med chem 2 exam 2

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Flashcards on med chem 2 exam 2, created by lola_smily on 17/03/2015.
lola_smily
Flashcards by lola_smily, updated more than 1 year ago
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Created by lola_smily over 9 years ago
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Question Answer
histidine
histamine
khellin antihistaminic inhibit histamine release chromone moiety from ammi visnaga bronchodilatory effect (don't reverse bronchoconstriction)
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
nedocromil sodium antihistaminic inhibit histamine release chromone derivative by inhalation: aerosol (for prophylaxis of asthma) ophthalmic solution (for seasonal, perennial allergic conjunctivitis)
lodoxamide antihistaminic mast cell stabilizer (inhibit immediate hypersensitivity reaction) topically: eye (for conjunctivitis)
pemirolast potassium antihistaminic inhibit histamine release pyrimidone
phenbenzamine H1 antihistaminic ethylenediamine SE: sedation, drowsiness, impair mental activity
Tripelennamine H1 antihistaminic ethylenediamine SE: sedation, drowsiness, impair mental activity
pyrilamine H1 antihistaminic ethylenediamine local anesthetic effect (tongue numbness) SE: sedation, drowsiness, impair mental activity
thonzylamine H1 antihistaminic ethylenediamine SE: sedation, drowsiness, impair mental activity
methapyrilene H1 antihistaminic ethylenediamine SE: sedation, drowsiness, impair mental activity
antazoline H1 antihistaminic ethylenediamine SE: sedation, drowsiness, impair mental activity
Diphenhydramine H1 antihistamine ethanolamine ether antihistaminic, antiemetic, antitussive, marked sedation, anticholinergic, antidyskinetic SE: sedation, drowsiness
bromodiphenhydramine H1 antihistamine ethanolamine ether more lipid soluble, more potent antihistaminic, antiemetic, antitussive, marked sedation, anticholinergic, antidyskinetic SE: sedation, drowsiness
chlorodiphenhydramine H1 antihistamine ethanolamine ether more lipid soluble, more potent antihistaminic, antiemetic, antitussive, marked sedation, anticholinergic, antidyskinetic SE: sedation, drowsiness
Doxylamine H1 antihistamine ethanolamine ether most potent CNS depressant hypnotic agent no abuse potential SE: sedation, drowsiness
Carbinoxamine H1 antihistamine ethanolamine ether potent - (rotoxamine)> + (available as racemic mixture) SE: sedation, drowsiness
clemastine H1 antihistamine aminoalkyl ether RR more potent long DOA less anticholinergic less sedation
clemastine H1 antihistamine aminoalkyl ether RR more potent long DOA less anticholinergic less sedation
setastine H1 antihistaminic aminoalkyl ether
cyclizine H1 antihistamine piperazine derivative for nausea, vomiting (from motion sickness and radiation sickness) cyclizine lactate IM injection moderately potent prolonged DOA anticholinergic effects
Chlorcyclizine H1 antihistamine piperazine derivative antiallergic (for urticaria and hay fever) more lipophilic moderately potent prolonged DOA anticholinergic effect
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
Cetirizine H1 antihistamine piperazine derivative 2nd generation ionized --> less absorbed antinauseant moderately potent prolonged DOA anticholinergic effects
Meclizine H1 antihistamine piperazine derivative for nausea (from motion sickness and radiation sickness) moderately potent prolonged DOA anticholinergic effects
buclizine H1 antihistamine piperazine derivative for nausea (from motion sickness and radiation sickness) moderately potent prolonged DOA anticholinergic effects
oxatomide H1 antihistamine piperazine derivative antimuscarinic, mast cell stabilizer (less release of histamine) moderately potent prolonged DOA anticholinergic effects
chlorpheniramine H1 antihistamine propylamine derivative 10X > potent than pheniramine + > - longer acting than pheniramine t 1/2 = 12-15 h
Dexchloropheniramine H1 antihistamine propylamine derivative dextropheniramine
bromopheninramine H1 antihistamine propylamine derivative 10X > potent than pheniramine + > - longer acting than chlorpheniramine t 1/2 = 25h
Dexbromopheniramine H1 antihistamine propylamine derivative
E-pyrrobutamine (pyronil) H1 antihistamine propylamine unsaturated pheniramine potent (E (165X) > Z) t1/2 = 12h --> long acting
triprolidine H1 antihistamine propylamine unsaturated pheniramine potent (E (100X) > Z) t1/2 = 12h --> long acting
demethindine H1 antihistamine propylamine unsaturated pheniramine potent (- > +)
phenindamine H1 antihistamine propylamine unsaturated pheniramine moderately potent cause CNS stimulation, insomnia
Promethazine H1 antihistamine tricyclic phenothiazine moderately potent antiemetic, antianxiety pronounced sedation potentiate analgesics long DOA drowsiness
pyrathiazine H1 antihistamine tricyclic phenothiazine moderately potent antiemetic, antianxiety pronounced sedation potentiate analgesics long DOA drowsiness
trimeprazine H1 antihistamine tricyclic phenothiazine less antihistaminic, more neuroleptic activity (spacer 3 C) moderately potent antiemetic, antianxiety pronounced sedation potentiate analgesics long DOA drowsiness
methdiazine H1 antihistamine tricyclic phenothiazine less antihistaminic, more neuroleptic activity (spacer 3 C) moderately potent antiemetic, antianxiety pronounced sedation potentiate analgesics long DOA drowsiness
pimethixene H1 antihistamine tricyclic thioxanthene derivative orally active
methixene H1 antihistamine tricyclic moderately potent anticholinergic usefull in parkinson
cyproheptadine H1 antihistamine tricyclic anticholinergic antiserotonergic appetite stimulating effect for anorexia nervosa
azatadine H1 antihistamine tricyclic aza isostere potent long acting anticholinergic
ketotifen H1 antihistamine tricyclic potent mast cell stabilizer topically (for seasonal allergic conjunctivitis) nasal spray (for allergic rhinitis)
terfenadine H1 antihistamine 2nd generation less or no: anticholinergic, sedation low affinity to adrenergic and serotonergic effects QT prolongation, torsade de pointes give fexofenadine
fexofenadine H1 antihistamine 2nd generation less or no: anticholinergic, sedation low affinity to adrenergic and serotonergic effects active safer
ebastine H1 antihistamine 2nd generation potent long acting less or no: anticholinergic, sedation low affinity to adrenergic and serotonergic effects from terfenadine
cetirizine H1 antihistamine 2nd generation metabolite of hydroxyzine levo (30X): levocetirizine > dextro less or no: anticholinergic, sedation low affinity to adrenergic and serotonergic effects
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
acrivastine H1 antihistamine 2nd generation metabolite of tripolidine lacks CNS effects less or no: anticholinergic, sedation low affinity to adrenergic and serotonergic effects
mizolastine H1 antihistamine 2nd generation long acting less or no: anticholinergic, sedation low affinity to adrenergic and serotonergic effects metabolized into inactive
astemizole H1 antihistamine 2nd generation less or no: anticholinergic, sedation low affinity to adrenergic and serotonergic effects
carebastine H1 antihistamine 2nd generation less or no: anticholinergic, sedation low affinity to adrenergic and serotonergic effects
desloratadine H1 antihistamine 2nd generation less or no: anticholinergic, sedation low affinity to adrenergic and serotonergic effects
burimamide H2 antihistamine 1st generation antiulcer thiurea derivative poor oral bioavailability low potency for GERD treatment
metiamide H2 antihistamine 1st generation antiulcer thiourea derivative orally active potent agranulocytosis for GERD treatment
cimetidine H2 antihistamine 1st generation antiulcer cyanoguanidine derivative orally active potent antiandrogenic effect, CYP inhibition metabolized to S-oxide (inactive) for GERD treatment
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
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
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
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
Esomeprazol antiulcer proton pump inhibitor(H+/K+ ATPase) 2-pyridylmethylsulfinylbenzimidazole derivative irreversible inhibitors S (-) omeprazole metabolized by CYP3A4
tenatoprazole antiulcer proton pump inhibitor(H+/K+ ATPase) irreversible inhibitors imidazopyridine derivative
lansoprazole antiulcer proton pump inhibitor(H+/K+ ATPase) 2-pyridylmethylsulfinylbenzimidazole derivative irreversible inhibitors
Rabeprazole antiulcer proton pump inhibitor(H+/K+ ATPase) 2-pyridylmethylsulfinylbenzimidazole derivative irreversible inhibitors thio ether
pantoprazole antiulcer proton pump inhibitor(H+/K+ ATPase) 2-pyridylmethylsulfinylbenzimidazole derivative irreversible inhibitors
misoprostol antiulcer semisynthetic prostaglandin E1 derivative ester prodrug abotifacient agent (causes abortion) de-esterification --> active metabolite (not by 16-hydroxydehydrogenase) abuse potential
prostaglandin E1 antiulcer maintain mucosal integrity, protect gastric wall
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
carbenoxolone antiulcer steroid like from licorice mineralocorticoid activity (SE) inhibit PG inactivation
pirenzepine antiulcer anticholinergic selective M1 receptor antagonist decrease GI acid secretion, intestinal mobility
telenzepine antiulcer anticholinergic selective M1 receptor antagonist decrease GI acid secretion, intestinal mobility
steroid backbone
steroid template
phenantrene
cholestane template
5-beta-cholestane cis isomer
5-beta-cholestane cis isomer
5-alpha-cholestane trans isomer
5-alpha-cholestane trans isomer precursor of cholesterol
5-alpha-pregnane steroid precursor of progesterone and hydrocortisone (cortisol)
5-alpha-androstane steroid precursor of testosterone and dehydroepiandrosterone
5-alpha-estrane steroid precursor of estradiol
cholesterol steroid adrenocorticoid cholest-5-en-3-beta-ol formed from acetyl CoA and acetoacetyl CoA forms pregnenolone, bile acids (glycocholic acid, taurocholic acid)
progesterone steroid adrenocorticoid pregn-4-ene-3,20-dione
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
testosterone steroid 17-beta-hydroxyandrost-4-ene-3-one
dehydroepiandrosterone DHEA steroid
17-beta-estradiol steroid 1,3,5(10)-estratien-3,17-beta-diol
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
estrone steroid 1,3,5(10)-estratrien-3-ol-17-one
pregnenolone steroid adrenocorticoid metabolite of oxidation of cholesterol active
aldosterone steroid adrenocorticoid from cholesterol active
11-epicortisol steroid first analogue
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
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
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
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
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
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
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
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
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
prednisolone steroid delta 1-hydrocortisone longer acting more glucocorticoid act (3-4) than mineralocorticoid act. (1) 4-5X more potent less salt retention
6-beta-hydroxyprednisolone steroid metabolite of prednisolone active
16-alpha-hydroxyprednisolone steroid metabolite of prednisolone active
20-hydroxyprednisolone steroid metabolite of prednisolone inactive
Prednisolone acetate steroid delta corticosteroid
prednisolone t-butylacetate steroid delta corticosteroid
prednisolone sodium phosphate steroid delta corticosteroid
methylprednisolone steroid methyl corticoid 6-alpha-methyl analogue of prednisolone potent glucocorticoid negligible mineralocorticoid
methylprednisolone 21-acetate steroid methyl corticoid
methylprednisolone sodium succinate steroid methyl corticoid
triamcinolone steroid 9-alpha fluro-16-alpha OH prednisolone more potent less water retention SE: anorexia, weight loss, nausea, dizziness, muscle weakness
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
Dexamethasone 21-acetate steroid
dexamethasone sodium phosphate steroid
betamethasone steroid 9-alpha fluro-16-beta CH3 no advantage same potency, same SE as dexamethasone
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
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
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
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
desonide steroid topical glucocorticoid high lipid solubility (acetonides) potent local/topical antiinflammatory effect (for short duration) metabolized in liver excreted in bile or urine
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
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
alcometasone steroid topical glucocorticoid low potent (for chronic use) metabolized in liver excreted in bile or urine
flumethasone steroid topical glucocorticoid high activity potent local/topical antiinflammatory effect (for short duration) metabolized in liver excreted in bile or urine
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
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
beclomethasone steroid topical glucocorticoid high lipid solubility potent local/topical antiinflammatory effect (for short duration) metabolized in liver excreted in bile or urine
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
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
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
prednicarbate steroid topical glucocorticoid low potency (for chronic use) metabolized in liver excreted in bile or urine
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
triamcinolone acetonide steriod inhaled/intranasal corticosteroid high activity high potency
flunisolide steriod inhaled/intranasal corticosteroid high activity high potency
fluticasone propionate steriod inhaled/intranasal corticosteroid high activity high potency
budesonide steriod inhaled/intranasal corticosteroid high potency
mometasone furoate steriod inhaled/intranasal corticosteroid
androstenedione steroid precursor of testosterone and estradiol
estrone steroid precursor of estradiol
testosterone steroid precursor of estradiol
estradiol steroid estra-1,3,5(10)-triene-3,17beta-diol most potent
estriol steroid metabolite of estradiol least active least potent
estradiol steroid estrogen derivative
estriol steroid estrogen derivative
estrone steroid estrogen derivative
estradiol 3-benzoate steroid estrogen derivative prodrug IM
estradiol 17-valerate steroid estrogen derivative prodrug IM
estradiol 17-cypionate steroid estrogen derivative prodrug IM
ethinyl estradiol steroid estrogen derivative orally active similar potency to estradiol (injection) more potent (15-20X) than estradiol (orally)
mestranol ethinyl estradiol 3-methylether steroid estrogen derivative prodrug oral contraceptive metabolized to ethinyl estradiol
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
sodium estrone sulfate steroid conjugated estrogen hydrolyzed to estrone
equilin sodium sulfate steroid conjugated estrogen low activity (unsaturation in ring B)
sodium equilenin sulfate steroid conjugated estrogen low activity (unsaturated ring B)
piperazine estrone sulfate steroid conjugates estrogen salt
diethylstilbestrol non steroidal estrogen orally active slowly metabolized long term use in pregnancy: increase risk of breast cancer diphosphate form used for: prostate cancer
dienestrol nonsteroidal estrogen
benzestrol non steroidal estrogen no double bonds
hexestrol non steroidal estrogen no double bonds trans better
coumestrol phytoestrogen natural plant substance from legumes
genistein phytoestrogen natural plant substance from soybean and clover example of flavonoids
daidzein phytoestrogen natural plant substance from soybean example of flavonoids
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
N-demethyltamoxifen metabolite of tamoxifen by 3A4 active
4-hydroxytamoxifen metabolite of tamoxifen by 2D6 more active than tamoxifen
toremifene antiestrogen triphenylethylene chlorotamoxifen metabolized by CYP3A4, deamination-hydroxylation in liver (caution if liver disease) SE: hot flashes, nausea, platelet reduction, endometrial cancer
N-demethyltoremifene metabolite of toremifene by CYP3A4 active
ospemifene metabolite of toremifene by deamination-hydroxylation active
enclomiphene antiestrogen E isomer stimulate ovulation in women desiring pregnancy
zuclomiphene antiestrogen Z isomer stimulate ovulation in women desiring pregnancy
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
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
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
formestane aromatase (estrogen biosynthesis) inhibitor irreversible inhibitor steroidal derivative (type 1 inhibitors) 4-hydroxyandrostenedione for breast cancer given parenterally (no oral activity)
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
letrozole aromatase (estrogen biosynthesis) inhibitor triazole (type 2 inhibitors) selective decrease estrogen: 75-90% in 2-3 days metabolized to inactive
progesterone steroid female sex hormone t1/2= 5-10min renally excreted: glucuronide (miscarriage index), sulfate conjugate (5-beta-pregnanediol)
20-alpha/beta-hydroxyprogesterone steroid metabolite of progesterone by reduction of 20 ketone
5-beta-pregnanediol steroid metabolite of progesterone by reduction of 4,5 double bond
6-alpha-hydroxyprogesterone steroid metabolite of progesterone by hydroxylation at C6
ethisterone steroid testosterone derivative 17-alpha alkyl derivative orally active
dimethisterone steroid testosterone derivative 17-alpha alkyl derivative orally active
19-norprogesterone steroid testosterone derivative
norethindrone steroid 19-nortestosterone derivative potent (10x > norethynodrel) orally active
norethindrone acetate steroid 19-nortestosterone derivative orally administered/ transdermally metabolized by deacetylation (rapidly,completely) in GI and liver--> norethindrone
norethynodrel steroid 19-nortestosterone derivative potent orally active
ethynodiol diacetate steroid 19-nortestosterone derivative prodrug
norgestrel steroid 19-nortestosterone derivative orally active (oral contraceptives)
levonorgestrel steroid 19-nortestosterone derivative active isomer orally active (OC) weak androgenic activity no glucocorticoid, mineralocorticoid act.
norgestimate steroid levonorgestrel derivative prodrug metabolized to 2 active metabolites (norelgestromine (in intestine, liver), levonorgestrel (in liver)) in mono, triphasic OC few androgenic SE
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
etonogestrel steroid levonorgestrel derivative active metabolite of desogestrel
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
17-alpha-acetoxyprogesterone steroid progesterone derivative limited activity orally undergoes 6-alpha hydroxylation
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)
megestrol acetate steroid progesterone derivative from medroxyprogesterone acetate progestin activity for treatment of breast, endometrial cancer/ hormone dependent carcinoma
dienogest steroid 19-nortestosterone estrane skeleton, C17 cyanomethyl group, C9,10 double bond in OC preparation
drospirenone steroid 19-norprogesterone from spironolactone antimineralocorticoid activity (5x affinity to receptor > aldosterone) antiandrogenic action progestin activity (10% of levonorgestrel)
elcometrine steroid 19-norprogesterone derivative potent SQ (100x more potent than orally), intravaginally, transdermally antiestrogenic action no androgenic/antiandrogenic activity
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
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
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
onapristone steroid progesterone antagonist less antiglucocorticoid act for hormone dependent breast cancer
telapristone acetate steroid progesterone antagonist for hormone dependent breast cancer
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
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..)
5-alpha-dihydrotestosterone steroid metabolite of testosterone most potent endogenous androgen
17-alpha-methyltestosterone steroid testosterone derivative DOA: 24h
oxymesterone steroid testosterone derivative
methandrostenolone steroid testosterone derivative
fluoxymesterone steroid testosterone derivative DOA: 24h
testosterone 17-beta-propionate steroid testosterone derivative DOA: 1-2w
testosterone 17-beta-enanthate steroid testosterone derivative depot ester DOA: 2-4 w
testosterone 17-beta-undecanoate steroid testosterone derivative DOA: 10h
testosterone 17-beta-cyclopentylpropionate (cypionate) steroid testosterone derivative depot ester DOA: 2-4 w
oxandrolone steroid 17-alkylated derivative 2-oxasteroid analogue with lactone moiety 3x anabolic act (>17-methyltestosterone) slight androgenic act
stanozolol steroid 17-alkylated derivative pyrazole derivative anabolic act
testolactone steroid 17-alkylated derivative 18-oxasteroid anabolic act little androgenic act irreversible aromatase inhibitor
norethandrolone steroid 19-norandrogens better anabolic act
nandrolone decanoate steroid 19-norandrogen IM slow hydrolysis
nandrolone phenylpropionate steroid 19-norandrogen IM slow hydrolysis
methenolone acetate steroid potent anabolic act no alkyl on C17 orally/injection
oxymetholone steroid 17-alkylated derivative anabolic act
chlortestosterone acetate steroid anabolic act
ethylestrenol steroid 17-alkylated derivative anabolic act
desoxymethyltestosterone steroid illegal anabolic agent difficult to trace
tetrahydrogestrinone steroid illegal anabolic agent difficult to trace to build up cattle
gestrinone steroid illegal anabolic agent difficult to trace
trenbolone steroid illegal anabolic agent difficult to trace
3-trifluoromethyl-4-nitroaniline antiandrogens precursor
flutamide antiandrogens nonsteroidal synthetic Competitive inhibitors (to testosterone and DHT) of androgen receptor given 3x/day
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
nilutamide antiandrogens nonsteroidal synthetic Competitive inhibitors (to testosterone and DHT) of androgen receptor SE: vasomotor flushing, gynecomastia, decreases libido, decreased potency, hepatotoxicity
hydroxyflutamide metabolite of flutamide more potent antiandrogen
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
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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