Osanetant HCl

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 414640

CAS#: 173050-51-6 (HCl)

Description: Osanetant HCl is the (R)-enantiomer; neurokinin-3 receptor antagonist


Chemical Structure

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Osanetant HCl
CAS# 173050-51-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 414640
Name: Osanetant HCl
CAS#: 173050-51-6 (HCl)
Chemical Formula: C35H42Cl3N3O2
Exact Mass: 641.2343
Molecular Weight: 643.09
Elemental Analysis: C, 65.37; H, 6.58; Cl, 16.54; N, 6.53; O, 4.98

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 173050-51-6 (HCl); 160492-56-8 (free base)  

Synonym: Osanetant hydrochoride; Osanetant HCl; SR142801; SR-142801; SR 142801

IUPAC/Chemical Name: Acetamide, N-(1-(3-((3R)-1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl)propyl)-4-phenyl-4-piperidinyl)-N-methyl-, monohydrochloride

InChi Key: NKFREVJOQXEZID-GXUZKUJRSA-N

InChi Code: InChI=1S/C35H41Cl2N3O2.ClH/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;1H/t34-;/m0./s1

SMILES Code: 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.[H]Cl

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

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.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 643.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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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.