17—Doxylamine
H1 antihistamine
ethanolamine ether
most potent CNS depressant
hypnotic agent
no abuse potential
SE: sedation, drowsiness
- 18—Carbinoxamine
H1 antihistamine
ethanolamine ether
potent
- (rotoxamine)> + (available as racemic mixture)
SE: sedation, drowsiness
- 19—clemastine
H1 antihistamine
aminoalkyl ether
RR more potent
long DOA
less anticholinergic
less sedation
- 20—clemastine
H1 antihistamine
aminoalkyl ether
RR more potent
long DOA
less anticholinergic
less sedation
- 21—setastine
H1 antihistaminic
aminoalkyl ether
- 22—cyclizine
H1 antihistamine
piperazine derivative
for nausea, vomiting (from motion sickness and radiation sickness)
cyclizine lactate IM injection
moderately potent
prolonged DOA
anticholinergic effects
- 23—Chlorcyclizine
H1 antihistamine
piperazine derivative
antiallergic (for urticaria and hay fever)
more lipophilic
moderately potent
prolonged DOA
anticholinergic effect
- 24—Hydroxyzine
H1 antihistaminic
piperazine derivative
marked sedation
antiemetic, antiallergic (for pruritis)
at high dose: for anxiety and emotional stress
moderately potent
prolonged DOA
anticholinergic effects
- 25—Cetirizine
H1 antihistamine
piperazine derivative
2nd generation
ionized --> less absorbed
antinauseant
moderately potent
prolonged DOA
anticholinergic effects
- 26—Meclizine
H1 antihistamine
piperazine derivative
for nausea (from motion sickness and radiation sickness)
moderately potent
prolonged DOA
anticholinergic effects
- 27—buclizine
H1 antihistamine
piperazine derivative
for nausea (from motion sickness and radiation sickness)
moderately potent
prolonged DOA
anticholinergic effects
- 28—oxatomide
H1 antihistamine
piperazine derivative
antimuscarinic, mast cell stabilizer (less release of histamine)
moderately potent
prolonged DOA
anticholinergic effects
- 29—chlorpheniramine
H1 antihistamine
propylamine derivative
10X > potent than pheniramine
+ > -
longer acting than pheniramine
t 1/2 = 12-15 h
- 30—Dexchloropheniramine
H1 antihistamine
propylamine derivative
dextropheniramine
- 31—bromopheninramine
H1 antihistamine
propylamine derivative
10X > potent than pheniramine
+ > -
longer acting than chlorpheniramine
t 1/2 = 25h
- 32—Dexbromopheniramine
H1 antihistamine
propylamine derivative
- 33—E-pyrrobutamine (pyronil)
H1 antihistamine
propylamine
unsaturated pheniramine
potent (E (165X) > Z)
t1/2 = 12h --> long acting
- 34—triprolidine
H1 antihistamine
propylamine
unsaturated pheniramine
potent (E (100X) > Z)
t1/2 = 12h --> long acting
- 35—demethindine
H1 antihistamine
propylamine
unsaturated pheniramine
potent (- > +)
- 36—phenindamine
H1 antihistamine
propylamine
unsaturated pheniramine
moderately potent
cause CNS stimulation, insomnia
- 37—Promethazine
H1 antihistamine
tricyclic phenothiazine
moderately potent
antiemetic, antianxiety
pronounced sedation
potentiate analgesics
long DOA
drowsiness
- 38—pyrathiazine
H1 antihistamine
tricyclic phenothiazine
moderately potent
antiemetic, antianxiety
pronounced sedation
potentiate analgesics
long DOA
drowsiness
- 39—trimeprazine
H1 antihistamine
tricyclic phenothiazine
less antihistaminic, more neuroleptic activity (spacer 3 C)
moderately potent
antiemetic, antianxiety
pronounced sedation
potentiate analgesics
long DOA
drowsiness
- 40—methdiazine
H1 antihistamine
tricyclic phenothiazine
less antihistaminic, more neuroleptic activity (spacer 3 C)
moderately potent
antiemetic, antianxiety
pronounced sedation
potentiate analgesics
long DOA
drowsiness
- 41—pimethixene
H1 antihistamine
tricyclic thioxanthene derivative
orally active
- 42—methixene
H1 antihistamine
tricyclic
moderately potent
anticholinergic
usefull in parkinson
- 43—cyproheptadine
H1 antihistamine
tricyclic
anticholinergic
antiserotonergic
appetite stimulating effect
for anorexia nervosa
- 44—azatadine
H1 antihistamine
tricyclic
aza isostere
potent
long acting
anticholinergic
- 45—ketotifen
H1 antihistamine
tricyclic
potent
mast cell stabilizer
topically (for seasonal allergic conjunctivitis)
nasal spray (for allergic rhinitis)
- 46—terfenadine
H1 antihistamine
2nd generation
less or no: anticholinergic, sedation
low affinity to adrenergic and serotonergic effects
QT prolongation, torsade de pointes
give fexofenadine
- 47—fexofenadine
H1 antihistamine
2nd generation
less or no: anticholinergic, sedation
low affinity to adrenergic and serotonergic effects
active
safer
- 48—ebastine
H1 antihistamine
2nd generation
potent
long acting
less or no: anticholinergic, sedation
low affinity to adrenergic and serotonergic effects
from terfenadine
- 49—cetirizine
H1 antihistamine
2nd generation
metabolite of hydroxyzine
levo (30X): levocetirizine > dextro
less or no: anticholinergic, sedation
low affinity to adrenergic and serotonergic effects
- 50—loratadine
H1 antihistamine
2nd generation
metabolite of azatadine
long acting tricyclic
less or no: anticholinergic, sedation
low affinity to adrenergic and serotonergic effects
forms desloratadine
- 51—acrivastine
H1 antihistamine
2nd generation
metabolite of tripolidine
lacks CNS effects
less or no: anticholinergic, sedation
low affinity to adrenergic and serotonergic effects
- 52—mizolastine
H1 antihistamine
2nd generation
long acting
less or no: anticholinergic, sedation
low affinity to adrenergic and serotonergic effects
metabolized into inactive
- 53—astemizole
H1 antihistamine
2nd generation
less or no: anticholinergic, sedation
low affinity to adrenergic and serotonergic effects
- 54—carebastine
H1 antihistamine
2nd generation
less or no: anticholinergic, sedation
low affinity to adrenergic and serotonergic effects
- 55—desloratadine
H1 antihistamine
2nd generation
less or no: anticholinergic, sedation
low affinity to adrenergic and serotonergic effects
- 56—burimamide
H2 antihistamine 1st generation
antiulcer
thiurea derivative
poor oral bioavailability
low potency
for GERD treatment
- 57—metiamide
H2 antihistamine 1st generation
antiulcer
thiourea derivative
orally active
potent
agranulocytosis
for GERD treatment
- 58—cimetidine
H2 antihistamine 1st generation
antiulcer
cyanoguanidine derivative
orally active
potent
antiandrogenic effect, CYP inhibition
metabolized to S-oxide (inactive)
for GERD treatment
- 59—Ranitidine
H2 antihistamine 2nd generation
antiulcer
orally active (30-80% bioavailable)
potent (4-10X more than cimetidine)
weaker inhibitor of CYP enzymes
no antiandrogenic effects
renal elimination
metabolized: N-desmethyl, S-oxide, N-oxide
for GERD treatment
- 60—nizatidine
H2 antihistamine 2nd generation
antiulcer
orally active (75-100% bioavailable)
potent (5-18X more than cimetidine)
not an inhibitor of CYP enzymes
no antiandrogenic effects
renal elimination
metabolized: N-desmethyl, S-oxide, N-oxide
for GERD treatment
- 61—famotidine
H2 antihistamine 2nd generation
antiulcer
orally active (40-45% bioavailable)
more potent
not an inhibitor of CYP enzymes
no antiandrogenic effects
for GERD treatment
- 62—omeprazole
antiulcer
proton pump inhibitor (H+/K+ ATPase)
2-pyridylmethylsulfinylbenzimidazole derivative
irreversible inhibitors
for activation: acidic media--> sulfenic acid, sulfenamide (active, bind irreversibly by covalent bond)
metabolites: methyl hydroxylation, O-demethylation (CYP2C19)
sulfoxidation (CYP3A4)
clearance: R(+) --> rapidly, metabolized by CYP2C19
S(-)--> esomeprazole, metabolized by CYP3A4
- 63—Esomeprazol
antiulcer
proton pump inhibitor(H+/K+ ATPase)
2-pyridylmethylsulfinylbenzimidazole derivative
irreversible inhibitors
S (-) omeprazole
metabolized by CYP3A4
- 64—tenatoprazole
antiulcer
proton pump inhibitor(H+/K+ ATPase)
irreversible inhibitors
imidazopyridine derivative
- 65—lansoprazole
antiulcer
proton pump inhibitor(H+/K+ ATPase)
2-pyridylmethylsulfinylbenzimidazole derivative
irreversible inhibitors
- 66—Rabeprazole
antiulcer
proton pump inhibitor(H+/K+ ATPase)
2-pyridylmethylsulfinylbenzimidazole derivative
irreversible inhibitors
thio ether
- 67—pantoprazole
antiulcer
proton pump inhibitor(H+/K+ ATPase)
2-pyridylmethylsulfinylbenzimidazole derivative
irreversible inhibitors
- 68—misoprostol
antiulcer
semisynthetic prostaglandin E1 derivative
ester prodrug
abotifacient agent (causes abortion)
de-esterification --> active metabolite (not by 16-hydroxydehydrogenase)
abuse potential
- 69—prostaglandin E1
antiulcer
maintain mucosal integrity, protect gastric wall
- 70—sucralfate
antiulcer
aluminium hydroxide complex of octasulfate ester of sucrose
small amount absorbed systematically
synthesize: prostaglandin, bicarbonate, epidermal, fibroblast growth factors
decrease absorption of: H2 antihistamine, quinolone antibiotic, phenytoin, warfarin
- 71—carbenoxolone
antiulcer
steroid like
from licorice
mineralocorticoid activity (SE)
inhibit PG inactivation
- 72—pirenzepine
antiulcer
anticholinergic
selective M1 receptor antagonist
decrease GI acid secretion, intestinal mobility
- 73—telenzepine
antiulcer
anticholinergic
selective M1 receptor antagonist
decrease GI acid secretion, intestinal mobility
- 74—steroid backbone
- 75—steroid template
- 76—phenantrene
- 77—cholestane template
- 78—5-beta-cholestane
cis isomer
- 79—5-beta-cholestane
cis isomer
- 80—5-alpha-cholestane
trans isomer
- 81—5-alpha-cholestane
trans isomer
precursor of cholesterol
- 82—5-alpha-pregnane
steroid
precursor of progesterone and hydrocortisone (cortisol)
- 83—5-alpha-androstane
steroid
precursor of testosterone and dehydroepiandrosterone
- 84—5-alpha-estrane
steroid
precursor of estradiol
- 85—cholesterol
steroid
adrenocorticoid
cholest-5-en-3-beta-ol
formed from acetyl CoA and acetoacetyl CoA
forms pregnenolone, bile acids (glycocholic acid, taurocholic acid)
- 86—progesterone
steroid
adrenocorticoid
pregn-4-ene-3,20-dione
- 87—hydrocortisone (cortisol)
steroid
adrenocorticoid
11-beta-17-alpha-21-trihydroxy-pregn-4-ene-3,20-dione
short acting
active
metabolized to cortisone, inactive metabolites
orally: completely absorbed (>95% bioavailability)
t1/2 = 1-2h
IM (acetate): slowly absorbed
longer duration of action
intrarectally: poorly absorbed
- 88—testosterone
steroid
17-beta-hydroxyandrost-4-ene-3-one
- 89—dehydroepiandrosterone DHEA
steroid
- 90—17-beta-estradiol
steroid
1,3,5(10)-estratien-3,17-beta-diol
- 91—cortisone
steroid
17-alpha-21-dihydroxypregn-4-ene-3,11,20-trione
natural
short acting
t1/2= 1-1.5h
active
orally/ IM (21-acetate): slowly absorbed, longer duration
SE: Na/H2O retention, K excretion, increase gastric acid secretion, gluconeogenesis, increase nitrogen excretion
- 92—estrone
steroid
1,3,5(10)-estratrien-3-ol-17-one
- 93—pregnenolone
steroid
adrenocorticoid
metabolite of oxidation of cholesterol
active
- 94—aldosterone
steroid
adrenocorticoid
from cholesterol
active
- 95—11-epicortisol
steroid
first analogue
- 96—hydrocortisone acetate
steroid
mineralocorticoid and glucocorticoid act.
for replacement therapy (adrenocortical deficiency)
for rheumatoid arthritis --> caus abnormal metabolic function
SE: Na/H2O retention, K excretion, increase gastric acid secretion, gluconeogenesis, increase nitrogen excretion
- 97—hydrocortisone cypionate
steroid
21-(3-cyclopentylpropionate) ester
water insoluble
orally
mineralocorticoid and glucocorticoid act.
for replacement therapy (adrenocortical deficiency)
for rheumatoid arthritis --> caus abnormal metabolic function
SE: Na/H2O retention, K excretion, increase gastric acid secretion, gluconeogenesis, increase nitrogen excretion
- 98—hydrocortisone butyrate
steroid
17-alpha-butyrate-ester
topically
mineralocorticoid and glucocorticoid act.
for replacement therapy (adrenocortical deficiency)
for rheumatoid arthritis --> caus abnormal metabolic function
SE: Na/H2O retention, K excretion, increase gastric acid secretion, gluconeogenesis, increase nitrogen excretion
- 99—hydrocortisone buteprate
steroid
17-alpha-butyrate, 21-propionate ester
mineralocorticoid and glucocorticoid act.
for replacement therapy (adrenocortical deficiency)
for rheumatoid arthritis --> caus abnormal metabolic function
SE: Na/H2O retention, K excretion, increase gastric acid secretion, gluconeogenesis, increase nitrogen excretion
- 100—hydrocortisone valerate
steroid
17-alpha-valerate ester
topically
mineralocorticoid and glucocorticoid act.
for replacement therapy (adrenocortical deficiency)
for rheumatoid arthritis --> caus abnormal metabolic function
SE: Na/H2O retention, K excretion, increase gastric acid secretion, gluconeogenesis, increase nitrogen excretion
- 101—hydrocortisone sodium succinate
steroid
21-sodium succinate ester
extremely water soluble
IV/IM
slowly and incompletely hydrolyzed
t1/2= 30minmineralocorticoid and glucocorticoid act.
for replacement therapy (adrenocortical deficiency)
for rheumatoid arthritis --> caus abnormal metabolic function
SE: Na/H2O retention, K excretion, increase gastric acid secretion, gluconeogenesis, increase nitrogen excretion
- 102—hydrocortisone sodium phosphate
steroid
21-sodium phosphate ester
extremely water soluble
IV/IM
completely and rapidly metabolized
t1/2= 10min
mineralocorticoid and glucocorticoid act.
for replacement therapy (adrenocortical deficiency)
for rheumatoid arthritis --> caus abnormal metabolic function
SE: Na/H2O retention, K excretion, increase gastric acid secretion, gluconeogenesis, increase nitrogen excretion
- 103—fludrocortisone
steroid
orally active
high glucocorticoid activity
increase stability of 11-beta-OH
if Br at 9: increase 11X glucocorticoid, increase 300-800X mineralocorticoid
for adrenocortical insufficiency: addison's disease
- 104—fludrocortisone acetate
steroid
orally active
high glucocorticoid activity
increase stability of 11-beta-OH
if Br at 9: increase 11X glucocorticoid, increase 300-800X mineralocorticoid
for adrenocortical insufficiency: addison's disease
- 105—prednisolone
steroid
delta 1-hydrocortisone
longer acting
more glucocorticoid act (3-4) than mineralocorticoid act. (1)
4-5X more potent
less salt retention
- 106—6-beta-hydroxyprednisolone
steroid
metabolite of prednisolone
active
- 107—16-alpha-hydroxyprednisolone
steroid
metabolite of prednisolone
active
- 108—20-hydroxyprednisolone
steroid
metabolite of prednisolone
inactive
- 109—Prednisolone acetate
steroid
delta corticosteroid
- 110—prednisolone t-butylacetate
steroid
delta corticosteroid
- 111—prednisolone sodium phosphate
steroid
delta corticosteroid
- 112—methylprednisolone
steroid
methyl corticoid
6-alpha-methyl analogue of prednisolone
potent glucocorticoid
negligible mineralocorticoid
- 113—methylprednisolone 21-acetate
steroid
methyl corticoid
- 114—methylprednisolone sodium succinate
steroid
methyl corticoid
- 115—triamcinolone
steroid
9-alpha fluro-16-alpha OH prednisolone
more potent
less water retention
SE: anorexia, weight loss, nausea, dizziness, muscle weakness
- 116—Dexamethasone
steroid
9-alpha fluro-16-alpha methyl
higher stability of 20-keto group
5X more potent as anti-inflammatory (compared to prednisolone, hydrocortisone)
SE: excessive appetite, weight gain, abdominal distention
- 117—Dexamethasone 21-acetate
steroid
- 118—dexamethasone sodium phosphate
steroid
- 119—betamethasone
steroid
9-alpha fluro-16-beta CH3
no advantage
same potency, same SE as dexamethasone
- 120—flurandrenolide
steroid
topical glucocorticoid
high activity
high lipid solubility (acetonides)
potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 121—fluocinolone acetonide
steroid
topical glucocorticoid
high activity
high lipid solubility (acetonides)
potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 122—fluocinonide
steroid
topical glucocorticoid
high activity
high lipid solubility (acetonides)
potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 123—halcinonide
steroid
topical glucocorticoid
high activity
high lipid solubility (acetonides)
potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 124—desonide
steroid
topical glucocorticoid
high lipid solubility (acetonides)
potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 125—amcinonide
steroid
topical glucocorticoid
high activity
high lipid solubility (acetonides)
potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 126—clobetasol propionate
steroid
topical glucocorticoid
high activity
high lipid solubility
very potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 127—alcometasone
steroid
topical glucocorticoid
low potent (for chronic use)
metabolized in liver
excreted in bile or urine
- 128—flumethasone
steroid
topical glucocorticoid
high activity
potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 129—diflorasone diacetate
steroid
topical glucocorticoid
high activity
high lipid solubility
very potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 130—desoximetasone
steroid
topical glucocorticoid
high activity
high lipid solubility
potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 131—beclomethasone
steroid
topical glucocorticoid
high lipid solubility
potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 132—beclomethasone dipropionate
steroid
topical glucocorticoid
high lipid solubility
very potent local/topical antiinflammatory effect (for short duration)
5000X more potent than hydrocortisone
500X more potent than betamethasone
5X more potent than fluocinolone acetonide or triamcinolone acetonide
metabolized in liver
excreted in bile or urine
- 133—halobetasol propionate
steroid
topical glucocorticoid
high lipid solubility
very potent local/topical antiinflammatory effect (for short duration)
6% systemically absorbed
metabolized in liver
excreted in bile or urine
- 134—diflucortolone pivalate
steroid
topical glucocorticoid
high activity
high lipid solubility
potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 135—prednicarbate
steroid
topical glucocorticoid
low potency (for chronic use)
metabolized in liver
excreted in bile or urine
- 136—fluorometholone acetate
steroid
topical glucocorticoid
high activity
high lipid solubility
potent local/topical antiinflammatory effect (for short duration)
metabolized in liver
excreted in bile or urine
- 137—triamcinolone acetonide
steriod
inhaled/intranasal corticosteroid
high activity
high potency
- 138—flunisolide
steriod
inhaled/intranasal corticosteroid
high activity
high potency
- 139—fluticasone propionate
steriod
inhaled/intranasal corticosteroid
high activity
high potency
- 140—budesonide
steriod
inhaled/intranasal corticosteroid
high potency
- 141—mometasone furoate
steriod
inhaled/intranasal corticosteroid
- 142—androstenedione
steroid
precursor of testosterone and estradiol
- 143—estrone
steroid
precursor of estradiol
- 144—testosterone
steroid
precursor of estradiol
- 145—estradiol
steroid
estra-1,3,5(10)-triene-3,17beta-diol
most potent
- 146—estriol
steroid
metabolite of estradiol
least active
least potent
- 147—estradiol
steroid
estrogen derivative
- 148—estriol
steroid
estrogen derivative
- 149—estrone
steroid
estrogen derivative
- 150—estradiol 3-benzoate
steroid
estrogen derivative
prodrug
IM
- 151—estradiol 17-valerate
steroid
estrogen derivative
prodrug
IM
- 152—estradiol 17-cypionate
steroid
estrogen derivative
prodrug
IM
- 153—ethinyl estradiol
steroid
estrogen derivative
orally active
similar potency to estradiol (injection)
more potent (15-20X) than estradiol (orally)
- 154—mestranol
ethinyl estradiol 3-methylether
steroid
estrogen derivative
prodrug
oral contraceptive
metabolized to ethinyl estradiol
- 155—quinestrol
steroid
estrogen derivative
3-cyclopentyl ether of ethinyl estradiol
prodrug
most orally active
long acting
hydrolyzed by dealkylation
lipid soluble (stored in body fat), slowly released
- 156—sodium estrone sulfate
steroid
conjugated estrogen
hydrolyzed to estrone
- 157—equilin sodium sulfate
steroid
conjugated estrogen
low activity (unsaturation in ring B)
- 158—sodium equilenin sulfate
steroid
conjugated estrogen
low activity (unsaturated ring B)
- 159—piperazine estrone sulfate
steroid
conjugates estrogen
salt
- 160—diethylstilbestrol
non steroidal estrogen
orally active
slowly metabolized
long term use in pregnancy: increase risk of breast cancer
diphosphate form used for: prostate cancer
- 161—dienestrol
nonsteroidal estrogen
- 162—benzestrol
non steroidal estrogen
no double bonds
- 163—hexestrol
non steroidal estrogen
no double bonds
trans better
- 164—coumestrol
phytoestrogen
natural plant substance
from legumes
- 165—genistein
phytoestrogen
natural plant substance
from soybean and clover
example of flavonoids
- 166—daidzein
phytoestrogen
natural plant substance
from soybean
example of flavonoids
- 167—tamoxifen
estrogen antagonist
antiestrogen
orally active
Z isomer
SERM (selective estrogen receptor modifier)
estrogen antagonist in breast (for estrogen dependent breast cancer)
estrogen agonist in uterus and bones
metabolized by CYP3A4, 2D6
- 168—N-demethyltamoxifen
metabolite of tamoxifen by 3A4
active
- 169—4-hydroxytamoxifen
metabolite of tamoxifen by 2D6
more active than tamoxifen
- 170—toremifene
antiestrogen
triphenylethylene
chlorotamoxifen
metabolized by CYP3A4, deamination-hydroxylation in liver (caution if liver disease)
SE: hot flashes, nausea, platelet reduction, endometrial cancer
- 171—N-demethyltoremifene
metabolite of toremifene by CYP3A4
active
- 172—ospemifene
metabolite of toremifene by deamination-hydroxylation
active
- 173—enclomiphene
antiestrogen
E isomer
stimulate ovulation in women desiring pregnancy
- 174—zuclomiphene
antiestrogen
Z isomer
stimulate ovulation in women desiring pregnancy
- 175—raloxifene
antiestrogen
benzothiophene
SERM
estrogen antagonist: on endometrium and breast tissues
estrogen agonist: on bones and cardiovascular
to treat and prevent osteoporosis in postmenopausal
extensive first pass metabolism (to active) --> low oral bioavailability
- 176—fulvestrant
pure antiestrogen
hydrophobic side chain
poor oral bioavailability
IM
prevent growth of tamoxifen resistant breast cancer
metabolized to active and less active
for pregnant women taking anticoagulant/ have thrombocytopenia
SE: GI symptoms, headache, hot flashes
- 177—exemestane
aromatase (estrogen biosynthesis) inhibitor
steroidal derivative (type 1 inhibitors)
10-beta-propynylestr-4-ene-3,17-dione
for breast cancer
decrease estrogen: 85-95% in 2-3 days
no CYP effect
metabolite: 17-hydroxy metabolite --> active, higher affinity to receptor
- 178—formestane
aromatase (estrogen biosynthesis) inhibitor
irreversible inhibitor
steroidal derivative (type 1 inhibitors)
4-hydroxyandrostenedione
for breast cancer
given parenterally (no oral activity)
- 179—anastrozole
aromatase (estrogen biosynthesis) inhibitor
triazole (type 2 inhibitors)
selective
first line in advanced breast cancer in postmenopausal women
decrease estrogen: 80% in 2 weeks
long t1/2 = 50h (once daily)
metabolized to inactive
inhibit CYP 1A2, 2C9, 3A4
- 180—letrozole
aromatase (estrogen biosynthesis) inhibitor
triazole (type 2 inhibitors)
selective
decrease estrogen: 75-90% in 2-3 days
metabolized to inactive
- 181—progesterone
steroid
female sex hormone
t1/2= 5-10min
renally excreted: glucuronide (miscarriage index), sulfate conjugate (5-beta-pregnanediol)
- 182—20-alpha/beta-hydroxyprogesterone
steroid
metabolite of progesterone by reduction of 20 ketone
- 183—5-beta-pregnanediol
steroid
metabolite of progesterone by reduction of 4,5 double bond
- 184—6-alpha-hydroxyprogesterone
steroid
metabolite of progesterone by hydroxylation at C6
- 185—ethisterone
steroid
testosterone derivative
17-alpha alkyl derivative
orally active
- 186—dimethisterone
steroid
testosterone derivative
17-alpha alkyl derivative
orally active
- 187—19-norprogesterone
steroid
testosterone derivative
- 188—norethindrone
steroid
19-nortestosterone derivative
potent (10x > norethynodrel)
orally active
- 189—norethindrone acetate
steroid
19-nortestosterone derivative
orally administered/ transdermally
metabolized by deacetylation (rapidly,completely) in GI and liver--> norethindrone
- 190—norethynodrel
steroid
19-nortestosterone derivative
potent
orally active
- 191—ethynodiol diacetate
steroid
19-nortestosterone derivative
prodrug
- 192—norgestrel
steroid
19-nortestosterone derivative
orally active (oral contraceptives)
- 193—levonorgestrel
steroid
19-nortestosterone derivative
active isomer
orally active (OC)
weak androgenic activity
no glucocorticoid, mineralocorticoid act.
- 194—norgestimate
steroid
levonorgestrel derivative
prodrug
metabolized to 2 active metabolites (norelgestromine (in intestine, liver), levonorgestrel (in liver))
in mono, triphasic OC
few androgenic SE
- 195—desogestrel
steroid
levonorgestrel derivative
prodrug
metabolized rapidly to active metabolite (etenogestrel) in intestinal mucosa and first pass
oral bioavailability: 84%
in mono and triphasic OC
few androgenic SE
- 196—etonogestrel
steroid
levonorgestrel derivative
active metabolite of desogestrel
- 197—gestodene
steroid
levonorgestrel derivative
oral bioavailability: 100% (not prodrug)
excellent progesterone receptor binding affinity
in mono and triphasic OC--> small increase in triglyceride/total cholest levels
- 198—17-alpha-acetoxyprogesterone
steroid
progesterone derivative
limited activity orally
undergoes 6-alpha hydroxylation
- 199—medroxyprogesterone acetate
steroid
progesterone derivative
25X active > ethisterone
orally administered
completely, rapidly metabolized by first pass (deacetylation) --> medroxyprogesterone (metabolized like progesterone)
metabolites excreted in urine (glucuronide conjugates)
- 200—megestrol acetate
steroid
progesterone derivative
from medroxyprogesterone acetate
progestin activity
for treatment of breast, endometrial cancer/ hormone dependent carcinoma
- 201—dienogest
steroid
19-nortestosterone
estrane skeleton, C17 cyanomethyl group, C9,10 double bond
in OC preparation
- 202—drospirenone
steroid
19-norprogesterone
from spironolactone
antimineralocorticoid activity (5x affinity to receptor > aldosterone)
antiandrogenic action
progestin activity (10% of levonorgestrel)
- 203—elcometrine
steroid
19-norprogesterone derivative
potent
SQ (100x more potent than orally), intravaginally, transdermally
antiestrogenic action
no androgenic/antiandrogenic activity
- 204—nomegestrol acetate
steroid
19-norprogesterone derivative
better selectivity, more potent (than medroxyprogesterone acetate)
in OC preparations
no glucocorticoid/antimineralocorticoid/ androgenic act
has significant antiandrogenic action
- 205—trimegestone
steroid
19-norprogesterone derivative
most potent
high affinity to progesterone receptor
weak affinity to mineralocorticoid receptor
no glucocorticoid/androgenic/ antiandrogenic act
metabolic hydroxylation --> metabolites with progestogenic action
- 206—mifepristone
steroid
progesterone antagonist
orally active
rapidly absorbed
bioavailability: 70%
antiglucocorticoid act
metabolism: mono,di-dealkylation, 17-propyl hydroxylation-->inactive metabolite
fecal elimination (83%)
for hormone dependent breast cancer
- 207—onapristone
steroid
progesterone antagonist
less antiglucocorticoid act
for hormone dependent breast cancer
- 208—telapristone acetate
steroid
progesterone antagonist
for hormone dependent breast cancer
- 209—ulipristal acetate
steroid
progesterone antagonist
very high affinity to progesterone receptor (selective)
reduce effect of hormonal contraceptive
delay/inhibit ovulation
alter endometrium to prevent uterine implantation
metabolism: mono --> active, di-dealkylation
- 210—testosterone
steroid
male sex hormone
from androstenedione
do nitrogen retention: increasing the rate of protein synthesis and muscle mass,
decrease in the rate of protein catabolism
have androgenic activity (development of male reproductive tissues) / anabolic activity (cell growth,protein synthesis..)
- 211—5-alpha-dihydrotestosterone
steroid
metabolite of testosterone
most potent endogenous androgen
- 212—17-alpha-methyltestosterone
steroid
testosterone derivative
DOA: 24h
- 213—oxymesterone
steroid
testosterone derivative
- 214—methandrostenolone
steroid
testosterone derivative
- 215—fluoxymesterone
steroid
testosterone derivative
DOA: 24h
- 216—testosterone 17-beta-propionate
steroid
testosterone derivative
DOA: 1-2w
- 217—testosterone 17-beta-enanthate
steroid
testosterone derivative
depot ester
DOA: 2-4 w
- 218—testosterone 17-beta-undecanoate
steroid
testosterone derivative
DOA: 10h
- 219—testosterone 17-beta-cyclopentylpropionate (cypionate)
steroid
testosterone derivative
depot ester
DOA: 2-4 w
- 220—oxandrolone
steroid
17-alkylated derivative
2-oxasteroid analogue with lactone moiety
3x anabolic act (>17-methyltestosterone)
slight androgenic act
- 221—stanozolol
steroid
17-alkylated derivative
pyrazole derivative
anabolic act
- 222—testolactone
steroid
17-alkylated derivative
18-oxasteroid
anabolic act
little androgenic act
irreversible aromatase inhibitor
- 223—norethandrolone
steroid
19-norandrogens
better anabolic act
- 224—nandrolone decanoate
steroid
19-norandrogen
IM
slow hydrolysis
- 225—nandrolone phenylpropionate
steroid
19-norandrogen
IM
slow hydrolysis
- 226—methenolone acetate
steroid
potent anabolic act
no alkyl on C17
orally/injection
- 227—oxymetholone
steroid
17-alkylated derivative
anabolic act
- 228—chlortestosterone acetate
steroid
anabolic act
- 229—ethylestrenol
steroid
17-alkylated derivative
anabolic act
- 230—desoxymethyltestosterone
steroid
illegal anabolic agent
difficult to trace
- 231—tetrahydrogestrinone
steroid
illegal anabolic agent
difficult to trace
to build up cattle
- 232—gestrinone
steroid
illegal anabolic agent
difficult to trace
- 233—trenbolone
steroid
illegal anabolic agent
difficult to trace
- 234—3-trifluoromethyl-4-nitroaniline
antiandrogens precursor
- 235—flutamide
antiandrogens
nonsteroidal
synthetic
Competitive inhibitors (to testosterone and DHT) of androgen receptor
given 3x/day
- 236—bicalutamide
antiandrogens
nonsteroidal
synthetic
orally active
Competitive inhibitors (to testosterone and DHT) of androgen receptor
metabolized: hydroxyl metabolite -->active (in liver)
less hepatotoxicity
SE: vasomotor flushing, gynecomastia, decreases libido, decreased potency
- 237—nilutamide
antiandrogens
nonsteroidal
synthetic
Competitive inhibitors (to testosterone and DHT) of androgen receptor
SE: vasomotor flushing, gynecomastia, decreases libido, decreased potency, hepatotoxicity
- 238—hydroxyflutamide
metabolite of flutamide
more potent antiandrogen
- 239—finasteride
steroid
5-alpha reductase inhibitor (tightly)
irreversible competitive inhibition
relatively selective for type II
potent
slow
t1/2=30d
1mg suppress DHT (70% in plasma, 85-90% in prostate in 24h)
metabolism: CYP3A4 (liver)
elimination: renal (40%), fecal
- 240—dutasteride
steroid
5-alpha reductase inhibitor (tightly)
irreversible competitive inhibition
for 2 types
orally active
more potent
0.5mg/day for 2w suppress DHT (90% in plasma)
to treat BPH
metabolism: CYP3A4 (liver), parahydroxy metabolite --> active
elimination: renal, fecal (40%)
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- Flashcards on med chem 2 exam 2, created by lola_smily on 17/03/2015.
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