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
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
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
|---|---|---|
| Selective inhibition of mammalian lanosterol 14 alpha-demethylase: a possible strategy for cholesterol lowering. | 1993 Jul 23 |
|
| Selective inhibition of mammalian lanosterol 14 alpha-demethylase by RS-21607 in vitro and in vivo. | 1994 Apr 19 |
|
| 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 Jan |
|
| Roles of gonadotropins and meiosis-activating sterols in meiotic resumption of cultured follicle-enclosed mouse oocytes. | 2004 Apr 15 |
|
| Synthesis and evaluation of azalanstat analogues as heme oxygenase inhibitors. | 2005 Mar 1 |
|
| The source of endogenous carbon monoxide formation in human placental chorionic villi. | 2005 Oct 3 |
|
| Meiosis activating sterol (MAS) regulate FSH-induced meiotic resumption of cumulus cell-enclosed porcine oocytes via PKC pathway. | 2006 Apr 25 |
|
| Imidazole-dioxolane compounds as isozyme-selective heme oxygenase inhibitors. | 2006 Jul 13 |
|
| Lanosterol 14alpha-demethylase expression in the mouse ovary and its participation in cumulus-enclosed oocyte spontaneous meiotic maturation in vitro. | 2006 Sep 15 |
|
| Inhibition of angiogenesis by the antifungal drug itraconazole. | 2007 Apr 24 |
|
| 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 |
|
| Inhibition of heme oxygenase activity in newborn mice by azalanstat. | 2008 Oct |
|
| Synthesis and evaluation of imidazole-dioxolane compounds as selective heme oxygenase inhibitors: effect of substituents at the 4-position of the dioxolane ring. | 2009 Mar 15 |
|
| Structural characterization of human heme oxygenase-1 in complex with azole-based inhibitors. | 2010 Mar |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:32:39 GMT 2023
by
admin
on
Fri Dec 15 15:32:39 GMT 2023
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| Record UNII |
X30J960B4D
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29703
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X30J960B4D
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CHEMBL70611
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FF-53
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143484-82-6
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6918262
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C80126
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ACTIVE MOIETY |