CAS No.595-33-5,Megestrol acetate Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	595-33-5
Name:	Megestrol acetate
Article Data:	30

Formula:	C₂₄H₃₂O₄
Molecular Weight:	384.516
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;
EINECS:	209-864-5
Density:	1.15 g/cm³
Melting Point:	214 °C
Boiling Point:	507.1 °C at 760 mmHg
Flash Point:	218.5 °C
Appearance:	Crystalline Solid
Hazard Symbols:	Xn
Risk Codes:	40-48
Safety:	22-24/25
PSA:	60.44000
LogP:	4.57530

Synthetic route

: 74-83-9
methyl bromide

: C27H38O7

: 595-33-5
Megestrol acetate

Conditions

Conditions	Yield
Stage #1: methyl bromide; C27H38O7 With magnesium In tetrahydrofuran at 30 - 55℃; Inert atmosphere; Stage #2: With hydrogenchloride In water at 60 - 65℃;	69.8%

: 4382-76-7
methoxymethyl acetate

: 4134-58-1, 17308-02-0, 41460-93-9, 41460-97-3, 630-56-8, 302-23-8
hydroxyprogesterone acetate

: 595-33-5
Megestrol acetate

Conditions

Conditions	Yield
With sodium acetate; trichlorophosphate In chloroform at 70℃; for 0.166667h;	51%
With sodium acetate; trichlorophosphate In chloroform

: 71-58-9
Medroxyprogesterone acetate

: 595-33-5
Megestrol acetate

Conditions

Conditions	Yield
With chloranil
With 2-methyl-propan-1-ol; chloranil Heating;
With chloranil
Multi-step reaction with 2 steps 1: TsOH / dioxane 2: (tBuO)2CrO2, Ac2O / CCl4 View Scheme

: 71-58-9
Medroxyprogesterone acetate

: 118-75-2
chloranil

: 64-19-7
acetic acid

: 141-78-6
ethyl acetate

: 595-33-5
Megestrol acetate

...Expand

: 71-58-9
Medroxyprogesterone acetate

: 118-75-2
chloranil

: 75-65-0
tert-butyl alcohol

: 595-33-5
Megestrol acetate

...Expand

: 1104-99-0
3-Methoxy-17α-acetoxy-6-methyl-pregnadien-(3,5)-on-(20)

: 595-33-5
Megestrol acetate

Conditions

Conditions	Yield
With acetic anhydride In tetrachloromethane

: 2381-48-8
6-methylpregn-5-ene-3β,17α-diol-20-one 17-acetate

: 595-33-5
Megestrol acetate

Conditions

Conditions	Yield
With aluminum tri-tert-butoxide; p-benzoquinone

: 1863-39-4
3β-acetoxy-17α-hydroxy-5-pregnen-20-one

: 595-33-5
Megestrol acetate

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: benzene; toluene-4-sulfonic acid 2: peroxybenzoic acid; chloroform 3: benzene; diethyl ether 4: aqueous methanol.H2SO4 5: CrO3; pyridine 6: aqueous HCl 7: acetic acid; toluene-4-sulfonic acid 8: tetrachloro-<1,4>benzoquinone View Scheme

: 520-85-4
Medroxyprogesterone

: 595-33-5
Megestrol acetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; toluene-4-sulfonic acid 2: tetrachloro-<1,4>benzoquinone View Scheme

: 113665-92-2
3β,5,17-trihydroxy-6β-methyl-5α-pregnan-20-one

: 595-33-5
Megestrol acetate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: CrO3; pyridine 2: aqueous HCl 3: acetic acid; toluene-4-sulfonic acid 4: tetrachloro-<1,4>benzoquinone View Scheme

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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%