Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C31H35Cl2N3O2.C4H6O4 |
| Molecular Weight | 670.623 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC(O)=O.CN(C[C@@H](CCN1CCC(CC1)(NC(C)=O)C2=CC=CC=C2)C3=CC=C(Cl)C(Cl)=C3)C(=O)C4=CC=CC=C4
InChI
InChIKey=RCPXXEKUUCEFEI-UFTMZEDQSA-N
InChI=1S/C31H35Cl2N3O2.C4H6O4/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;5-3(6)1-2-4(7)8/h3-14,21,26H,15-20,22H2,1-2H3,(H,34,37);1-2H2,(H,5,6)(H,7,8)/t26-;/m1./s1
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
| Title | Date | PubMed |
|---|---|---|
| A potent and selective non-peptide antagonist of the neurokinin A (NK2) receptor. | 1992 |
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| Influence of (+/-)-CP-96,345 and SR 48968 on electrical field stimulation of the isolated guinea-pig main bronchus. | 1992 Dec 2 |
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| Characterization of the binding sites of [3H]SR 48968, a potent nonpeptide radioligand antagonist of the neurokinin-2 receptor. | 1993 Mar 31 |
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| Expression of rat NK-2 (neurokinin A) receptor in E. coli. | 1994 |
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| Characterization of the capsaicin-sensitive component of cyclophosphamide-induced inflammation in the rat urinary bladder. | 1994 Apr |
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| Capsaicin-induced bladder hyperactivity in normal conscious rats. | 1994 Aug |
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| The non-peptide tachykinin NK2 receptor antagonist SR 48968 interacts with human, but not rat, cloned tachykinin NK3 receptors. | 1994 Feb 15 |
|
| The inhibitory modulation of guinea-pig intestinal peristalsis caused by capsaicin involves calcitonin gene-related peptide and nitric oxide. | 1995 Dec |
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| Prostaglandin E2-induced bladder hyperactivity in normal, conscious rats: involvement of tachykinins? | 1995 Jun |
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| Effects of neurokinin receptor antagonists on L-dopa induced bladder hyperactivity in normal conscious rats. | 1995 Oct |
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| 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 |
|
| Role of tachykinins in castor oil diarrhoea in rats. | 1997 Jun |
|
| Effect of tachykinin receptor antagonists in experimental neuropathic pain. | 1998 Nov 20 |
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| Acetylcholine and tachykinin receptor antagonists attenuate wood smoke-induced bronchoconstriction in guinea pigs. | 1998 Nov 6 |
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| Role of supraspinal tachykinins for volume- and L-dopa-induced bladder activity in normal conscious rats. | 2000 |
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| Effect of a tachykinin NK(2) receptor antagonist, nepadutant, on cardiovascular and gastrointestinal function in rats and dogs. | 2001 Mar 9 |
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| 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 |
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| 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 |
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| 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 |
|
| Role of capsaicin-sensitive afferents and sensory neuropeptides in endotoxin-induced airway inflammation and consequent bronchial hyperreactivity in the mouse. | 2007 Jun 7 |
|
| Capsaicin-evoked bradycardia in anesthetized guinea pigs is mediated by endogenous tachykinins. | 2008 Apr 10 |
|
| Occurrence and pharmacological characterization of four human tachykinin NK2 receptor variants. | 2008 Aug 15 |
|
| 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 |
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| Contractile effect of tachykinins on Suncus murinus (house musk shrew) isolated ileum. | 2008 Oct-Dec |
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| Behavioral effects of saredutant, a tachykinin NK2 receptor antagonist, in experimental models of mood disorders under basal and stress-related conditions. | 2008 Sep |
|
| Multifaceted approach to determine the antagonist molecular mechanism and interaction of ibodutant ([1-(2-phenyl-1R-[[1-(tetrahydropyran-4-ylmethyl)-piperidin-4-ylmethyl]-carbamoyl]-ethylcarbamoyl)-cyclopentyl]-amide) at the human tachykinin NK2 receptor. | 2009 May |
|
| Characterization of species-related differences in the pharmacology of tachykinin NK receptors 1, 2 and 3. | 2009 May 1 |
|
| Saredutant, an NK2 receptor antagonist, has both antidepressant-like effects and synergizes with desipramine in an animal model of depression. | 2010 Aug |
|
| 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 |
|
| Contractile responses induced by physalaemin, an analogue of substance P, in the rat esophagus. | 2010 Feb 25 |
|
| 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 |
|
| Neurokinin-1 receptor antagonist treatment in polymicrobial sepsis: molecular insights. | 2010 Sep 20 |
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DTXSID80170119
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6FE8PG636R
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11534823
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176381-98-9
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ACTIVE MOIETY
SUBSTANCE RECORD
