MedKoo Cat#: 562331 | Name: Relcovaptan
Featured

Description:

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

Relcovaptan is a selective non-peptide vasopressin V1A receptor antagonist. Relcovaptan has shown initial positive results in the treatment of Raynaud's disease, dysmenorrhoea, and tocolysis. Relcovaptan prevented CRPC emergence and decreased CRPC orthotopic and bone metastatic growth in mouse models.

Chemical Structure

Relcovaptan
Relcovaptan
CAS#150375-75-0

Theoretical Analysis

MedKoo Cat#: 562331

Name: Relcovaptan

CAS#: 150375-75-0

Chemical Formula: C28H27Cl2N3O7S

Exact Mass: 619.0947

Molecular Weight: 620.49

Elemental Analysis: C, 54.20; H, 4.39; Cl, 11.43; N, 6.77; O, 18.05; S, 5.17

Price and Availability

Size Price Availability Quantity
5mg USD 300.00
25mg USD 860.00
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Relcovaptan; SR-49059; SR 49059; SR49059;
IUPAC/Chemical Name
(2S)-1-[[(2R,3S)-5-Chloro-3-(2-chlorophenyl)-1-[(3,4-dimethoxyphenyl)sulfonyl]-2,3-dihydro-3-hydroxy-1H-indol-2-yl]carbonyl]-2-pyrrolidinecarboxamide
InChi Key
CEBYCSRFKCEUSW-NAYZPBBASA-N
InChi Code
InChI=1S/C28H27Cl2N3O7S/c1-39-23-12-10-17(15-24(23)40-2)41(37,38)33-21-11-9-16(29)14-19(21)28(36,18-6-3-4-7-20(18)30)25(33)27(35)32-13-5-8-22(32)26(31)34/h3-4,6-7,9-12,14-15,22,25,36H,5,8,13H2,1-2H3,(H2,31,34)/t22-,25-,28+/m0/s1
SMILES Code
O=C([C@H]1N(C([C@@H]2N(S(=O)(C3=CC=C(OC)C(OC)=C3)=O)C4=C(C=C(Cl)C=C4)[C@@]2(C5=CC=CC=C5Cl)O)=O)CCC1)N
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
Biological target:
Relcovaptan is a potent and selective non-peptide vasopressin V1A receptor antagonist; devoid of agonist activity. Relcovaptan displays high affinity and efficacy at both rat (Ki = 1.6 nM) and human (Ki = 1.1 - 6.3 nM) V1A receptors. It potently antagonizes arginine vasopressin-induced effects in vitro (IC50 = 3.7 nM for inhibition of human platelet aggregation) and is orally active in vivo.
In vitro activity:
Relcovaptan fully inhibited Swiss 3T3 fibroblast proliferation. Through direct interaction at AVP V1a receptors, relcovaptan exerts the most potent antiproliferative effect yet described for any V1a antagonist on Swiss 3T3 cells. Reference: Biochem Pharmacol. 1994 Feb 11;47(4):633-41. https://pubmed.ncbi.nlm.nih.gov/8129742/
In vivo activity:
Relcovaptan may be a novel strategy for decreasing risk of ovarian hyperstimulation syndrome by inhibition of vasopressin-induced VEGF secretion through V1A receptor antagonist. Reference: Eur J Obstet Gynecol Reprod Biol. 2014 Mar;174:86-90. https://pubmed.ncbi.nlm.nih.gov/24405730/
Solvent mg/mL mM
Solubility
DMSO 18.6 30.00
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 620.49 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:
1. Serradeil-Le Gal C, Bourrié B, Raufaste D, Carayon P, Garcia C, Maffrand JP, Le Fur G, Casellas P. Effect of a new, potent, non-peptide V1a vasopressin antagonist, SR 49059, on the binding and the mitogenic activity of vasopressin on Swiss 3T3 cells. Biochem Pharmacol. 1994 Feb 11;47(4):633-41. doi: 10.1016/0006-2952(94)90125-2. PMID: 8129742. 2. Serradeil-Le Gal C, Herbert JM, Delisee C, Schaeffer P, Raufaste D, Garcia C, Dol F, Marty E, Maffrand JP, Le Fur G. Effect of SR-49059, a vasopressin V1a antagonist, on human vascular smooth muscle cells. Am J Physiol. 1995 Jan;268(1 Pt 2):H404-10. doi: 10.1152/ajpheart.1995.268.1.H404. PMID: 7840290. 3. Cenksoy C, Cenksoy PO, Erdem O, Sancak B, Gursoy R. A potential novel strategy, inhibition of vasopressin-induced VEGF secretion by relcovaptan, for decreasing the incidence of ovarian hyperstimulation syndrome in the hyperstimulated rat model. Eur J Obstet Gynecol Reprod Biol. 2014 Mar;174:86-90. doi: 10.1016/j.ejogrb.2013.12.001. Epub 2013 Dec 12. PMID: 24405730. 4. Steinwall M, Bossmar T, Brouard R, Laudanski T, Olofsson P, Urban R, Wolff K, Le-Fur G, Akerlund M. The effect of relcovaptan (SR 49059), an orally active vasopressin V1a receptor antagonist, on uterine contractions in preterm labor. Gynecol Endocrinol. 2005 Feb;20(2):104-9. doi: 10.1080/09513590400021144. PMID: 15823830.
In vitro protocol:
1. Serradeil-Le Gal C, Bourrié B, Raufaste D, Carayon P, Garcia C, Maffrand JP, Le Fur G, Casellas P. Effect of a new, potent, non-peptide V1a vasopressin antagonist, SR 49059, on the binding and the mitogenic activity of vasopressin on Swiss 3T3 cells. Biochem Pharmacol. 1994 Feb 11;47(4):633-41. doi: 10.1016/0006-2952(94)90125-2. PMID: 8129742. 2. Serradeil-Le Gal C, Herbert JM, Delisee C, Schaeffer P, Raufaste D, Garcia C, Dol F, Marty E, Maffrand JP, Le Fur G. Effect of SR-49059, a vasopressin V1a antagonist, on human vascular smooth muscle cells. Am J Physiol. 1995 Jan;268(1 Pt 2):H404-10. doi: 10.1152/ajpheart.1995.268.1.H404. PMID: 7840290.
In vivo protocol:
1. Cenksoy C, Cenksoy PO, Erdem O, Sancak B, Gursoy R. A potential novel strategy, inhibition of vasopressin-induced VEGF secretion by relcovaptan, for decreasing the incidence of ovarian hyperstimulation syndrome in the hyperstimulated rat model. Eur J Obstet Gynecol Reprod Biol. 2014 Mar;174:86-90. doi: 10.1016/j.ejogrb.2013.12.001. Epub 2013 Dec 12. PMID: 24405730. 2. Steinwall M, Bossmar T, Brouard R, Laudanski T, Olofsson P, Urban R, Wolff K, Le-Fur G, Akerlund M. The effect of relcovaptan (SR 49059), an orally active vasopressin V1a receptor antagonist, on uterine contractions in preterm labor. Gynecol Endocrinol. 2005 Feb;20(2):104-9. doi: 10.1080/09513590400021144. PMID: 15823830.
1: Lemmens-Gruber R, Kamyar M. Vasopressin antagonists. Cell Mol Life Sci. 2006 Aug;63(15):1766-79. doi: 10.1007/s00018-006-6054-2. PMID: 16794787; PMCID: PMC11136164. 2: Steinwall M, Bossmar T, Brouard R, Laudanski T, Olofsson P, Urban R, Wolff K, Le-Fur G, Akerlund M. The effect of relcovaptan (SR 49059), an orally active vasopressin V1a receptor antagonist, on uterine contractions in preterm labor. Gynecol Endocrinol. 2005 Feb;20(2):104-9. doi: 10.1080/09513590400021144. PMID: 15823830. 3: Decaux G, Soupart A, Vassart G. Non-peptide arginine-vasopressin antagonists: the vaptans. Lancet. 2008 May 10;371(9624):1624-32. doi: 10.1016/S0140-6736(08)60695-9. PMID: 18468546. 4: Izumi Y, Miura K, Iwao H. Therapeutic potential of vasopressin-receptor antagonists in heart failure. J Pharmacol Sci. 2014;124(1):1-6. doi: 10.1254/jphs.13r13cp. Epub 2014 Jan 7. PMID: 24401675. 5: Cenksoy C, Cenksoy PO, Erdem O, Sancak B, Gursoy R. A potential novel strategy, inhibition of vasopressin-induced VEGF secretion by relcovaptan, for decreasing the incidence of ovarian hyperstimulation syndrome in the hyperstimulated rat model. Eur J Obstet Gynecol Reprod Biol. 2014 Mar;174:86-90. doi: 10.1016/j.ejogrb.2013.12.001. Epub 2013 Dec 12. PMID: 24405730. 6: Brydges NM, Hall J, Best C, Rule L, Watkin H, Drake AJ, Lewis C, Thomas KL, Hall J. Childhood stress impairs social function through AVP-dependent mechanisms. Transl Psychiatry. 2019 Dec 9;9(1):330. doi: 10.1038/s41398-019-0678-0. PMID: 31819033; PMCID: PMC6901493. 7: McDougall ARA, Hastie R, Goldstein M, Tuttle A, Ammerdorffer A, Gülmezoglu AM, Vogel JP. New medicines for spontaneous preterm birth prevention and preterm labour management: landscape analysis of the medicine development pipeline. BMC Pregnancy Childbirth. 2023 Jul 18;23(1):525. doi: 10.1186/s12884-023-05842-9. PMID: 37464260; PMCID: PMC10354994. 8: Lemmens-Gruber R, Kamyar M. Pharmakologie und klinische Bedeutung von Vasopressinantagonisten [Pharmacology and clinical relevance of vasopressin antagonists]. Internist (Berl). 2008 May;49(5):628, 629-30, 632-4. German. doi: 10.1007/s00108-008-2017-z. PMID: 18335184. 9: Zurfluh L, Duvaud L, Inci N, Potterat O, Simões-Wüst AP, Mosbacher J. Bryophyllum pinnatum Inhibits Oxytocin and Vasopressin Signaling in Myometrial Cells. Planta Med. 2024 Aug;90(10):757-765. doi: 10.1055/a-2303-9608. Epub 2024 Apr 10. PMID: 38599625. 10: Serradeil-Le Gal C, Wagnon J, Valette G, Garcia G, Pascal M, Maffrand JP, Le Fur G. Nonpeptide vasopressin receptor antagonists: development of selective and orally active V1a, V2 and V1b receptor ligands. Prog Brain Res. 2002;139:197-210. doi: 10.1016/s0079-6123(02)39017-4. PMID: 12436936. 11: Haass M. Vaptane und Herzinsuffizienz [Vasopressin receptor antagonists and heart failure]. Ther Umsch. 2009 Nov;66(11):735-40. German. doi: 10.1024/0040-5930.66.11.735. PMID: 19885790. 12: Usta IM, Khalil A, Nassar AH. Oxytocin antagonists for the management of preterm birth: a review. Am J Perinatol. 2011 Jun;28(6):449-60. doi: 10.1055/s-0030-1270111. Epub 2010 Dec 17. PMID: 21170825. 13: Pierzynski P. Oxytocin and vasopressin V(1A) receptors as new therapeutic targets in assisted reproduction. Reprod Biomed Online. 2011 Jan;22(1):9-16. doi: 10.1016/j.rbmo.2010.09.015. Epub 2010 Oct 14. PMID: 21130036. 14: Zhao N, Peacock SO, Lo CH, Heidman LM, Rice MA, Fahrenholtz CD, Greene AM, Magani F, Copello VA, Martinez MJ, Zhang Y, Daaka Y, Lynch CC, Burnstein KL. Arginine vasopressin receptor 1a is a therapeutic target for castration- resistant prostate cancer. Sci Transl Med. 2019 Jun 26;11(498):eaaw4636. doi: 10.1126/scitranslmed.aaw4636. PMID: 31243151; PMCID: PMC7864378. 15: Streefkerk JO, van Zwieten PA. Vasopressin receptor antagonists: pharmacological tools and potential therapeutic agents. Auton Autacoid Pharmacol. 2006 Apr;26(2):141-8. doi: 10.1111/j.1474-8673.2006.00361.x. PMID: 16553642. 16: García-Arroyo FE, Muñoz-Jiménez I, Gonzaga G, Tapia E, Osorio-Alonso H, Roncal-Jiménez CA, Iroz A, Vecchio M, Reyes-García JG, Johnson RJ, Sánchez- Lozada LG. A Role for Both V1a and V2 Receptors in Renal Heat Stress Injury Amplified by Rehydration with Fructose. Int J Mol Sci. 2019 Nov 16;20(22):5764. doi: 10.3390/ijms20225764. PMID: 31744099; PMCID: PMC6888540. 17: Garofalo NA, Teixeira Neto FJ, Pereira CD, Pignaton W, Vicente F, Alvaides RK. Cardiorespiratory and neuroendocrine changes induced by methadone in conscious and in isoflurane anaesthetised dogs. Vet J. 2012 Dec;194(3):398-404. doi: 10.1016/j.tvjl.2012.03.019. Epub 2012 Jun 29. PMID: 22750283. 18: Cragg B, Ji G, Neugebauer V. Differential contributions of vasopressin V1A and oxytocin receptors in the amygdala to pain-related behaviors in rats. Mol Pain. 2016 Nov 11;12:1744806916676491. doi: 10.1177/1744806916676491. PMID: 27837170; PMCID: PMC5117246. 19: Erdem Tuncdemir B, Mergen H, Saglar Ozer E. Evaluation of pharmacochaperone- mediated rescue of mutant V2 receptor proteins. Eur J Pharmacol. 2019 Dec 15;865:172803. doi: 10.1016/j.ejphar.2019.172803. Epub 2019 Nov 15. PMID: 31738937. 20: Everett NA, McGregor IS, Baracz SJ, Cornish JL. The role of the vasopressin V1A receptor in oxytocin modulation of methamphetamine primed reinstatement. Neuropharmacology. 2018 May 1;133:1-11. doi: 10.1016/j.neuropharm.2017.12.036. Epub 2018 Jan 17. PMID: 29353054.