AZACOSTEROL

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H44N2O
Molecular Weight	388.6297
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCCN(C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

InChIKey=FMTFZYKYVZBISL-HUVRVWIJSA-N

InChI=1S/C25H44N2O/c1-24-13-11-19(28)17-18(24)7-8-20-21-9-10-23(25(21,2)14-12-22(20)24)27(5)16-6-15-26(3)4/h7,19-23,28H,6,8-17H2,1-5H3/t19-,20-,21-,22-,23-,24-,25-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C25H44N2O
Molecular Weight	388.6297
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://books.google.ru/books?id=_J2ti4EkYpkC&pg=PA463&lpg=PA463&dq=AZACOSTEROL retrieved from Pharmaceutical Manufacturing Encyclopedia, 3rd Edition By William Andrew Publishing, p.463 | https://www.ncbi.nlm.nih.gov/pubmed/28985619 | https://www.ncbi.nlm.nih.gov/pubmed/12507656 | https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C79819 | https://www.ncbi.nlm.nih.gov/pubmed/14346416 | https://www.ncbi.nlm.nih.gov/pubmed/7294732

Azacosterol (Ornitrol, 20,25-diazacholesterol dihydrochloride, SC 12937) is a cholesterol-lowering drug (hypocholesteremic) which was marketed previously but has since been discontinued. Azacosterol is a sterol derivative of cholesterol with two nitrogen atoms replacing two carbon atoms that acts as a hypocholesteremic agent by blocking delta-24-reductase. Azacosterol has the unintended side effect of causing myotonia. It is an avian contraceptive compound, which reduces fertility by inhibiting cholesterol synthesis. Azacosterol is also useful in the control of rodent populations.

Originator

Approval Year

PubMed

Title	Date	PubMed
Effectiveness of twenty, twenty-five diazacholesterol, avian gonadotropin-releasing hormone, and chicken riboflavin carrier protein for inhibiting reproduction in Coturnix quail.	2004-02	14979575
Antispermatogenic and antifertility effects of 20,25-diazacholesterol dihydrochloride in mice.	2003-01-01	12507656
Desmosterol: a biomarker for the efficient development of 20,25-diazacholesterol as a contraceptive for pest wildlife.	2003-01-01	12502398
Determination of DiazaCon in quail feed and quail serum by ion pair reversed-phase chromatography.	2001-06-22	11417624
Structure-activity relationship of aza-steroids as PI-PLC inhibitors.	2001-05	11377165
Clofibrate-induced myotonia in the rat.	1978-12-15	729726

Patents

Sample Use Guides

In Vivo Use Guide

The effect of intraperitoneal administration for 28 days of 10, 20, and 30 mg/kg body weight per day of 20,25-diazacholesterol dihydrochloride on the testis of Parkes (P) strain mice was investigated. Histologically, testes in mice treated with 10 or 20 mg/kg body weight of SC 12937 showed non-uniform degenerative changes in the seminiferous tubules. Testes in mice treated with 30 mg/kg body weight of the drug exhibited a degenerated appearance of germ cells in all seminiferous tubules.

Route of Administration: Intraperitoneal

In Vitro Use Guide

The epimeric mixtures 22,25-diazacholesterol (Azacosterol) and 3beta-hydroxy-22,25-diazacholestane were among the most active of phosphatidylinositol phospholipase C (PI-PLC) inhibitors, with IC(50) values of 7.4 and 7.5 uM, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:23:13 GMT 2025` Edited by `admin` on `Mon Mar 31 18:23:13 GMT 2025`
Record UNII	EPT876J73A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZACOSTEROL [MI]

Preferred Name

English

AZACOSTEROL

Official Name

English

20,25-DIAZACHOLESTEROL

Systematic Name

English

17.BETA.-((3-(DIMETHYLAMINO)-PROPYL)METHYLAMINO)ANDROST-5-EN-3.BETA.-OL

Systematic Name

English

ANDROST-5-EN-3-OL, 17-((3-(DIMETHYLAMINO)PROPYL)METHYLAMINO)-, (3.BETA.,17.BETA.)-

Systematic Name

English

azacosterol [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29703