AZACOSTEROL HYDROCHLORIDE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H44N2O.2ClH
Molecular Weight	461.552
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.[H][C@@]12CC[C@H](N(C)CCCN(C)C)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC=C4C[C@@H](O)CC[C@]34C

InChI

InChIKey=BZFBDUQOBQHBSZ-DLCQERRASA-N

InChI=1S/C25H44N2O.2ClH/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;2*1H/t19-,20-,21-,22-,23-,24-,25-;;/m0../s1

HIDE SMILES / InChI

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
Clofibrate-induced myotonia in the rat.	1978 Dec 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.

Name

Type

Language

AZACOSTEROL HYDROCHLORIDE

Official Name

English

AZACOSTEROL DIHYDROCHLORIDE [MI]

Common Name

English

AZACOSTEROL DIHYDROCHLORIDE

Common Name

English

AZACOSTEROL HYDROCHLORIDE [USAN]

Common Name

English

SC-12937

Code

English

ANDROST-5-EN-3-OL, 17-((3-(DIMETHYLAMINO)PROPYL)METHYL)AMINO)-, DIHYDROCHLORIDE, (3.BETA.,17.BETA.)-

Common Name

English

AZACOSTEROL HCL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29703