tetomilast   Click here for help

GtoPdb Ligand ID: 9877

Synonyms: compound 19f [PMID: 7830278] | OPC-6535 | OPC6535
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Tetomilast is a PDE4 inhibitor. Inhibition of PDE4 blocks the oxidative burst in human neutrophils, which is a major mediator of tissue injury in inflammatory diseases. Tetomilast (OPC-6535) was originally identified as an inhibitor of superoxide production by human neutrophils [1]. The clinical potential of PDE4 inhibition in inflammatory bowel disease was reviewed by Salari and Abdollahiin 2012 [2].
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 109.78
Molecular weight 370.1
XLogP 1.21
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 CCOc1cc(ccc1OCC)c1scc(n1)c1cccc(n1)C(=O)O
Isomeric SMILES CCOc1cc(ccc1OCC)c1scc(n1)c1cccc(n1)C(=O)O
InChI InChI=1S/C19H18N2O4S/c1-3-24-16-9-8-12(10-17(16)25-4-2)18-21-15(11-26-18)13-6-5-7-14(20-13)19(22)23/h5-11H,3-4H2,1-2H3,(H,22,23)
InChI Key XDBHURGONHZNJF-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. Chihiro M, Nagamoto H, Takemura I, Kitano K, Komatsu H, Sekiguchi K, Tabusa F, Mori T, Tominaga M, Yabuuchi Y. (1995)
Novel thiazole derivatives as inhibitors of superoxide production by human neutrophils: synthesis and structure-activity relationships.
J Med Chem, 38 (2): 353-8. [PMID:7830278]
2. Salari P, Abdollahi M. (2012)
Phosphodiesterase inhibitors in inflammatory bowel disease.
Expert Opin Investig Drugs, 21 (3): 261-4. [PMID:22303952]
3. Schreiber S, Keshavarzian A, Isaacs KL, Schollenberger J, Guzman JP, Orlandi C, Hanauer SB. (2007)
A randomized, placebo-controlled, phase II study of tetomilast in active ulcerative colitis.
Gastroenterology, 132 (1): 76-86. [PMID:17241861]