AZALANSTAT

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H24ClN3O2S
Molecular Weight	429.963
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=CC=C(SC[C@@H]2CO[C@](CCC3=CC=C(Cl)C=C3)(CN4C=CN=C4)O2)C=C1

InChI

InChIKey=VYNIUBZKEWJOJP-UNMCSNQZSA-N

InChI=1S/C22H24ClN3O2S/c23-18-3-1-17(2-4-18)9-10-22(15-26-12-11-25-16-26)27-13-20(28-22)14-29-21-7-5-19(24)6-8-21/h1-8,11-12,16,20H,9-10,13-15,24H2/t20-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H24ClN3O2S
Molecular Weight	429.963
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800002302 | https://www.ncbi.nlm.nih.gov/pubmed/7646560 | https://www.ncbi.nlm.nih.gov/pubmed/8161528

Azalanstat is a synthetic imidazole. It has been shown to inhibit cholesterol synthesis in HepG2 cells, human fibroblasts, hamster hepatocytes and hamster liver, by inhibiting the cytochrome P450 enzyme lanosterol 14 alpha-demethylase. In hamsters it lowered serum cholesterol in a dose-dependent manner. Azalanstat preferentially lowered low density lipoprotein (LDL) cholesterol and apo B relative to high density lipoprotein (HDL) cholesterol and apo A-1. Azalanstat inhibited hepatic microsomal hydroxymethylglutaryl-CoA (HMG-CoA) reductase activity in hamsters in a dose-dependent manner and this was highly correlated with serum cholesterol lowering. In vitro studies with HepG2 cells indicated that this modulation of reductase activity was indirect, occurring at a post-transcriptional step. Azalanstat has been in preclinical phase for the treatment of hyperlipidaemia but this research has been discontinued.

Approval Year

PubMed

Title	Date	PubMed
Selective inhibition of mammalian lanosterol 14 alpha-demethylase: a possible strategy for cholesterol lowering.	1993 Jul 23	8340925
Synthesis and evaluation of azalanstat analogues as heme oxygenase inhibitors.	2005 Mar 1	15713406
Meiosis activating sterol (MAS) regulate FSH-induced meiotic resumption of cumulus cell-enclosed porcine oocytes via PKC pathway.	2006 Apr 25	16500744
3',5'-cyclic adenosine monophosphate response element binding protein up-regulated cytochrome P450 lanosterol 14alpha-demethylase expression involved in follicle-stimulating hormone-induced mouse oocyte maturation.	2008 Jul	18467523
Inhibition of heme oxygenase activity in newborn mice by azalanstat.	2008 Oct	18841169
Structural characterization of human heme oxygenase-1 in complex with azole-based inhibitors.	2010 Mar	19917515

Sample Use Guides

In Vivo Use Guide

30 mg/kg once daily for 7 days

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:03:56 GMT 2023` Edited by `admin` on `Sat Dec 16 17:03:56 GMT 2023`
Record UNII	2NL79NI1WS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZALANSTAT

Official Name

English

BENZENAMINE, 4-(((2-(2-(4-CHLOROPHENYL)ETHYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHYL)THIO)-, (2S-CIS)-

Common Name

English

1-(((2S,4S)-4-(((P-AMINOPHENYL)THIO)METHYL)-2-(P-CHLOROPHENETHYL)-1,3-DIOXOLAN-2-YL)METHYL)IMIDAZOLE

Common Name

English

azalanstat [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29703