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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 of AZACOSTEROL

SMILES

[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=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

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

Unknown
139594
PubMed

PubMed

TitleDatePubMed
Clofibrate-induced myotonia in the rat.
1978 Dec 15
Structure-activity relationship of aza-steroids as PI-PLC inhibitors.
2001 May
Determination of DiazaCon in quail feed and quail serum by ion pair reversed-phase chromatography.
2001 May-Jun
Desmosterol: a biomarker for the efficient development of 20,25-diazacholesterol as a contraceptive for pest wildlife.
2003 Jan 1
Antispermatogenic and antifertility effects of 20,25-diazacholesterol dihydrochloride in mice.
2003 Jan-Feb
Effectiveness of twenty, twenty-five diazacholesterol, avian gonadotropin-releasing hormone, and chicken riboflavin carrier protein for inhibiting reproduction in Coturnix quail.
2004 Feb
Patents

Patents

JPH01311025A
6

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 Fri Dec 15 16:15:31 GMT 2023
Edited
by admin
on Fri Dec 15 16:15:31 GMT 2023
Record UNII
EPT876J73A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZACOSTEROL
INN   MI  
INN  
Official Name English
20,25-DIAZACHOLESTEROL
Systematic Name English
AZACOSTEROL [MI]
Common 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
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
Code System Code Type Description
MESH
D001373
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY
EVMPD
SUB05627MIG
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID1058509
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL1615357
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY
INN
2126
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY
PUBCHEM
10023199
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY
FDA UNII
EPT876J73A
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY
SMS_ID
100000086887
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY
CAS
313-05-3
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY
WIKIPEDIA
AZACOSTEROL
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY
MERCK INDEX
m1017
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C79819
Created by admin on Fri Dec 15 16:15:31 GMT 2023 , Edited by admin on Fri Dec 15 16:15:31 GMT 2023
PRIMARY
Related Record Type Details
Structure of AZACOSTEROL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of AZACOSTEROL
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