Chlormethenmadinone acetate

Chemical compound

Chlormethenmadinone acetate
Clinical data

Trade names	Biogest, Sterolibrin, Antigest B, Agelin
Other names	SCH-12600; 6-Chloromethylenedehydroacetoxyprogesterone; 17α-Acetoxy-6-chloro-16-methylene-6-dehydroprogesterone; 16-Methylenechlormadinone acetate; 17α-Acetoxy-6-chloro-16-methylenepregna-4,6-diene-3,20-dione
Drug class	Progestogen; Progestin; Progestogen ester
Identifiers
IUPAC name [(8R,9S,10R,13S,14S,17R)-17-Acetyl-6-chloro-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number	6799-23-1
PubChem CID	175513
ChemSpider	152916
ChEMBL	ChEMBL3276150
CompTox Dashboard (EPA)	DTXSID00987408
Chemical and physical data
Formula	C₂₄H₂₉ClO₄
Molar mass	416.94 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=O)[C@]1(C(=C)C[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=C(C4=CC(=O)CC[C@]34C)Cl)C)OC(=O)C
InChI InChI=1S/C24H29ClO4/c1-13-10-19-17-12-21(25)20-11-16(28)6-8-22(20,4)18(17)7-9-23(19,5)24(13,14(2)26)29-15(3)27/h11-12,17-19H,1,6-10H2,2-5H3/t17-,18+,19+,22-,23+,24+/m1/s1 Key:MDTBKPVVPCIBIT-USYNNDFZSA-N

Chlormethenmadinone acetate (CMMA), also known as chlorsuperlutin, is a progestin medication which was developed in Czechoslovakia in the 1960s.^[1] It has been used in combination with mestranol in birth control pills under the brand names Biogest, Sterolibrin, and Antigest B,^[2]^[3] and in veterinary medicine under the brand name Agelin.^[4] Analogues of CMMA include bromethenmadinone acetate (bromsuperlutin), which was assessed but was never marketed,^[3]^[5] and melengestrol acetate (methylsuperlutin), which is used in veterinary medicine.^[6]

References

^ Sterba R (1968). "New biological application of contraceptive steroids". Endocrinologia Experimentalis. 2 (2): 101–110. Archived from the original on 16 September 2018.
^ Melich H (July 1972). "[Biogest]". Casopis Lekaru Ceskych (in Czech). 111 (30): 694–695. PMID 5079918. Archived from the original on 2018-09-16. Retrieved 2018-09-16.
^ ^a ^b Stĕrba R (March 1970). "[Towards a more physiological hormonal contraception]". Zentralblatt Fur Gynakologie (in German). 92 (10): 303–312. PMID 4096927. Archived from the original on 2018-09-16. Retrieved 2018-09-16.
^ Bekeová E, Krajnicáková M, Hendrichovský V, Maracek I (November 1995). "[Thyroid and ovarian hormones in ewes treated with gestagens and PMSG in the spring season]". Veterinarni Medicina (in Slovak). 40 (11): 345–352. PMID 8659087. Archived from the original on 2018-09-16. Retrieved 2018-09-16.
^ Štěrba, R. (1971). "On the Way to a More Physiological Hormonal Contraception". Current Problems in Fertility. pp. 154–158. doi:10.1007/978-1-4615-8651-7_28. ISBN 978-1-4615-8653-1. Archived from the original on 2018-09-16. Retrieved 2018-09-16.
^ von Kunz W (8 March 2013). "Über neue Arzneimittel". In Denkewalter RG, Tishler M, Ehrhart G, Biel JH, Lum BK, Büchi J, Winter CA, Münzel K, Kunz W, Ariëns EJ, Labhardt F (eds.). Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 407–. ISBN 978-3-0348-7059-7.

Progestogens and antiprogestogens

Progestogens
(and progestins)

PRTooltip Progesterone receptor agonists	Progesterone derivatives: Progesterone Quingestrone Retroprogesterone derivatives: Dydrogesterone Trengestone 17α-Hydroxyprogesterone (and closely related) derivatives: 17α-Hydroxylated: Acetomepregenol (mepregenol diacetate) Algestone acetophenide (dihydroxyprogesterone acetophenide) Anagestone acetate Chlormadinone acetate Chlormethenmadinone acetate Cyproterone acetate Delmadinone acetate Flugestone acetate (flurogestone acetate) Flumedroxone acetate Hydroxyprogesterone acetate Hydroxyprogesterone caproate Hydroxyprogesterone heptanoate Medroxyprogesterone acetate^# Megestrol acetate Melengestrol acetate Methenmadinone acetate Osaterone acetate Pentagestrone acetate Proligestone; 17α-Methylated: Medrogestone; Others: Haloprogesterone 19-Norprogesterone derivatives: 17α-Hydroxylated: Gestonorone caproate (gestronol hexanoate) Nomegestrol acetate Norgestomet Segesterone acetate (nestorone, elcometrine); 17α-Methylated: Demegestone Promegestone Trimegestone Testosterone derivatives: Estranes: Danazol Dimethisterone Ethisterone 19-Nortestosterone derivatives: Estranes: Allylestrenol Altrenogest Dienogest Etynodiol diacetate Lynestrenol Norethisterone (norethindrone)^# Norethisterone acetate Norethisterone enanthate Noretynodrel Norgesterone Norgestrienone Normethandrone (methylestrenolone) Norvinisterone Oxendolone Quingestanol acetate Tibolone; Gonanes: Desogestrel Etonogestrel Gestodene Gestrinone Levonorgestrel^# Norelgestromin Norgestimate Norgestrel Spirolactone derivatives: Drospirenone Others: Anabolic–androgenic steroids (e.g., nandrolone and esters, trenbolone and esters, ethylestrenol, norethandrolone, others)

PRTooltip Progesterone receptor agonists

Progesterone derivatives: Progesterone
Quingestrone

Retroprogesterone derivatives: Dydrogesterone
Trengestone

17α-Hydroxyprogesterone (and closely related) derivatives: 17α-Hydroxylated: Acetomepregenol (mepregenol diacetate)
Algestone acetophenide (dihydroxyprogesterone acetophenide)
Anagestone acetate
Chlormadinone acetate
Chlormethenmadinone acetate
Cyproterone acetate
Delmadinone acetate
Flugestone acetate (flurogestone acetate)
Flumedroxone acetate
Hydroxyprogesterone acetate
Hydroxyprogesterone caproate
Hydroxyprogesterone heptanoate
Medroxyprogesterone acetate^#
Megestrol acetate
Melengestrol acetate
Methenmadinone acetate
Osaterone acetate
Pentagestrone acetate
Proligestone; 17α-Methylated: Medrogestone; Others: Haloprogesterone

19-Norprogesterone derivatives: 17α-Hydroxylated: Gestonorone caproate (gestronol hexanoate)
Nomegestrol acetate
Norgestomet
Segesterone acetate (nestorone, elcometrine); 17α-Methylated: Demegestone
Promegestone
Trimegestone

Testosterone derivatives: Estranes: Danazol
Dimethisterone
Ethisterone

19-Nortestosterone derivatives: Estranes: Allylestrenol
Altrenogest
Dienogest
Etynodiol diacetate
Lynestrenol
Norethisterone (norethindrone)^#
Norethisterone acetate
Norethisterone enanthate
Noretynodrel
Norgesterone
Norgestrienone
Normethandrone (methylestrenolone)
Norvinisterone
Oxendolone
Quingestanol acetate
Tibolone; Gonanes: Desogestrel
Etonogestrel
Gestodene
Gestrinone
Levonorgestrel^#
Norelgestromin
Norgestimate
Norgestrel

Spirolactone derivatives: Drospirenone

Others: Anabolic–androgenic steroids (e.g., nandrolone and esters, trenbolone and esters, ethylestrenol, norethandrolone, others)

Antiprogestogens

SPRMsTooltip Selective progesterone receptor modulators	Telapristone^§ Ulipristal acetate
PRTooltip Progesterone receptor antagonists	Aglepristone Mifepristone

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Progesterone receptor modulators; Androgens and antiandrogens; Estrogens and antiestrogens; List of progestogens

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