32634-95-0

Basic information

• Product Name: 17-hydroxy-6-methylenepregn-4-ene-3,20-dione 17-acetate
• Synonyms: 17-hydroxy-6-methylenepregn-4-ene-3,20-dione 17-acetate;17-Acetoxy-6-methylene-4-pregnene-3,20-dione;17-Acetyloxy-6-methyleneprogn-4-ene-3,20-dione;17-(Acetyloxy)-6-methylenepregn-4-ene-3,20-dione;6-Methylene-17-acetoxypregna-4-ene-3,20-dione;Dehydromedroxyprogesterone acetate;Einecs 251-133-8;Nsc 58799
• CAS NO: 32634-95-0
• Molecular Formula: C₂₄H₃₂O₄
• Molecular Weight: 384.50848
• EINECS: 251-133-8
• Product Categories: API
• Mol File: 32634-95-0.mol

Chemical Properties

• Melting Point: 248-251℃ (methanol )
• Boiling Point: 507.6 °C at 760 mmHg
• Flash Point: 218.7 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 2E-10mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• Water Solubility: 300μg/L at 20℃
• CAS DataBase Reference: 17-hydroxy-6-methylenepregn-4-ene-3,20-dione 17-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 17-hydroxy-6-methylenepregn-4-ene-3,20-dione 17-acetate(32634-95-0)
• EPA Substance Registry System: 17-hydroxy-6-methylenepregn-4-ene-3,20-dione 17-acetate(32634-95-0)

Safety Data

• Hazardous Substances Data: 32634-95-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
17-Hydroxy-6-methylenepregn-4-ene-3,20-dione 17-acetate is used as an impurity in the production of Medroxyprogesterone 17-Acetate (M203560) for pharmaceutical applications. Medroxyprogesterone 17-Acetate is a synthetic progestin hormone with various medical uses, including hormone replacement therapy, treatment of endometriosis, and contraception. As an impurity, 17-Hydroxy-6-methylenepregn-4-ene-3,20-dione 17-acetate is essential for maintaining the quality and efficacy of the final product, ensuring that it meets the required standards as per the European Pharmacopeia (EP).

InChI:InChI=1/C24H32O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h13,18-20H,1,6-12H2,2-5H3

Upstream product

• 109-87-5 Dimethoxymethane 
• 4134-58-1 hydroxyprogesterone acetate 
• 462-95-3 formaldehyde diethyl acetal 
• 1054-64-4 17α-acetoxy-3-methoxypregna-3,5-dien-20-one 
• 2568-89-0 diisopropoxymethane 
• 50-00-0 formaldehyd 
• 68-96-2 17-hydroxyprogesterone 
• 4954-07-8 pregna-3,5-dien-20-one, 3,17-dihydroxy-, diacetate 
• 1498-51-7 ethyl phosphodichloridite 
• 53476-47-4 3-Methoxy-20-oxo-6-hydroxymethyl-17α-acetoxy-pregnadien-(3,5) 
• 57361-81-6 17α-acetoxy-6-formyl-3-methoxypregna-3,5-dien-20-one 

Downstream Products

• 595-33-5 Megestrol acetate 
• 71-58-9 Medroxyprogesterone acetate 

Relevant articles and documents

Preparation method of 6-methylene-17alpha-hydroxyprogesterone acetate

The invention discloses a preparation method of 6-methylene-17alpha-hydroxyprogesterone acetate. The preparation method comprises the following steps: (1) enabling 17alpha-hydroxyl progesterone to have acylation reaction with 0.025 to 0.1 time of amount of substance of catalyst and 1 to 10 times of amount of substance of acetic anhydride, then adding 1 to 1.5 times of amount of substance of Mannich reagent into 2 to 10 times of mass ratio of solvent to have reaction, wherein the reaction temperature is -10 DEG C to 60 DEG C, the reaction time is 3 to 10 hours, and obtaining 6-methylene-17alpha-hydroxyprogesterone acetate tertiary amine; and (2) enabling the 6-methylene-17alpha-hydroxyprogesterone acetate tertiary amine to have reaction with 1 to 10 times of amount of substance of acid, wherein the reaction temperature is -10 DEG C to 70 DEG C, the reaction time is 1 to 5 hours, thus obtaining the product 6-methylene-17alpha-hydroxyprogesterone acetate. By adopting the preparation method, medroxyprogesterone and megestrol acetate progestational hormone can be conveniently prepared. The preparation method has the characteristics of good quality, high yield and easiness in industrialization, and has important significance on preparing sterides drugs.

PROCESS FOR PREPARING 17ALPHA-ACETOXY-6-METHYLENEPREGN-4-ENE-3,20-DIONE, MEDROXYPROGESTERONE ACETATE AND MEGESTROL ACETATE

The present invention relates to a process for preparing 17α-acetoxy-6-methylenepregn-4-ene-3,20-dione (4) as an intermediate, and to processes for preparing medroxyprogesterone acetate (1) (17α-acetoxy-6α-methylpregn-4-ene-3,20-dione) and megestrol acetate (2) (17α-acetoxy-6-methylpregna-4,6-diene-3,20-dione) via this intermediate (4).

Novel 17 substituted pregnadiene derivatives as 5α-reductase inhibitors and their binding affinity for the androgen receptor

The in vitro antiandrogenic activity of four new progesterone derivatives: 4, 5, 6 and 7 (8 is a known compound) was determined. These compounds were evaluated as 5α-reductase inhibitors as well as by their capacity to bind to the androgen receptor in gonadectomized hamster prostate. The IC50 value was determined using increasing concentrations of 4, 5, 6, 7 and 8 in the presence of [3H]T and the microsomal fraction of the hamster prostate containing the 5α-reductase enzyme. In this paper we also demonstrated the effect of increasing concentrations of the novel steroids upon [3H]DHT binding to the androgen receptors from hamster prostate which produces competition for the androgen receptor sites. The in vitro studies showed that steroids 4, 5, 6, 7 and 8 had an inhibitory activity for the 5α-reductase with IC50 of: 4 (0.17 μM), 5 (0.19 μM), 6 (1 μM), 7 (4.2 μM), and 8 (2.7 μM). On the other hand, the IC 50 value for compounds 4, 5, 6, 7, 8 and DHT showed the following order of affinity for the androgen receptor: 6>7>5>DHT. Surprisingly compounds 4 and 8 did not bind to the androgen receptor. The overall data indicate that all synthesized compounds are inhibitors for the enzyme 5α-reductase present in the hamster prostate. In contrast, compounds 5, 6 and 7, which have a cyclohexyl group in the side chain showed a high affinity for the androgen receptor.

Molecular interactions of new pregnenedione derivatives.

The in vitro inhibitory activity of five new progesterone derivatives: 17alpha-hydroxy-16beta-methylpregna-1,4,6-triene-3,20-dione 1; 16beta-methyl-17alpha-toluoyloxypregna-1,4,6-triene-3,20-dione 2; 17alpha-hydroxy-6-methylenepregn-4-ene-3,20-dione 3; 6-methylene-17alpha-toluoyloxypregn-4ene-3,20-dione 4 and 17alpha-(p-bromobenzoyloxy)-6-methylenepregn-4-ene-3,20-dione 5 was determined. These compounds were evaluated as 5alpha-reductase inhibitors as well as antagonists for the androgen receptor. Compounds 1, 2, 3, 4 and 5 showed the following inhibitory activity for the 5alpha-reductase enzyme with IC(50) values of: 1 (1.65 microM), 2 (10 microM), 3 (19 nM), 4 (100 nM) and 5 (100 nM). The results of this study also showed the effect of increasing concentrations of the novel steroids upon [(3)H]dihydrotestosterone binding to androgen receptors from male hamster prostate. The K(i) values for compounds 1, 2, 3, 4, 5 and dihydrotestosterone showed the following order of affinity for the androgen receptor: 4>5>dihydrotestosterone>2>3>1. The overall data indicated that all synthesized compounds 1, 2, 3, 4 and 5 are inhibitors of the 5alpha-reductase enzyme present in the hamster prostate. In addition compounds 1, 2, 3, 4 and 5 also presented an affinity for the androgen receptor.

Process for preparing 6-methylene steroids

A process for preparing a 6-methylene-Δ4 -3-keto steroid of the formula STR1 wherein R is hydrogen, alkoxy of up to 6 carbon atoms or acyloxy of up to 6 carbon atoms wherein the acyl group is that of a carboxylic acid, and R' is the CD-ring system of a steroid of the androstane or pregnane series, comprising reacting the corresponding Δ4 -3-keto steroid of the formula STR2 with a formaldehyde derivative of the formula wherein n is 1, 3 or an integer on the order of 100-1000, and X is C1-5 alkoxy and Y is C1-5 alkyl when n is 1, X and Y represent a single bond between the terminal C atom and the terminal O atom when n is 3, and X is hydroxy and Y is hydrogen when n is an integer on the order of 100-1000, in an inert solvent in the presence of a condensation agent which is a strong acid a strongly acidic cation exchanger or a phosphoric acid derivative.

Phosphate catalyzed acylation of steroidal tertiary alcohols

The process of the invention permits acylation of hindered steroidal tertiary alcohols without the undesirable side reactions which accompany previously known acylation reactions.