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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H35Cl2N3O2
Molecular Weight 552.5355
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SAREDUTANT

SMILES

CC(=NC1(CCN(CC[C@]([H])(CN(C)C(=O)c2ccccc2)c3ccc(c(c3)Cl)Cl)CC1)c4ccccc4)O

InChI

InChIKey=PGKXDIMONUAMFR-AREMUKBSSA-N
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

HIDE SMILES / InChI

Molecular Formula C31H35Cl2N3O2
Molecular Weight 552.5355
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Sanofi aventis developed saredutant (also known as SR 48968C) as a tachykinin neurokinin-2 (NK2) receptor antagonist for the treatment of depressive disorders and generalized anxiety disorder. This drug participated in phase III clinical trials in patients with a generalized anxiety disorder and as Combination Treatment for major depressive disorder, however, the drug failed to meet efficacy endpoints. It is known that NK-2 receptor mediates airway obstruction that is why saredutant was studied as a potential treatment of asthma. However, all studies of the drug were discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
A potent and selective non-peptide antagonist of the neurokinin A (NK2) receptor.
1992
Influence of (+/-)-CP-96,345 and SR 48968 on electrical field stimulation of the isolated guinea-pig main bronchus.
1992 Dec 2
Characterization of the capsaicin-sensitive component of cyclophosphamide-induced inflammation in the rat urinary bladder.
1994 Apr
'Sensory-efferent' neural control of mucus secretion: characterization using tachykinin receptor antagonists in ferret trachea in vitro.
1994 Dec
Role of intrathecal tachykinins for micturition in unanaesthetized rats with and without bladder outlet obstruction.
1994 Sep
Prostaglandin E2-induced bladder hyperactivity in normal, conscious rats: involvement of tachykinins?
1995 Jun
The non-peptide tachykinin NK1- and NK2-receptor antagonists SR 140333 and SR 48968 prevent castor-oil induced diarrhea in rats.
1996
Further evidence for the involvement of tachykinin receptor subtypes in formalin and capsaicin models of pain in mice.
1997 Aug
Nonpeptide tachykinin receptor antagonists: I. Pharmacological and pharmacokinetic characterization of SB 223412, a novel, potent and selective neurokinin-3 receptor antagonist.
1997 Jun
Effect of tachykinin receptor antagonists in experimental neuropathic pain.
1998 Nov 20
Role of supraspinal tachykinins for volume- and L-dopa-induced bladder activity in normal conscious rats.
2000
SCH 206272: a potent, orally active tachykinin NK(1), NK(2), and NK(3) receptor antagonist.
2002 Aug 23
Actions of endothelin and corticotropin releasing factor in the guinea-pig ileum: no evidence for an interaction with capsaicin-sensitive neurons.
2003 Aug
Targeting tachykinins for the treatment of obstructive airways disease.
2004
Inducible nitric oxide synthase evoked nitric oxide counteracts capsaicin-induced airway smooth muscle contraction, but exacerbates plasma extravasation.
2005 Apr 18
Antidepressant-like effects of neurokinin receptor antagonists in the forced swim test in the rat.
2005 Jan 10
Pharmacology of an original and selective nonpeptide antagonist ligand for the human tachykinin NK2 receptor.
2005 Jun 1
Selective blockade of NK2 or NK3 receptors produces anxiolytic- and antidepressant-like effects in gerbils.
2006 Apr
Tachykinin receptors antagonists: from research to clinic.
2006 Aug
Capsaicin-evoked bradycardia in anesthetized guinea pigs is mediated by endogenous tachykinins.
2008 Apr 10
Additional evidence for anxiolytic- and antidepressant-like activities of saredutant (SR48968), an antagonist at the neurokinin-2 receptor in various rodent-models.
2008 Mar
Role of tachykinin NK(1) and NK(2) receptors in colonic sensitivity and stress-induced defecation in gerbils.
2008 Mar 17
Contractile effect of tachykinins on Suncus murinus (house musk shrew) isolated ileum.
2008 Oct-Dec
Involvement of sensory nerves and TRPV1 receptors in the rat airway inflammatory response to two environment pollutants: diesel exhaust particles (DEP) and 1,2-naphthoquinone (1,2-NQ).
2010 Feb
Effects of intra-hippocampal injections of the NK2 receptor antagonist saredutant on the elevated plus maze, and the mouse defense test battery.
2010 Nov 26
ACS chemical neuroscience molecule spotlight on Saredutant.
2010 Oct 20

Sample Use Guides

Saredutant 100 mg once daily in the morning for a maximum of 8 weeks
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:56:49 UTC 2021
Edited
by admin
on Sat Jun 26 05:56:49 UTC 2021
Record UNII
720U2QK8I5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SAREDUTANT
INN   WHO-DD  
INN  
Official Name English
BENZAMIDE, N-((2S)-4-(4-(ACETYLAMINO)-4-PHENYL-1-PIPERIDINYL)-2-(3,4-DICHLOROPHENYL)BUTYL)-N-METHYL-
Systematic Name English
SAREDUTANT [INN]
Common Name English
SR-48968
Common Name English
SAREDUTANT [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Sat Jun 26 05:56:50 UTC 2021 , Edited by admin on Sat Jun 26 05:56:50 UTC 2021
Code System Code Type Description
EVMPD
SUB10449MIG
Created by admin on Sat Jun 26 05:56:50 UTC 2021 , Edited by admin on Sat Jun 26 05:56:50 UTC 2021
PRIMARY
INN
7487
Created by admin on Sat Jun 26 05:56:50 UTC 2021 , Edited by admin on Sat Jun 26 05:56:50 UTC 2021
PRIMARY
PUBCHEM
104974
Created by admin on Sat Jun 26 05:56:50 UTC 2021 , Edited by admin on Sat Jun 26 05:56:50 UTC 2021
PRIMARY
CAS
142001-63-6
Created by admin on Sat Jun 26 05:56:50 UTC 2021 , Edited by admin on Sat Jun 26 05:56:50 UTC 2021
PRIMARY
EPA CompTox
142001-63-6
Created by admin on Sat Jun 26 05:56:50 UTC 2021 , Edited by admin on Sat Jun 26 05:56:50 UTC 2021
PRIMARY
IUPHAR
2111
Created by admin on Sat Jun 26 05:56:50 UTC 2021 , Edited by admin on Sat Jun 26 05:56:50 UTC 2021
PRIMARY
DRUG BANK
DB06660
Created by admin on Sat Jun 26 05:56:50 UTC 2021 , Edited by admin on Sat Jun 26 05:56:50 UTC 2021
PRIMARY
NCI_THESAURUS
C152301
Created by admin on Sat Jun 26 05:56:50 UTC 2021 , Edited by admin on Sat Jun 26 05:56:50 UTC 2021
PRIMARY
FDA UNII
720U2QK8I5
Created by admin on Sat Jun 26 05:56:50 UTC 2021 , Edited by admin on Sat Jun 26 05:56:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL308148
Created by admin on Sat Jun 26 05:56:50 UTC 2021 , Edited by admin on Sat Jun 26 05:56:50 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Tachykinin NK2 receptor antagonist that was developed by Sanofi-Aventis for anti-depressant potential
IC50
Related Record Type Details
ACTIVE MOIETY