Osanetant
Osanetant is a tachykinin NK3 antagonist potentially for the treatment of schizophrenia.
For research use only. We do not sell to patients.
Chemical Information
| Name | Osanetant |
|---|---|
| Iupac Chemical Name | (R)-N-(1-(3-(1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl)propyl)-4-phenylpiperidin-4-yl)-N-methylacetamide |
| Synonyms | SR-142801; SR142801; SR 142801 |
| Molecular Formula | C35H41Cl2N3O2 |
| Molecular Weight | 606.62 |
| Smile | CC(N(C1(C2=CC=CC=C2)CCN(CCC[C@@]3(C4=CC=C(Cl)C(Cl)=C4)CN(C(C5=CC=CC=C5)=O)CCC3)CC1)C)=O |
| InChiKey | DZOJBGLFWINFBF-UMSFTDKQSA-N |
| InChi | InChI=1S/C35H41Cl2N3O2/c1-27(41)38(2)35(29-13-7-4-8-14-29)19-23-39(24-20-35)21-9-17-34(30-15-16-31(36)32(37)25-30)18-10-22-40(26-34)33(42)28-11-5-3-6-12-28/h3-8,11-16,25H,9-10,17-24,26H2,1-2H3/t34-/m0/s1 |
| CAS Number | 160492-56-8 (free base) |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Solubility | Soluble in DMSO |
| Handling | |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| HS Code |
| Targets | |
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| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
1: Malherbe P, Kratzeisen C, Marcuz A, Zenner MT, Nettekoven MH, Ratni H, Wettstein JG, Bissantz C. Identification of a critical residue in the transmembrane domain 2 of tachykinin neurokinin 3 receptor affecting the dissociation kinetics and antagonism mode of osanetant (SR 142801) and piperidine-based structures. J Med Chem. 2009 Nov 26;52(22):7103-12. doi: 10.1021/jm900948q. PubMed PMID: 19817444.
2: Malherbe P, Bissantz C, Marcuz A, Kratzeisen C, Zenner MT, Wettstein JG, Ratni H, Riemer C, Spooren W. Me-talnetant and osanetant interact within overlapping but not identical binding pockets in the human tachykinin neurokinin 3 receptor transmembrane domains. Mol Pharmacol. 2008 Jun;73(6):1736-50. doi: 10.1124/mol.107.042754. PubMed PMID: 18308898.
3: 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. PubMed PMID: 17172464.
4: Daoui S, Cui YY, Lagente V, Emonds-Alt X, Advenier C. A tachykinin NK3 receptor antagonist, SR 142801 (osanetant), prevents substance P-induced bronchial hyperreactivity in guinea-pigs. Pulm Pharmacol Ther. 1997 Oct-Dec;10(5-6):261-70. PubMed PMID: 9778489.
5: Kamali F. Osanetant Sanofi-Synthélabo. Curr Opin Investig Drugs. 2001 Jul;2(7):950-6. Review. PubMed PMID: 11757797.
6: Kronenberg G, Berger P, Tauber RF, Bandelow B, Henkel V, Heuser I. Randomized, double-blind study of SR142801 (Osanetant). A novel neurokinin-3 (NK3) receptor antagonist in panic disorder with pre- and posttreatment cholecystokinin tetrapeptide (CCK-4) challenges. Pharmacopsychiatry. 2005 Jan;38(1):24-9. PubMed PMID: 15706463.
7: Bert L, Rodier D, Bougault I, Allouard N, Le-Fur G, Soubrié P, Steinberg R. Permissive role of neurokinin NK(3) receptors in NK(1) receptor-mediated activation of the locus coeruleus revealed by SR 142801. Synapse. 2002 Jan;43(1):62-9. PubMed PMID: 11746734.
8: Pinto FM, Saulnier JP, Faisy C, Naline E, Molimard M, Prieto L, Martin JD, Emonds-Alt X, Advenier C, Candenas ML. SR 142801, a tachykinin NK(3) receptor antagonist, prevents beta(2)-adrenoceptor agonist-induced hyperresponsiveness to neurokinin A in guinea-pig isolated trachea. Life Sci. 2002 Dec 6;72(3):307-20. PubMed PMID: 12427489.
9: Nénan S, Germain N, Lagente V, Emonds-Alt X, Advenier C, Boichot E. Inhibition of inflammatory cell recruitment by the tachykinin NK(3)-receptor antagonist, SR 142801, in a murine model of asthma. Eur J Pharmacol. 2001 Jun 15;421(3):201-5. PubMed PMID: 11516437.
10: Guo JZ, Yoshioka K, Otsuka M. Effects of a tachykinin NK3 receptor antagonist, SR 142801, studied in isolated neonatal rat spinal cord. Neuropeptides. 1998 Dec;32(6):537-42. PubMed PMID: 9920451.
11: Beaujouan JC, Saffroy M, Torrens Y, Glowinski J. Potency and selectivity of the tachykinin NK3 receptor antagonist SR 142801. Eur J Pharmacol. 1997 Jan 29;319(2-3):307-16. PubMed PMID: 9042606.
12: Werkman TR, McCreary AC, Kruse CG, Wadman WJ. NK3 receptors mediate an increase in firing rate of midbrain dopamine neurons of the rat and the guinea pig. Synapse. 2011 Aug;65(8):814-26. doi: 10.1002/syn.20908. PubMed PMID: 21218451.
13: Malherbe P, Knoflach F, Marcuz A, Bohnert C, Weber M, Knust H, Ratni H, Spooren W, Ballard TM, Bissantz C. Mapping the binding pocket of a novel, high-affinity, slow dissociating tachykinin NK3 receptor antagonist: biochemical and electrophysiological characterization. Neuropharmacology. 2014 Nov;86:259-72. doi: 10.1016/j.neuropharm.2014.07.017. PubMed PMID: 25107588.
14: Pasichnichenko OM, Skok VI. [The effect of SR 142801, a blocker of tachykinin NK-3 receptors, on synaptic transmission in the rat caudal mesenteric ganglion]. Fiziol Zh. 1999;45(4):55-60. Ukrainian. PubMed PMID: 10474803.
15: Giuliani S, Maggi CA. Effect of SR 142801 on nitric oxide-dependent and independent responses to tachykinin NK3 receptor agonists in isolated guinea-pig colon. Naunyn Schmiedebergs Arch Pharmacol. 1995 Nov;352(5):512-9. PubMed PMID: 8751080.
16: Roccon A, Marchionni D, Nisato D. Study of SR 142801, a new potent non-peptide NK3 receptor antagonist on cardiovascular responses in conscious guinea-pig. Br J Pharmacol. 1996 Jul;118(5):1095-102. PubMed PMID: 8818331; PubMed Central PMCID: PMC1909579.
17: Patacchini R, Barthò L, Holzer P, Maggi CA. Activity of SR 142801 at peripheral tachykinin receptors. Eur J Pharmacol. 1995 May 4;278(1):17-25. PubMed PMID: 7545122.
18: Andero R, Dias BG, Ressler KJ. A role for Tac2, NkB, and Nk3 receptor in normal and dysregulated fear memory consolidation. Neuron. 2014 Jul 16;83(2):444-54. doi: 10.1016/j.neuron.2014.05.028. PubMed PMID: 24976214; PubMed Central PMCID: PMC4103970.
19: Nguyen-Le XK, Nguyen QT, Gobeil F, Pheng LH, Emonds-Alt X, Brelière JC, Regoli D. Pharmacological characterization of SR 142801: a new non-peptide antagonist of the neurokinin NK-3 receptor. Pharmacology. 1996 May;52(5):283-91. PubMed PMID: 8807672.
20: Salomé N, Stemmelin J, Cohen C, Griebel G. Selective blockade of NK2 or NK3 receptors produces anxiolytic- and antidepressant-like effects in gerbils. Pharmacol Biochem Behav. 2006 Apr;83(4):533-9. PubMed PMID: 16624395.
Chemical Structure
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