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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
MOL RATIO 1 MOL RATIO (average)
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

PubMed

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
Record UNII
EPT876J73A
Record Status Validated (UNII)
Record Version