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

MedKoo Cat#: 529118 | Name: Osanetant free base

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Description:

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

Osanetant (SR142801) is a potent and selective non-peptide antagonist of the tachykinin NK3 receptor. It exhibits high affinity with a Ki of about 1.1–3.6 nM for the human NK3 receptor and shows over 500-fold selectivity versus NK1 and NK2 receptors. In preclinical studies, osanetant effectively blocks NK3 receptor-mediated responses, such as neurokinin B-induced contractions and hormone release. For example, it has been shown to inhibit NK3 receptor agonist–induced LH release in rodents and primates.

Chemical Structure

Osanetant free base

CAS#160492-56-8 (free base)

Theoretical Analysis

MedKoo Cat#: 529118

Name: Osanetant free base

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

Chemical Formula: C35H41Cl2N3O2

Exact Mass: 605.2576

Molecular Weight: 606.63

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 450.00	2 Weeks
25mg	USD 1,075.00	2 Weeks

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Related CAS #

160492-56-8 (free base) 173050-51-6 (HCl)

Synonym

SR-142801; SR142801; SR 142801; Osanetant free base;

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

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	66.7	109.90

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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:

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.

1: Cieri-Hutcherson NE, Marji EK, Hutcherson TC. Systematic review of neurokinin-3 receptor antagonists for the management of vasomotor symptoms of menopause. Menopause. 2024 Apr 1;31(4):342-354. doi: 10.1097/GME.0000000000002328. Epub 2024 Mar 11. PMID: 38471077. 2: Wiedmann F, Paasche A, Nietfeld J, Kraft M, Meyer AL, Warnecke G, Karck M, Frey N, Schmidt C. Activation of neurokinin-III receptors modulates human atrial TASK-1 currents. J Mol Cell Cardiol. 2023 Nov;184:26-36. doi: 10.1016/j.yjmcc.2023.09.010. Epub 2023 Oct 2. PMID: 37793594. 3: Florido A, Moreno E, Canela EI, Andero R. Nk3R blockade has sex-divergent effects on memory in mice. Biol Sex Differ. 2022 Jun 11;13(1):28. doi: 10.1186/s13293-022-00437-z. PMID: 35690790; PMCID: PMC9188709. 4: Florido A, Velasco ER, Soto-Faguás CM, Gomez-Gomez A, Perez-Caballero L, Molina P, Nadal R, Pozo OJ, Saura CA, Andero R. Sex differences in fear memory consolidation via Tac2 signaling in mice. Nat Commun. 2021 May 3;12(1):2496. doi: 10.1038/s41467-021-22911-9. Erratum in: Nat Commun. 2024 Jul 18;15(1):6051. doi: 10.1038/s41467-024-50516-5. PMID: 33941789; PMCID: PMC8093426. 5: Zhang J, He C, Pi X, Wang Y, Zhou L, Dong S. MCRT, a chimeric peptide based on morphiceptin and PFRTic-NH2, regulates the depressor effects induced by endokinin A/B. Eur J Pharmacol. 2016 Dec 5;792:33-37. doi: 10.1016/j.ejphar.2016.10.028. Epub 2016 Oct 23. PMID: 27784644. 6: Andero R, Daniel S, Guo JD, Bruner RC, Seth S, Marvar PJ, Rainnie D, Ressler KJ. Amygdala-Dependent Molecular Mechanisms of the Tac2 Pathway in Fear Learning. Neuropsychopharmacology. 2016 Oct;41(11):2714-22. doi: 10.1038/npp.2016.77. Epub 2016 May 26. PMID: 27238620; PMCID: PMC5026739. 7: Duarte FS, Duzzioni M, Leme LR, Smith Sde P, De Lima TC. Evidence for involvement of NK₃ receptors in the anxiogenic-like effect of SP6-11(C-terminal), a metabolite of substance P, in rats evaluated in the elevated plus-maze. Behav Brain Res. 2016 Apr 15;303:168-75. doi: 10.1016/j.bbr.2016.02.003. Epub 2016 Feb 3. PMID: 26851555. 8: Burbiel JC. Primary prevention of posttraumatic stress disorder: drugs and implications. Mil Med Res. 2015 Oct 26;2:24. doi: 10.1186/s40779-015-0053-2. PMID: 26504586; PMCID: PMC4620711. 9: Zhou L, Yang Q, He C, Wei C, Yang Y, Dong S. Interaction of endokinin A/B and (Mpa(6))-γ2-MSH-6-12 in pain regulation in mice. Neuropeptides. 2015 Oct;53:79-84. doi: 10.1016/j.npep.2015.06.007. Epub 2015 Jun 25. PMID: 26145509. 10: Gwynne RM, Clarke AJ, Furness JB, Bornstein JC. Both exogenous 5-HT and endogenous 5-HT, released by fluoxetine, enhance distension evoked propulsion in guinea-pig ileum in vitro. Front Neurosci. 2014 Sep 19;8:301. doi: 10.3389/fnins.2014.00301. PMID: 25285066; PMCID: PMC4168689. 11: 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. Epub 2014 Aug 5. PMID: 25107588. 12: 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):444-454. doi: 10.1016/j.neuron.2014.05.028. Epub 2014 Jun 26. PMID: 24976214; PMCID: PMC4103970. 13: Sendur P, Ceranowicz P, Sendur R, Cieszkowski J, Warzecha Z, Dembiński A. Udział endogennych tachykinin w powstawaniu uszkodzeń błony śluzowej jelita czczego wywołanych niesterydowymi lekami przeciwzapalnymi [Involvement of endogenous tachykinins in the development of jejunal mucosa injury induced by on-steroidal anti-inflammatory drugs]. Przegl Lek. 2013;70(2):48-52. Polish. PMID: 23879003. 14: de Croft S, Boehm U, Herbison AE. Neurokinin B activates arcuate kisspeptin neurons through multiple tachykinin receptors in the male mouse. Endocrinology. 2013 Aug;154(8):2750-60. doi: 10.1210/en.2013-1231. Epub 2013 Jun 6. PMID: 23744641. 15: Zhou L, Jin Q, Yang Y, Liu Z, Li X, Dong S, Zhao L. Effects of endokinin A/B and endokinin C/D on the antinociception properties of hemopressin in mice. Peptides. 2012 Nov;38(1):70-80. doi: 10.1016/j.peptides.2012.08.006. Epub 2012 Aug 20. PMID: 22951322. 16: Tauer U, Zhao Y, Hunt SP, Culman J. Are biological actions of neurokinin A in the adult brain mediated by a cross-talk between the NK1 and NK2 receptors? Neuropharmacology. 2012 Nov;63(6):958-65. doi: 10.1016/j.neuropharm.2012.06.041. Epub 2012 Jul 6. PMID: 22771977. 17: Corboz MR, Rivelli MA, Fernandez X, Greenfeder S. Neuromodulation mediated by the tachykinin NK3-receptor agonist [MePhe7]-neurokinin B in the isolated perfused lung of nonsensitized nonchallenged and ovalbumin-sensitized and -challenged guinea pig. Exp Lung Res. 2012 Jun;38(5):233-49. doi: 10.3109/01902148.2012.673050. Epub 2012 Apr 26. PMID: 22536826. 18: Malherbe P, Ballard TM, Ratni H. Tachykinin neurokinin 3 receptor antagonists: a patent review (2005 - 2010). Expert Opin Ther Pat. 2011 May;21(5):637-55. doi: 10.1517/13543776.2011.568482. Epub 2011 Mar 21. PMID: 21417773. 19: Hassanzadeh P, Hassanzadeh A. Involvement of the neurotrophin and cannabinoid systems in the mechanisms of action of neurokinin receptor antagonists. Eur Neuropsychopharmacol. 2011 Dec;21(12):905-17. doi: 10.1016/j.euroneuro.2011.01.002. Epub 2011 Feb 12. PMID: 21316930. 20: 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.