Algestone

Chemical compound

None

Legal statusLegal status

In general: ℞ (Prescription only)

Identifiers

IUPAC name

(8R,9S,10R,13S,14S,16R,17S)-17-acetyl-16,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one

CAS Number

595-77-7

PubChem CID

11687

ChemSpider

11196

UNII

3JEB53B3WT

ChEBI

CHEBI:763^Y

CompTox Dashboard (EPA)

DTXSID40208200

ECHA InfoCard100.008.974

Chemical and physical dataFormulaC₂₁H₃₀O₄Molar mass346.467 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@](O)(C(=O)C)[C@H](O)C[C@H]3[C@@H]1CC2)C)(C)CC4

InChI

InChI=1S/C21H30O4/c1-12(22)21(25)18(24)11-17-15-5-4-13-10-14(23)6-8-19(13,2)16(15)7-9-20(17,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15-,16+,17+,18-,19+,20+,21-/m1/s1
Key:CXDWHYOBSJTRJU-SRWWVFQWSA-N

Algestone (INNTooltip International Nonproprietary Name), also known as alphasone or alfasone, as well as dihydroxyprogesterone, is a progestin which was never marketed.^[1] Another progestin, algestone acetophenide, in contrast, has been marketed as a hormonal contraceptive.^[1]

Chemistry

Algestone, also known as 16α,17α-dihydroxyprogesterone or as 16α,17α-dihydroxypregn-4-ene-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone.^[1] Closely related analogues of algestone include 16α-hydroxyprogesterone, algestone acetonide, and algestone acetophenide.^[2]

References

^ ^a ^b ^c Roberts AD (1991). Dictionary of Steroids: Chemical Data, Structures, and Bibliographies. CRC Press. p. 336. ISBN 978-0-412-27060-4. Retrieved 25 May 2012.
^ "16α-hydroxyprogesterone". ChemicalBook. 438-07-3 (16ALPHA-Hydroxyprogesterone) Related Search

Progesterone receptor modulators

PRTooltip Progesterone receptor

Agonists	Progesterone derivatives: 3β-Dihydroprogesterone 5α-Dihydroprogesterone 6α-Methylprogesterone 9α-Bromo-11-ketoprogesterone 11-Dehydroprogesterone 11-Deoxycorticosterone 16α-Hydroxyprogesterone 17α-Methyl-11-deoxycorticosterone acetate 20α-Dihydroprogesterone 20β-Dihydroprogesterone Dimepregnen Diosgenin P1-185 Progesterone Progesterone 3-acetyl enol ether Quingestrone Retroprogesterone derivatives: 20α-Dihydrodydrogesterone 20α-Dihydrotrengestone DU-41164 DU-41165 Dydrogesterone Retroprogesterone Ro 6-3129 Trengestone 17α-Substituted progesterone derivatives: 6α-Methyl-17α-bromoprogesterone 15β-Hydroxycyproterone acetate 16-Methylene-17α-hydroxyprogesterone acetate 17α-Bromoprogesterone 17α-Hydroxyprogesterone (hydroxyprogesterone) 17α-Methylprogesterone Acetomepregenol (mepregenol diacetate) Algestone Algestone acetonide Algestone acetophenide Anagestone Anagestone acetate Bromethenmadinone Bromethenmadinone acetate Butagest (buterol) Chlormadinone Chlormadinone acetate Chlormadinone caproate Chlormethenmadinone Chlormethenmadinone acetate Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clomegestone acetate Cymegesolate Cyproterone acetate Delmadinone Delmadinone acetate Edogestrone Flugestone Flugestone acetate Fluorometholone Fluorometholone acetate Flumedroxone Flumedroxone acetate Fluoromedroxyprogesterone acetate Gestaclone Gestobutanoyl Haloprogesterone Hydromadinone Hydromadinone acetate Hydroxyprogesterone acetate Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate) Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate) Hydroxyprogesterone heptanoate benzilic acid hydrazone Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Medroxyprogesterone caproate Megestrol Megestrol acetate Megestrol caproate Melengestrol Melengestrol acetate Methenmadinone Methenmadinone acetate Methenmadinone caproate Mometasone Mometasone furoate Osaterone Osaterone acetate Pentagestrone Pentagestrone acetate Pentarane A Proligestone Triamcinolone acetonide 19-Norprogesterone derivatives: 17α-Methyl-19-norprogesterone 18-Methylsegesterone acetate 19-Norprogesterone Amadinone Amadinone acetate Demegestone Fluoro ethyl norprogesterone Fluoro furanyl norprogesterone Gestadienol Gestadienol acetate Gestonorone acetate (gestronol acetate) Gestonorone caproate (gestronol hexanoate) Gestronol (gestonorone) Nomegestrol Nomegestrol acetate Norgestomet ORG-2058 Oxogestone Oxogestone phenpropionate (xinogestone) Promegestone Segesterone Segesterone acetate (nestorone) Trimegestone Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone 6,6-Difluoronorethisterone acetate 17α-Allyl-19-nortestosterone Allylestrenol Altrenogest Chloroethynylnorgestrel Cingestol Danazol Desogestrel Dienogest Ethinylandrostenediol Ethandrostate Ethisterone Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel esters (e.g., levonorgestrel butanoate) Lynestrenol Lynestrenol phenylpropionate Metynodiol Metynodiol diacetate Norelgestromin Norethisterone (norethindrone) Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate) Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tibolone Tigestol Tosagestin; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione 19-Nordehydroepiandrosterone Bolandiol Bolandiol dipropionate Bolandione Dimethisterone Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethyldienolone Dimethyltrienolone Ethyldienolone Ethylestrenol (ethylnandrol) Methyldienolone Metribolone (R-1881) Methoxydienone (methoxygonadiene) Mibolerone Nandrolone Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate) Norethandrolone Normethandrone (methylestrenolone, normethandrolone, normethisterone) RU-2309 Tetrahydrogestrinone Trenbolone (trienolone) Trenbolone esters (e.g., trenbolone acetate, trenbolone enanthate) Trendione Trestolone Trestolone acetate Spirolactone derivatives: Canrenoic acid Canrenone Drospirenone Mespirenone Potassium canrenoate Prorenone SC-5233 (spirolactone) SC-8109 Spironolactone Spirorenone Nonsteroidal: 3,8-Dihydrodiligustilide LG-2527 LG-100128 Riligustilide RWJ-26819 RWJ-49853 RWJ-60130 Tanaproget ZM-182345 Unknown: ORG-47241 ORG-201745
Mixed (SPRMsTooltip Selective progesterone receptor modulators)	Steroidal: Dihydroethisterone 5α-Dihydrolevonorgestrel 5α-Dihydronorethisterone Asoprisnil Asoprisnil ecamate Guggulsterone J1042 LG-120838 Metapristone (RU-42633) Mifepristone (RU-486) ORF-9371 ORF-9326 ORG-31710 ORG-33628 RMI-12936 Telapristone Ulipristal acetate Vilaprisan ZK-137316 Nonsteroidal: Apigenin Kaempferol LG-120920 Naringenin PRA-910 Syringic acid
Antagonists	Steroidal: Aglepristone Lilopristone Lonaprisan Onapristone ORG-31710 ORG-31806 ORG-33628 RTI 3021–022 Toripristone Zanoterone Nonsteroidal: Darolutamide LG-001447 LG-100127 LG-100128 LG-120830 LG-121046 Valproic acid ZM-150271 ZM-172406

mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)

Agonists	5α-Dihydroprogesterone 5β-Dihydroprogesterone 11-Deoxycortisone (21-hydroxyprogesterone) 11-Deoxycortisol (17α,21-dihydroxyprogesterone) 17α-Hydroxyprogesterone Allopregnanolone Mifepristone Pregnenolone Progesterone
Antagonists	Mifepristone

See also: Receptor/signaling modulators; Progestogens and antiprogestogens; Androgen receptor modulators; Estrogen receptor modulators; List of progestogens