Details
| Stereochemistry | UNKNOWN |
| 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)
| Molecular Formula | C17H13ClN4 |
| Molecular Weight | 308.765 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL5141 |
540.0 nM [IC50] | ||
Target ID: CHEMBL1978 |
5.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| 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 |
|---|---|---|
| Discovery of inhibitors of MCF-7 tumor cell adhesion to endothelial cells and investigation on their mode of action. | 2004 Dec |
|
| Novel tetralone-derived retinoic acid metabolism blocking agents: synthesis and in vitro evaluation with liver microsomal and MCF-7 CYP26A1 cell assays. | 2005 Nov 17 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:01:25 GMT 2023
by
admin
on
Sat Dec 16 11:01:25 GMT 2023
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| Record UNII |
090Y06W08H
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| Record Status |
Validated (UNII)
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| Record Version |
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090Y06W08H
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60652
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RACEMATE -> ENANTIOMER | |||
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ENANTIOMER -> ENANTIOMER |
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