U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H22N2O2
Molecular Weight 382.4544
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TALNETANT

SMILES

CC[C@H](NC(=O)C1=C(O)C(=NC2=C1C=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=BIAVGWDGIJKWRM-FQEVSTJZSA-N
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

HIDE SMILES / InChI
Molecular Formula C25H22N2O2
Molecular Weight 382.4544
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800009015 https://en.wikipedia.org/wiki/Talnetant

Talnetant (SB-223412) is a selective, orally active neurokinin 3 receptor antagonist and is under development for the potential treatment of several disorders, including irritable bowel syndrome, schizophrenia, chronic obstructive pulmonary disease, cough, overactive bladder and urinary incontinence. The most common adverse effects were headache, fatigue, and nausea.

CNS Activity

CNS Penetrant
2554
Curator's Comment: SB223412 crosses the blood-brain barrier to a significant extent.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 1.0 nM [Ki]
Antagonist
2778
 144.0 nM [Ki]
Antagonist
2778
 100.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.56 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18755817/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TALNETANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
600 mg 2 times / day multiple, oral
Studied dose
Dose: 600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00103727
unhealthy, ADULT
n = 275
Health Status: unhealthy
Condition: schizophrenia
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 275
Sources:
https://clinicaltrials.gov/ct2/show/NCT00103727
Sources:
https://clinicaltrials.gov/ct2/show/NCT00103727
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P0020AX
https://www.1pchem.com/search?query=1P0020AX
A2B Chem
AA92905
http://a2bchem.com/prod/AA92905
AA Blocks
AA001ZRH
http://aablocks.com/goods/Goods/detail?id=AA001ZRH
AK Scientific
4080AH
https://aksci.com/item_detail.php?cat=4080AH
AbovChem LLC
HY-14552A
http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-14552A
Angene
AGN-PC-0O4XVX
http://www.angenechemical.com/productshow/AGN-PC-0O4XVX.html
ApexBio Technology
A3854
https://www.apexbt.com/catalogsearch/result/?q=A3854
AstaTech
56181
http://astatechinc.com/CPSResult.php?CRNO=56181
BLD Pharm
BD262311
http://www.bldpharm.com/search/Search.html?keyword=BD262311
BLD Pharm
BD630526
http://www.bldpharm.com/search/Search.html?keyword=BD630526
BOC Sciences
174636-32-9
http://www.bocsci.com/description.asp?cas=174636-32-9
Chem Scene
CS-1638
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1638
ChemShuttle
169552
https://www.chemshuttle.com/catalogsearch/result/?q=169552
Excenen
EX-A894
http://www.excenen.com/searchresultlist.php?id=EX-A894
KeyOrganics
AS-72166
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-72166
Lab Network
LN01311468
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01311468
MedChem Express
HY-14552
https://www.medchemexpress.com/search.html?q=HY-14552&ft=&fa=&fp=
MolPort
MolPort-006-170-148
https://www.molport.com/shop/molecule-link/MolPort-006-170-148
MolPort
MolPort-035-758-899
https://www.molport.com/shop/molecule-link/MolPort-035-758-899
MuseChem
I002280
https://www.musechem.com/product/I002280.html
Princeton BioMolecular Research
PBMR240802
http://www.princetonbio.com/order_online?common_id=PBMR240802
Tocris
4672
https://www.tocris.com/search.php?Type=QuickSearch&Value=4672
Wonderchem
WD02VGS
http://www.wonder-chem.com/search.html?text=WD02VGS
eMolecules
266610510
https://orderbb.emolecules.com/search/#?query=266610510
eMolecules
301145200
https://orderbb.emolecules.com/search/#?query=301145200
eMolecules
49837486
https://orderbb.emolecules.com/search/#?query=49837486
eMolecules
50283866
https://orderbb.emolecules.com/search/#?query=50283866
eMolecules
70145128
https://orderbb.emolecules.com/search/#?query=70145128
mcule
MCULE-3991197012
https://mcule.com/MCULE-3991197012/
mcule
MCULE-7106959917
https://mcule.com/MCULE-7106959917/
mcule
MCULE-7135163856
https://mcule.com/MCULE-7135163856/
mcule
MCULE-8672750156
https://mcule.com/MCULE-8672750156/
PubMed

PubMed

TitleDatePubMed
2-Phenyl-4-quinolinecarboxamides: a novel class of potent and selective non-peptide competitive antagonists for the human neurokinin-3 receptor.
1996 Jun 7
Nonpeptide tachykinin receptor antagonists: I. Pharmacological and pharmacokinetic characterization of SB 223412, a novel, potent and selective neurokinin-3 receptor antagonist.
1997 Jun
Molecular and pharmacological characterization of the murine tachykinin NK(3) receptor.
2001 Feb 16
Synthesis and biological evaluation of novel fluoro and iodo quinoline carboxamides as potential ligands of NK-3 receptors for in vivo imaging studies.
2004 Aug 15
Testicular toxicity induced by a triple neurokinin receptor antagonist in male dogs.
2011 May
Patents

Patents

06277862
2
06355654
2

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/17727393 25 or 100 mg over 14-17 days.
0.1 mg to 1000 mg as single doses; up to 800 mg twice daily on repeat doses.
Route of Administration: Oral
In Vitro Use Guide
SB223412 antagonized senktide-induced contraction of rabbit isolated iris sphincter muscle (KB = 1.6 nM), and inhibited NK-3 receptorinduced membrane depolarization in guinea-pig bronchial parasympathetic ganglia and substantia nigra pars compacta in guinea pig. SB223412 inhibited senktide-induced miosis in rabbits when given iv (ED50 = 0.44mg/kg) and by 53% when given orally (25 mg/kg, PO).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:00:54 GMT 2023
Edited
by admin
on Fri Dec 15 16:00:54 GMT 2023
Record UNII
CZ3T9T146K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TALNETANT
INN   WHO-DD  
INN  
Official Name English
Talnetant [WHO-DD]
Common Name English
N-((S)-.ALPHA.-ETHYLBENZYL)-3-HYDROXY-2-PHENYLCINCHONINAMIDE
Systematic Name English
talnetant [INN]
Common Name English
(S)-3-HYDROXY-2-PHENYL-N-(1-PHENYLPROPYL)-4-QUINOLINECARBOXAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29698
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
Code System Code Type Description
WIKIPEDIA
TALNETANT
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL10188
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
PRIMARY
INN
7872
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
PRIMARY
DRUG BANK
DB06429
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
PRIMARY
EVMPD
SUB34015
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
PRIMARY
SMS_ID
100000127876
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID00870124
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
PRIMARY
PUBCHEM
5311424
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
PRIMARY
NCI_THESAURUS
C76464
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
PRIMARY
CAS
174636-32-9
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
PRIMARY
FDA UNII
CZ3T9T146K
Created by admin on Fri Dec 15 16:00:54 GMT 2023 , Edited by admin on Fri Dec 15 16:00:54 GMT 2023
PRIMARY
Related Record Type Details
NEUROMEDIN-K RECEPTOR
TARGET -> INHIBITOR
Structure of TALNETANT HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of TALNETANT
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
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