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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H24ClN3O2S.2ClH
Molecular Weight 502.885
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZALANSTAT DIHYDROCHLORIDE

SMILES

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

InChI

InChIKey=UTHWWPSFKXCLMU-HWELVIDPSA-N
InChI=1S/C22H24ClN3O2S.2ClH/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;2*1H/t20-,22-;;/m0../s1

HIDE SMILES / InChI
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

PubMed

TitleDatePubMed
Selective inhibition of mammalian lanosterol 14 alpha-demethylase by RS-21607 in vitro and in vivo.
1994 Apr 19
Meiosis activating sterol (MAS) regulate FSH-induced meiotic resumption of cumulus cell-enclosed porcine oocytes via PKC pathway.
2006 Apr 25
Inhibition of heme oxygenase activity in newborn mice by azalanstat.
2008 Oct

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Hamsters data
30 mg/kg once daily for 7 days
Route of Administration: Oral
Name Type Language
AZALANSTAT DIHYDROCHLORIDE
USAN  
USAN  
Official Name English
RS-21607-197
Code English
AZALANSTAT DIHYDROCHLORIDE [USAN]
Common Name English
1-(((2S,4S)-4-(((P-AMINOPHENYL)THIO)METHYL)-2-(P-CHLOROPHENETHYL)-1,3-DIOXOLAN-2-YL)METHYL)IMIDAZOLE DIHYDROCHLORIDE
Common Name English
BENZENAMINE, 4-(((2-(2-(4-CHLOROPHENYL)ETHYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHYL)THIO)-, DIHYDROCHLORIDE, (2S-CIS)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29703
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
Code System Code Type Description
FDA UNII
X30J960B4D
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
ChEMBL
CHEMBL70611
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
USAN
FF-53
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
CAS
143484-82-6
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
PUBCHEM
6918262
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY
NCI_THESAURUS
C80126
Created by admin on Fri Dec 15 15:32:39 GMT 2023 , Edited by admin on Fri Dec 15 15:32:39 GMT 2023
PRIMARY