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Chemical compound
Melengestrol acetate
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
[(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
PubChem
CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (
EPA )
ECHA InfoCard
100.018.964
Formula C 25 H 32 O 4
Molar mass 396.527 g·mol−1 3D model (
JSmol )
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=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 Tooltip United States Adopted Name and
USP Tooltip United States Pharmacopeia .
[1]
[2] Melengestrol is the
INN Tooltip International Nonproprietary Name and
BAN Tooltip 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 .
PR Tooltip Progesterone receptor
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RU-2309
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