1054-64-4

Basic information

• Product Name: 17-(Acetyloxy)-3-Methoxy-pregna-3,5-dien-20-one
• Synonyms: 17-(Acetyloxy)-3-Methoxy-pregna-3,5-dien-20-one;Chlormadinone acetate impurity H
• CAS NO: 1054-64-4
• Molecular Formula: C₂₄H₃₄O₄
• Molecular Weight: 386.52436
• Mol File: 1054-64-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 17-(Acetyloxy)-3-Methoxy-pregna-3,5-dien-20-one(CAS DataBase Reference)
• NIST Chemistry Reference: 17-(Acetyloxy)-3-Methoxy-pregna-3,5-dien-20-one(1054-64-4)
• EPA Substance Registry System: 17-(Acetyloxy)-3-Methoxy-pregna-3,5-dien-20-one(1054-64-4)

Safety Data

• Hazardous Substances Data: 1054-64-4(Hazardous Substances Data)

Usage

General Description

17-(Acetyloxy)-3-Methoxy-pregna-3,5-dien-20-one is a synthetic steroid compound that belongs to the class of pregnane derivatives. It is also known as 17-O-acetyl 3-O-methyl progesterone and is commonly used in the pharmaceutical industry as an intermediate for the synthesis of various steroid-based drugs. This chemical is a progestin, which means it has progesterone-like effects, and it is often utilized in hormonal contraception and hormone replacement therapy. It has a molecular formula of C24H32O4 and a molecular weight of 384.5 g/mol. 17-(Acetyloxy)-3-Methoxy-pregna-3,5-dien-20-one has potential medical applications and is an important component in the production of various pharmaceutical products.

Upstream product

• 4134-58-1 hydroxyprogesterone acetate 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 302-22-7 chlormadinone acetate 
• 57361-81-6 17α-acetoxy-6-formyl-3-methoxypregna-3,5-dien-20-one 
• 425-51-4 17-acetoxy-pregna-4,6-diene-3,20-dione 
• 32634-95-0 17α-Acetoxy-6-methylene-pregn-4-ene-3,20-dione 

Relevant articles and documents

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.

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.