Product Name

  • Name

    Megestrol acetate

  • EINECS 209-864-5
  • CAS No. 595-33-5
  • Article Data30
  • CAS DataBase
  • Density 1.15 g/cm3
  • Solubility
  • Melting Point 214 °C
  • Formula C24H32O4
  • Boiling Point 507.1 °C at 760 mmHg
  • Molecular Weight 384.516
  • Flash Point 218.5 °C
  • Transport Information
  • Appearance Crystalline Solid
  • Safety 22-24/25
  • Risk Codes 40-48
  • Molecular Structure Molecular Structure of 595-33-5 (Megestrol acetate)
  • Hazard Symbols HarmfulXn
  • 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;
  • PSA 60.44000
  • LogP 4.57530

Synthetic route

methyl bromide
74-83-9

methyl bromide

C27H38O7

C27H38O7

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
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%
methoxymethyl acetate
4382-76-7

methoxymethyl acetate

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

hydroxyprogesterone acetate

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
With sodium acetate; trichlorophosphate In chloroform at 70℃; for 0.166667h;51%
With sodium acetate; trichlorophosphate In chloroform
Medroxyprogesterone acetate
71-58-9

Medroxyprogesterone acetate

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
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
Medroxyprogesterone acetate
71-58-9

Medroxyprogesterone acetate

chloranil
118-75-2

chloranil

acetic acid
64-19-7

acetic acid

ethyl acetate
141-78-6

ethyl acetate

Megestrol acetate
595-33-5

Megestrol acetate

...Expand
Medroxyprogesterone acetate
71-58-9

Medroxyprogesterone acetate

chloranil
118-75-2

chloranil

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Megestrol acetate
595-33-5

Megestrol acetate

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

3-Methoxy-17α-acetoxy-6-methyl-pregnadien-(3,5)-on-(20)

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
With acetic anhydride In tetrachloromethane
6-methylpregn-5-ene-3β,17α-diol-20-one 17-acetate
2381-48-8

6-methylpregn-5-ene-3β,17α-diol-20-one 17-acetate

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
With aluminum tri-tert-butoxide; p-benzoquinone
3β-acetoxy-17α-hydroxy-5-pregnen-20-one
1863-39-4

3β-acetoxy-17α-hydroxy-5-pregnen-20-one

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
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
Medroxyprogesterone
520-85-4

Medroxyprogesterone

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; toluene-4-sulfonic acid
2: tetrachloro-<1,4>benzoquinone
View Scheme
3β,5,17-trihydroxy-6β-methyl-5α-pregnan-20-one
113665-92-2

3β,5,17-trihydroxy-6β-methyl-5α-pregnan-20-one

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
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
5,17-dihydroxy-6β-methyl-5α-pregnane-3,20-dione
23706-51-6

5,17-dihydroxy-6β-methyl-5α-pregnane-3,20-dione

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous HCl
2: acetic acid; toluene-4-sulfonic acid
3: tetrachloro-<1,4>benzoquinone
View Scheme
20,20-ethanediyldioxy-6β-methyl-5α-pregnane-3β,5,17-triol
19699-76-4

20,20-ethanediyldioxy-6β-methyl-5α-pregnane-3β,5,17-triol

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: aqueous methanol.H2SO4
2: CrO3; pyridine
3: aqueous HCl
4: acetic acid; toluene-4-sulfonic acid
5: tetrachloro-<1,4>benzoquinone
View Scheme
3β-acetoxy-20,20-ethanediyldioxy-pregn-5-en-17-ol
19699-74-2

3β-acetoxy-20,20-ethanediyldioxy-pregn-5-en-17-ol

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: peroxybenzoic acid; chloroform
2: benzene; diethyl ether
3: aqueous methanol.H2SO4
4: CrO3; pyridine
5: aqueous HCl
6: acetic acid; toluene-4-sulfonic acid
7: tetrachloro-<1,4>benzoquinone
View Scheme
3β-acetoxy-20,20-ethanediyldioxy-5,6α-epoxy-5α-pregnan-17-ol
19699-75-3

3β-acetoxy-20,20-ethanediyldioxy-5,6α-epoxy-5α-pregnan-17-ol

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: benzene; diethyl ether
2: aqueous methanol.H2SO4
3: CrO3; pyridine
4: aqueous HCl
5: acetic acid; toluene-4-sulfonic acid
6: tetrachloro-<1,4>benzoquinone
View Scheme
17α-Acetoxy-6-methylene-pregn-4-ene-3,20-dione
32634-95-0

17α-Acetoxy-6-methylene-pregn-4-ene-3,20-dione

Megestrol acetate
595-33-5

Megestrol acetate

Conditions
ConditionsYield
With sodium acetate; palladium on activated charcoal; 4-methylcyclohexene In ethanol Heating / reflux;
Megestrol acetate
595-33-5

Megestrol acetate

17α-acetoxy-3-β-hydroxy-6-methylpregna-4,6-dien-20-one
2233-58-1

17α-acetoxy-3-β-hydroxy-6-methylpregna-4,6-dien-20-one

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 5h;97%
With sodium tetrahydroborate In methanol for 0.5h;94.5%
With lithium tri(t-butoxy)aluminum hydride In tetrahydrofuran at 0℃;
Megestrol acetate
595-33-5

Megestrol acetate

megestrol
3562-63-8

megestrol

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 1.5h; Heating;94%
With sodium methylate
With sodium hydroxide In methanol; water
Megestrol acetate
595-33-5

Megestrol acetate

6-Methyl-1,4,6-pregnatrien-17α-ol-3,20-dione Acetate

6-Methyl-1,4,6-pregnatrien-17α-ol-3,20-dione Acetate

Conditions
ConditionsYield
With bunazosin In 1,4-dioxane; ethyl acetate90%

Megestrol acetate Chemical Properties

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.

Megestrol acetate Uses

Efficacy of medroxyprogesterone acetate (MPA) intermediates

Megestrol acetate 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.

Megestrol acetate 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 .

Megestrol acetate 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) .

Megestrol acetate 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.

Megestrol acetate Standards and Recommendations

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

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