Vinorelbine

Vinorelbine

File:Vinorelbin.svg
Clinical data
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	intravenous, oral
ATC code	L01CA04 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	43 ± 14% (oral)
Protein binding	79 to 91%
Metabolism	Hepatic (CYP3A4-mediated)
Elimination half-life	27.7 to 43.6 hours
Excretion	Fecal (46%) and renal (18%)
Identifiers
IUPAC name 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-methyl-,methyl ester, (2beta,3beta,4beta,5alpha,12R,19alpha)- aspidospermidine-3-carboxylic acid
CAS Number	71486-22-1
PubChem CID	60780
DrugBank	APRD00101
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C45H54N4O8
Molar mass	778.932 g/mol

Vinorelbine (Navelbine®) is an anti-mitotic chemotherapy drug that is given as a treatment for some types of cancer, including breast cancer and non-small cell lung cancer.

Pharmacology

Vinorelbine is the first 5´NOR semi-synthetic vinca alkaloid. It is obtained by semi-synthesis from alkaloids extracted from the rosy periwinkle, Catharanthus roseus.

History

Vinorelbine was invented by the Pharmacist Pierre Potier and his team from the CNRS in France in the 1980s and was licensed to the oncology department of the Pierre Fabre Group. The drug was approved in France in 1989 under the brand name Navelbine for the treatment of bronchial cancer. It gained approval to treat non-small cell lung cancer in 1991. The drug is now primarily used to treat this cancer. Vinorelbine received approval by the United States Food and Drug Administration (FDA) in December 1994 sponsored by GlaxoSmithKline. The drug went generic in the U.S. in February 2003.
In Europe is approved to treat non-small cell lung cancer, breast cancer and, in some countries, prostate cancer.
Since 2004 an oral formulation has been marketed and registered in Europe for the same settings. It has been shown a similar efficacy and safety profile between both intravenous and per os formulations, avoiding local toxicity induced by the intravenous vinorelbine.

Side effects

Vinorelbine has a number of side-effects that can limit its use:

Lowered resistance to infection, bruising or bleeding, anaemia, constipation, diarrhoea, nausea, numbness or tingling in hands or feet (peripheral neuropathy), tiredness and a general feeling of weakness (asthenia), inflammation of the vein into which it was injected (phlebitis).

Less common effects are hair loss and allergic reaction.