Melengestrol acetate

Melengestrol acetate
Clinical data
Trade names	Heifermax, MGA
Other names	MGA; MLA; MLGA; Melengesterol acetate; Methylsuperlutin; U-21240; BDH-1921; 17α-Acetoxy-16-methylene-6-methyl-6-dehydroprogesterone; 17α-Acetoxy-16-methylene-6-methylpregna-4,6-diene-3,20-dione
Drug class	Progestogen; Progestin; Progestogen ester
ATC code	None;
Identifiers
	IUPAC name [(8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate;
CAS Number	2919-66-6;
PubChem CID	250948;
DrugBank	DB14659;
ChemSpider	219803;
UNII	4W5HDS3936;
KEGG	D04900;
CompTox Dashboard (EPA)	DTXSID5048184 ;
ECHA InfoCard	100.018.964
Chemical and physical data
Formula	C25H32O4
Molar mass	396.527 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4\C=C3\C(=C/[C@@H]1[C@H](CC[C@@]2([C@](OC(=O)C)(C(=C)\C[C@@H]12)C(=O)C)C)[C@@]3(C)CC4)C;
	InChI InChI=1S/C25H32O4/c1-14-11-19-20(23(5)9-7-18(28)13-21(14)23)8-10-24(6)22(19)12-15(2)25(24,16(3)26)29-17(4)27/h11,13,19-20,22H,2,7-10,12H2,1,3-6H3/t19-,20+,22+,23-,24+,25+/m1/s1; Key:UDKABVSQKJNZBH-DWNQPYOZSA-N;

Melengestrol acetate (MLGA), sold under the brand names Heifermax and MGA among others, is a progestin medication which is used in animal reproduction.[1][2] It is not approved for use in humans, and is instead used as an implantable contraceptive for captive animals in zoos and other refuges,[3] and is also used as a feed additive to promote growth in cattle, a purpose it is licensed for in the United States and Canada.[4]

Uses

Animal reproduction

MLGA is used in animal reproduction.[3][4]

Pharmacology

Pharmacodynamics

MLGA is a progestogen, and hence is an agonist of the progesterone receptor.[5] It has been found to possess 73% of the affinity of progesterone for the progesterone receptor in rhesus monkey uterus.[5]

Chemistry

MLGA, also known as 17α-acetoxy-16-methylene-6-dehydro-6-methylprogesterone or as 17α-acetoxy-16-methylene-6-methylpregna-4,6-diene-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone.[1][2] It is specifically a derivative of 17α-hydroxyprogesterone with a methyl group at the C6 position, a methylene group at the C16 position, a double bond between the C6 and C7 positions, and an acetate ester at the C17α position.[1][2] As such, it is also a derivative of 16-methylene-17α-hydroxyprogesterone acetate. MLGA is the acetate ester of melengestrol, which in contrast, has never been marketed.[1] Analogues of MLGA include other 17α-hydroxyprogesterone derivatives such as chlormadinone acetate, chlormethenmadinone acetate, cyproterone acetate, delmadinone acetate, hydroxyprogesterone caproate, medroxyprogesterone acetate, megestrol acetate, methenmadinone acetate, and osaterone acetate.[1] The only structural difference between MLGA and megestrol acetate is the presence of the C16 methylene group in the former.[1]

Society and culture

Generic names

Melengestrol acetate is the generic name of the drug and its USAN and USP.[1][2] Melengestrol is the INN and BAN of the unesterified free alcohol form.[1][2]

Brand names

MLGA is marketed under the brand names Heifermax and MGA among others.[1][2]

References

J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 764–. ISBN 978-1-4757-2085-3.
Asa, C.S.; Porton, I.J. (2010). "Chapter 34: Contraception as a Management Tool for Controlling Surplus Animals". In Kleiman, D.G.; Thompson, K.V.; Baer, C.K. (eds.). Wild Mammals in Captivity: Principles and Techniques for Zoo Management (2nd ed.). Chicago, IL: University of Chicago Press. pp. 469–482. ISBN 9780226440118. Retrieved 17 March 2016.
Jack F. Kay (26 November 2009). Analyses for Hormonal Substances in Food-Producing Animals. Royal Society of Chemistry. p. 139. ISBN 978-0-85404-198-5. Retrieved 27 May 2012.
Illingworth DV, Elsner C, De Groot K, Flickinger GL, Mikhail G (February 1977). "A specific progesterone receptor of myometrial cytosol from the rhesus monkey". J. Steroid Biochem. 8 (2): 157–60. doi:10.1016/0022-4731(77)90040-1. PMID 405534.

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[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 764–. ISBN 978-1-4757-2085-3.

[AsaContra10-3] Asa, C.S.; Porton, I.J. (2010). "Chapter 34: Contraception as a Management Tool for Controlling Surplus Animals". In Kleiman, D.G.; Thompson, K.V.; Baer, C.K. (eds.). Wild Mammals in Captivity: Principles and Techniques for Zoo Management (2nd ed.). Chicago, IL: University of Chicago Press. pp. 469–482. ISBN 9780226440118. Retrieved 17 March 2016.

[Kay2009-4] Jack F. Kay (26 November 2009). Analyses for Hormonal Substances in Food-Producing Animals. Royal Society of Chemistry. p. 139. ISBN 978-0-85404-198-5. Retrieved 27 May 2012.

[pmid405534-5] Illingworth DV, Elsner C, De Groot K, Flickinger GL, Mikhail G (February 1977). "A specific progesterone receptor of myometrial cytosol from the rhesus monkey". J. Steroid Biochem. 8 (2): 157–60. doi:10.1016/0022-4731(77)90040-1. PMID 405534.