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MedKoo Cat#: 561753 | Name: Nelivaptan
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Description:

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

Nelivaptan is a non-peptide vasopressin receptor antagonist that is selective for the V1B subtype. SSR149415 ameliorates spermatogenesis function in a mouse model of chronic social defeat stress. SSR149415 has long-lasting antidepressant effects in the olfactory bulbectomy-induced hyperactivity depression model. SSR149415 blocks aggressive behaviors in hamsters. The combination of V1b antagonist SSR149415 with NTN at individual subthreshold doses shows potential in alcoholism treatment, possibly with less adverse effects.

Chemical Structure

Nelivaptan
Nelivaptan
CAS#439687-69-1

Theoretical Analysis

MedKoo Cat#: 561753

Name: Nelivaptan

CAS#: 439687-69-1

Chemical Formula: C30H32ClN3O8S

Exact Mass: 629.1599

Molecular Weight: 630.11

Elemental Analysis: C, 57.19; H, 5.12; Cl, 5.63; N, 6.67; O, 20.31; S, 5.09

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 Weeks
25mg USD 1,450.00 2 Weeks
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Related CAS #
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Synonym
Nelivaptan; SSR149415; SR-149415; SR 149415;
IUPAC/Chemical Name
(2S,4R)-1-[(3R)-5-Chloro-1-(2,4-dimethoxyphenyl)sulfonyl-3-(2-methoxyphenyl)-2-oxoindol-3-yl]-4-hydroxy-N,N-dimethylpyrrolidine-2-carboxamide
InChi Key
NJXZWIIMWNEOGJ-WEWKHQNJSA-N
InChi Code
InChI=1S/C30H32ClN3O8S/c1-32(2)28(36)24-15-19(35)17-33(24)30(21-8-6-7-9-25(21)41-4)22-14-18(31)10-12-23(22)34(29(30)37)43(38,39)27-13-11-20(40-3)16-26(27)42-5/h6-14,16,19,24,35H,15,17H2,1-5H3/t19-,24+,30+/m1/s1
SMILES Code
O=C([C@H]1N([C@]2(C3=CC=CC=C3OC)C(N(S(=O)(C4=CC=C(OC)C=C4OC)=O)C5=C2C=C(Cl)C=C5)=O)C[C@H](O)C1)N(C)C
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:
Nelivaptan is a non-peptide vasopressin receptor antagonist that is selective for the V1B subtype.
In vitro activity:
TBD
In vivo activity:
Microinjection of vasopressin into the PVN increased mean arterial pressure, heart rate and renal sympathetic nerve activity in rats, all of which were inhibited by pre-injection of the PVN with the V1b antagonist, nelivaptan. Pre-injection of the PVN with the selective V1b receptor antagonist, nelivaptan, did not alter baseline values but blocked the responses to VP. Reference: Exp Physiol. 2015 Apr 20;100(5):553-65. https://pubmed.ncbi.nlm.nih.gov/25605313/
Solvent mg/mL mM
Solubility
Ethanol 63.0 100.00
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 630.11 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
Formulation protocol:
El-Werfali W, Toomasian C, Maliszewska-Scislo M, Li C, Rossi NF. Haemodynamic and renal sympathetic responses to V1b vasopressin receptor activation within the paraventricular nucleus. Exp Physiol. 2015 Apr 20;100(5):553-65. doi: 10.1113/expphysiol.2014.084426. PMID: 25605313.
In vitro protocol:
TBD
In vivo protocol:
El-Werfali W, Toomasian C, Maliszewska-Scislo M, Li C, Rossi NF. Haemodynamic and renal sympathetic responses to V1b vasopressin receptor activation within the paraventricular nucleus. Exp Physiol. 2015 Apr 20;100(5):553-65. doi: 10.1113/expphysiol.2014.084426. PMID: 25605313.
1: Zhou Y, Rubinstein M, Low MJ, Kreek MJ. V1b Receptor Antagonist SSR149415 and Naltrexone Synergistically Decrease Excessive Alcohol Drinking in Male and Female Mice. Alcohol Clin Exp Res. 2018 Jan;42(1):195-205. doi: 10.1111/acer.13544. Epub 2017 Nov 28. PMID: 29105118; PMCID: PMC5750120. 2: Wang B, Zhou J, Zhuang YY, Wang LL, Pu JX, Huang YH, Xia F, Lv JX. The Non- Peptide Vasopressin V1b Receptor Antagonist, SSR149415, Ameliorates Spermatogenesis Function in a Mouse Model of Chronic Social Defeat Stress. J Cell Biochem. 2017 Nov;118(11):3891-3898. doi: 10.1002/jcb.26040. Epub 2017 Jun 7. PMID: 28390185. 3: Qi X, Guzhva L, Ji Y, Bruijnzeel AW. Chronic treatment with the vasopressin 1b receptor antagonist SSR149415 prevents the dysphoria associated with nicotine withdrawal in rats. Behav Brain Res. 2015 Oct 1;292:259-65. doi: 10.1016/j.bbr.2015.06.031. Epub 2015 Jun 22. PMID: 26112757; PMCID: PMC4558258. 4: Griebel G, Beeské S, Stahl SM. The vasopressin V(1b) receptor antagonist SSR149415 in the treatment of major depressive and generalized anxiety disorders: results from 4 randomized, double-blind, placebo-controlled studies. J Clin Psychiatry. 2012 Nov;73(11):1403-11. doi: 10.4088/JCP.12m07804. Epub 2012 Oct 16. PMID: 23146246. 5: Hernandez VS, Ruíz-Velazco S, Zhang L. Differential effects of osmotic and SSR149415 challenges in maternally separated and control rats: the role of vasopressin on spatial learning. Neurosci Lett. 2012 Oct 24;528(2):143-7. doi: 10.1016/j.neulet.2012.09.002. Epub 2012 Sep 12. PMID: 22982556. 6: Amikishieva AV, Ilnitskaya SI, Nikolin VP, Popova NA. Effect of vasopressin V1b receptor antagonist, SSR149415, on anxiety-like behavior and Lewis lung carcinoma metastasis in mice. Exp Oncol. 2011 Sep;33(3):126-9. PMID: 21956463. 7: Urani A, Philbert J, Cohen C, Griebel G. The corticotropin-releasing factor 1 receptor antagonist, SSR125543, and the vasopressin 1b receptor antagonist, SSR149415, prevent stress-induced cognitive impairment in mice. Pharmacol Biochem Behav. 2011 May;98(3):425-31. doi: 10.1016/j.pbb.2011.02.019. Epub 2011 Feb 26. PMID: 21356230. 8: Schönberger M, Leggett C, Kim SW, Hooker JM. Synthesis of [11C]SSR149415 and preliminary imaging studies using positron emission tomography. Bioorg Med Chem Lett. 2010 May 15;20(10):3103-6. doi: 10.1016/j.bmcl.2010.03.108. Epub 2010 Apr 2. PMID: 20400305. 9: Breuer ME, van Gaalen MM, Wernet W, Claessens SE, Oosting RS, Behl B, Korte SM, Schoemaker H, Gross G, Olivier B, Groenink L. SSR149415, a non-peptide vasopressin V1b receptor antagonist, has long-lasting antidepressant effects in the olfactory bulbectomy-induced hyperactivity depression model. Naunyn Schmiedebergs Arch Pharmacol. 2009 Jan;379(1):101-6. doi: 10.1007/s00210-008-0336-1. Epub 2008 Jul 31. PMID: 18668225. 10: Serradeil-Le Gal C, Raufaste D, Derick S, Blankenstein J, Allen J, Pouzet B, Pascal M, Wagnon J, Ventura MA. Biological characterization of rodent and human vasopressin V1b receptors using SSR-149415, a nonpeptide V1b receptor ligand. Am J Physiol Regul Integr Comp Physiol. 2007 Aug;293(2):R938-49. doi: 10.1152/ajpregu.00062.2007. Epub 2007 May 23. PMID: 17522130. 11: Hodgson RA, Higgins GA, Guthrie DH, Lu SX, Pond AJ, Mullins DE, Guzzi MF, Parker EM, Varty GB. Comparison of the V1b antagonist, SSR149415, and the CRF1 antagonist, CP-154,526, in rodent models of anxiety and depression. Pharmacol Biochem Behav. 2007 Mar;86(3):431-40. doi: 10.1016/j.pbb.2006.12.021. Epub 2007 Jan 9. PMID: 17291571. 12: Iijima M, Chaki S. An arginine vasopressin V1b antagonist, SSR149415 elicits antidepressant-like effects in an olfactory bulbectomy model. Prog Neuropsychopharmacol Biol Psychiatry. 2007 Apr 13;31(3):622-7. doi: 10.1016/j.pnpbp.2006.12.008. Epub 2006 Dec 15. PMID: 17229509. 13: Shimazaki T, Iijima M, Chaki S. The pituitary mediates the anxiolytic-like effects of the vasopressin V1B receptor antagonist, SSR149415, in a social interaction test in rats. Eur J Pharmacol. 2006 Aug 14;543(1-3):63-7. doi: 10.1016/j.ejphar.2006.06.032. Epub 2006 Jun 27. PMID: 16843459. 14: Claustre Y, Rouquier L, Desvignes C, Leonetti M, Montégut J, Aubin N, Allouard N, Bougault I, Oury-Donat F, Steinberg R. Effects of the vasopressin (V1b) receptor antagonist, SSR149415, and the corticotropin-releasing factor 1 receptor antagonist, SSR125543, on FG 7142-induced increase in acetylcholine and norepinephrine release in the rat. Neuroscience. 2006 Sep 1;141(3):1481-8. doi: 10.1016/j.neuroscience.2006.05.006. Epub 2006 Jun 15. PMID: 16781820. 15: Salomé N, Stemmelin J, Cohen C, Griebel G. Differential roles of amygdaloid nuclei in the anxiolytic- and antidepressant-like effects of the V1b receptor antagonist, SSR149415, in rats. Psychopharmacology (Berl). 2006 Aug;187(2):237-44. doi: 10.1007/s00213-006-0424-1. Epub 2006 Jun 2. PMID: 16779555. 16: Louis C, Cohen C, Depoortère R, Griebel G. Antidepressant-like effects of the corticotropin-releasing factor 1 receptor antagonist, SSR125543, and the vasopressin 1b receptor antagonist, SSR149415, in a DRL-72 s schedule in the rat. Neuropsychopharmacology. 2006 Oct;31(10):2180-7. doi: 10.1038/sj.npp.1301036. Epub 2006 Feb 1. PMID: 16452986. 17: Overstreet DH, Griebel G. Antidepressant-like effects of the vasopressin V1b receptor antagonist SSR149415 in the Flinders Sensitive Line rat. Pharmacol Biochem Behav. 2005 Sep;82(1):223-7. doi: 10.1016/j.pbb.2005.07.021. Epub 2005 Sep 21. PMID: 16181667. 18: Griffante C, Green A, Curcuruto O, Haslam CP, Dickinson BA, Arban R. Selectivity of d[Cha4]AVP and SSR149415 at human vasopressin and oxytocin receptors: evidence that SSR149415 is a mixed vasopressin V1b/oxytocin receptor antagonist. Br J Pharmacol. 2005 Nov;146(5):744-51. doi: 10.1038/sj.bjp.0706383. PMID: 16158071; PMCID: PMC1751202. 19: Serradeil-Le Gal C, Wagnon J 3rd, Tonnerre B, Roux R, Garcia G, Griebel G, Aulombard A. An overview of SSR149415, a selective nonpeptide vasopressin V(1b) receptor antagonist for the treatment of stress-related disorders. CNS Drug Rev. 2005 Spring;11(1):53-68. doi: 10.1111/j.1527-3458.2005.tb00035.x. PMID: 15867952; PMCID: PMC6741711. 20: Blanchard RJ, Griebel G, Farrokhi C, Markham C, Yang M, Blanchard DC. AVP V1b selective antagonist SSR149415 blocks aggressive behaviors in hamsters. Pharmacol Biochem Behav. 2005 Jan;80(1):189-94. doi: 10.1016/j.pbb.2004.10.024. Epub 2004 Dec 15. PMID: 15652395.

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