17308-02-0

Basic information

• Product Name: 3,20-Dioxopregn-4-en-17-beta-yl acetate
• Synonyms: 17-HYDROXYPROGESTERONE ACETATE;17-ALPHA-HYDROXYPROGESTERONE 17-ACETATE;17ALPHA-HYDROXYPROGESTERONE ACETATE;17ALPHA-HYDROXY-4-PREGNENE-3,20-DIONE 17-ACETATE;17ALPHA-ACETOXYPROGESTERONE;17-ACETOXYPROGESTERONE;17ALPHA-ACETOXY-4-PREGNENE-3,20-DIONE;ACETIC ACID (8R,9S,10R,13S,14S,17R)-17-ACETYL-10,13-DIMETHYL-3-OXO-2,3,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-17-YL ESTER
• CAS NO: 17308-02-0
• Molecular Formula: C₂₃H₃₂O₄
• Molecular Weight: 372.5
• EINECS: 206-119-6
• Mol File: 17308-02-0.mol

Chemical Properties

• Melting Point: 198 °C
• Boiling Point: 490.2 °C at 760 mmHg
• Flash Point: 211.576 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.543
• CAS DataBase Reference: 3,20-Dioxopregn-4-en-17-beta-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3,20-Dioxopregn-4-en-17-beta-yl acetate(17308-02-0)
• EPA Substance Registry System: 3,20-Dioxopregn-4-en-17-beta-yl acetate(17308-02-0)

Safety Data

• Hazard Codes: Xn
• Statements: 40-48
• Safety Statements: 22-24/25-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: TU5074000
• Hazardous Substances Data: 17308-02-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,20-Dioxopregn-4-en-17-beta-yl acetate is used as an anti-inflammatory and immunosuppressive drug for the treatment of a wide range of conditions. It is particularly effective in managing asthma, uveitis, pyoderma gangrenosum, rheumatoid arthritis, ulcerative colitis, temporal arteritis, Crohn's disease, Bell's palsy, multiple sclerosis, cluster headaches, and autoimmune hepatitis. The drug works by suppressing the immune system's response to different stimuli, thereby reducing inflammation and alleviating symptoms associated with these conditions.
Used in Medical Treatments:
3,20-Dioxopregn-4-en-17-beta-yl acetate is used as a therapeutic agent in the management of various inflammatory and autoimmune diseases. Its potent anti-inflammatory and immunosuppressive properties make it a valuable tool in the treatment of conditions such as asthma, uveitis, and rheumatoid arthritis. By dampening the body's immune response, it helps to control the symptoms and prevent the progression of these diseases.

InChI:InChI=1/C23H32O4/c1-14(24)23(27-15(2)25)12-9-20-18-6-5-16-13-17(26)7-10-21(16,3)19(18)8-11-22(20,23)4/h13,18-20H,5-12H2,1-4H3/t18-,19+,20+,21+,22+,23+/m1/s1

Upstream product

• 68-96-2 17-hydroxyprogesterone 
• 108-24-7 acetic anhydride 
• 4954-07-8 pregna-3,5-dien-20-one, 3,17-dihydroxy-, diacetate 
• 1600-27-7 mercury(II) diacetate 
• 65851-76-5 17α-ethynyl-17β-nitro-oxy-4-androsten-3-one 
• 434-03-7 levonorgestrel 
• 141-78-6 ethyl acetate 
• 2542-26-9 (8R,9S,10R,13S,14S,17R)-17-ethynyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate 
• 109-63-7 trifluoroborane diethyl ether 
• 64-19-7 acetic acid 
• 1250-99-3 3β.17-diacetoxy-17βH-pregnen-(5)-yne-(20) 
• 40264-22-0 21-bromo-17-acetoxy-17βH-pregnene-(4)-dione-(3.20) 
• 127-09-3 sodium acetate 
• 1176-21-2 3β,17-diacetoxy-17βH-pregn-5-en-20-one 

Downstream Products

• 4954-07-8 pregna-3,5-dien-20-one, 3,17-dihydroxy-, diacetate 
• 32634-95-0 17α-Acetoxy-6-methylene-pregn-4-ene-3,20-dione 
• 16319-93-0 17-acetoxy-3-ethoxy-pregna-3,5-dien-20-one 
• 1054-64-4 17α-acetoxy-3-methoxypregna-3,5-dien-20-one 
• 13583-20-5 4-chloro-17-α hydroxy-4-pregnene-3,20-dione 
• 89202-94-8 3β,17α-Dihydroxypregna-4,6-dien-20-one 17-acetate 3-caproate 
• 2477-60-3 17α-hydroxypregna-4,6-diene-3,20-dione 
• 81480-72-0 17α-benzoyloxy-4,6-pregnadiene-3,20-dione 
• 1190878-46-6 17α-p-fluorobenzoyloxy-4,6-pregnadiene-3,20-dione 
• 1190878-47-7 17α-p-chlorobenzoyloxy-4,6-pregnadiene-3,20-dione 
• 1190878-48-8 17α-p-bromobenzoyloxy-4,6-pregnadiene-3,20-dione 
• 1616932-84-3 17α-p-iodobenzoiloxy-4,6-pregnadien-3,20-dione 
• 1616932-85-4 17α-phenylcarbamoiloxypregn-4,6-dien-3,20-dione 
• 1616932-86-5 17α-p-fluorophenylcarbamoiloxypregn-4,6-dien-3,20-dione 

Relevant articles and documents

Preparation process of 17a-hydroxyprogesterone acetate

The invention discloses a preparation process of 17a-hydroxyprogesterone acetate. According to the invention, high-purity 17a-hydroxyprogesterone acetate is obtained sequentially through an acylation reaction, a hydrolysis reaction, a neutralization reaction, centrifugation and refining. Therefore, a process procedure is shortened, raw material input is reduced, and cost is saved.

Further syntheses of cyproterone acetate

The present invention relates to improved methods for synthesising cyproterone acetate (17α-Acetoxy-6-chloro-1α, 2α-methylene-4,6-pregnadiene-3,20-dione) from solasodine. The methods of the invention are shorter as those of the prior art and therefore more economic.

Microwave induced selective enolization of steroidal ketones and efficient acetylation of sterols in semisolid state

Under microwave irradiation steroidal enones, more specifically, position three carbonyls were efficiently and selectively converted to the corresponding enol acetates in the presence of additional enolizable carbonyl functions at other positions, using acetic anhydride and a catalytic amount of toluene-p-sulfonic acid. Acetylation of hydroxyl groups of the sterols, including those at the hindered positions, was near quantitative. Strictly anhydrous conditions were not a pre-requisite for acetylation and the reaction system easily tolerated up to 10% (v/v) moisture.

15β-Hydroxysteroids (part V). Steroids of the human perinatal period: The synthesis of 3β, 15β, 17α-trihydroxy-5-pregnen-20- one from 15β, 17α-dihydroxy-4-pregnen-3,20-dione

A simple three-step synthetic method is reported on the conversion of Δ4-3-ketosteroids to the corresponding 3β- hydroxy-Δ5-steroid analogues. 17α-Hydroxy-4-pregnen-3,20-dione (10a) was used as a model to develop a method for the synthesis of 3β,17α-dihydroxy-5-pregnen-20-one (16). The major problem being the synthesis of 3,17α-diacetoxy-3,5-pregnadien-20-one (14) was solved by acetylating using a mixture of acetic anhydride and perchloric acid. The conversion of 15β,17α-dihydroxy-4-pregnen- 3,20-dione (8), product of Penicillium citrinum fermentation, to the desired 3β, 15β, 17α-trihydroxy-5-pregnen-20-one (1), is described using a modification of this method. Reaction of 8 with acetic anhydride and perchloric acid in ethyl acetate gave 3,15β,17α-triacetoxy-3,5-pregnadien-20-one (17) which on reduction with sodium borohydrice gave 5-pregnen-3β,15β,17α, 20(S + R)-tetrols (18a and 18b); however, reduction of 17 with a mixture of sodium borohydride and potassium bicarbonate gave after basic hydrolysis with metanolic sodium hydroxide the desired product 3β,15β,17α-trihydroxy-5-pregnen-20-one (1) in good yield (54%).

Anti-glaucomatous pharmaceutical composition and the process for obtaining them

The invention relates to the domain of medicinal chemistry. It concerns more particularly that of the preparation of pharmaceutical compositions for ocular use. A subject of the invention is pharmaceutical compositions for ocular use characterized in that they contain at least one selected compound of steroidal structure in combination with or admixed with a pharmaceutically-acceptable, inert carrier or vehicle. The compositions according to the invention are intended to the treatment of glaucoma.

REDUCTIVE DEHALOGENATION OF 21-IODO DERIVATIVES OF CORTICOSTEROIDS

In the reactions of 21-iodo derivatives of corticosteroids with hydrogen sulfide and thiol-containing reagents in a medium of dipolar aprotic and amide protogenic solvents at room temperature reductive-deiodination reactions occur with the formation of 21-deoxycorticosteroids in quantitative yield.Reactions of solutions of 21-iodomethyl ketones, heated to 80 deg C, with hydrogen sulfide and thiol-containing reagents give not only reduction products, but also products of nucleophilic substitution at C21 in yields of 20-30percent.

A NEW PROCEDURE TO Δ4-3-KETOSTEROIDS FROM 5β-3-KETOSTEROIDS

A convenient two-step process for the conversion of 5β-3-Ketosteroid series into the corresponding Δ4-enones is described.This transformation was achieved by first forming the corresponding Δ3-enol acetate which in turn was oxidized to the enone with chromium oxidizing reagents.

Mercury removal process

Oxymercuration reaction products (I) and/or mercury contaminated steroids (I) are purified by dissolving the compound in a suitable solvent and contacting with a metal dust selected from zinc, copper or iron and a suitable acid.

Process for preparing 17α-hydroxy-pregn-4-en-3,20-dione derivatives

The invention relates to a novel process for the preparation of pregnane derivatives of formula I, STR1 wherein R1 stands for a methyl or an ethyl group, R2 represents a hydrogen atom or a methyl group, and X is a hydrogen atom or a formyl or acetyl group, and the bond indicated by a dotted and a continuous line stands for a single or a double bond between the two neighboring carbon atoms. According to the invention a trifluoroacetate ester of formula II, STR2 wherein R1 and R2 are as defined above, is reacted with formic acid or acetic acid in the presence of a catalytic amount of a mercury salt in a dipolar proton-free or basic solvent. The formyl or acetyl group being in the place of X can be split off in a way known per se. The process provides a novel advantageous method for building up the pregnane side chain characteristic of corticoids.

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.