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Megestrol acetate

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Megestrol acetate Basic information
Megestrol acetate Chemical Properties
  • Melting point:214°C
  • alpha D24 +5° (chloroform)
  • Boiling point:431.17°C (rough estimate)
  • Density 1.0474 (rough estimate)
  • refractive index 11 ° (C=2, CHCl3)
  • storage temp. Refrigerator
  • solubility Practically insoluble in water, soluble in acetone, sparingly soluble in alcohol.
  • form neat
  • Merck 14,5805
  • BRN 1917291
  • CAS DataBase Reference595-33-5(CAS DataBase Reference)
  • NIST Chemistry ReferenceMegestrol acetate(595-33-5)
  • EPA Substance Registry SystemMegestrol acetate (595-33-5)
Safety Information
  • Hazard Codes Xn
  • Risk Statements 40-48
  • Safety Statements 22-24/25
  • WGK Germany 3
  • RTECS TU4075000
  • HS Code 29372390
  • ToxicityLD50 intravenous in mouse: 56mg/kg
MSDS
Megestrol acetate Usage And Synthesis
  • Chemical PropertiesCrystalline Solid
  • OriginatorMegestat,Bristol,W. Germany,1964
  • UsesOrally active progestogen; formerly used in combinations as oral contraceptive
  • UsesProgestogen;Progesterone receptor agonist
  • UsesMegestrol acetate USP (Megace) is used to treat Carcinoma of the breast or endorometrium.
  • Manufacturing ProcessThe following preparation is given in US Patent 3,356,573. 17α-Acetoxy-3βhydroxy-6-methylpregn-5-ene-20-one (1 g), aluminum tert-butoxide (1 g) and p-benzoquinone (6 g) were dissolved in dry benzene (100 ml) and the mixture was heated under reflux for 30 minutes. The reaction mixture was cooled and washed with potassium hydroxide solution until the benzene layer was colorless. The benzene was washed with water, dried and evaporated to dryness under reduced pressure. The residue crystallized from aqueous methanol to give 17α-acetoxy-6-methylpregna-4,6-diene-3,20-dione, needles, MP 214° to 216°C.
  • brand nameMegace (Bristol-Myers Squibb); Megace (Par).
  • Therapeutic FunctionCancer chemotherapy
  • General DescriptionMegestrol acetate, 17-hydroxy-6-methylpregna-4,6-diene-3,20-dione acetate(Megace), is a progestin used primarily for the palliativemanagement of recurrent, inoperable, or metastatic endometrialor breast carcinoma. Megestrol acetate has also beenindicated for appetite enhancement in patients with AIDS.The biochemical basis for this use of megestrol is unclear.
  • Clinical UseProgestin activity is further enhanced when a double bond is introduced between positions 6 and 7, as is found in megestrol acetate. Megestrol is used primarily in the treatment of breast and endometrial carcinomas and in postmenopausal women with advanced hormone-dependent carcinoma.
  • Safety ProfileSuspected carcinogen with experimental carcinogenic and teratogenic data. Poison by intravenous route. Human reproductive effects bp 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.
  • Veterinary Drugs and TreatmentsMegestrol acetate (Ovaban?—Schering) is approved by FDA for use in dogs only for the postponement of estrus and the alleviation of false pregnancy. In male dogs, it has been used for benign prostatic hypertrophy. It is used clinically for many dermatologic and behavior- related conditions, primarily in the cat. See the Dosage section for specific indications and dosages for both dogs and cats.
    Megestrol acetate is indicated in humans for the palliative treatment of advanced carcinoma of the breast or endometrium.
  • Metabolism Less than 10% of an oral dose undergoes metabolism. Several major metabolites appear in the urine (e.g., 2-hydroxy and 6-hydroxymethyl megestrol and their glucuronide conjugates).
Megestrol acetate Preparation Products And Raw materials
Megestrol acetate (595-33-5)Related Product Information
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