osanetant   Click here for help

GtoPdb Ligand ID: 2110

Synonyms: SB-236984 | SR 142,806 | SR 142801 | SR-142,801 | SR-142801 | SR-142806 | SR142801
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 10
Topological polar surface area 43.86
Molecular weight 605.26
XLogP 7.05
No. Lipinski's rules broken 1
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Canonical SMILES O=C(N1CCCC(C1)(CCCN1CCC(CC1)(c1ccccc1)N(C(=O)C)C)c1ccc(c(c1)Cl)Cl)c1ccccc1
Isomeric SMILES O=C(N1CCC[C@](C1)(CCCN1CCC(CC1)(c1ccccc1)N(C(=O)C)C)c1ccc(c(c1)Cl)Cl)c1ccccc1
InChI InChI=1S/C35H41Cl2N3O2/c1-27(41)38(2)35(29-13-7-4-8-14-29)19-23-39(24-20-35)21-9-17-34(30-15-16-31(36)32(37)25-30)18-10-22-40(26-34)33(42)28-11-5-3-6-12-28/h3-8,11-16,25H,9-10,17-24,26H2,1-2H3/t34-/m0/s1
1. Anthes JC, Chapman RW, Richard C, Eckel S, Corboz M, Hey JA, Fernandez X, Greenfeder S, McLeod R, Sehring S et al.. (2002)
SCH 206272: a potent, orally active tachykinin NK(1), NK(2), and NK(3) receptor antagonist.
Eur J Pharmacol, 450 (2): 191-202. [PMID:12206858]
2. Beaujouan JC, Saffroy M, Torrens Y, Glowinski J. (1997)
Potency and selectivity of the tachykinin NK3 receptor antagonist SR 142801.
Eur J Pharmacol, 319 (2-3): 307-16. [PMID:9042606]
3. Chung FZ, Wu LH, Tian Y, Vartanian MA, Lee H, Bikker J, Humblet C, Pritchard MC, Raphy J, Suman-Chauhan N. (1995)
Two classes of structurally different antagonists display similar species preference for the human tachykinin neurokinin3 receptor.
Mol Pharmacol, 48 (4): 711-6. [PMID:7476898]
4. Emonds-Alt X, Bichon D, Ducoux JP, Heaulme M, Miloux B, Poncelet M, Proietto V, Van Broeck D, Vilain P, Neliat G. (1995)
SR 142801, the first potent non-peptide antagonist of the tachykinin NK3 receptor.
Life Sci, 56 (1): PL27-32. [PMID:7830490]
5. Kamali F. (2001)
Osanetant Sanofi-Synthélabo.
Curr Opin Investig Drugs, 2 (7): 950-6. [PMID:11757797]
6. Oury-Donat F, Carayon P, Thurneyssen O, Pailhon V, Emonds-Alt X, Soubrié P, Le Fur G. (1995)
Functional characterization of the nonpeptide neurokinin3 (NK3) receptor antagonist, SR142801 on the human NK3 receptor expressed in Chinese hamster ovary cells.
J Pharmacol Exp Ther, 274 (1): 148-54. [PMID:7616392]
7. Sarau HM, Feild JA, Ames RS, Foley JJ, Nuthulaganti P, Schmidt DB, Buckley PT, Elshourbagy NA, Brawner ME, Luttmann MA et al.. (2001)
Molecular and pharmacological characterization of the murine tachykinin NK(3) receptor.
Eur J Pharmacol, 413 (2-3): 143-50. [PMID:11226387]
8. Sarau HM, Griswold DE, Potts W, Foley JJ, Schmidt DB, Webb EF, Martin LD, Brawner ME, Elshourbagy NA, Medhurst AD et al.. (1997)
Nonpeptide tachykinin receptor antagonists: I. Pharmacological and pharmacokinetic characterization of SB 223412, a novel, potent and selective neurokinin-3 receptor antagonist.
J Pharmacol Exp Ther, 281 (3): 1303-11. [PMID:9190866]
9. Tian Y, Wu LH, Oxender DL, Chung FZ. (1996)
The unpredicted high affinities of a large number of naturally occurring tachykinins for chimeric NK1/NK3 receptors suggest a role for an inhibitory domain in determining receptor specificity.
J Biol Chem, 271 (34): 20250-7. [PMID:8702757]