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
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)
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL5141 |
540.0 nM [IC50] | ||
Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20413308 |
5.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.67 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10763459 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23.9 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10763459 |
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
Title | Date | PubMed |
---|---|---|
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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24102348
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1374473
In vitro, liarozole (IC50, 2.2 uM) suppressed the P-450-mediated conversion of RA to more polar metabolites by hamster liver microsomes.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C2018
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FDA ORPHAN DRUG |
183904
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EU-Orphan Drug |
EU/3/03/144
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100000077092
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CHEMBL389433
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C061121
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C1433
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115575-11-6
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SUB14356MIG
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DB13066
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m6798
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Liarozole
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60652
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K0Q29TGV9Y
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DTXSID9048277
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)