13074-00-5

Basic information

• Product Name: Azastene
• Synonyms: Azastene;4,4,17-Trimethylandrost-2-eno[2,3-d]isoxazol-5-en-17β-ol;4,4,17α-Trimethylandrost-2-eno[2,3-d]isoxazol-5-en-17β-ol;Win-17625;(17b)-4,4,17-Trimethylandrosta-2,5-dieno[2,3-d]isoxazol-17-ol
• CAS NO: 13074-00-5
• Molecular Formula: C23H33NO2
• Molecular Weight: 355.519
• Mol File: 13074-00-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 178.5°C
• Boiling Point: 488.52°C (rough estimate)
• Flash Point: 233.5°C
• Appearance: /
• Density: 1.14
• Vapor Pressure: 2.36E-09mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• CAS DataBase Reference: Azastene(CAS DataBase Reference)
• NIST Chemistry Reference: Azastene(13074-00-5)
• EPA Substance Registry System: Azastene(13074-00-5)

Safety Data

• Hazardous Substances Data: 13074-00-5(Hazardous Substances Data)

Usage

Originator

Azastene,ZYF Pharm Chemical

Manufacturing Process

A solution of 4,4,17α-trimethyl-androsta-2,5-dien-17β-ol-3-one in benzene was added to sodium methoxide (from sodium and of absolute methanol, concentrating the solution and drying the residue for 1 h at 150°-160°C and 15 mm). Ethyl formate was then added with stirring in a nitrogen atmosphere. The reaction mixture was stirred for 4 h at room temperature, allowed to stand for about 15 h, stirred for 2 h and then poured into water. The reaction mixture was extracted with benzene, the aqueous layer warmed until clear, filtered and cooled below room temperature. Concentrated hydrochloric acid and ice were added to the filtrate until the mixture was acid to Congo red, and the product was extracted with chloroform. The chloroform extracts were washed with water, dried over anhydrous sodium sulfate, filtered and concentrated vacuum, whereupon there separated 2-hydroxymethylene- 4,4,17α-trimethyl-androsta-2,5-dien-17β-ol-3-one. To a solution of sodium acetate in acetic acid was added hydroxylamine hydrochloride, and methanol was added until solution resulted. This solution was added to a solution of 2-hydroxymethylene-4,4,17α-trimethyl-androsta- 2,5-dien-17β-ol-3-one in absolute methanol, and the combined solution was refluxed for 40 min on a steam bath. The reaction mixture was concentrated, the residue extracted with ethyl acetate, and the ethyl acetate extracts were washed with ethyl acetate, and the ethyl acetate extracts were washed with 5% hydrochloric acid, dried over anhydrous sodium sulfate and concentrated whereupon there separated solid material. The mother liquors were concentrated to dryness and the residue recrystallized from ether to give solid product. The latter was chromatographed on a column of silica gel in benzene solution, recrystallized from ethyl acetate and dried at 75°C for 20 h to give 17β-hydroxy-4,4,17α- trimethyl-androsta-2,5-dien[2,3-d]isoxazole. The crude product was chromatographed on silica gel in benzene solution, eluted with benzene containing 5% of ether and recrystallized from ethanol to give 17β-hydroxy-4,4,17α-trimethyl-androsta-2,5-dien[2,3-d]isoxazole.

Therapeutic Function

Contraceptive

InChI:InChI=1/C23H33NO2/c1-20(2)18-7-6-15-16(21(18,3)12-14-13-24-26-19(14)20)8-10-22(4)17(15)9-11-23(22,5)25/h7,13,15-17,25H,6,8-12H2,1-5H3/t15?,16-,17-,21?,22?,23-/m0/s1

Upstream product

• 87425-81-8 17β-hydroxy-4,4,17α-trimethyl-3-oxo-androst-5-ene-2-carbaldehyde 

Downstream Products

• 4248-66-2 cyanoketone 

Related news

SCIENTIFIC ARTICLESInterceptive Activity of Azastene (cas 13074-00-5) in Rhesus Monkeys*09/10/2019

Azastene is an orally effective “luteolytic” agent in rhesus monkeys. In nonpregnant monkeys it reverses the human chorionic gonadotropin-stimulated increase in progesterone production and delay in the onset of menstruation, and in inseminated monkeys, it prevents pregnancy if given for 5 days...detailed

Antifertility effect of Azastene (cas 13074-00-5) mediated by prostaglandin09/09/2019

Azastene, a synthetic steroid of the androstano (2,3-d) isoxazole family, has been shown to terminate pregnancy in the rat and in the primate. Its antifertility effect in the rat is associated with a decrease of progesterone and an increase in prostaglandin F (PGF). Its mechanism of action has b...detailed

Relevant articles and documents

STEROIDAL HETEROCYCLES. VII. ANDROSTANO(2,3-D)ISOXAZOLES AND RELATED

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