Tosagestin

Chemical compound

Tosagestin
Clinical data

Other names	ORG-30659; Exogestin; Letogestin;^[1] 11-Methylene-δ¹⁵-norethisterone; 17α-Ethynyl-11-methylene-19-nor-δ¹⁵-testosterone
Routes of administration	By mouth
Identifiers
IUPAC name (1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyl-17-methylidenetetracyclo[8.7.0.0^2,7.0^11,15]heptadeca-6,12-dien-5-one
CAS Number	110072-15-6
PubChem CID	159355
ChemSpider	140146
UNII	YS7Z529O22
KEGG	D06197
ChEMBL	ChEMBL2107658
CompTox Dashboard (EPA)	DTXSID50891344
Chemical and physical data
Formula	C₂₁H₂₄O₂
Molar mass	308.421 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC12CC(=C)C3C(C1C=CC2(C#C)O)CCC4=CC(=O)CCC34
InChI InChI=1S/C21H24O2/c1-4-21(23)10-9-18-17-7-5-14-11-15(22)6-8-16(14)19(17)13(2)12-20(18,21)3/h1,9-11,16-19,23H,2,5-8,12H2,3H3/t16-,17-,18-,19+,20-,21-/m0/s1 Key:YJSTYQGZKJHXLN-OLGWUGKESA-N

Tosagestin (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name) (developmental code name ORG-30659), also known as 11-methylene-δ¹⁵-norethisterone or 17α-ethynyl-11-methylene-19-nor-δ¹⁵-testosterone, is a progestin of the 19-nortestosterone group which was under development by Organon in the United States and Europe as a hormonal contraceptive (in combination with ethinylestradiol) and for the treatment of menopausal symptoms but was never marketed.^[2]^[3]^[4]^[5]^[6]

References

^ Negwer M, Scharnow HG (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 2104. ISBN 978-3-527-30247-5.
^ World Health Organization (2013), The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances (PDF), p. 95, archived from the original (PDF) on August 8, 2016
^ "Tosagestin", AdisInsight, Springer Nature Switzerland AG, retrieved 12 July 2016
^ Verhoeven CH, Krebbers SF, Wagenaars GN, Booy CJ, Groothuis GM, Olinga P, Vos RM (November 1998). "In vitro and in vivo metabolism of the progestagen Org 30659 in several species". Drug Metabolism and Disposition. 26 (11): 1102–1112. PMID 9806953.
^ de Visser SJ, Uchida N, van Vliet-Daskalopoulou E, Fukazawa I, van Doorn MB, van den Heuvel MW, et al. (September 2003). "Pharmacokinetic differences between Caucasian and Japanese subjects after single and multiple doses of a potential combined oral contraceptive (Org 30659 and EE)". Contraception. 68 (3): 195–202. doi:10.1016/S0010-7824(03)00140-9. PMID 14561540.
^ Obruca A, Korver T, Huber J, Killick SR, Landgren B, Struijs MJ (July 2001). "Ovarian function during and after treatment with the new progestagen Org 30659". Fertility and Sterility. 76 (1): 108–115. doi:10.1016/S0015-0282(01)01824-6. PMID 11438328.

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