Methenmadinone acetate

Methenmadinone acetate
Clinical data
Trade names	Superlutin, Antigest
Other names	Superlutin; Superlutine; MMA; Methylenedehydroacetoxyprogesterone; MDAP; 17α-Hydroxy-16-methylene-δ6-progesterone 17α-acetate; 17α-Acetoxy-16-methylenepregna-4,6-diene-3,20-dione
Routes of; administration	By mouth
Drug class	Progestogen; Progestin; Progestogen ester
Identifiers
	IUPAC name [(8R,9S,10R,13S,14S,17R)-17-Acetyl-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate;
CAS Number	805-84-5;
PubChem CID	188952;
ChemSpider	164183;
UNII	KUR23M82TZ;
CompTox Dashboard (EPA)	DTXSID701001282 ;
Chemical and physical data
Formula	C24H30O4
Molar mass	382.500 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=CC4=CC(=O)CC[C@]34C)C)OC(=O)C;
	InChI InChI=1S/C24H30O4/c1-14-12-21-19-7-6-17-13-18(27)8-10-22(17,4)20(19)9-11-23(21,5)24(14,15(2)25)28-16(3)26/h6-7,13,19-21H,1,8-12H2,2-5H3/t19-,20+,21+,22+,23+,24+/m1/s1; Key:UXRDAJMOOGEIAQ-CKOZHMEPSA-N;

Methenmadinone acetate (MMA), also known as methylenedehydroacetoxyprogesterone (MDAP) and sold under the brand names Superlutin and Antigest, is a progestin medication which was developed in Czechoslovakia in the 1960s.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]^[9]^[10]^[11]^[12]^[13] It is the C17α acetate ester of methenmadinone.^[1]

Quick facts Clinical data, Trade names ...

MMA given orally shows about 13-fold the progestogenic activity of parenteral progesterone in animal bioassays.^[14]

Analogues of methenmadinone acetate include methenmadinone caproate (MMC), which was studied in combination with estradiol valerate as a combined injectable contraceptive (tentative brand name Lutofollin);^[15]^[16]^[17] chlormethenmadinone acetate (chlorsuperlutin; SCH-12600; 6-chloro-MMA),^[18] which has been used in combination with mestranol in birth control pills (brand names Biogest, Sterolibrin, Antigest B)^[19]^[20] and in veterinary medicine (brand name Agelin);^[21] bromethenmadinone acetate (bromsuperlutin; 6-bromo-MMA), which was assessed but was never marketed;^[20]^[22] and melengestrol acetate (methylsuperlutin; 6-methyl-MMA), which is used in veterinary medicine.^[6]

See also