10384. Lixivaptan

Nomenclature

CAS number: 168079-32-1
N-[3-Chloro-4-(5H-pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)-ylcarbonyl)phenyl]-5-fluoro-2-methylbenzamide; CL-347985; VPA-985.
C27H21ClFN3O2; mol wt 473.93.
C 68.43%, H 4.47%, Cl 7.48%, F 4.01%, N 8.87%, O 6.75%.

Description and references

Arginine vasopressin V2-receptor antagonist; increases water excretion and normalizes serum sodium levels. Prepn: J. D. Albright et al., EP 636625; eidem, US 5516774 (1995, 1996 both to Am. Cyan.); J. D. Albright et al., J. Med. Chem. 41, 2442 (1998) DOI PubMed. Metabolism: A. J. Molinari et al., Bioorg. Med. Chem. Lett. 17, 5796 (2007) DOI PubMed. Clinical effect on serum sodium concentration in hyponatremia: F. Wong et al., Hepatology 37, 182 (2003) DOI PubMed. Aquaretic effect in chronic heart failure: W. T. Abraham et al., J. Am. Coll. Cardiol. 47, 1615 (2006) DOI PubMed. Review of pharmacology and clinical development: A. Martinez-Castelao, Curr. Opin. Investig. Drugs 2, 525-530 (2001) PubMed.

Chemical structure

Properties

Crystals from ethyl acetate, mp 191-195°.

Therapeutic Category

In treatment of congestive heart failure.

Keywords

Vasopressin Receptor Antagonist