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Talnetant

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Identification

Generic Name
Talnetant
DrugBank Accession Number
DB06429
Background

Talnetant (SB-223,412) is a neurokinin 3 receptor antagonist developed by GlaxoSmithKline, which is being researched for several different functions, primarily for irritable bowel syndrome and as a potential antipsychotic drug for the treatment of schizophrenia.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 382.4544
Monoisotopic: 382.168127958
Chemical Formula
C25H22N2O2
Synonyms
  • Talnetant
External IDs
  • SB 223412
  • SB-223412
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Pharmacology

Indication

Investigated for use/treatment in schizophrenia and schizoaffective disorders, irritable bowel syndrome (IBS), and chronic obstructive pulmonary disease (COPD).

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ANeuromedin-K receptor
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Talnetant hydrochlorideC1ZIJ8F59E204519-66-4BHCSUEHQURQVLD-BDQAORGHSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Phenylquinolines
Direct Parent
Phenylquinolines
Alternative Parents
Quinoline carboxamides / Phenylpyridines / Pyridinecarboxylic acids and derivatives / Phenylpropanes / Hydroxypyridines / Vinylogous acids / Heteroaromatic compounds / Secondary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
2-phenylpyridine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyridine / Monocyclic benzene moiety
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
CZ3T9T146K
CAS number
174636-32-9
InChI Key
BIAVGWDGIJKWRM-UHFFFAOYSA-N
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)
IUPAC Name
3-hydroxy-2-phenyl-N-(1-phenylpropyl)quinoline-4-carboxamide
SMILES
CCC(NC(=O)C1=C(O)C(=NC2=CC=CC=C12)C1=CC=CC=C1)C1=CC=CC=C1

References

General References
  1. Dawson LA, Cato KJ, Scott C, Watson JM, Wood MD, Foxton R, de la Flor R, Jones GA, Kew JN, Cluderay JE, Southam E, Murkitt GS, Gartlon J, Pemberton DJ, Jones DN, Davies CH, Hagan J: 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. 2008 Jun;33(7):1642-52. Epub 2007 Aug 29. [Article]
  2. Houghton LA, Cremonini F, Camilleri M, Busciglio I, Fell C, Cox V, Alpers DH, Dewit OE, Dukes GE, Gray E, Lea R, Zinsmeister AR, Whorwell PJ: Effect of the NK(3) receptor antagonist, talnetant, on rectal sensory function and compliance in healthy humans. Neurogastroenterol Motil. 2007 Sep;19(9):732-43. [Article]
  3. Evangelista S: Talnetant GlaxoSmithKline. Curr Opin Investig Drugs. 2005 Jul;6(7):717-21. [Article]
PubChem Compound
133090
ChemSpider
117450
BindingDB
50074819
ChEMBL
CHEMBL275544
Wikipedia
Talnetant

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data
2CompletedTreatmentIrritable Bowel Syndrome (IBS)1somestatusstop reasonjust information to hide
2CompletedTreatmentSchizophrenia3somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00127 mg/mLALOGPS
logP4.98ALOGPS
logP6.25Chemaxon
logS-5.5ALOGPS
pKa (Strongest Acidic)8.03Chemaxon
pKa (Strongest Basic)2.73Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area62.22 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity114.25 m3·mol-1Chemaxon
Polarizability42.55 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8041
Caco-2 permeable+0.5113
P-glycoprotein substrateSubstrate0.538
P-glycoprotein inhibitor INon-inhibitor0.9114
P-glycoprotein inhibitor IINon-inhibitor0.839
Renal organic cation transporterNon-inhibitor0.9087
CYP450 2C9 substrateNon-substrate0.7074
CYP450 2D6 substrateNon-substrate0.7435
CYP450 3A4 substrateNon-substrate0.5685
CYP450 1A2 substrateInhibitor0.7106
CYP450 2C9 inhibitorInhibitor0.6508
CYP450 2D6 inhibitorNon-inhibitor0.884
CYP450 2C19 inhibitorNon-inhibitor0.5573
CYP450 3A4 inhibitorNon-inhibitor0.6319
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7766
Ames testNon AMES toxic0.765
CarcinogenicityNon-carcinogens0.8585
BiodegradationNot ready biodegradable0.986
Rat acute toxicity2.4383 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9816
hERG inhibition (predictor II)Non-inhibitor0.735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1409000000-57abffaad808752ea22c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0089-0169000000-429cb88818fdbc543269
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-1901000000-ec0b9ae64491ddd22a4a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01x1-1194000000-c469f3c161fc33e3d8fc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0g5d-3491000000-9f8e1e2805ece4b7db3d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-4492000000-98f4b4039307da8ddad0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-188.77867
predicted
DeepCCS 1.0 (2019)
[M+H]+191.13667
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.68695
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Neuromedin-K receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
This is a receptor for the tachykinin neuropeptide neuromedin-K (neurokinin B). It is associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of affinity of this receptor to tachykinins is: neuromedin-K > substance K > substance P
Specific Function
tachykinin receptor activity
Gene Name
TACR3
Uniprot ID
P29371
Uniprot Name
Neuromedin-K receptor
Molecular Weight
52201.35 Da
References
  1. Tian G, Wilkins D, Scott CW: Neurokinin-3 receptor-specific antagonists talnetant and osanetant show distinct mode of action in cellular Ca2+ mobilization but display similar binding kinetics and identical mechanism of binding in ligand cross-competition. Mol Pharmacol. 2007 Mar;71(3):902-11. Epub 2006 Dec 15. [Article]
  2. Dawson LA, Cato KJ, Scott C, Watson JM, Wood MD, Foxton R, de la Flor R, Jones GA, Kew JN, Cluderay JE, Southam E, Murkitt GS, Gartlon J, Pemberton DJ, Jones DN, Davies CH, Hagan J: 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. 2008 Jun;33(7):1642-52. Epub 2007 Aug 29. [Article]
  3. Sarau HM, Griswold DE, Potts W, Foley JJ, Schmidt DB, Webb EF, Martin LD, Brawner ME, Elshourbagy NA, Medhurst AD, Giardina GA, Hay DW: 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. 1997 Jun;281(3):1303-11. [Article]
  4. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at March 19, 2008 16:33 / Updated at February 21, 2021 18:52