Epostane

Epostane
Names

Other names Win-32729
Identifiers
InChI InChI=1S/C22H31NO3/c1-18-8-6-16-14(15(18)7-9-20(18,3)25)5-10-22-19(16,2)11-13(12-23)17(24)21(22,4)26-22/h14-16,24-25H,5-11H2,1-4H3/t14-,15-,16-,18-,19+,20-,21+,22-/m0/s1 Key: CETKWEWBSMKADK-GSXVSZIWSA-N
Jmol-3D images	Image
PubChem	6917713
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@]45[C@@]3(CC(=C([C@]4(O5)C)O)C#N)C
Properties
Molecular formula	C₂₂H₃₁NO₃
Molar mass	357.49 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Epostane is a progestogen biosynthesis inhibitor.^[1]

Synthesis

Epostane synthesis: Sterling Drug, R. G. Christiansen, DE 2855091 (1979).

References

↑ Frye, CA; Vongher, JM (2001). "Progesterone and 3alpha,5alpha-THP enhance sexual receptivity in mice". Behavioral neuroscience 115 (5): 1118–28. doi:10.1037/0735-7044.115.5.1118. PMID 11584925.

Steroidergics

Androgenics

Receptor

AR (A, B)

Agonists: 1-Androstenediol
1-Testosterone
1,4-Androstenedione
4-Androstenediol
4-Androstenedione
4-Chlordehydromethyltestosterone
4-Hydroxytestosterone
5-Androstenediol
5-Androstenedione
5α-Androst-1-ene-3,17-dione
11-Ketotestosterone
17-((1-Oxoheptyl)oxy)androstan-3-one
17-((1-Oxopentyl)oxy)androstan-3-one
17-(1-Oxopropoxy)androstan-3-one
17β-Hydroxyandrost-2-ene-2-carbonitrile
19-Norandrostenediol
19-Norandrostenedione
19-Norandrosterone
19-Nordehydrotestosterone
Adrenosterone
Androisoxazole
Androstanolone
Bolandiol
Bolasterone
Bolazine
Boldenone
Boldione
Bolenol
Bolmantalate
Calusterone
Cl-4AS-1
Clostebol
Cloxotestosterone
Danazol
Desogestrel
Desoxymethyltestosterone
DHT
Drostanolone
Enestebol
Epitiostanol
Ethisterone
Ethyldienolone
Ethylestrenol
Fluoxymesterone
Formebolone
Furazabol
Hexabolan
Hydroxystenozole
Levonorgestrel
Mebolazine
Medroxyprogesterone acetate
Mepitiostane
Mesabolone
Mestanolone
Mesterolone
Metandienone/Methandrostenolone
Metenolone
Metenolone acetate
Metenolone enanthate
Methandriol
Methandriol propionate
Methasterone
Methylestrenolone
Methyltestosterone
Metribolone
Mibolerone
Nandrolone
Nandrolone caproate
Nandrolone cypionate
Nandrolone cyclohexane carboxylate
Nandrolone cyclohexylpropionate
Nandrolone cyclotate
Nandrolone decanoate
Nandrolone furylpropionate
Nandrolone hexyloxyphenylpropionate
Nandrolone hydrogen succinate
Nandrolone laurate
Nandrolone phenylpropionate
Nandrolone propionate
Nandrolone undecyclate
Norboletone
Norclostebol
Norethandrolone
Norethisterone
Norgestrel
Oxabolone
Oxabolone cypionate
Oxandrolone
Oxendolone
Oxymesterone
Oxymetholone
Penmesterol
Propetandrol
Quinbolone
Quingestanol acetate
Roxibolone
Silandrone
Stanozolol
Stenbolone
Stenbolone acetate
Testolactone
Testosterone
Testosterone enanthate
Testosterone isocaproate
Testosterone ketolaurate
Testosterone nicotinate
Testosterone propionate
Testosterone undecanoate
THG
Thiomesterone
Tibolone
Tiomesterone
Trenboloneca
Trenbolone acetate
Trestolone

Enzyme

See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase).

Others

Indirect: Antigonadotropins (e.g., estrogens, progestogens, prolactin)
GnRH agonists (e,g, GnRH, leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Gonadotropins (e.g., FSH, hCG, LH)
Kisspeptin
Plasma proteins (ABP, albumin, SHBG)

See also: Estrogenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics

Estrogenics

Receptor

ER (α, β)	Agonists: 5α-Androstane-3β,17β-diol 16α-Hydroxyestrone 17α-Estradiol (alfatradiol) 17β-Estradiol (estradiol) Alestramustine Almestrone Benzestrol Bifluranol Broparestrol Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Chlorotrianisene Cloxestradiol Coumestans (e.g., coumestrol, psoralidin) DHEA Deoxymiroestrol Dienestrol Diethylstilbestrol Diethylstilbestrol diphosphate Diosgenin Doisynoestrol DPN DY-131 (GSK-9089) Epiestriol Epimestrol ERB-041 Etamestrol (eptamestrol) ERB-041 Equilenin Equilin Estetrol Estradiol benzoate Estradiol butyrylacetate Estradiol cypionate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol hemihydrate Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol palmitate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol stearate Estradiol succinate Estradiol undecylate Estradiol valerate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol succinate Estriol tripropionate Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone sulfate Estrone tetraacetylglucoside Estropipate Etamestrol Ethinylestradiol Ethinylestradiol 3-isopropylsulfonate Etynodiol diacetate FERb 033 Fenestrel Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Fosfestrol Furostilbestrol GSK-4716 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate Hydroxyestrone diacetate Lignans (e.g., enterodiol, enterolactone) Mestranol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Miroestrol Moxestrol Nilestriol Orestrate Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate PPT Promestriene Promethoestrol Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranal (zearalanol)) Quinestradol Quinestrol Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenol A (BPA), DDT, parabens, PBBs, phthalates, PCBs) (R,R)-THC WAY-200070 Mixed (SERMs): 2-Hydroxyestrone (Z)-4-Hydroxytamoxifen Acolbifene Afimoxifene Arzoxifene Bazedoxifene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Epimestrol Femarelle Fispemifene GW5638 Idoxifene Lasofoxifene Levormeloxifene Menerba Mepitiostane Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Pipendoxifene Prinaberel Raloxifene SS1010 Sivifene Tamoxifen TAS-108 Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene Antagonists: Fulvestrant ICI-164384 ICI-182780 MPP PHTPP RU-58668 SS1020 (R,R)-THC XCT-790 ZK-164015 ZK-191703

GPER	Agonists: Estradiol Fulvestrant G-1 Genistein ICI-182780 Quercetin Tamoxifen Tectoridin Antagonists: G-15

Enzyme

See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase).

Others

Precursors/prohormones: Cholesterol
22R-Hydroxycholesterol
20α,22R-Dihydroxycholesterol
Pregnenolone
Pregnenolone sulfate
17-Hydroxypregnenolone
Progesterone
17-Hydroxyprogesterone
11-Deoxycortisol (cortodoxone)
DHEA
DHEA sulfate
16-Hydroxy-DHEA sulfate
5-Androstenediol
4-Androstenedione
16-Hydroxyandrostenedione
Testosterone

Indirect: Antigonadotropins (e.g., estrogens, progestogens, prolactin)
Calcitriol (vitamin D)
GnRH agonists (e,g, GnRH, leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Gonadotropins (e.g., FSH, hCG, LH)
Kisspeptin
Plasma proteins (ABP, albumin, SHBG)

See also: Androgenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics

Glucocorticoidics

Receptor

Agonists: 11-Deoxycorticosterone
11-Deoxycortisol (cortodoxone)
Acrocinonide
Alclometasone
Amcinafal
Amcinafide
Amcinonide
Amebucort
Amelometasone
Amicinonide
Anecortave
Beclometasone
Beclometasone dipropionate
Betamethasone
Betamethasone acibutate
Betamethasone dipropionate
Budesonide
Butixocort
Chloroprednisone
Ciclesonide
Cicortonide
Ciprocinonide
Clobetasol
Clobetasol propionate
Clobetasone
Clocortolone
Cloprednol
Cloticasone
Cormetasone
Corticosterone
Cortisone
Cortisuzol
Cortivazol
Deflazacort
Deprodone
Descinolone
Desonide
Desoximetasone
Desoxycortone
Dexbudesonide
Dexamethasone
Dexamethasone acefurate
Dexamethasone cipecilate
Dexamethasone isonicotinate
Dichlorisone
Diflorasone
Difluocortolone
Difluocortolone valerate
Difluprednate
Domoprednate
Doxibetasol
Drocinonide
Etiprednol dicloacetate
Fluazacort
Fluclorolone
Fluclorolone (flucloronide)
Fludrocortisone
Fludroxycortide
Flumoxonide
Flumetasone
Flunisolide
Fluocinolone
Fluocinolone acetonide
Fluocinonide
Fluocortin
Fluocortolone
Fluorometholone
Fluperolone
Fluperolone acetate
Fluprednidene
Fluprednidene acetate
Fluprednisolone
Fluticasone
Fluticasone furoate
Fluticasone propionate
Formocortal
GSK-9027
Halcinonide
Halocortolone
Halometasone
Halopredone
Hydrocortamate
Hydrocortisone (cortisol)
Hydrocortisone aceponate
Hydrocortisone buteprate
Hydrocortisone-17-butyrate
Hydrocortisone-21-butyrate
Icometasone enbutate
Isoflupredone
Isoprednidene
Itrocinonide
Locicortolone dicibate
Loteprednol
Mazipredone
Meclorisone
Medrysone
Meprednisone
Methylprednisolone
Methylprednisolone aceponate
Methylprednisolone suleptanate
Mometasone
Mometasone furoate
Naflocort
Nicocortonide
Nivacortol
Oxisopred
Paramethasone
Prednazate
Prednazoline
Prednicarbate
Prednimustine
Prednisolamate
Prednisolone
Prednisolone steaglate
Prednisone
Prednylidene
Procinonide
Resocortol
Rimexolone
Rofleponide
Timobesone
Tipredane
Tixocortol
Tixocortol pivalate
Tralonide
Triamcinolone
Triamcinolone acetonide
Triamcinolone benetonide
Triamcinolone furetonide
Triamcinolone hexacetonide
Triclonide
Ulobetasol (halobetasol)

Mixed (SEGRAs): Mapracorat
PF-04171327

Antagonists: Aglepristone
Asoprisnil
C108297
C113176
CORT-108297
Cyproterone acetate
Ketoconazole
Lilopristone
LLY-2707
Mifepristone
Onapristone
Org 34850
PCN
Telapristone
Toripristone
Ulipristal acetate

Enzyme

See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 11β-HSD, 21-hydroxylase, 11β-hydroxylase, and 18-hydroxylase).

Others

See also: Androgenics • Estrogenics • Mineralocorticoidics • Progestogenics

Mineralocorticoidics

Receptor

Agonists: 11-Deoxycorticosterone (desoxycortone)
11-Deoxycortisol (cortodoxone)
16α,18-Dihydroxy-11-deoxycorticosterone
17-Hydroxyaldosterone
18-Hydroxy-11-deoxycorticosterone
19-Norprogesterone
Aldosterone
Corticosterone
Desoxycortone acetate
Desoxycortone enanthate
Desoxycortone glucoside
Desoxycortone pivalate
Hydrocortisone (cortisol)
Fludrocortisone
Fludrocortisone acetate

Antagonists: 6β-Hydroxy-7α-thiomethylspironolactone
7α-Thiomethylspironolactone
17-Hydroxyprogesterone
Benidipine
Canrenoate potassium (potassium canrenoate)
Canrenoic acid
Canrenone
Dicirenone
Drospirenone
Eplerenone
Mespirenone
Mexrenoate potassium
Mexrenoic acid
Mexrenone
Oxprenoic acid
Oxprenoate potassium (RU-28318)
Pregnenolone
Progesterone
Prorenoate potassium
Prorenoic acid (prorenoate)
Prorenone
RU-26752
Spirorenone
Spironolactone
Spiroxasone

Enzyme

See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 11β-HSD, 21-hydroxylase, 11β-hydroxylase, and 18-hydroxylase).

Others

Indirect: ACTH (corticotropin)
CRH
Plasma proteins (albumin, transcortin)
Vasopressin

See also: Androgenics • Estrogenics • Glucocorticoidics • Progestogenics

Progestogenics

Receptor

PR (A, B)

Agonists: 5α-Dihydroprogesterone
11-Dehydroprogesterone
11-Deoxycorticosterone
17-Hydroxyprogesterone
19-Norprogesterone
Algestone
Algestone acetonide
Algestone acetophenide
Allylestrenol
Altrenogest
Amadinone
Amadinone acetate
Anagestone
Anagestone acetate
Chlormadinone
Chlormadinone acetate
Cingestol
Cismadinone
Cismadinone acetate
Clogestone
Clogestone acetate
Clomegestone
Cyproterone acetate
Delmadinone
Delmadinone acetate
Demegestone
Desogestrel
Dienogest
Dimethisterone
Drospirenone
Dydrogesterone
Edogesterone
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Flugestone
Flugestone acetate
Gestaclone
Gestadienol
Gestodene
Gestonorone
Gestonorone caproate
Gestovister
Gestronol
Haloprogesterone
Hydromadinone
Hydroxyprogesterone acetate
Hydroxyprogesterone caproate
Hydroxyprogesterone heptanoate
Hydroxyprogesterone hexanoate
Levonorgestrel
Lutenyl
Lynestrenol
Medrogestone
Medroxyprogesterone
Medroxyprogesterone acetate
Megestrol
Megestrol acetate
Melengestrol
Melengestrol acetate
Methylestrenolone
Methynodiol
Methynodiol diacetate
Metogest
Mometasone furoate
Nandrolone
Nestorone
Nomegestrol
Nomegestrol acetate
Norelgestromin
Norethisterone/Norethindrone
Norethisterone acetate
Norethisterone acetate oxime
Norethisterone enanthate
Norethynodrel
Norgesterone
Norgestimate
Norgestomet
Norgestrel
Norgestrienone
Norvinisterone
Org-2058
Oxogestone
Oxogestone phenpropionate
Pentagestrone
Progesterone
Proligestone
Promegestone
Quingestanol
Quingestanol acetate
Quingestrone
Segesterone
Spironenone
Spironolactone
Tanaproget
Tibolone
Tigestol
Tosagestin
Trengestone
Trimegestone
ZM-182,345

Mixed (SPRMs): Asoprisnil
Asoprisnil ecamate
Gestrinone
J1042
LG-120,838
Telapristone; Antagonistic: Mifepristone
Org-31710
Org-33628
Ulipristal acetate
ZK-137,316
ZK-230,211

Antagonists: Aglepristone
BAY-1002670
Lilopristone
Lonaprisan
Onapristone
Toripristone
ZM-150,271
ZM-172,406

Enzyme

See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, and 21-hydroxylase).

Others

Indirect: Antigonadotropins (e.g., estrogens, progestogens, prolactin)
GnRH agonists (e,g, GnRH, leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Gonadotropins (e.g., FSH, hCG, LH)
Kisspeptin
Plasma proteins (ABP, albumin, SHBG)

See also: Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics