talnetant   Click here for help

GtoPdb Ligand ID: 2132

Synonyms: SB 223412 | SB-223,412 | SB-223412 | SB223412
Compound class: Synthetic organic
Comment: Talnetant (SB-223412) is an orally active, selective neurokinin-3 (NK3) receptor antagonist that was developed as a potential anti-schizophrenia drug [2-4,6,8].
There is some ambiguity in the stereochemical representation of talnetant as shown on other databases. The structure shown above is the same as the INN-assigned structure and shows the (S)-isomer of the compound.
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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

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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 3
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 62.22
Molecular weight 382.17
XLogP 6.61
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 CCC(c1ccccc1)NC(=O)c1c(O)c(nc2c1cccc2)c1ccccc1
Isomeric SMILES CC[C@@H](c1ccccc1)NC(=O)c1c(O)c(nc2c1cccc2)c1ccccc1
InChI InChI=1S/C25H22N2O2/c1-2-20(17-11-5-3-6-12-17)27-25(29)22-19-15-9-10-16-21(19)26-23(24(22)28)18-13-7-4-8-14-18/h3-16,20,28H,2H2,1H3,(H,27,29)/t20-/m0/s1
InChI Key BIAVGWDGIJKWRM-FQEVSTJZSA-N
References
1. Bennacef I, Tymciu S, Dhilly M, Lasne MC, Debruyne D, Perrio C, Barré L. (2004)
Synthesis and biological evaluation of novel fluoro and iodo quinoline carboxamides as potential ligands of NK-3 receptors for in vivo imaging studies.
Bioorg Med Chem, 12 (16): 4533-41. [PMID:15265501]
2. Dawson LA, Cato KJ, Scott C, Watson JM, Wood MD, Foxton R, de la Flor R, Jones GA, Kew JN, Cluderay JE et al.. (2008)
In vitro and in vivo characterization of the non-peptide NK3 receptor antagonist SB-223412 (talnetant): potential therapeutic utility in the treatment of schizophrenia.
Neuropsychopharmacology, 33 (7): 1642-52. [PMID:17728699]
3. de la Flor R, Dawson LA. (2009)
Augmentation of antipsychotic-induced neurochemical changes by the NK3 receptor antagonist talnetant (SB-223412).
Neuropharmacology, 56 (2): 342-9. [PMID:18822303]
4. Giardina GA, Raveglia LF, Grugni M, Sarau HM, Farina C, Medhurst AD, Graziani D, Schmidt DB, Rigolio R, Luttmann M et al.. (1999)
Discovery of a novel class of selective non-peptide antagonists for the human neurokinin-3 receptor. 2. Identification of (S)-N-(1-phenylpropyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (SB 223412).
J Med Chem, 42 (6): 1053-65. [PMID:10090788]
5. Giardina GA, Sarau HM, Farina C, Medhurst AD, Grugni M, Foley JJ, Raveglia LF, Schmidt DB, Rigolio R, Vassallo M et al.. (1996)
2-Phenyl-4-quinolinecarboxamides: a novel class of potent and selective non-peptide competitive antagonists for the human neurokinin-3 receptor.
J Med Chem, 39 (12): 2281-4. [PMID:8691422]
6. Liem-Moolenaar M, Gray FA, de Visser SJ, Franson KL, Schoemaker RC, Schmitt JA, Cohen AF, van Gerven JM. (2010)
Psychomotor and cognitive effects of a single oral dose of talnetant (SB223412) in healthy volunteers compared with placebo or haloperidol.
J Psychopharmacol (Oxford), 24 (1): 73-82. [PMID:18755817]
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]