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
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
| 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 |
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 |
|---|---|---|
| Structural characterization of human heme oxygenase-1 in complex with azole-based inhibitors. | 2010-03 |
|
| Synthesis and evaluation of imidazole-dioxolane compounds as selective heme oxygenase inhibitors: effect of substituents at the 4-position of the dioxolane ring. | 2009-03-15 |
|
| Inhibition of heme oxygenase activity in newborn mice by azalanstat. | 2008-10 |
|
| 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. | 2008-07 |
|
| Inhibition of angiogenesis by the antifungal drug itraconazole. | 2007-04-24 |
|
| Lanosterol 14alpha-demethylase expression in the mouse ovary and its participation in cumulus-enclosed oocyte spontaneous meiotic maturation in vitro. | 2006-09-15 |
|
| Imidazole-dioxolane compounds as isozyme-selective heme oxygenase inhibitors. | 2006-07-13 |
|
| Meiosis activating sterol (MAS) regulate FSH-induced meiotic resumption of cumulus cell-enclosed porcine oocytes via PKC pathway. | 2006-04-25 |
|
| The source of endogenous carbon monoxide formation in human placental chorionic villi. | 2005-10-03 |
|
| Synthesis and evaluation of azalanstat analogues as heme oxygenase inhibitors. | 2005-03-01 |
|
| Roles of gonadotropins and meiosis-activating sterols in meiotic resumption of cultured follicle-enclosed mouse oocytes. | 2004-04-15 |
|
| Role of meiosis-activating sterols in rat oocyte maturation: effects of specific inhibitors and changes in the expression of lanosterol 14alpha-demethylase during the preovulatory period. | 2001-01 |
|
| Selective inhibition of mammalian lanosterol 14 alpha-demethylase by RS-21607 in vitro and in vivo. | 1994-04-19 |
|
| Selective inhibition of mammalian lanosterol 14 alpha-demethylase: a possible strategy for cholesterol lowering. | 1993-07-23 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 08:43:54 GMT 2025
by
admin
on
Wed Apr 02 08:43:54 GMT 2025
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| Record UNII |
2NL79NI1WS
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| Record Status |
Validated (UNII)
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| Record Version |
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| Name | Type | Language | ||
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Official Name | English | ||
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Preferred Name | English | ||
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Common Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C29703
Created by
admin on Wed Apr 02 08:43:54 GMT 2025 , Edited by admin on Wed Apr 02 08:43:54 GMT 2025
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| Code System | Code | Type | Description | ||
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C082410
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AZALANSTAT
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DTXSID401029427
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SUB05630MIG
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7373
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60876
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100000086908
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CHEMBL70611
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C79817
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2NL79NI1WS
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143393-27-5
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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ACTIVE MOIETY |
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