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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key PGKXDIMONUAMFR-AREMUKBSSA-N
References
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]