Osanetant | CAS# 160492-56-8 (free base) | tachykinin NK3 antagonist

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

MedKoo CAT#: 529118

CAS#: 160492-56-8 (free base)

Description: Osanetant is a tachykinin NK3 antagonist potentially for the treatment of schizophrenia.

Chemical Structure

Osanetant

CAS# 160492-56-8 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 529118
Name: Osanetant
CAS#: 160492-56-8 (free base)
Chemical Formula: C35H41Cl2N3O2
Exact Mass: 605.26
Molecular Weight: 606.632
Elemental Analysis: C, 69.30; H, 6.81; Cl, 11.69; N, 6.93; O, 5.27

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 340
25mg	USD 920
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

Synonym: SR-142801; SR142801; SR 142801

IUPAC/Chemical Name: (R)-N-(1-(3-(1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl)propyl)-4-phenylpiperidin-4-yl)-N-methylacetamide

InChi Key: DZOJBGLFWINFBF-UMSFTDKQSA-N

InChi Code: 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

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

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: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Osanetant (SR142801) is a selective NK3 receptor antagonist.
In vitro activity:	The NK3 receptor antagonist SR-142801 (100 nM) significantly inhibited both SP-induced depolarization and the stimulation-evoked slow EPSP, as did NK3 receptor desensitization with senktide. The capsaicin-induced depolarization was significantly attenuated in the presence of SR-142801. Reference: Am J Physiol Gastrointest Liver Physiol. 2001 Aug;281(2):G357-64. https://pubmed.ncbi.nlm.nih.gov/11447015/
In vivo activity:	The selective NK3 receptor antagonist osanetant (100 nM) was able to partly block the senktide-induced increase in firing rates of dopamine neurons and shifted the concentration-response relation curves for senktide to the right (pA₂ values were ~7.5). The fractional block of the senktide responses by osanetant appeared to be larger in guinea pig dopamine neurons, indicating that osanetant is a more potent blocker of NK3 receptor-mediated responses with noncompetitive properties in the guinea pig. Reference: Synapse. 2011 Aug;65(8):814-26. https://pubmed.ncbi.nlm.nih.gov/21218451/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	66.7	109.90

Preparing Stock Solutions

The following data is based on the product molecular weight 606.63 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.

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

Formulation protocol:	1. Manning BP, Mawe GM. Tachykinins mediate slow excitatory postsynaptic transmission in guinea pig sphincter of Oddi ganglia. Am J Physiol Gastrointest Liver Physiol. 2001 Aug;281(2):G357-64. doi: 10.1152/ajpgi.2001.281.2.G357. PMID: 11447015. 2. Barbieri M, Nistri A. Depression of windup of spinal neurons in the neonatal rat spinal cord in vitro by an NK3 tachykinin receptor antagonist. J Neurophysiol. 2001 Apr;85(4):1502-11. doi: 10.1152/jn.2001.85.4.1502. PMID: 11287474. 3. 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. Epub 2011 Mar 21. PMID: 21218451. 4. 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. doi: 10.1016/s0014-2999(01)01036-6. PMID: 11516437.
In vitro protocol:	1. Manning BP, Mawe GM. Tachykinins mediate slow excitatory postsynaptic transmission in guinea pig sphincter of Oddi ganglia. Am J Physiol Gastrointest Liver Physiol. 2001 Aug;281(2):G357-64. doi: 10.1152/ajpgi.2001.281.2.G357. PMID: 11447015. 2. Barbieri M, Nistri A. Depression of windup of spinal neurons in the neonatal rat spinal cord in vitro by an NK3 tachykinin receptor antagonist. J Neurophysiol. 2001 Apr;85(4):1502-11. doi: 10.1152/jn.2001.85.4.1502. PMID: 11287474.
In vivo protocol:	1. 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. Epub 2011 Mar 21. PMID: 21218451. 2. 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. doi: 10.1016/s0014-2999(01)01036-6. PMID: 11516437.

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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.

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