Tigestol

Short description: Chemical compound

Tigestol

Identifiers

IUPAC name

* (8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

CAS Number|

* 896-71-9

PubChem CID|

* 13471

ChemSpider|

* 12892

UNII|

* 1WAE0P123G

KEGG|

* D06145

ChEMBL|

* ChEMBL2105440

Chemical and physical data
Formula| C20H28O
Molar mass| 284.443 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* CC12CCC3C(C1CCC2(C#C)O)CCC4=C3CCCC4

InChI

* InChI=InChI=1S/C20H28O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h1,16-18,21H,4-13H2,2H3/t16-,17-,18+,19+,20+/m1/s1

* Key:DHOKBGHAEUVRMO-SLHNCBLASA-N

Tigestol (INN, USAN), also known as 17α-ethynylestr-5(10)-en-17β-ol,[1] is a steroidal progestin of the 19-nortestosterone group that was developed by Organon in the 1960s but was never marketed.[2][3][4][5] It is an isomer of the related 19-nortestosterone derivative progestins lynestrenol and cingestol.[6]

## References

1. ↑ Chemikalien und Drogen Teil C: T–Z. Springer-Verlag. 12 March 2013. pp. 179–. ISBN 978-3-642-67085-5. https://books.google.com/books?id=t4qfBgAAQBAJ&pg=PA179.
2. ↑ Dictionary of Steroids. CRC Press. 23 May 1991. pp. 424–. ISBN 978-0-412-27060-4. https://books.google.com/books?id=AI7EnUyeEtUC&pg=PA424.
3. ↑ United States Adopted Names (USAN).. United States Pharmacopeial Convention.. 1969. p. 65,85. https://books.google.com/books?id=1-dsAAAAMAAJ.
4. ↑ The Organic Chemistry of Drug Synthesis. John Wiley & Sons. 13 May 1980. pp. 145–. ISBN 978-0-471-04392-8. https://books.google.com/books?id=r-eqWrMoO18C&pg=PA145.
5. ↑ Strategies for Organic Drug Synthesis and Design. Wiley. 1998. p. 95. ISBN 978-0-471-19657-0. https://books.google.com/books?id=e7zwAAAAMAAJ.
6. ↑ "New 19-Nor-Steroid Compounds and process for the preparation thereof" GB patent 841411, published 1960-07-13

* v
* t
* e

Progesterone receptor modulators

PR|

| Agonists|

* Progesterone derivatives: 3β-Dihydroprogesterone
* 5α-Dihydroprogesterone
* 9α-Bromo-11-ketoprogesterone
* 11-Dehydroprogesterone
* 11-Deoxycorticosterone
* 16α-Hydroxyprogesterone
* 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
* 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

* 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
* 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
(SPRMs)|

* 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

mPR
(PAQR)|

| 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

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Original source: https://en.wikipedia.org/wiki/Tigestol. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Tigestol&oldid=872980"
*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[PR]: Progesterone receptor
*[SPRMs]: Selective progesterone receptor modulators
*[mPR]: Membrane progesterone receptor
*[PAQR]: Progestin and adipoQ receptor