MELENGESTROL ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H32O4
Molecular Weight	396.5192
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC(=C)[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])C=C(C)C4=CC(=O)CC[C@]34C

InChI

InChIKey=UDKABVSQKJNZBH-DWNQPYOZSA-N

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

HIDE SMILES / InChI

Description
Sources: http://vahs.net/wp-content/uploads/Stefanie-Anderson-Melengestrol-acetate-MGA.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2676933 and http://www.fda.gov/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm064715.htm

Melengestrol is a steroidal progestin and antineoplastic agent which was never marketed. An acylated derivative, melengestrol acetate, is used as a growth promoter in animals. Melengestrol acetate (MGA) is one of six steroidal hormone growth promoters approved for use in Canada and USA. These products are used to improve growth rate and feed efficiency, as well as to suppress estrus in beef heifers (CFIA 2008). They are not approved for use in any species other than beef cattle meant for slaughter. MGA is the only drug of its kind that is administered in animal feed, and its labelled dose in Canada is 0.4mg per heifer per day (CFIA 2008). A mandatory withdrawal of 2 days before slaughter is applied to any animal that is administered MGA.

Approval Year

Targets

Primary Target	Pharmacology	Potency
C. albicans growth 3 Target ID: C. albicans growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/24277040	Inhibitor 8297
Progesterone receptor 61 Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15713363	Agonist 2678	0.418 nM [IC50]
Rat prostatic tumor growth 2 Target ID: Rat prostatic tumor growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/2268413	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Suppression of estrus in Heifers 2 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm061809.pdf	Preventing		Approved 8429	HEIFERMAX 500 Approved Use For increased rate of weight gain, improved feed efficiency, suppression of estrus in Heifers. Launch Date 2004
Prostate cancer 178 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2268413	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The watershed as a conceptual framework for the study of environmental and human health.	2009 Feb 18	20508751
Roles of hCG in Advancing Follicular Growth to Ovulation after Concurrent Injections of PGF(2α) and GnRH in Postpubertal Holstein Heifers Bearing a CL.	2010 Dec 1	21151654

Patents

Sample Use Guides

In Vivo Use Guide

Melengestrol (HEIFERMAX® 500) should be thoroughly mixed in liquid Type C medicated feed which must be fed at 0.5 to 2.0 pounds per head daily to provide 0.25 to 0.5 mg of melengestrol acetate per head per day. Average daily intakes approximating the middle of this range provide the most optimal and economical improvements in rate of weight gain and feed utilization. Constant daily intakes of 0.35 to 0.50 mg per head per day give a high degree of estrus suppression. Levels of 0.25 to 0.35 mg provide a lower but still effective degree of estrus suppression.

Route of Administration: Oral

In Vitro Use Guide

Total body mass and snout-vent length of X. laevis larvae were significantly reduced by the 100 ng/L melengestrol

Name

Type

Language

MELENGESTROL ACETATE

Official Name

English

MELENGESTROL ACETATE [USAN]

Common Name

English

MELENGESTROL ACETATE [USP-RS]

Common Name

English

NSC-70968

Code

English

BDH 1921

Code

English

17-Hydroxy-6-methyl-16-methylenepregna-4,6-diene-3,20-dione acetate

Common Name

English

MELENGESTROL ACETATE [USP MONOGRAPH]

Common Name

English

MELENGESTROL ACETATE [GREEN BOOK]

Common Name

English

PREGNA-4,6-DIENE-3,20-DIONE, 17-(ACETYLOXY)-6-METHYL-16-METHYLENE-

Systematic Name

English

MELENGESTROL ACETATE [MART.]

Common Name

English

5373

Code

English

MELENGESTROL ACETATE [MI]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 556.380