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Basic information

  • Name:

  • Megestrol acetate

  • CAS No.:

  • 595-33-5

  • Formula:
  • C24H32O4
  • Synonyms:
  • Megace ES;Pregna-4,6-diene-3,20-dione, 17-(acetyloxy)-6-methyl-;Ovarid;Megace;Ovaban (Veterinary);Megeron;6-Methyl-delta4,6-pregnadien-17alpha-ol-3,20-dione acetate;6-Methyl-6-dehydro-17.alpha.-acetoxyprogesterone;Megace (TN);SC 10363;Megestryl acetate;Pregna-4,6-diene-3, 20-dione, 17-hydroxy-6-methyl-, acetate;Pallace;Ovaban;S4;6-Methyl-17-alpha-hydroxy-delta(sup 6)-progesterone acetate;SC-10363;SC10363;Niagestin;Progesterone, 6-dehydro-17-hydroxy-6-methyl-, acetate;6-Methyl-delta(sup 4,6)-pregnadien-17-alpha-ol-3,20-dione acetate;Megestrol acetate [USAN];17alpha-Acetoxy-6-dehydro-6-methylprogesterone;Megestrol acetate (USAN);Megestat;6-Dehydro-6-methyl-17.alpha.-acetoxyprogesterone;17-Hydroxy-6-methylpregna-4,6-diene-3,20-dione acetate;Megestrol acetole [Progestins];6-MethleneProgesterone Acetate;Pregna-4,6-diene-3, 20-dione, 17- (acetyloxy)-6-methyl-;BDH 1298;

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Chemistry

Name:17-Acetyloxy-6-methylpregna-4,6-diene-3,20-dione
Other names:Megestrol acetate;6-diene-3,20-dione;17-hydroxy-6-methyl-pregna-acetate;17- (acetyloxy)-6-methylpregna-4 ,6-dien-3,20-dione;17-acetoxy-6-methylpregna-4, 6-dien-3;20-dione;megestrol acetate acetate; 17α-acetoxy-6-methyl-pregn-4 ,6-diene-;6-methyl-pregn-4 ,6-dien-17 alpha-ol ,20 - dione-17-acetate
17α-hydroxy-6-methyl-;16-4,6-diene; 20-dione-17-acetate
Molecular formula : C24H32O4
MW : 384.52
refractive index: 11°C (C=2, CHCl3)
Melting point:214-216 °C
ACD/LogP(pH 5.5): 3.82
ACD/LogP(pH 5.5): 3.82
ACDXLogP: 3.90 

nature : a white or slightly yellow crystalline powder in methanol, tasteless, odorless.Soluble acetone, ethanol-soluble, ether, do not dissolve in water.

Uses

Efficacy of medroxyprogesterone acetate (MPA) intermediates

Production

available 16-17α-dione by the open-loop hydrogen bromide and nickel Catalytic Reduction of bromine, in the production of 17 alpha-hydroxy progesterone, and then acetylated and acid hydrolysis of the production of 17 alpha-acetoxy progesterone, and then to the original three formic acid and ethyl ether of Vilsmeier reacted 3-ethoxy-6-formyl-17α- acetoxy ,16 ,5-diene-20-one, and the final KBH4, acid hydrolysis, dehydration and transposition of the goods obtained.

Toxicity Data With Reference

1.   

dns-mus-scu 200 mg/kg

   JOENAK    Journal of Endocrinology. 60 (1974),167.
2.   

dni-mus-scu 200 mg/kg

   JOENAK    Journal of Endocrinology. 60 (1974),167.
3.   

ivn-mus LD50:56 mg/kg

   CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#00931 .

Consensus Reports

IARC Cancer Review: Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 ,1979,p. 431.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) .

Safety Profile

Suspected carcinogen with experimental carcinogenic and teratogenic data. Poison by intravenous route. Human reproductive effects by ingestion and implant routes: effects on ovaries and fallopian tubes, menstrual cycle changes, and female fertility index changes. Mutation data reported. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. An FDA proprietary drug used to treat endometriosis and breast cancer. A steroid.

Standards and Recommendations

Megestrol Acetate, Micronized, USP, 97.0-103.0%
Megestrol Acetate, 99% 
Megestrol acetate, 98% 

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