pecazine   Click here for help

GtoPdb Ligand ID: 9782

Synonyms: mepazine | nothiazine | Pacatal®
Approved drug Immunopharmacology Ligand
pecazine is an approved drug
Compound class: Synthetic organic
Comment: Pecazine is a phenothiazine derivative that was historically used as an antipsychotic/tranquillizer, but use has replaced by newer drugs. Pecazine is also an allosteric inhibitor of MALT1 protease activity [1-2], and a RANKL inhibitor. It may be used experimentally as the acetate or hydrochloride.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 31.78
Molecular weight 310.15
XLogP 4.68
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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Canonical SMILES CN1CCCC(C1)CN1c2ccccc2Sc2c1cccc2
Isomeric SMILES CN1CCCC(C1)CN1c2ccccc2Sc2c1cccc2
InChI InChI=1S/C19H22N2S/c1-20-12-6-7-15(13-20)14-21-16-8-2-4-10-18(16)22-19-11-5-3-9-17(19)21/h2-5,8-11,15H,6-7,12-14H2,1H3
InChI Key CBHCDHNUZWWAPP-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. Nagel D, Spranger S, Vincendeau M, Grau M, Raffegerst S, Kloo B, Hlahla D, Neuenschwander M, Peter von Kries J, Hadian K et al.. (2012)
Pharmacologic inhibition of MALT1 protease by phenothiazines as a therapeutic approach for the treatment of aggressive ABC-DLBCL.
Cancer Cell, 22 (6): 825-37. [PMID:23238017]
2. Schlauderer F, Lammens K, Nagel D, Vincendeau M, Eitelhuber AC, Verhelst SH, Kling D, Chrusciel A, Ruland J, Krappmann D et al.. (2013)
Structural analysis of phenothiazine derivatives as allosteric inhibitors of the MALT1 paracaspase.
Angew Chem Int Ed Engl, 52 (39): 10384-7. [PMID:23946259]