Megestrol acetate

Megestrol acetate Basic information
Product Name:Megestrol acetate
Synonyms:Megesgtrol Acetate ;Megestrol Acetate (250 mg);6-MethleneProgesterone Acetate;* Megestrol acetate acetate;Megestrol acetate, progesterone;17-(acetyloxy)-6-methylpregna-4,6-diene-3,20-dione;17-Acetoxy-6-methylpregna-4,6-diene-3,20-dione;17-alpha-acetoxy-6-dehydro-6-methylprogesterone
CAS:595-33-5
MF:C24H32O4
MW:384.51
EINECS:209-864-5
Product Categories:SARMs(Selective androgen receptor modulator);Active Pharmaceutical Ingredients;Antitumors for Research and Experimental Use;Biochemistry;Hydroxyketosteroids;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labeled Compounds;Isotope Labelled Compounds;Steroid and Hormone;Megace, Megace ES;Hormone Drugs;595-33-5
Mol File:595-33-5.mol
Megestrol acetate Structure
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. Sealed in dry,Room Temperature
solubility Practically insoluble in water, soluble in acetone, sparingly soluble in alcohol.
form neat
color White
Merck 14,5805
BRN 1917291
InChIKeyRQZAXGRLVPAYTJ-GQFGMJRRSA-N
SMILESC1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)[C@@](OC(C)=O)(C(=O)C)CC3)C=C2C
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 Information
ProviderLanguage
SigmaAldrich English
Megestrol acetate Usage And Synthesis
DescriptionMegestrol Acetate is the acetate salt form of megestrol, a synthetic derivative of the naturally occurring female sex hormone progesterone with potential anti-estrogenic and antineoplastic activity. It is frequently used in the treatment of patients with metastatic breast cancer. It is generally well tolerated, except that it may cause undesirable weight gain. Subsequently, it was shown that megestrol acetate produced weight gain in a variety of cachectic cancer patients. Significant reduction inserum levels of IL-1a and b,IL-2,IL-6, and TNF-o were observed in cancer patientstreated with megestrol acetate which may bear on the mechanism of improved appetite and body weight gain.It has also been postulated that the effect is, at least in part,mediated by NPY,a potent central appetite stimulant.
Chemical PropertiesCrystalline Solid
OriginatorMegestat,Bristol,W. Germany,1964
UsesMegestrol acetate USP (Megace) is used to treat Carcinoma of the breast or endorometrium.
UsesMegestrol acetate (Megace), a semi-synthetic progestational steroid, is the most effective known appetite stimulant at present. Previously used in patients with cancer and acquired immunodeficiency syndrome, only a few studies have considered the applicability of this drug in malnourished older persons.
Megestrol acetate is useful if profound anorexia is the main manifestation of cachexia and if expected survival is weeks to months. Megace has been shown to significantly increase appetite, but not survival. In patients with a shorter predicted survival, a brief course of corticosteroids may be useful to stimulate appetite and have positive effects on nausea, pain, and asthenia.
DefinitionChEBI: Megestrol acetate is a steroid ester resulting from the formal condensation of the hydroxy group of megestrol with the carboxy group of acetic acid. It is an appetite stimulant used for the treatment of anorexia and cachexia. Also used for birth control and for the treatment of breast cancer. It has a role as an antineoplastic agent, an appetite enhancer, a contraceptive drug, a progestin and a synthetic oral contraceptive. It is a steroid ester, an acetate ester, a 20-oxo steroid and a 3-oxo-Delta(4) steroid. It derives from a megestrol.
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.
MetabolismLess 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).
storageStore at RT
references[1] zhang k1, chow pk. the effect of megestrol acetate on growth of hepg2 cells in vitro and in vivo. clin cancer res. 2004 aug 1; 10(15):5226-32.
Megestrol Medroxyprogesterone Acetate Methyl cyclopentenolone ETHYLENEDIAMINE TETRAKIS(PROPOXYLATE-BLOCK-ETHOXYLATE) TETROL Diphenolic acid 4-(Diethylamino)salicylaldehyde POLY(VINYL ACETATE) 6-Methyl-5-hepten-2-one Cellulose acetate Norandrostenedione DL-α-Tocopherol Allyl methacrylate Ethyl acetate Cyproterone acetate Vinyl acetate Ammonium acetate METHYLCYCLOPENTADIENE DIMER Megestrol acetate

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.