9990. Vinorelbine

Nomenclature

CAS number: 71486-22-1
(2β,3β,4β,5α,12R,19α)-4-(Acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic acid methyl ester; 3′,4′-didehydro-4′-deoxy-C′-norvincaleukoblastine; nor-5′-anhydrovinblastine; NVB; KW-2307.
C45H54N4O8; mol wt 778.93.
C 69.39%, H 6.99%, N 7.19%, O 16.43%.

Description and references

Semi-synthetic Vinca alkaloid; structurally related to vinblastine, q.v. Prepn: JP Kokai 80 31096; N. Langlois et al., US 4307100 (1980, 1981 both to Agence Nat. Valorisation Recherche); P. Mangeney et al., Tetrahedron 35, 2175 (1979). Pharmacology: G. Mathé, P. Reizenstein, Cancer Lett. 27, 285 (1985). HPLC determn in biological fluids: F. Jehl et al., J. Chromatogr. 525, 225 (1990). Veterinary trial in dogs with spontaneous neoplasia: V. J. Poirier et al., J. Vet. Intern. Med. 18, 536 (2004). Symposium: Semin. Oncol. 16, Suppl. 4, 1-45 (1989). Review of early clinical development: M. Marty et al., Nouv. Rev. Fr. Hematol. 31, 77-84 (1989); of clinical pharmacokinetics: D. Leveque, F. Jehl, Clin. Pharmacokinet. 31, 184-197 (1996); of use in advanced non-small cell lung cancer: M. P. Curran, G. L. Plosker, Drugs Aging 19, 695-721 (2002).

Chemical structure

Properties

Residue. [α]D20 +52.4° (c = 0.3 in CHCl3). uv max (ethanol): 215, 268, 282, 293, 310 nm (ε 3700, 11000, 9500, 7600, 4400). Partition coefficient (octanol/buffer pH 7.2): 16. LD50 in mice (mg/m2): 72 i.v.; 78 orally (Mathé, Reizenstein).

Derivative

Ditartrate.

Nomenclature

CAS number: 125317-39-7
Eunades (Pfizer); Navelbine (Fabre).
C45H54N4O8.2C4H6O6; mol wt 1079.11.
C 58.99%, H 6.16%, N 5.19%, O 29.65%.

Properties

Yellow-white amorphous powder. Sol in water and ethanol.

Therapeutic Category

Antineoplastic.

Therapeutic Category (Veterinary)

Antineoplastic.

Keywords

Antineoplastic; Alkaloids/Natural Products; Vinca Alkaloids