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110 Cards in this Set
- Front
- Back
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Phenanthrene |
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cylopentanoperhydrophenanthrene Gonane (C-17) or Sterane |
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5-alpha-cholestane -a cholestane: C27 -2 methyl groups at C13 and C10 -8-carbon side chain attached at C17 |
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5-alpha-androstane -an androstane: C19 -2 methyl groups at C13 and C10 -no side chain at C17 |
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5-alpha-pregnane -a pregnane: C21 -2 methyl groups at C13 and C10 -2 carbon side chain at C17 |
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5-alpha-gonane (19-nor steroid) -no methyls -no side chain |
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5-alpha-estrane -an estrane: C18 -single methyl at C13 -no side chain at C17 |
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cortisone -inactive -converted from active cortisol (hydrocortisone) by 11 beta-hydroxysteroid dehydrogenase |
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17-beta-estradiol -converted from testosterone by aromatase |
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cholesterol -C27 |
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R=? |
R= H Cortisol (Hydrocortisone) R= CH3CO- Hydrocortisone acetate R= C3H7CO- Hydrocortisone Butyrate R= C2H5CO-; 17-alpha-C3H7CO- buteprate |
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R= H Cortisone R= CH3CO- Cortisone Acetate Inactive |
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Prednisone inactive metabolite/pro-drug |
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R=H Prednisolone R= CH3CO- Prednisolone acetate R= (CH3)3CCH2CO- Prednisolone t-butylacetate -conversion of prednisone by 11-beta-hydroxysteroid dehydrogenase |
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R= H Fludrocortisone R= CH3CO- Fludrocortisone acetate mineralocorticoids |
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Triamcinolone -looks like fludrocortisone but has 2 double bonds in the A ring |
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R= H Methylprednisolone R= CH3CO- Methylprednisolone 21-acetate
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Betamethasone looks like Dexamethasone but different orientation of the 16-methyl |
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R=H Dexamethasone R=CH3CO- Dexamethasone 21-acetate
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Testosterone cyclopentylpropionate - increased lipid solubility compared to testosterone -important for delayed release of repo preparation and increased skin absorption |
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Triamcinolone Acetonide -increased topical activity compared to triamcinolone -more lipid soluble than triamcinolone -ideal inhaled/intra-nasal steroid |
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Methylprednisolone Sodium Succinate -sodium salt increases water solubility -can be used for IV injection |
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Testosterone -not orally active
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17-apha-methyltestosterone -orally active -17-methyl blocks oxidation from occurring
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androstenedione -oxidation of testosterone -reduced activity compared to testosterone |
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Flurandrenolide -class III -fluoride substitution at 6 position -no double bond between 1&2--> less potent |
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R=H Flucinonide R= CH3CO Flucinolone acetonide -halogenated= potent |
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Halcinonide -class II -fluorinated and chlorinated -no double bond at 1,2 position -makes it less potent than clobetasol |
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Desonide -class IV -not halogenated or fluorinated -not potent -standard glucocorticoid |
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Amcinonide |
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Clobetasol propionate -class I -very potent -has fluorine, chlorine, 2 double bonds |
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Alclometasone |
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Flumethasone |
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Desoximethasone |
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R=H beclomethasone R=C2H5CO beclomethasone dipropionate |
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Halobetasol propionate |
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Diflucortolone pivalate |
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Prednicarbate |
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diflorasone diacetate |
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Flunisolide -fluoride in 6 position (the unknown position)--> more activity -ideal inhaled/intranasal |
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Fluticasone Propionate -androstane (not pregnane b/c carbothiolate) -ideal inhaled/intra-nasal |
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Budesonide -ideal inhaled/intranasal |
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Mometasone Furoate -halogenated (Cl) in position 9 -ideal inhaled/intranasal |
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Ciclesonide (Alvesco for asthma, Omnaris for allergy) -prodrug -de-esterified to free C-21 OH -ring substituent makes metabolism hard -tends to be one of the longest acting steroids -lipid conjugated- stays in the lungs -ideal inhaled/intranasal |
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Fluorometholone -only available for topical/ophthalmic use
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Loteprednol (Lotemax/Alrex) -chlorine on chain -only available for topical/ophthalmic use |
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Difluprednate (Durezol) -halogenated, pretty potent -only available for topical/ophthalmic use |
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Cytadren -aminoglutethimide -adrenocortical antagonist -blocks conversion of cholesterol to pregnenolone blocks aromatase and estrogen production -used in Cushing's |
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Ketoconazole -adrenocortical antagonist -non-selective inhibitor of adrenal and gonadal steroid synthesis -inhibits cholesterol side chain cleavage -used in Cushing's |
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Mifepristone (RU-486) -adrenocortical antagonist -inhibits glucocorticoid receptor -used in adrenal carcinoma and Cushing's -anti-progestational agent (abortion pill) -triple bond helps oral activity -very lipophilic ring attached -korlym (300mg), mifeprex (200mg) |
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Mitotane (Lysodren) -adrenocortical antagonist -for adrenocortical cancers and Cushing's -binds to zona reticularis and fasciculata mitochondrial proteins and disrupts protein synthesis |
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Estradiol -most potent endogenous estrogen
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Estrone -natural steroid |
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Estriol -natural steroid |
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Ethinyl estradiol -synthetic steroid -in 99% of oral contraceptives -triple bond makes it more orally active |
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Mestranol -metabolized to ethinyl estradiol -synthetic steroid -like a prodrug |
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Equilenin -conjugated estrogen (ex. premarin) -synthetic steroid -extracted from the urine of pregnant horses
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Diethylstilbestrol (DES) -non-steroidal synthetic -very potent estrogen agonist -fits into estrogen receptor very well even though it doesn't have the steroid nucleus -used to be given to prevent premature birth -linked to cancers in female-offspring |
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Trans-stilbene -proof that you don't need estrogen ring scheme to have estrogen activity
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Bisphenol A (BPA) -proof that entire steroid nucleus is not needed for estrogenic activity
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Clomiphene -E and Z isomers have different activity -E (trans) is antagonist, Z (cis) is partial agonist -mixture of both is used as fertility enhancer -SERM |
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Tamoxifen -SERM -used to cure and prevent breast cancer in people with particular mutation of breast receptor |
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Raloxifene -SERM |
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Letrozole -triazole aromatase inhibitor -typically used for breast cancer, adjunct therapy -CN groups |
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Exemestane -steroidal aromatase inhibitor (irreversible) -has some use as anti-cancer agent |
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Anastrazole -triazole aromatase inhibitor -typically used for breast cancer, adjunct therapy |
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Ospemifene -estrogen agonist and antagonist -used for dyspareunia (painful intercourse) |
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Fulvestrant -estrogen receptor down regulator and ER degradation -pure estrogen-receptor antagonist |
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Ethisterone -1st generation progesterone -triple bond makes it orally active -ketone at 3 position fits progesterone receptor |
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R=H Norethindrone R= acetate Norethindrone acetate -first generation progesterone |
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ethynodiol diacetate -first generation progesterone |
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medroxyprogesterone acetate (6,7dihydro-6alpha-CH3) (MPA, Depo-Provera) megestrol acetate (6,7-dehydro) anti-cancer -1st generation progesterone -methyl on 6 position NOT orally active -more lipophilic since it's an injection |
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norgestrel (13-dextro/levo) levonorgestrel (13-levo)- Plan B, Mirena IUD -2nd generation progesterone
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Norgestimate Norelgestromin (C17 desacetyl) -3rd generation progesterone |
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Desogestrel (R1=R2=H) Etonogestrol (R1 and R2=O) (3-ketodesogestrel) vaginal rings, implants -3rd generation progesterone |
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Dienogest -4th generation progesterone |
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Drospirenone -4th generation progesterone -has spiro carbon like spironolactone -has some mineralocorticoid activity -inhibits testosterone production by ovaries and adrenal glands, as well as some peripheral testosterone activity -increased risk of blood clots |
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Nomegestrol acetate -4th generation progesterone
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Progesterone -orally inactive -no substituent on C-17 to prevent metabolism |
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17-alpha-hydroxyprogesterone caproate (Makena) -injection approved for reducing risk of pre-term delivery in women with a history of this issue -used alone, not in combination |
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Norelgesteromin -progestin of high pro gestational, slight estrogenic, and low androgenic activity -primary active metabolite produced after oral administration of norgestimate (acetate at C-17) -found in Evra path, applied weekly |
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Mifepristone (RU-486, Mifeprex) -inhibits glucocorticoid receptor activation -used in adrenal carcinoma and Cushing's, also antiprogestational agent -inhibits early stages of pregnancy |
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Ulipristal (EllaOne) -SPRM (selective progesterone receptor modulator) -partial agonist and antagonist at progesterone receptor -emergency contraception up to 5 days after unprotected intercourse |
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Danazol (Danocrine) -isoxazole derivative of ethisterone -used for control of endometriosis -may inhibit synthesis of sex hormones peripherally and inhibits pituitary-ovarian axis by decreasing output of gonadotropins -weakly androgenic |
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epiT -17-alpha-HSD -found in urine of all males -may act as anti-androgen but it's not made in huge amount |
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Dihydrotestosterone -active metabolite of testosterone -converted by 5-alpha-reductase |
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androsterone -inactive metabolite of testosterone -converted by 5-alpha-reductase |
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estradiol -active metabolite of testosterone -converted by aromatase
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etiocholanolone -inactive metabolite of testosterone -converted by aromatase |
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testosterone enanathate (delatestryl) -testosterone ester -parenteral
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testosterone cypionate (depo-testosterone) -testosterone ester -parenteral |
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testosterone undecanoate (andriol) -testosterone ester |
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methyltestosterone (oretin methyl) -17-alpha-alkylated androgen -oral |
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oxymesterone -17-alpha-alkylated androgen -oral |
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fluoxymesterone (halotestin) -17-alpha-alkylated androgen -oral |
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oxandrolone -anabolic steroid -on order of 100 times the androgenic activity as testosterone |
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Norethandrolone -anabolic steroid |
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Nandrolone -R=CH3(CH2)8CO deconate -anabolic steroid -parenteral |
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methandrostenolone -anabolic steroid
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oxymetholone -anabolic steroid |
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Flutamide: X=H 2-hydroxyflutamide: X-OH Eulexin -nonsteroidal antiandrogen (pharmacologic castration) |
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Nilutamide: X=H Hydroxynilutamide: X=OH Nilandron -nonsteroidal antiandrogen (pharmacologic castration) |
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Bicalutamide (Casodex) -nonsteroidal antiandrogen (pharmacologic castration) |
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Finasteride (Proscar, Propecia) -5-alpha-reductase inhibitor -treatment of BPH and alopecia |
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Dutasteride (Avodart) -5-alpha-reductase inhibitor |
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Abiraterone Acetate (Zytiga) -CYP17 (17-alpha-hydroxylase/C17,20-lyase) inhibitor -prodrug metabolized by CYP3A4 -treatment of prostate cancer |
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Tricyclin quinoline -nonsteroidal SARM pharmacophore -only effect one type of tissue (selective) |
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Tetrahydroquinoline -nonsteroidal SARM pharmacophore -only effect one type of tissue (selective) |
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Aryl propionamide -nonsteroidal SARM pharmacophore -only effect one type of tissue (selective) |
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Bicyclic hydrantoin -nonsteroidal SARM pharmacophore -only effect one type of tissue (selective) |