Medroxyprogesterone 17-acetate supplier

Name
Medroxyprogesterone 17-acetate
EINECS 200-757-9
CAS No. 71-58-9
Article Data32
CAS DataBase
Density 1.13 g/cm³
Solubility <0.1 g/100 mL at 23 °C in water
Melting Point 206-207 °C(lit.)
Formula C₂₄H₃₄O₄
Boiling Point 496.4 °C at 760 mmHg
Molecular Weight 386.532
Flash Point 213.2 °C
Transport Information
Appearance white crystalline powder
Safety 22-36/37/39-45
Risk Codes 40-48
Molecular Structure
Hazard Symbols Xn
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride

: 520-85-4
Medroxyprogesterone

: 108-24-7
acetic anhydride

: 71-58-9
Medroxyprogesterone acetate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 151-68-8
17-acetoxy-6α-methyl-pregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
With pyridine; selenium(IV) oxide; tert-butyl alcohol

: 71-58-9
Medroxyprogesterone acetate

: 520-85-4
Medroxyprogesterone

Conditions

Conditions	Yield
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

...Expand

: 71-58-9
Medroxyprogesterone acetate

: 118-75-2
chloranil

: 75-65-0
tert-butyl alcohol

: 595-33-5
Megestrol acetate

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
(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

Conditions	Yield
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

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

...Expand

: 71-58-9
Medroxyprogesterone acetate

: 69688-15-9
17α-acetoxy-6α-methyl-5β-pregnane-3,20-dione

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
(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

Conditions	Yield
With triethylamine In ethanol

...Expand

: 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

Conditions	Yield
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

...Expand

: 71-58-9
Medroxyprogesterone acetate

: 113891-97-7
17α-acetoxy-3α-hydroxy-6α-methyl-5α-pregnan-20-one

Conditions

Conditions	Yield
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

Medroxyprogesterone 17-acetate Chemical Properties

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

Medroxyprogesterone 17-acetate 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.

Medroxyprogesterone 17-acetate Safety Profile

Hazard Codes: Harmful Xn
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

Medroxyprogesterone 17-acetate 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.

Product Name

Medroxyprogesterone 17-acetate

Synthetic route

Medroxyprogesterone 17-acetate Chemical Properties

Medroxyprogesterone 17-acetate Toxicity Data With Reference

Medroxyprogesterone 17-acetate Safety Profile

Medroxyprogesterone 17-acetate Specification

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