9989. Vinflunine

Nomenclature

CAS number: 162652-95-1
(2β,3β,4β,5α,12R,19α)-4-(Acetyloxy)-6,7-didehydro-15-[(2R,4R,6S,8S)-4-(1,1-difluoroethyl)-1,3,4,5,6,7,8,9-octahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic acid methyl ester; 4′-deoxy-20′,20′-difluoro-8′-norvincaleukoblastine; 20′,20′-difluoro-3′,4′-dihydrovinorelbine.
C45H54F2N4O8; mol wt 816.93.
C 66.16%, H 6.66%, F 4.65%, N 6.86%, O 15.67%.

Description and references

Semisynthetic Vinca alkaloid with microtubule destabilizing and antiangiogenic activity; derivative of vinorelbine, q.v. Prepn: J.-C. Jacquesy et al., FR 2707988; eidem, US 5620985 (1995, 1997 both to Pierre Fabre); J. Fahy et al., J. Am. Chem. Soc. 119, 8576 (1997). NMR study of tubulin binding: C. Fabre et al., Biochem. Pharmacol. 64, 733 (2002). Clinical pharmacokinetics and evaluation in solid tumors: J. Bennouna et al., Ann. Oncol. 14, 630 (2003). Clinical evaluation in bladder cancer: S. Culine et al., Br. J. Cancer 2006, 1. Review of clinical development and mechanism of action: A. Kruczynski, B. T. Hill, Crit. Rev. Oncol. Hematol. 40, 159-173 (2001); J. Bennouna et al. Expert Opin. Invest. Drugs 14, 1259-1267 (2005).

Chemical structure

Derivative

Ditartrate.

Nomenclature

CAS number: 194468-36-5
Javlor (Fabre).
C45H54F2N4O8.2C4H6O6; mol wt 1117.10.
C 56.98%, H 5.96%, F 3.40%, N 5.02%, O 28.64%.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkaloids/Natural Products; Vinca Alkaloids