Med Chem Iii Test 2

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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=?

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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)