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Wikipedia

Melengestrol acetate

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]

Melengestrol acetate
Clinical data
Trade namesHeifermax, MGA
Other namesMGA; 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 classProgestogen; Progestin; Progestogen ester
ATC code
  • None
Identifiers
  • [(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 InfoCard100.018.964
Chemical and physical data
FormulaC25H32O4
Molar mass396.527 g·mol−1
3D model (JSmol)
  • 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=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

Uses edit

Animal reproduction edit

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

Pharmacology edit

Pharmacodynamics edit

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 edit

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 edit

Generic names edit

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 edit

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

References edit

  1. ^ 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.
  2. ^ a b c d e f . Drugs.com. Archived from the original on 30 July 2017.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.

melengestrol, acetate, confused, with, megestrol, acetate, mlga, sold, under, brand, names, heifermax, among, others, progestin, medication, which, used, animal, reproduction, approved, humans, instead, used, implantable, contraceptive, captive, animals, zoos,. Not to be confused with Megestrol acetate 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 Melengestrol acetateClinical dataTrade namesHeifermax MGAOther namesMGA MLA MLGA Melengesterol acetate Methylsuperlutin U 21240 BDH 1921 17a Acetoxy 16 methylene 6 methyl 6 dehydroprogesterone 17a Acetoxy 16 methylene 6 methylpregna 4 6 diene 3 20 dioneDrug classProgestogen Progestin Progestogen esterATC codeNoneIdentifiersIUPAC 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 acetateCAS Number2919 66 6PubChem CID250948DrugBankDB14659ChemSpider219803UNII4W5HDS3936KEGGD04900CompTox Dashboard EPA DTXSID5048184ECHA InfoCard100 018 964Chemical and physical dataFormulaC 25H 32O 4Molar mass396 527 g mol 13D model JSmol Interactive imageSMILES 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 CInChI 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 s1Key UDKABVSQKJNZBH DWNQPYOZSA N Contents 1 Uses 1 1 Animal reproduction 2 Pharmacology 2 1 Pharmacodynamics 3 Chemistry 4 Society and culture 4 1 Generic names 4 2 Brand names 5 ReferencesUses editAnimal reproduction edit MLGA is used in animal reproduction 3 4 Pharmacology editPharmacodynamics edit 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 editSee also List of progestogens Progestogen ester and List of progestogen esters MLGA also known as 17a acetoxy 16 methylene 6 dehydro 6 methylprogesterone or as 17a 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 17a 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 C17a position 1 2 As such it is also a derivative of 16 methylene 17a hydroxyprogesterone acetate MLGA is the acetate ester of melengestrol which in contrast has never been marketed 1 Analogues of MLGA include other 17a 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 editGeneric names edit 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 edit MLGA is marketed under the brand names Heifermax and MGA among others 1 2 References edit 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 Retrieved from https en wikipedia org w index php title Melengestrol acetate amp oldid 1192049417, wikipedia, wiki, book, books, library,

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