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Details

Stereochemistry RACEMIC
Molecular Formula C17H13ClN4
Molecular Weight 308.765
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LIAROZOLE

SMILES

ClC1=CC=CC(=C1)C(N2C=CN=C2)C3=CC=C4N=CNC4=C3

InChI

InChIKey=UGFHIPBXIWJXNA-UHFFFAOYSA-N
InChI=1S/C17H13ClN4/c18-14-3-1-2-12(8-14)17(22-7-6-19-11-22)13-4-5-15-16(9-13)21-10-20-15/h1-11,17H,(H,20,21)

HIDE SMILES / InChI
Liarozole is an imidazole-containing compound that inhibits the cytochrome P-450-dependent metabolism of all-trans-retinoic acid (RA). Liarozole, a retinoic acid (RA) metabolism-blocking agent (RAMBA) in clinical development, has been granted orphan drug designation for congenital ichthyosis by the European Commission and the U.S. Food and Drug Administration. Later, based on the mixed results from a phase II/III trial of liarozole for the treatment of ichthyosis, Barrier decided to discontinue the development of liarozole. Liarozole displays antitumor activity against androgen-dependent and independent rat prostate carcinomas.A large phase III international study was completed comparing liarozole 300 mg twice daily with cyproterone acetate (CPA) 100 mg twice daily in a total of 321 patients with metastatic prostate cancer in relapse after first-line endocrine therapy. The results indicate that liarozole might be a possible treatment option for prostate cancer (PCA) following failure of first-line endocrine therapy.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.67 mg/L
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LIAROZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
23.9 mg × h/L
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LIAROZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
PubMed

PubMed

TitleDatePubMed
Small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26): synthesis and biological evaluation of imidazole methyl 3-(4-(aryl-2-ylamino)phenyl)propanoates.
2011 Apr 28
Synthesis and biological evaluation of 3-(1H-imidazol- and triazol-1-yl)-2,2-dimethyl-3-[4-(naphthalen-2-ylamino)phenyl]propyl derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26).
2011 Oct 13
Patents

Sample Use Guides

Patients aged ≥ 14 years with moderate/severe lamellar ichthyosis [Investigator's Global Assessment (IGA) score ≥ 3] were randomized 3 : 3 : 1 to receive oral liarozole (75 or 150 mg) or placebo once daily for 12 weeks. Compared with placebo, oral liarozole, 75 or 150 mg, once daily for 12 weeks, reduced the overall severity of ichthyosis and scaling, but not erythema or pruritus, and improved DLQI in patients with moderate or severe lamellar ichthyosis.
Route of Administration: Oral
In Vitro Use Guide
In vitro, liarozole (IC50, 2.2 uM) suppressed the P-450-mediated conversion of RA to more polar metabolites by hamster liver microsomes.
Name Type Language
LIAROZOLE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
LIAROZOLE [MI]
Common Name English
1H-BENZIMIDAZOLE, 5-((3-CHLOROPHENYL)-1H-IMIDAZOL-1-YLMETHYL)-, (±)-
Systematic Name English
liarozole [INN]
Common Name English
(±)-5-(M-CHLORO-.ALPHA.-IMIDAZOL-1-YLBENZYL)BENZIMIDAZOLE
Systematic Name English
6-((3-CHLOROPHENYL)-1H-IMIDAZOL-1-YLMETHYL)-1H-BENZIMIDAZOLE
Common Name English
LIAROZOLE [MART.]
Common Name English
Liarozole [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2018
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
FDA ORPHAN DRUG 183904
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
EU-Orphan Drug EU/3/03/144
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
Code System Code Type Description
SMS_ID
100000077092
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL389433
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY
MESH
C061121
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY
NCI_THESAURUS
C1433
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY
CAS
115575-11-6
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY
EVMPD
SUB14356MIG
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY
INN
6478
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY
DRUG BANK
DB13066
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY
MERCK INDEX
m6798
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
Liarozole
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY
PUBCHEM
60652
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY
FDA UNII
K0Q29TGV9Y
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID9048277
Created by admin on Fri Dec 15 16:03:56 GMT 2023 , Edited by admin on Fri Dec 15 16:03:56 GMT 2023
PRIMARY