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71-58-9

Basic Information
CAS No.: 71-58-9
Name: Medroxyprogesterone 17-acetate
Molecular Structure:
Molecular Structure of 71-58-9 (Medroxyprogesterone 17-acetate)
Formula: C24H34O4
Molecular Weight: 386.58
Synonyms: Pregn-4-ene-3,20-dione,17-hydroxy-6a-methyl-, acetate(7CI,8CI);Progesterone, 17-hydroxy-6a-methyl-, acetate (6CI);17a-Acetoxy-6a-methylprogesterone;17a-Hydroxy-6a-methyl-4-pregnene-3,20-dione17-acetate;17a-Hydroxy-6a-methylprogesteroneacetate;6a-Methyl-17-acetoxyprogesterone;6a-Methyl-17a-acetoxy-D4-pregnene-3,20-dione;6a-Methyl-17a-acetoxypregn-4-ene-3,20-dione;Amen;CBP 1011;Clinovir;Colirest;Curretab;Cycrin;DMPA;Depo-Prodasone;Depo-Ralovera;Depo-promone;Depomedroxyprogesterone acetate;Farlutal;Farlutin;Lutoral;Medroprogesterone acetate;
EINECS: 200-757-9
Density: 1.13 g/cm3
Melting Point: 206-207 °C(lit.)
Boiling Point: 496.4 °C at 760 mmHg
Flash Point: 213.2 °C
Solubility: <0.1 g/100 mL at 23 °C in water
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 40-48
Safety: 22-36/37/39-45
Transport Information:
PSA: 60.44000
LogP: 4.51270
Synthetic route
32634-95-0

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

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
With ethanol; 5%-palladium/activated carbon In cyclohexene at 75 - 78℃; for 5h; Reagent/catalyst; Temperature;87.5%
With sodium acetate; cyclohexene; palladium on activated charcoal In ethanol; water Heating / reflux;
809-01-8

3-cycloethylenedioxy-6-methyl-17α-acetoxy-pregn-5-ene-20-one

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
With silica gel; copper(II) sulfate In chloroform for 2h; Heating;81%
2381-48-8

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

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
With cyclohexanone; aluminum isopropoxide; toluene
With aluminum isopropoxide
986-96-9

3,17-diacetoxy-6-methyl-pregna-3,5-dien-20-one

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
With hydrogenchloride
520-85-4

Medroxyprogesterone

108-24-7

acetic anhydride

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid; acetic acid

6-Formil-3-(2'-chloro-etossi)-Δ3,5-pregnadien-17α-ol-20-one acetato

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol
1863-39-4

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

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 7 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
View Scheme
113665-92-2

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

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CrO3; pyridine
2: aqueous HCl
3: acetic acid; toluene-4-sulfonic acid
View Scheme
23706-51-6

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

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous HCl
2: acetic acid; toluene-4-sulfonic acid
View Scheme
Multi-step reaction with 2 steps
1: HCl; CHCl3
2: acetic acid; toluene-4-sulfonic acid
View Scheme
Multi-step reaction with 3 steps
1: pyridine; aq. NaOH solution
2: HCl; CHCl3
3: acetic acid; toluene-4-sulfonic acid
View Scheme
19699-76-4

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

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aqueous methanol.H2SO4
2: CrO3; pyridine
3: aqueous HCl
4: acetic acid; toluene-4-sulfonic acid
View Scheme
19699-74-2

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

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 6 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
View Scheme
19699-75-3

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

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: benzene; diethyl ether
2: aqueous methanol.H2SO4
3: CrO3; pyridine
4: aqueous HCl
5: acetic acid; toluene-4-sulfonic acid
View Scheme
60446-57-3

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

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous methanol. HCl
2: cyclohexanone; aluminium isopropylate; toluene
View Scheme
80996-18-5

17-hydroxy-6β-methyl-pregn-4-ene-3,20-dione

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl; CHCl3
2: acetic acid; toluene-4-sulfonic acid
View Scheme
3386-01-4

3,3;20,20-bis-ethanediyldioxy-6β-methyl-5α-pregnane-5,17-diol

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetone / saure Hydrolyse
2: HCl; CHCl3
3: acetic acid; toluene-4-sulfonic acid
View Scheme
Multi-step reaction with 4 steps
1: acetone / saure Hydrolyse
2: pyridine; aq. NaOH solution
3: HCl; CHCl3
4: acetic acid; toluene-4-sulfonic acid
View Scheme
3386-00-3

17-hydroxy-5-pregnene-3,20-dione 3,20-bisethylene ketal

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: peroxyacetic acid
2: tetrahydrofuran
3: acetone / saure Hydrolyse
4: HCl; CHCl3
5: acetic acid; toluene-4-sulfonic acid
View Scheme
Multi-step reaction with 6 steps
1: peroxyacetic acid
2: tetrahydrofuran
3: acetone / saure Hydrolyse
4: pyridine; aq. NaOH solution
5: HCl; CHCl3
6: acetic acid; toluene-4-sulfonic acid
View Scheme
3496-78-4

3,3;20,20-bis-ethanediyldioxy-5,6α-epoxy-5α-pregnan-17-ol

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrahydrofuran
2: acetone / saure Hydrolyse
3: HCl; CHCl3
4: acetic acid; toluene-4-sulfonic acid
View Scheme
Multi-step reaction with 5 steps
1: tetrahydrofuran
2: acetone / saure Hydrolyse
3: pyridine; aq. NaOH solution
4: HCl; CHCl3
5: acetic acid; toluene-4-sulfonic acid
View Scheme
520-85-4

Medroxyprogesterone

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; toluene-4-sulfonic acid
2: methanol.HCl
View Scheme

3β-Formyloxy-6-methyl-Δ5-pregnen-17α-acetoxy-20-on

71-58-9

Medroxyprogesterone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. HCl
2: Al(OiPr)3
View Scheme
95-20-5

2-methyl-1H-indole

71-58-9

Medroxyprogesterone acetate

1233478-27-7

C33H43NO4

Conditions
ConditionsYield
With rhodium(III) chloride hydrate In methanol for 2.5h; Michael addition; Reflux; diastereoselective reaction;95%
603-76-9

1-methylindole

71-58-9

Medroxyprogesterone acetate

1233478-26-6

C33H43NO4

Conditions
ConditionsYield
With rhodium(III) chloride hydrate In methanol for 6h; Michael addition; Reflux; diastereoselective reaction;78%
71-58-9

Medroxyprogesterone acetate

11β-hydroxy-medroxyprogesterone acetate

Conditions
ConditionsYield
With Absidia griseollavar. igachii In ethanol at 25℃; for 240h; Reagent/catalyst; Temperature; Microbiological reaction; regioselective reaction;63%
71-58-9

Medroxyprogesterone acetate

17α-acetyloxy-6-methylpregna-3,5-dien-20-one

Conditions
ConditionsYield
Stage #1: Medroxyprogesterone acetate With C19H26ClIrN3O(1+)*Cl(1-) In water at 80℃; for 0.166667h;
Stage #2: With formic acid In water at 80℃; for 4h; regioselective reaction;
62%
71-58-9

Medroxyprogesterone 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
71-58-9

Medroxyprogesterone acetate

151-68-8

17-acetoxy-6α-methyl-pregna-1,4-diene-3,20-dione

Conditions
ConditionsYield
With pyridine; selenium(IV) oxide; tert-butyl alcohol
71-58-9

Medroxyprogesterone acetate

520-85-4

Medroxyprogesterone

Conditions
ConditionsYield
With potassium hydroxide
With water; sodium hydroxide In methanol for 5h; Reflux;
71-58-9

Medroxyprogesterone acetate

118-75-2

chloranil

64-19-7

acetic acid

141-78-6

ethyl acetate

595-33-5

Megestrol acetate

71-58-9

Medroxyprogesterone acetate

118-75-2

chloranil

75-65-0

tert-butyl alcohol

595-33-5

Megestrol acetate

71-58-9

Medroxyprogesterone acetate

123-62-6

propionic acid anhydride

114552-99-7

17-acetoxy-6-methyl-3-propionyloxy-pregna-3,5-dien-20-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid
71-58-9

Medroxyprogesterone acetate

A

anti-6α-Methyl-17α-acetoxy-Δ4-pregnen-20-on-3-N-chlorimin

B

syn-6α-Methyl-17α-acetoxy-Δ4-pregnen-20-on-3-N-chlorimin

Conditions
ConditionsYield
(i) MeNH2, MeOH, (ii) aq. Ca(OCl)2, NH3, OTs; Multistep reaction;
71-58-9

Medroxyprogesterone acetate

4124-31-6

trichloroacetic acid anhydride

22223-98-9

17α-Acetoxy-3-trichloracetoxy-6-methyl-Δ3,5-pregnadien-20-on

71-58-9

Medroxyprogesterone acetate

57-16-9

6α-methylpregn-4-ene-3β,17α-diol-20-one 17-acetate

Conditions
ConditionsYield
With lithium tri(t-butoxy)aluminum hydride In tetrahydrofuran at 0℃;
71-58-9

Medroxyprogesterone acetate

A

113891-97-7

17α-acetoxy-3α-hydroxy-6α-methyl-5α-pregnan-20-one

B

113891-98-8

17α-acetoxy-3β-hydroxy-6α-methyl-5α-pregnan-20-one

C

71315-38-3

17α-acetoxy-3α-hydroxy-6α-methyl-5β-pregnan-20-one

D

71315-40-7

17α-acetoxy-3β-hydroxy-6α-methyl-5β-pregnan-20-one

Conditions
ConditionsYield
With hydrogen; Rh on carbon In ethanol; acetic acid for 48h; Yield given. Yields of byproduct given;
71-58-9

Medroxyprogesterone acetate

69688-15-9

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

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate
With hydrogen; Lindlar's catalyst In pyridine for 24h;6.9 g
71-58-9

Medroxyprogesterone acetate

113846-17-6

6α-methylpregn-4-ene-3α,17α-diol-20-one 17-acetate

Conditions
ConditionsYield
With lithium tri-sec-butyl(hydrido)borate In tetrahydrofuran at -78℃;
71-58-9

Medroxyprogesterone acetate

3-Cloro-6-metil-Δ3,5-pregnadien-17α-ol-20-one acetato

Conditions
ConditionsYield
With N,N-dimethyl-formamide; trichlorophosphate
71-58-9

Medroxyprogesterone acetate

A

3α-Hydroxy-6α-methyl-5β-androstan-17-on

B

3β-Hydroxy-6α-methyl-5α-androstan-17-on

Conditions
ConditionsYield
(i) H2, Pd-C, AcOEt, (ii) LiAlH4, Et2O, (iii) aq. NaIO4, AcOH, EtOH; Multistep reaction;
50-00-0

formaldehyd

71-58-9

Medroxyprogesterone acetate

108-98-5

thiophenol

17α-Acetoxy-6β-methyl-4-phenylmercaptomethyl-progesteron

Conditions
ConditionsYield
With triethylamine In ethanol
71-58-9

Medroxyprogesterone acetate

149-73-5

trimethyl orthoformate

1104-99-0

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane
110-86-1

pyridine

7446-08-4

selenium(IV) oxide

71-58-9

Medroxyprogesterone acetate

75-65-0

tert-butyl alcohol

151-68-8

17-acetoxy-6α-methyl-pregna-1,4-diene-3,20-dione

71-58-9

Medroxyprogesterone acetate

113891-97-7

17α-acetoxy-3α-hydroxy-6α-methyl-5α-pregnan-20-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium tri-t-butoxyaluminium hydride / tetrahydrofuran / 0 °C
2: 47 mg / H2 / Rh-C / ethanol; acetic acid / 48 h
View Scheme
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    CAS:71-58-9 Medroxyprogesterone 17-acetate

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    Medroxyprogesterone 17-acetate

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    Medroxyprogesterone Acetate

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  • Medroxyprogesterone Acetate

  • Casno:

    71-58-9

    Medroxyprogesterone Acetate

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Chemistry

The Molecular Structure of Medroxyprogesterone Acetate (CAS NO.71-58-9):

Empirical Formula: C24H34O4
Molecular Weight: 386.5244
Appearance: white crystalline powder
Nominal Mass: 386 
Average Mass: 386.5244
Monoisotopic Mass: 386.24571
Index of Refraction: 1.538
Molar Refractivity: 106.71 cm3
Molar Volume: 340.8 cm3 
Surface Tension: 43.2 dyne/cm
Density: 1.13 g/cm3
Flash Point: 213.2 °C
Enthalpy of Vaporization: 76.41 kJ/mol
Boiling Point: 496.4 °C at 760 mmHg
Vapour Pressure: 5.44E-10 mmHg at 25 °C 
Water Solubility:  <0.1 g/100 mL at 23 °C 
Melting Point: 206-207 °C 
Stability: Stable, but weakly air and light sensitive. Incompatible with strong oxidizing agents
Classification Code: Antineoplastic Agents; Antineoplastic agents, hormonal; Contraceptive Agents; Contraceptive agents, female; Contraceptive agents, male; Drug / Therapeutic Agent; Hormone; Human Data; Mutation data; Progestin; Reproductive Control Agents; Reproductive Effect; Tumor data
IUPAC Name:  [(6S,8R,9S,10R,13S,14S,17R)-17-Acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate   
Synonyms: (6-Alpha)-17-(acetyloxy)-6-methylpreg-4-ene-3,20-dione ; 17-(Acetyloxy)-6-methyl-(6-alpha)-pregn-4-ene-20-dione ; 17-(Acetyloxy)-6-methyl-20-dion(6alpha)-pregn-4-ene- ; 17-Acetoxy-6-alpha-methylprogesterone ; 17-Alpha-hydroxy-6-alpha-methylpregn-4-ene-3,20-dioneacetate ; 17-Alpha-hydroxy-6-alpha-methyl-progesteronacetate ; 17-Alpha-hydroxy-6-alpha-methylprogesteroneacetate ; 17-Hydroxy-6-alpha-methylpregn-4-ene-3,20-dioneacetate  

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. -, Pg. 1196, 1990.
mouse LD50 intraperitoneal > 1500mg/kg (1500mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 18, Pg. 6135, 1984.
mouse LD50 oral > 16gm/kg (16000mg/kg) ENDOCRINE: ADRENAL CORTEX HYPOPLASIA Kiso to Rinsho. Clinical Report. Vol. 18, Pg. 6135, 1984.
mouse LD50 subcutaneous > 1500mg/kg (1500mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 18, Pg. 6135, 1984.
rat LD50 intraperitoneal > 900mg/kg (900mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 18, Pg. 6135, 1984.
rat LD50 oral > 6400mg/kg (6400mg/kg) LIVER: OTHER CHANGES Kiso to Rinsho. Clinical Report. Vol. 18, Pg. 6135, 1984.
rat LD50 subcutaneous > 900mg/kg (900mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 18, Pg. 6135, 1984.
women TDLo intravenous 10mg/kg (10mg/kg) SENSE ORGANS AND SPECIAL SENSES: INCREASED INTRAOCULAR PRESSURE: EYE Advances in Planned Parenthood. Vol. 8, Pg. 103, 1972.
women TDLo intravenous 21mg/kg (21mg/kg) SENSE ORGANS AND SPECIAL SENSES: INCREASED INTRAOCULAR PRESSURE: EYE Advances in Planned Parenthood. Vol. 8, Pg. 103, 1972.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 40-48 
R40: Limited evidence of a carcinogenic effect
R48: Danger of serious damage to health by prolonged exposur
Safety Statements: 22-36/37/39-45 
S22: Do not breathe dust
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection

S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS: TU5010000

Specification

Incompatibilities: Flammable and/or toxic gases are generated by combination with with alkali metals, nitrides, and strong reducing agents Reacts with oxoacids and carboxylic acids to form esters plus water Incompatible with oxidizing agents.