talarozole   Click here for help

GtoPdb Ligand ID: 11381

Synonyms: R-115866 | R115866 | Rambazole®
Compound class: Synthetic organic
Comment: Talarozole (R115866) is a cytochrome P450 CYP26 inhibitor. It was investigated for clinical efficacy as a treatment for cutaneous inflammation, including psoriasis.

talarozole is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 83.87
Molecular weight 377.17
XLogP 4.89
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCC(C(n1cncn1)c1ccc(cc1)Nc1nc2c(s1)cccc2)CC
Isomeric SMILES CCC(C(n1cncn1)c1ccc(cc1)Nc1nc2c(s1)cccc2)CC
InChI InChI=1S/C21H23N5S/c1-3-15(4-2)20(26-14-22-13-23-26)16-9-11-17(12-10-16)24-21-25-18-7-5-6-8-19(18)27-21/h5-15,20H,3-4H2,1-2H3,(H,24,25)
InChI Key SNFYYXUGUBUECJ-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Thatcher JE, Buttrick B, Shaffer SA, Shimshoni JA, Goodlett DR, Nelson WL, Isoherranen N. (2011)
Substrate specificity and ligand interactions of CYP26A1, the human liver retinoic acid hydroxylase.
Mol Pharmacol, 80 (2): 228-39. [PMID:21521770]
2. Verfaille CJ, Coel M, Boersma IH, Mertens J, Borgers M, Roseeuw D. (2007)
Oral R115866 in the treatment of moderate to severe facial acne vulgaris: an exploratory study.
Br J Dermatol, 157 (1): 122-6. [PMID:17459036]
3. Verfaille CJ, Thissen CA, Bovenschen HJ, Mertens J, Steijlen PM, van de Kerkhof PC. (2007)
Oral R115866 in the treatment of moderate to severe plaque-type psoriasis.
J Eur Acad Dermatol Venereol, 21 (8): 1038-46. [PMID:17714122]