Melengestrol acetate

Last updated
Melengestrol acetate
Melengestrol acetate.svg
Clinical data
Trade names Heifermax, 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 class Progestogen; 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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.018.964 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C25H32O4
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]

Contents

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]

Related Research Articles

<span class="mw-page-title-main">17α-Hydroxyprogesterone</span> Chemical compound

17α-Hydroxyprogesterone (17α-OHP), also known as 17-OH progesterone (17-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. It is also a chemical intermediate in the biosynthesis of many other endogenous steroids, including androgens, estrogens, glucocorticoids, and mineralocorticoids, as well as neurosteroids.

<span class="mw-page-title-main">Medroxyprogesterone</span> Steroidal progestin drug

Medroxyprogesterone (MP), is a progestin which is not used medically. A derivative, medroxyprogesterone acetate (MPA), is used as a medication in humans, and is far more widely known in comparison. Medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate, and what is almost always being referred to when the term is used is MPA and not medroxyprogesterone.

<span class="mw-page-title-main">Melengestrol</span> Chemical compound

Melengestrol is a steroidal progestin of the 17α-hydroxyprogesterone group and an antineoplastic drug which was never marketed. An acylated derivative, melengestrol acetate, is used as a growth promoter in animals.

<span class="mw-page-title-main">Chlormadinone acetate</span> Chemical compound

Chlormadinone acetate (CMA), sold under the brand names Belara, Gynorelle, Lutéran, and Prostal among others, is a progestin and antiandrogen medication which is used in birth control pills to prevent pregnancy, as a component of menopausal hormone therapy, in the treatment of gynecological disorders, and in the treatment of androgen-dependent conditions like enlarged prostate and prostate cancer in men and acne and hirsutism in women. It is available both at a low dose in combination with an estrogen in birth control pills and, in a few countries like France and Japan, at low, moderate, and high doses alone for various indications. It is taken by mouth.

<span class="mw-page-title-main">Medrogestone</span> Chemical compound

Medrogestone, sold under the brand name Colprone among others, is a progestin medication which has been used in menopausal hormone therapy and in the treatment of gynecological disorders. It is available both alone and in combination with an estrogen. It is taken by mouth.

<span class="mw-page-title-main">Delmadinone acetate</span> Chemical compound

Delmadinone acetate (DMA), sold under the brand name Tardak among others, is a progestin and antiandrogen which is used in veterinary medicine to treat androgen-dependent conditions such as benign prostatic hyperplasia. It must be used with care as it has the potential to cause adrenal insufficiency via inhibition of adrenocorticotropic hormone (ACTH) secretion from the pituitary gland. DMA is the C17α acetate ester of delmadinone, which, in contrast to DMA, was never marketed for medical use.

<span class="mw-page-title-main">Segesterone acetate</span> Progestin medication

Segesterone acetate (SGA), sold under the brand names Nestorone, Elcometrine, and Annovera, is a progestin medication which is used in birth control and in the treatment of endometriosis in the United States, Brazil, and other South American countries. It is available both alone and in combination with an estrogen. It is not effective by mouth and must be given by other routes, most typically as a vaginal ring or implant that is placed into fat.

<span class="mw-page-title-main">Osaterone acetate</span> Chemical compound

Osaterone acetate, sold under the brand name Ypozane, is a medication which is used in veterinary medicine in Europe in the treatment of enlarged prostate in dogs. It is given by mouth.

<span class="mw-page-title-main">Hydroxyprogesterone acetate</span> Chemical compound

Hydroxyprogesterone acetate (OHPA), sold under the brand name Prodox, is an orally active progestin related to hydroxyprogesterone caproate (OHPC) which has been used in clinical and veterinary medicine. It has reportedly also been used in birth control pills.

<span class="mw-page-title-main">Progestogen ester</span>

A progestogen ester is an ester of a progestogen or progestin. The prototypical progestogen is progesterone, an endogenous sex hormone. Esterification is frequently employed to improve the pharmacokinetics of steroids, including oral bioavailability, lipophilicity, and elimination half-life. In addition, with intramuscular injection, steroid esters are often absorbed more slowly into the body, allowing for less frequent administration. Many steroid esters function as prodrugs.

<span class="mw-page-title-main">Acetomepregenol</span> Chemical compound

Acetomepregenol (ACM), also known as mepregenol diacetate and sold under the brand name Diamol, is a progestin medication which is used in Russia for the treatment of gynecological conditions and as a method of birth control in combination with an estrogen. It has also been studied in the treatment of threatened abortion. It has been used in veterinary medicine as well. It has been marketed since at least 1981.

<span class="mw-page-title-main">Butagest</span> Chemical compound

Butagest, also known as buterol, as well as 3β-hydroxy-6-methyl-17α-hydroxypregna-4,6-dien-20-one 3β-butanoate 17α-acetate or as 6-methyl-17α-hydroxy-δ6-progesterone 3β-butanoate 17α-acetate, is a steroidal progestin which was developed in Russia for potential clinical use but was never marketed. It is a modification of megestrol acetate in which the C3 ketone has been replaced with a C3β butanoyloxy moiety.

<span class="mw-page-title-main">Gestadienol acetate</span> Chemical compound

Gestadienol acetate an orally active progestin which was described in the literature in 1967 and was never marketed. It has no androgenic or estrogenic effects. The effects of gestadienol acetate on the endometrium and its general pharmacology were studied in a clinical trial in women. It has also been studied in a clinical trial for benign prostatic hyperplasia in men, but was ineffective.

<span class="mw-page-title-main">Cymegesolate</span> Chemical compound

Cymegesolate, also known as cypionyl megestrol acetate or as megestrol acetate 3β-cypionate, is a progestin medication which was never marketed. It was developed in China in the late 1970s and early to mid 1980s for use as a hormonal contraceptive. The medication was formulated at a dose of 50–100 mg in combination with a "trace" dose of 0.25–0.5 mg quinestrol as a long-lasting, once-a-month combined oral contraceptive pill. This combination has been studied in 1,213 women across a total of 9,651 menstrual cycles, with contraceptive effectiveness of over 99.13% and "very few side effects." At the high dose, it showed an anovulation rate of only about 60%, and instead mediated its contraceptive effects via a marked anti-implantation effect.

<span class="mw-page-title-main">Megestrol caproate</span> Chemical compound

Megestrol caproate, abbreviated as MGC, is a progestin medication which was never marketed. It was developed in Russia in 2002. In animals, MGC shows 10-fold higher progestogenic activity compared to progesterone when both are administered via subcutaneous injection. In addition, MGC has no androgenic, anabolic, or estrogenic activity. The medication was suggested as a potential contraceptive and therapeutic agent.

<span class="mw-page-title-main">Methenmadinone</span> Chemical compound

Methenmadinone, also known as deacetylsuperlutin or as 16-methylene-6-dehydro-17α-hydroxyprogesterone, is a pregnane steroid which was never marketed. It is a parent compound of methenmadinone acetate, melengestrol, and chlormethenmadinone.

<span class="mw-page-title-main">16-Methylene-17α-hydroxyprogesterone acetate</span> Chemical compound

16-Methylene-17α-hydroxyprogesterone acetate is a progestin of the 17α-hydroxyprogesterone group which was never marketed. Given orally, it shows about 2.5-fold the progestogenic activity of parenteral progesterone in animal bioassays. It is a parent compound of the following clinically used progestins:

<span class="mw-page-title-main">Bromethenmadinone acetate</span> Chemical compound

Bromethenmadinone acetate is a progestin medication which was developed in Czechoslovakia and was described in 1970 but was never marketed. Analogues of BMMA include chlormethenmadinone acetate, melengestrol acetate, and methenmadinone acetate.

References

  1. 1 2 3 4 5 6 7 8 9 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.
  2. 1 2 3 4 5 6 [ dead link ]
  3. 1 2 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.
  4. 1 2 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.
  5. 1 2 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.