saredutant   Click here for help

GtoPdb Ligand ID: 2111

Synonyms: SR 48,968 | SR 48968 | SR-48,968 | SR48968 | SR48968C
Compound class: Synthetic organic
Comment: Saredutant is a tachykinin NK2 receptor antagonist that was developed by Sanofi-Aventis for anti-depressant potential [5,7-8,10].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 52.65
Molecular weight 551.21
XLogP 6.27
No. Lipinski's rules broken 1
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Canonical SMILES CC(=O)NC1(CCN(CC1)CCC(c1ccc(c(c1)Cl)Cl)CN(C(=O)c1ccccc1)C)c1ccccc1
Isomeric SMILES CC(=O)NC1(CCN(CC1)CC[C@@H](c1ccc(c(c1)Cl)Cl)CN(C(=O)c1ccccc1)C)c1ccccc1
InChI InChI=1S/C31H35Cl2N3O2/c1-23(37)34-31(27-11-7-4-8-12-27)16-19-36(20-17-31)18-15-26(25-13-14-28(32)29(33)21-25)22-35(2)30(38)24-9-5-3-6-10-24/h3-14,21,26H,15-20,22H2,1-2H3,(H,34,37)/t26-/m1/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. Chung FZ, Wu LH, Vartanian MA, Watling KJ, Guard S, Woodruff GN, Oxender DL. (1994)
The non-peptide tachykinin NK2 receptor antagonist SR 48968 interacts with human, but not rat, cloned tachykinin NK3 receptors.
Biochem Biophys Res Commun, 198 (3): 967-72. [PMID:8117304]
3. Emonds-Alt X, Golliot F, Pointeau P, Le Fur G, Breliere JC. (1993)
Characterization of the binding sites of [3H]SR 48968, a potent nonpeptide radioligand antagonist of the neurokinin-2 receptor.
Biochem Biophys Res Commun, 191 (3): 1172-7. [PMID:7682062]
4. Emonds-Alt X, Vilain P, Goulaouic P, Proietto V, Van Broeck D, Advenier C, Naline E, Neliat G, Le Fur G, Brelière JC. (1992)
A potent and selective non-peptide antagonist of the neurokinin A (NK2) receptor.
Life Sci, 50 (15): PL101-6. [PMID:1313515]
5. Hopkins CR. (2010)
ACS chemical neuroscience molecule spotlight on Saredutant.
ACS Chem Neurosci, 1 (10): 653-4. [PMID:22776916]
6. Martin CA, Naline E, Emonds-Alt X, Advenier C. (1992)
Influence of (+/-)-CP-96,345 and SR 48968 on electrical field stimulation of the isolated guinea-pig main bronchus.
Eur J Pharmacol, 224 (2-3): 137-43. [PMID:1334836]
7. Overstreet DH, Naimoli VM, Griebel G. (2010)
Saredutant, an NK2 receptor antagonist, has both antidepressant-like effects and synergizes with desipramine in an animal model of depression.
Pharmacol Biochem Behav, 96 (2): 206-10. [PMID:20470817]
8. Rogacki N, Lopez-Grancha M, Naimoli V, Potestio L, Stevens RJ, Pichat P, Bergis OE, Cohen C, Varty GB, Griebel G. (2011)
The neurokinin NK2 antagonist, saredutant, ameliorates stress-induced conditions without impairing cognition.
Pharmacol Biochem Behav, 98 (3): 405-11. [PMID:21115031]
9. 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]
10. Tamburella A, Leggio GM, Micale V, Navarria A, Bucolo C, Cicirata V, Drago F, Salomone S. (2013)
Behavioural and neurochemical changes induced by stress-related conditions are counteracted by the neurokinin-2 receptor antagonist saredutant.
Int J Neuropsychopharmacol, 16 (4): 813-23. [PMID:22695046]