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Megestrol

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Megestrol Basic information
Product Name:Megestrol
Synonyms:17-hydroxy-6-methylpregna-4,6-diene-3,20-dione;20-dione,17-hydroxy-6-methyl-pregna-6-diene-3;4,6-PREGNADIEN-6-METHYL-17-OL-3,20-DIONE;17-ALPHA-HYDROXY-6-METHYL-4,6-PREGNADIENE-3,20-DIONE;MEGESTROL;17-alpha-hydroxy-6-methylpregna-4,6-diene-3,20-dione;Megestrol (base and/or unspecified salts);C07120
CAS:3562-63-8
MF:C22H30O3
MW:342.47
EINECS:222-628-6
Product Categories:Hormone Drugs;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;3562-63-8
Mol File:3562-63-8.mol
Megestrol Structure
Megestrol Chemical Properties
Melting point 207-208 °C(Solv: ethyl ether (60-29-7); acetone (67-64-1))
Boiling point 500.4±50.0 °C(Predicted)
density 1.15±0.1 g/cm3(Predicted)
storage temp. Refrigerator
solubility Chloroform (Slightly), Methanol (Slightly)
form Solid
pka13.00±0.70(Predicted)
color White to Off-White
InChIInChI=1S/C22H30O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h11-12,16-18,25H,5-10H2,1-4H3/t16-,17+,18+,20-,21+,22+/m1/s1
InChIKeyVXIMPSPISRVBPZ-NWUMPJBXSA-N
SMILESC1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)[C@@](O)(C(=O)C)CC3)C=C2C
CAS DataBase Reference3562-63-8(CAS DataBase Reference)
Safety Information
Hazardous Substances Data3562-63-8(Hazardous Substances Data)
MSDS Information
Megestrol Usage And Synthesis
Chemical PropertiesWhite Solid
UsesMegestrol is an orally active progestogen. Megestrol is used in combinations as oral contraceptive and as antineoplastic agent.
IndicationsAs a representitive of the compounds of the class of progestins, this drug is used for various forms of cancer, in particular cancer of the breast, kidneys, and others.
DefinitionChEBI: A 3-oxo Delta4-steroid that is pregna-4,6-diene-3,20-dione substituted by a hydroxy group at position 17.
Brand nameMegace (Bristol-Myers Squibb); Megace (Par);Citestrol;Co-ervonum;Combiquens;Femagest;Kombiquens;Megecat;Megeron;Megestat;Menoquens;Neo-delpregnin;Niaestine;Niagestine;Novaquin;Novokvens;Novolina;Novoquens;Oracolnal;Ovaban;Ovarid;Pallace;Serial 28;Volidan;Volplan.
World Health Organization (WHO)Megestrol acetate, a synthetic progestogen, was introduced in the early 1960s as a component in oral contraceptive preparations. In 1967, as a result of new regulations required by the United States Food and Drug Administration, megestrol acetate was submitted to long-term toxicity studies and by the early 1970s it was shown to be associated with an increased incidence of mammary tumours in beagle bitches which led to its withdrawal by several regulatory authorities. Subsequently the validity of the beagle bitch model as a predictor of carcinogenicity of steroid contraceptives has been contested by many national regulatory authorities and megestrol remains available in some countries for contraceptive purposes. In other countries its use is restricted to anticancer treatment. (Reference: (WHODI) WHO Drug Information, 1-3, 5-7, 1984)
SynthesisMegestrol, 17|á-hydroxy-6|á-methylpregna-4,6-dien-3,20-dione acetate (28.3.9), is a product of dehydrogenation medroxyprogesterone (28.3.7) with chloranil (tetrachloro-p-benzoquinone) in the presence of p-toluenesulfonic acid, which results in the formation of an additional double bond at position C6¨CC7, and subsequent acetylation of the product (28.3.8) leads to the desired megestrol (28.3.9) by acetic anhydride in the presence of p-toluenesulfonic acid.

Synthesis_3562-63-8

Megestrol Preparation Products And Raw materials
Preparation Products17-Hydroxy-6-methylpregn-4-ene-3,20-dione 17-acetate
Tag:Megestrol(3562-63-8) Related Product Information
CHLOROPHOSPHONAZO III MEGESTROL ACETATE,MEGESTROL 17-ACETATE,MEGESTROL ACETATE-D3,MEGESTROL 17-ACETATE VETRANAL, 100 MG,Megestrol Acetate, Micronized,Megestrol Acetate, Milled Powder Premarin 17-Hydroxy-6-methylpregn-4-ene-3,20-dione 17-acetate Megestrol acetate EP Impurity E (2β)-Methyl Megestrol Acetate 4,7-Dihydro Megestrol Acetate AQMUMBCTNJGBGC-FGPIKTEISA-N Hydroxyprogesterone acetate Medroxyprogesterone Acetate 17-hydroxy-6-methylenepregn-4-ene-3,20-dione 17-acetate Melengestrol acetate Progesterone melengestrol Megestrol Acetate 2-Methyl-1-megestrol Acetate (Megestrol Acetate Impurity) MEGESTROL ACETATE - REFERENCE SPECTRUM Megestrol

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