Melengestrol acetate
Chemical compound
- None
- [(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
- 2919-66-6
- 250948
- DB14659
- 219803
- 4W5HDS3936
- D04900
- DTXSID5048184
- Interactive image
- 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 USANTooltip United States Adopted Name and USPTooltip United States Pharmacopeia.[1][2] Melengestrol is the INNTooltip International Nonproprietary Name and BANTooltip British Approved Name 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
- ^ a b c d e f g h i Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 764–. ISBN 978-1-4757-2085-3.
- ^ a b c d e f "Melengestrol". Drugs.com. Archived from the original on 30 July 2017.
- ^ a b Asa CS, Porton IJ (2010). "Chapter 34: Contraception as a Management Tool for Controlling Surplus Animals". In Kleiman DG, Thompson KV, Baer CK (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.
- ^ a b Sharman M, van Ginkel L, MacNeil JD (26 November 2009). "Chapter 4: Current Analytical Methods Used for the Detection of Hormone Residues". In Kay JF (ed.). Analyses for Hormonal Substances in Food-Producing Animals. Royal Society of Chemistry. p. 139. doi:10.1039/9781849730723-00129. ISBN 978-0-85404-198-5. Retrieved 27 May 2012.
- ^ a b Illingworth DV, Elsner C, De Groot K, Flickinger GL, Mikhail G (February 1977). "A specific progesterone receptor of myometrial cytosol from the rhesus monkey". Journal of Steroid Biochemistry. 8 (2): 157–160. doi:10.1016/0022-4731(77)90040-1. PMID 405534.
- v
- t
- e
Progestogens and antiprogestogens
(and progestins)
| SPRMsTooltip Selective progesterone receptor modulators | |
|---|---|
| PRTooltip Progesterone receptor antagonists |
- #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
