Melengestrol acetate | CAS#2919-66-6 | Animal reproduction progestin

MedKoo Cat#: 464259 | Name: Melengestrol acetate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Melengestrol acetate (MLGA), sold under the brand names Heifermax and MGA among others, is a progestin medication which is used in animal reproduction. It is not approved for use in humans, and is instead used as an implantable contraceptive for captive animals in zoos and other refuges, 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.

Chemical Structure

Melengestrol acetate

CAS#2919-66-6

Theoretical Analysis

MedKoo Cat#: 464259

Name: Melengestrol acetate

CAS#: 2919-66-6

Chemical Formula: C25H32O4

Exact Mass: 396.2301

Molecular Weight: 396.53

Elemental Analysis: C, 75.73; H, 8.13; O, 16.14

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 350.00	2 Weeks
500mg	USD 850.00	2 Weeks

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Synonym

Melengestrol acetate; MGA 100; MGA-100; MGA 500; MGA-500; NSC 70968; NSC70968; NSC-70968; MLGA;

IUPAC/Chemical Name

(8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-16-methylene-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

InChi Key

UDKABVSQKJNZBH-DWNQPYOZSA-N

InChi Code

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

SMILES Code

CC(O[C@@]1(C(C[C@H]2[C@@H]3C=C(C4=CC(CC[C@@]4([C@H]3CC[C@]12C)C)=O)C)=C)C(C)=O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Melengestrol acetate is a progesterone derivative, acts as an orally active corticosteroid hormone.

In vitro activity:

This study’s hypothesis was that MGA (malengestrol acetate) may induce various populations of muscle-derived cells (MDC) to the adipogenic pathway in both a bovine and murine cell culture model.Treatment of cultures with 10 nM MGA increased C/EBPbeta levels (P < 0.05) in C2C12 myoblasts and tended (P = 0.08) to increase C/EBPbeta levels in 3T3-L1 preadipocytes. Reference: J Anim Sci. 2009 Dec;87(12):3897-904. https://pubmed.ncbi.nlm.nih.gov/19684257/

In vivo activity:

Growth of the AT3 rat tumors was suppressed by approximately 53% after 9 days of daily s.c. injections with MGA (melengestrol acetate) at 10 mg/kg body weight. MGA also caused a 54% weight reduction of the ventral prostate and a 53% reduction of the seminal vesicles. Adrenal weights were reduced by 42%. A 24-day oral treatment with MGA (at approximately 15-17 mg/(kg.day)) inhibited AT3 tumor growth by 59% and caused a weight reduction in the following tissues: prostate (46%), seminal vesicles (19%), testes (12%), and adrenals (52%). Reference: Biochem Cell Biol. 1990 Oct;68(10):1181-8. https://pubmed.ncbi.nlm.nih.gov/2268413/

	Solvent	mg/mL	mM
Solubility
	DMSO	17.5	44.13
	Ethanol	10.0	25.22

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 396.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Chung KY, Johnson BJ. Melengestrol acetate enhances adipogenic gene expression in cultured muscle-derived cells. J Anim Sci. 2009 Dec;87(12):3897-904. doi: 10.2527/jas.2008-1645. Epub 2009 Aug 14. PMID: 19684257. 2. Padilla GM, Yacullo RC, Padilla JJ, Payne B, Petrow V. Melengestrol acetate and megestrol acetate are prostatic tumor inhibiting agents. Biochem Cell Biol. 1990 Oct;68(10):1181-8. doi: 10.1139/o90-175. PMID: 2268413.

In vitro protocol:

Chung KY, Johnson BJ. Melengestrol acetate enhances adipogenic gene expression in cultured muscle-derived cells. J Anim Sci. 2009 Dec;87(12):3897-904. doi: 10.2527/jas.2008-1645. Epub 2009 Aug 14. PMID: 19684257.

In vivo protocol:

Padilla GM, Yacullo RC, Padilla JJ, Payne B, Petrow V. Melengestrol acetate and megestrol acetate are prostatic tumor inhibiting agents. Biochem Cell Biol. 1990 Oct;68(10):1181-8. doi: 10.1139/o90-175. PMID: 2268413.

1: McDonald MM, Agnew MK, Asa CS, Powell DM. Melengestrol acetate contraceptive implant use in colobus monkeys (Colobus guereza): Patterns through time and differences in reproductive potential and live births. Zoo Biol. 2020 Nov 25. doi: 10.1002/zoo.21581. Epub ahead of print. PMID: 33238048. 2: Gilroy ÈAM, Bartlett AJ, Gillis PL, Bendo NA, Salerno J, Hedges AM, Brown LR, Holman EAM, Stock NL, de Solla SR. Correction to: Toxicity of the pharmaceuticals finasteride and melengestrol acetate to benthic invertebrates. Environ Sci Pollut Res Int. 2021 Jan;28(3):3749. doi: 10.1007/s11356-020-11617-y. Erratum for: Environ Sci Pollut Res Int. 2020 Nov;27(33):41803-41815. PMID: 33216304; PMCID: PMC7852903. 3: Javed S, Atia-Tul-Wahab, Jabeen A, Zhumagaliyeva S, Abilov ZA, Atta-Ur- Rahman, Choudhary MI. Fungal mediated biotransformation of melengestrol acetate, and T-cell proliferation inhibitory activity of biotransformed compounds. Bioorg Chem. 2020 Nov;104:104313. doi: 10.1016/j.bioorg.2020.104313. Epub 2020 Sep 24. PMID: 33142425. 4: Gilroy ÈAM, Bartlett AJ, Gillis PL, Bendo NA, Salerno J, Hedges AM, Brown LR, Holman EAM, Stock NL, de Solla SR. Toxicity of the pharmaceuticals finasteride and melengestrol acetate to benthic invertebrates. Environ Sci Pollut Res Int. 2020 Nov;27(33):41803-41815. doi: 10.1007/s11356-020-10121-7. Epub 2020 Jul 22. Erratum in: Environ Sci Pollut Res Int. 2021 Jan;28(3):3749. PMID: 32696412; PMCID: PMC7679302. 5: Locke JWC, Thomas JM, Knickmeyer ER, Ellersieck MR, Yelich JV, Poock SE, Smith MF, Patterson DJ. Comparison of long-term progestin-based protocols to synchronize estrus prior to natural service or fixed-time artificial insemination in Bos indicus-influenced beef heifers. Anim Reprod Sci. 2020 Jul;218:106475. doi: 10.1016/j.anireprosci.2020.106475. Epub 2020 Apr 30. PMID: 32507258. 6: Knickmeyer ER, Thomas JM, Locke JWC, Bonacker RC, Ellersieck MR, Poock SE, Smith MF, Patterson DJ. Evaluation of split-time artificial insemination following administration of a long or short-term progestin-based estrus synchronization protocol in beef heifers. Theriogenology. 2019 Jul 15;133:179-186. doi: 10.1016/j.theriogenology.2019.04.011. Epub 2019 Apr 11. PMID: 31125868. 7: Zhang JN, Yang L, Zhang M, Liu YS, Zhao JL, He LY, Zhang QQ, Ying GG. Persistence of androgens, progestogens, and glucocorticoids during commercial animal manure composting process. Sci Total Environ. 2019 May 15;665:91-99. doi: 10.1016/j.scitotenv.2019.02.120. Epub 2019 Feb 8. PMID: 30772582. 8: Zhao HP, Cui XZ, Zhang W, Chen GX, Yang WY, Wang QW, Li CY. [Effect of anti- androgen and progesterone on development of regrowth antlers in 6 year old sika deer]. Zhongguo Zhong Yao Za Zhi. 2018 Jul;43(13):2713-2719. Chinese. doi: 10.19540/j.cnki.cjcmm.20180514.010. PMID: 30111021. 9: Thomson P, Langlois VS. Developmental profiles of progesterone receptor transcripts and molecular responses to gestagen exposure during Silurana tropicalis early development. Gen Comp Endocrinol. 2018 Sep 1;265:4-14. doi: 10.1016/j.ygcen.2018.05.017. Epub 2018 May 18. PMID: 29778442. 10: Oosthuizen N, Lansford AC, Canal LB, Fontes PLP, Sanford CD, Dahlen CR, DiLorenzo N, Funston RN, Lamb GC. Comparison of two alternate PGF2α products in two estrus synchronization protocols in beef heifers. J Anim Sci. 2018 Apr 14;96(4):1388-1395. doi: 10.1093/jas/sky059. PMID: 29648600; PMCID: PMC6140874. 11: Shum DW, Nykamp SG, Molter CM. What Is Your Diagnosis? J Am Vet Med Assoc. 2018 Apr 1;252(7):801-803. doi: 10.2460/javma.252.7.801. PMID: 29553900. 12: Shen X, Chang H, Sun D, Wang L, Wu F. Trace analysis of 61 natural and synthetic progestins in river water and sewage effluents by ultra-high performance liquid chromatography-tandem mass spectrometry. Water Res. 2018 Apr 15;133:142-152. doi: 10.1016/j.watres.2018.01.030. Epub 2018 Feb 3. PMID: 29407696. 13: Food Safety Commission of Japan. Melengestrol Acetate (Veterinary Medicinal Products). Food Saf (Tokyo). 2017 Dec 29;5(4):164-168. doi: 10.14252/foodsafetyfscj.2017009s. PMID: 32231940; PMCID: PMC6989191. 14: Havens SM, Hedman CJ, Hemming JD, Mieritz MG, Shafer MM, Schauer JJ. Influence of Acidification on the Partitioning of Steroid Hormones among Filtrate, Filter Media, and Retained Particulate Matter. J Environ Qual. 2016 Sep;45(5):1776-1781. doi: 10.2134/jeq2016.01.0017. PMID: 27695756. 15: Zhu Y, Xie S, Chen D, Pan Y, Qu W, Wang X, Liu Z, Peng D, Huang L, Tao Y, Yuan Z. Targeted analysis and determination of β-agonists, hormones, glucocorticoid and psychiatric drugs in feed by liquid chromatography with electrospray ionization tandem mass spectrometry. J Sep Sci. 2016 Jul;39(13):2584-94. doi: 10.1002/jssc.201600011. Epub 2016 Jun 7. PMID: 27145483. 16: Nachman KE, Smith TJ. Hormone Use in Food Animal Production: Assessing Potential Dietary Exposures and Breast Cancer Risk. Curr Environ Health Rep. 2015 Mar;2(1):1-14. doi: 10.1007/s40572-014-0042-8. PMID: 26231238. 17: Martins JH, Santos CS, Silva MA, Aguiar HM, França IG, Pereira HG, Ribeiro DL, Chaves RM, Souza JA, Monteiro BM, Sá Filho MF, Torres-Júnior JR. Impact of puberty status and melengestrol acetate supplementation before the breeding period on reproductive efficiency of Bos indicus beef heifers. J Anim Sci. 2015 Jun;93(6):2796-805. doi: 10.2527/jas.2015-8799. PMID: 26115267. 18: Blackwell BR, Wooten KJ, Buser MD, Johnson BJ, Cobb GP, Smith PN. Occurrence and Characterization of Steroid Growth Promoters Associated with Particulate Matter Originating from Beef Cattle Feedyards. Environ Sci Technol. 2015 Jul 21;49(14):8796-803. doi: 10.1021/acs.est.5b01881. Epub 2015 Jul 2. PMID: 26098147. 19: Di Donna L, Benabdelkamel H, Taverna D, Indelicato S, Aiello D, Napoli A, Sindona G, Mazzotti F. Determination of ketosteroid hormones in meat by liquid chromatography tandem mass spectrometry and derivatization chemistry. Anal Bioanal Chem. 2015 Jul;407(19):5835-42. doi: 10.1007/s00216-015-8772-5. Epub 2015 May 27. PMID: 26014285. 20: Tao Y, Paula R, Stolker AA, Chen D, Yuan Z. Simultaneous determination of seven gestagens in kidney fats by Ultra Performance Convergence Chromatography tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Apr 15;988:143-8. doi: 10.1016/j.jchromb.2015.02.034. Epub 2015 Mar 2. PMID: 25777477.