Lixivaptan
Lixivaptan, laso known as CRTX-080; VPA-985; WAY-VPA-985, is a potent, orally active, non-peptide, selective vasopressin 2 receptor antagonist. Lixivaptan works by reducing the action of the hormone vasopressin that blocks fluid excretion. Lixivaptan acts by blocking vasopressin, an anti-diuretic hormone that causes the kidneys to retain water. When the body needs to remain hydrated under certain conditions, vasopressin can have protective effects.
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Chemical Information
| Name | Lixivaptan |
|---|---|
| Iupac Chemical Name | N-(3-chloro-4-(10,11-dihydro-6H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5-carbonyl)phenyl)-5-fluoro-2-methylbenzamide |
| Synonyms | CRTX-080; CRTX080; CRTX 080; VPA-985; VPA985; VPA 985; WAY-VPA-985; Lixivaptan |
| Molecular Formula | C27H21ClFN3O2 |
| Molecular Weight | 473.93 |
| Smile | O=C(NC1=CC=C(C(C2=C3C(NCC4=CC=CN42)=CC=CC3)=O)C(Cl)=C1)C5=CC(F)=CC=C5C |
| InChiKey | UQSWTTDKNJDIRW-UHFFFAOYSA-N |
| InChi | InChI=1S/C27H21ClFN3O2/c1-16-8-9-17(29)13-22(16)27(34)31-18-10-11-20(23(28)14-18)26(33)25-21-6-2-3-7-24(21)30-15-19-5-4-12-32(19)25/h2-5,7-14,30H,6,15H2,1H3,(H,31,34) |
| CAS Number | 168079-32-1 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | 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 |
| Handling | |
| 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. |
| HS Code |
| Targets | |
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| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
1: Liamis G, Filippatos TD, Elisaf MS. Treatment of hyponatremia: the role of lixivaptan. Expert Rev Clin Pharmacol. 2014 Jul;7(4):431-41. doi: 10.1586/17512433.2014.911085. Epub 2014 Apr 28. Review. PubMed PMID: 24766294.
2: Bowman BT, Rosner MH. Lixivaptan - an evidence-based review of its clinical potential in the treatment of hyponatremia. Core Evid. 2013;8:47-56. doi: 10.2147/CE.S36744. Epub 2013 Jul 11. PubMed PMID: 23874242; PubMed Central PMCID: PMC3712664.
3: Ring T. Lixivaptan and hyponatremia. Kidney Int. 2013 Jun;83(6):1205-6. doi: 10.1038/ki.2013.39. PubMed PMID: 23728012.
4: Zmily HD, Alani A, Ghali JK. Evaluation of lixivaptan in euvolemic and hypervolemic hyponatremia and heart failure treatment. Expert Opin Drug Metab Toxicol. 2013 May;9(5):645-55. doi: 10.1517/17425255.2013.783566. Epub 2013 Apr 9. Review. PubMed PMID: 23570283.
5: Borne RT, Krantz MJ. Lixivaptan for hyponatremia--the numbers game. JAMA. 2012 Dec 12;308(22):2345-6. doi: 10.1001/jama.2012.54515. PubMed PMID: 23232892.
6: Rosner MH. Lixivaptan: a vasopressin receptor antagonist for the treatment of hyponatremia. Kidney Int. 2012 Dec;82(11):1154-6. doi: 10.1038/ki.2012.317. PubMed PMID: 23151986.
7: Allison SJ. Hyponatraemia: Lixivaptan for euvolaemic hyponatraemia. Nat Rev Nephrol. 2012 Nov;8(11):612. doi: 10.1038/nrneph.2012.204. Epub 2012 Sep 11. PubMed PMID: 22965690.
8: Abraham WT, Decaux G, Josiassen RC, Yagil Y, Kopyt N, Thacker HP, Mannelli M, Bichet DG, Orlandi C; HARMONY Study Group. Oral lixivaptan effectively increases serum sodium concentrations in outpatients with euvolemic hyponatremia. Kidney Int. 2012 Dec;82(11):1215-22. doi: 10.1038/ki.2012.274. Epub 2012 Aug 29. PubMed PMID: 22932122.
9: Abraham WT, Hensen J, Gross PA, Bichet DG, Josiassen RC, Chafekar DS, Orlandi C; LIBRA Study Group. Lixivaptan safely and effectively corrects serum sodium concentrations in hospitalized patients with euvolemic hyponatremia. Kidney Int. 2012 Dec;82(11):1223-30. doi: 10.1038/ki.2012.275. Epub 2012 Aug 29. PubMed PMID: 22932119.
10: Dahl E, Gluud LL, Kimer N, Krag A. Meta-analysis: the safety and efficacy of vaptans (tolvaptan, satavaptan and lixivaptan) in cirrhosis with ascites or hyponatraemia. Aliment Pharmacol Ther. 2012 Oct;36(7):619-26. doi: 10.1111/apt.12025. Epub 2012 Aug 21. PubMed PMID: 22908905.
11: Lim GB. Heart failure: Lixivaptan reduces volume overload in patients with heart failure. Nat Rev Cardiol. 2012 May 8;9(7):373. doi: 10.1038/nrcardio.2012.67. PubMed PMID: 22566061.
12: Ghali JK, Orlandi C, Abraham WT; CK-LX2401 Study Investigators. The efficacy and safety of lixivaptan in outpatients with heart failure and volume overload: results of a multicentre, randomized, double-blind, placebo-controlled, parallel-group study. Eur J Heart Fail. 2012 Jun;14(6):642-51. doi: 10.1093/eurjhf/hfs051. Epub 2012 Apr 17. PubMed PMID: 22510424.
13: Zmily HD, Khan NS, Daifallah S, Ghali JK. The potential role for lixivaptan in heart failure and in hyponatremia. Expert Opin Investig Drugs. 2011 Jun;20(6):831-48. doi: 10.1517/13543784.2011.579102. Epub 2011 May 9. Review. PubMed PMID: 21548825.
14: Ghali JK, Zmily HD, Farah JO, Daifallah S. Lixivaptan, a non-peptide vasopressin V2 receptor antagonist for the potential oral treatment of hyponatremia. IDrugs. 2010 Nov;13(11):782-92. Review. PubMed PMID: 21046526.
15: Abraham WT, Aranda JM, Boehmer JP, Elkayam U, Gilbert EM, Gottlieb SS, Hasenfuss G, Kukin M, Lowes BD, O'Connell JB, Tavazzi L, Feldman AM, Ticho B, Orlandi C. Rationale and design of the treatment of hyponatremia based on lixivaptan in NYHA class III/IV cardiac patient evaluation (THE BALANCE) study. Clin Transl Sci. 2010 Oct;3(5):249-53. doi: 10.1111/j.1752-8062.2010.00217.x. PubMed PMID: 20973922.
16: Ku E, Nobakht N, Campese VM. Lixivaptan: a novel vasopressin receptor antagonist. Expert Opin Investig Drugs. 2009 May;18(5):657-62. doi: 10.1517/13543780902889760 . Review. PubMed PMID: 19379124.
17: Molinari AJ, Trybulski EJ, Bagli J, Croce S, Considine J, Qi J, Ali K, Demaio W, Lihotz L, Cochran D. Identification and synthesis of major metabolites of Vasopressin V2-receptor agonist WAY-151932, and antagonist, Lixivaptan. Bioorg Med Chem Lett. 2007 Nov 1;17(21):5796-800. Epub 2007 Aug 28. PubMed PMID: 17855087.
18: Abraham WT, Shamshirsaz AA, McFann K, Oren RM, Schrier RW. Aquaretic effect of lixivaptan, an oral, non-peptide, selective V2 receptor vasopressin antagonist, in New York Heart Association functional class II and III chronic heart failure patients. J Am Coll Cardiol. 2006 Apr 18;47(8):1615-21. Epub 2006 Mar 29. PubMed PMID: 16630999.
19: Martinez-Castelao A. Lixivaptan (American Home Products). Curr Opin Investig Drugs. 2001 Apr;2(4):525-30. Review. PubMed PMID: 11566011.
Chemical Structure
