levocabastine   Click here for help

GtoPdb Ligand ID: 1586

Synonyms: levocobastine | Livostin®
Approved drug
levocabastine is an approved drug (FDA (1993))
Compound class: Synthetic organic
Comment: In addition to acting at the histamine H1 receptor, levocabastine is also a selective antagonist for the neurotensin receptor NTS2, and has been used to characterise the different receptor subtypes [5,5]. This ligand is represented on PubChem by CID 54385.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 64.33
Molecular weight 420.22
XLogP 5.03
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES N#CC1(CCC(CC1)N1CCC(C(C1)C)(C(=O)O)c1ccccc1)c1ccc(cc1)F
Isomeric SMILES N#C[C@@]1(CC[C@@H](CC1)N1CC[C@]([C@@H](C1)C)(C(=O)O)c1ccccc1)c1ccc(cc1)F
InChI InChI=1S/C26H29FN2O2/c1-19-17-29(16-15-26(19,24(30)31)21-5-3-2-4-6-21)23-11-13-25(18-28,14-12-23)20-7-9-22(27)10-8-20/h2-10,19,23H,11-17H2,1H3,(H,30,31)/t19-,23-,25-,26-/m1/s1
1. Botto JM, Chabry J, Sarret P, Vincent JP, Mazella J. (1998)
Stable expression of the mouse levocabastine-sensitive neurotensin receptor in HEK 293 cell line: binding properties, photoaffinity labeling, and internalization mechanism.
Biochem Biophys Res Commun, 243 (2): 585-90. [PMID:9480852]
2. Chalon P, Vita N, Kaghad M, Guillemot M, Bonnin J, Delpech B, Le Fur G, Ferrara P, Caput D. (1996)
Molecular cloning of a levocabastine-sensitive neurotensin binding site.
FEBS Lett, 386 (2-3): 91-4. [PMID:8647296]
3. Mazella J, Botto JM, Guillemare E, Coppola T, Sarret P, Vincent JP. (1996)
Structure, functional expression, and cerebral localization of the levocabastine-sensitive neurotensin/neuromedin N receptor from mouse brain.
J Neurosci, 16 (18): 5613-20. [PMID:8795617]
4. Richard F, Barroso S, Martinez J, Labbé-Jullié C, Kitabgi P. (2001)
Agonism, inverse agonism, and neutral antagonism at the constitutively active human neurotensin receptor 2.
Mol Pharmacol, 60 (6): 1392-8. [PMID:11723247]
5. Schotte A, Leysen JE, Laduron PM. (1986)
Evidence for a displaceable non-specific [3H]neurotensin binding site in rat brain.
Naunyn Schmiedebergs Arch Pharmacol, 333 (4): 400-5. [PMID:3022160]