CTEP   Click here for help

GtoPdb Ligand ID: 6409

Synonyms: compound 3 [PMID: 25565255]
Compound class: Synthetic organic
Comment: CTEP is a negative allosteric modulator (NAM) of the glutamate metabotropic receptor 5 (mGlu5) GPCR [1-2]. Structurally, CTEP and basimglurant and are analogues. CTEP has a notably longer half-life in rodents (49 hours) than basimglurant (~10 hours), so is better suited for rodents studies requiring chronic exposure/treatment.
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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 3
Topological polar surface area 39.42
Molecular weight 391.07
XLogP 5.85
No. Lipinski's rules broken 1
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Canonical SMILES Clc1nccc(c1)C#Cc1nc(n(c1C)c1ccc(cc1)OC(F)(F)F)C
Isomeric SMILES Clc1nccc(c1)C#Cc1nc(n(c1C)c1ccc(cc1)OC(F)(F)F)C
InChI InChI=1S/C19H13ClF3N3O/c1-12-17(8-3-14-9-10-24-18(20)11-14)25-13(2)26(12)15-4-6-16(7-5-15)27-19(21,22)23/h4-7,9-11H,1-2H3
1. Jaeschke G, Kolczewski S, Spooren W, Vieira E, Bitter-Stoll N, Boissin P, Borroni E, Büttelmann B, Ceccarelli S, Clemann N et al.. (2015)
Metabotropic glutamate receptor 5 negative allosteric modulators: discovery of 2-chloro-4-[1-(4-fluorophenyl)-2,5-dimethyl-1H-imidazol-4-ylethynyl]pyridine (basimglurant, RO4917523), a promising novel medicine for psychiatric diseases.
J Med Chem, 58 (3): 1358-71. [PMID:25565255]
2. Lindemann L, Jaeschke G, Michalon A, Vieira E, Honer M, Spooren W, Porter R, Hartung T, Kolczewski S, Büttelmann B et al.. (2011)
CTEP: a novel, potent, long-acting, and orally bioavailable metabotropic glutamate receptor 5 inhibitor.
J Pharmacol Exp Ther, 339 (2): 474-86. [PMID:21849627]