Details of the Drug

General Information of Drug (ID: DM4OYXE)

Drug Name

LIAROZOLE

Synonyms

Liarozole; Liazal; 115575-11-6; R-75251; LIAROZOLE FUMARATE; Liarozole [INN:BAN]; Liarozolum [INN-Latin]; Liarozol [INN-Spanish]; R 75251; R-61405; R085246; R 61405; R-085246; R 085246; 6-((3-chlorophenyl)(1H-imidazol-1-yl)methyl)-1H-benzo[d]imidazole; UNII-17NYD2210B; CHEMBL389433; UNII-090Y06W08H; 17NYD2210B; 090Y06W08H; Liarozolum; Liarozol; 1H-Benzimidazole, 5-((3-chlorophenyl)-1H-imidazol-1-ylmethyl)-; NCGC00181034-01; Liarozole, (-)-; Liarozole, (+)-; AC1L1TNN; AC1Q3M3B; SCHEMBL18597; GTPL5210; SCHEMBL15944205; DTXSID9048277

Indication

Disease Entry	ICD 11	Status	REF
Dermatological disease	DA24.Y	Phase 2/3	[1], [2]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

308.8

Topological Polar Surface Area (xlogp)

3.5

Rotatable Bond Count (rotbonds)

3

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

2

Chemical Identifiers

Formula: C17H13ClN4
IUPAC Name: 6-[(3-chlorophenyl)-imidazol-1-ylmethyl]-1H-benzimidazole
Canonical SMILES: C1=CC(=CC(=C1)Cl)C(C2=CC3=C(C=C2)N=CN3)N4C=CN=C4
InChI: 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)
InChIKey: UGFHIPBXIWJXNA-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 60652
ChEBI ID: CHEBI:135316
CAS Number: 115575-11-6
DrugBank ID: DB13066
TTD ID: D08UGX

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Aromatase (CYP19A1)	TTSZLWK	CP19A_HUMAN	Inhibitor	[3]
Cytochrome P450 26 (CYP26A1)	TTD7Q0R	CP26A_HUMAN	Inhibitor	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5210).
2	ClinicalTrials.gov (NCT00282724) Efficacy and Safety of Two Doses of Liarozole vs. Placebo for the Treatment of Lamellar Ichthyosis. U.S. National Institutes of Health.
3	Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19). Bioorg Med Chem Lett. 2010 May 15;20(10):3050-64.
4	Novel azolyl-(phenylmethyl)]aryl/heteroarylamines: potent CYP26 inhibitors and enhancers of all-trans retinoic acid activity in neuroblastoma cells. Bioorg Med Chem. 2008 Sep 1;16(17):8301-13.
5	Effective aromatase inhibition by anastrozole in a patient with gonadotropin-independent precocious puberty in McCune-Albright syndrome. J Pediatr Endocrinol Metab. 2002;15 Suppl 3:945-8.
6	Aromatase inhibitors--theoretical concept and present experiences in the treatment of endometriosis. Zentralbl Gynakol. 2003 Jul-Aug;125(7-8):247-51.
7	Aminoglutethimide-induced protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis. Chem Res Toxicol. 2007 Jul;20(7):1038-45.
8	Enantioselective nonsteroidal aromatase inhibitors identified through a multidisciplinary medicinal chemistry approach. J Med Chem. 2005 Nov 17;48(23):7282-9.
9	Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9.
10	Toremifene-atamestane; alone or in combination: predictions from the preclinical intratumoral aromatase model. J Steroid Biochem Mol Biol. 2008 Jan;108(1-2):1-7.
11	Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template. J Med Chem. 2010 Mar 11;53(5):2155-70.
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13	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800032111)
14	Emerging drugs for psoriasis. Expert Opin Emerg Drugs. 2009 Mar;14(1):145-63.
15	Novel retinoic acid metabolism blocking agents endowed with multiple biological activities are efficient growth inhibitors of human breast and pros... J Med Chem. 2004 Dec 30;47(27):6716-29.