1197900-95-0

Basic information

• Product Name: (17α)-7-Cyano-17-hydroxy-3-oxo-pregna-4,9(11)-diene-21-carboxylic acid γ-Lactone
• Synonyms: (17α)-7-Cyano-17-hydroxy-3-oxo-pregna-4,9(11)-diene-21-carboxylic acid γ-Lactone
• CAS NO: 1197900-95-0
• Molecular Formula: C23H27NO3
• Molecular Weight: 365.46538
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 1197900-95-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (17α)-7-Cyano-17-hydroxy-3-oxo-pregna-4,9(11)-diene-21-carboxylic acid γ-Lactone(CAS DataBase Reference)
• NIST Chemistry Reference: (17α)-7-Cyano-17-hydroxy-3-oxo-pregna-4,9(11)-diene-21-carboxylic acid γ-Lactone(1197900-95-0)
• EPA Substance Registry System: (17α)-7-Cyano-17-hydroxy-3-oxo-pregna-4,9(11)-diene-21-carboxylic acid γ-Lactone(1197900-95-0)

Safety Data

• Hazardous Substances Data: 1197900-95-0(Hazardous Substances Data)

Usage

Description

(17α)-7-Cyano-17-hydroxy-3-oxo-pregna-4,9(11)-diene-21-carboxylic acid γ-Lactone is a complex organic compound belonging to the steroid family. It is characterized by its unique molecular structure, featuring a γ-lactone ring and a cyano group at the 7α position. This yellow solid is known for its potential applications in the pharmaceutical industry, particularly in the development of 17-spirosteroids.

Uses

Used in Pharmaceutical Industry:
(17α)-7-Cyano-17-hydroxy-3-oxo-pregna-4,9(11)-diene-21-carboxylic acid γ-Lactone is used as a key intermediate in the synthesis of 17-spirosteroids, which are aldosterone receptor antagonists. These antagonists play a crucial role in treating various conditions related to fluid and electrolyte balance, such as hypertension, heart failure, and edema. (17α)-7-Cyano-17-hydroxy-3-oxo-pregna-4,9(11)-diene-21-carboxylic acid γ-Lactone's unique structure allows for the development of more effective and targeted therapies for these medical conditions.

Upstream product

• 95716-71-5 (17α)-17-hydroxy-3-oxo-pregna-4,6,9 (11)-triene-21-carboxylic acid γ-lactone 
• 5804-85-3 diethylaluminium cyanide 
• 95716-71-5 Δ⁹⁽¹¹⁾-canrenone 

Relevant articles and documents

ALDOSTERONE RECEPTOR ANTAGONISTS

Compounds of the formula (I), (R1 is one of a wide range of substituents; R2 = H, halogen and R3 = H, hydroxymethyl or CR2R3 = cyclopropyl ring; CR4R5 is one of formula (II), formula (III) and formula (IV) Ra and Rb are a bond between carbons 9 and 11 or an -O-, -S-, -CH2- or -CF2- bridge; R6 is H, alkyl, -CH2ORx, -CH2SRx, -CH2SO-alkyl, -CH2SO2-alkyl, -CH2NHRx, -CH2N(alkyl)(Rx), -C(=O)O-alkyl, -C(=O)-alkyl, -C(=O)NHRx or -C(=O)N(alkyl)(Rx); R7 = R8 = H or CR7R8 is a cyclopropyl ring; R9 and R9’ are H, halogen, alkyl or alkoxycarbonyl or a bond between carbons 22 and 23; R10 is H or -C(=O)ORx; Rx is H, alkyl or acyl; Ry is H, alkyl; Rz is H, alkyl) are provided. They are aldosterone receptor antagonists, useful for the treatment of aldosteronism including hypertension, cardiovascular disease, renal dysfunction, edema, cerebrovascular disease and insulinopathies.

Steroidal, aldosterone antagonists: Increased selectivity of 9α,11-epoxy derivatives

In the search for aldosterone antagonists with an optimal activity profile, twelve 9α,11-epoxy-steroids were prepared and compared with their 9α,11α-unsubstituted analogues in terms of steroid receptor binding in vitro and electrolyte excretion in vivo. Substitution of the parent structures by an epoxy group at positions 9α,11 resulted in marginal effects on mineralocorticoid receptor binding and electrolyte excretion, but greatly reduced androgen and gestagen receptor binding. This finding is reflected in the largely lacking unwanted anti-androgenic and gestagenic side effects in animal models of the three most interesting 9α,11-epoxy-spirolactones 4(CGP 33033), 18(CGP 29245), and 25(CGP 30083).