Vinorelbine
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Vinorelbine
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| Systematic (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 |
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| Identifiers | |
| CAS number | |
| ATC code | L01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C45H54N4O8 |
| Mol. mass | 778.932 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 43 ± 14% (oral)[1] |
| Protein binding | 79 to 91% |
| Metabolism | Hepatic (CYP3A4-mediated) |
| Half life | 27.7 to 43.6 hours |
| Excretion | Fecal (46%) and renal (18%) |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | intravenous, oral |
Vinorelbine (Navelbine®) is a chemotherapy drug that is given as a treatment for some types of cancer, including breast cancer and non-small cell lung cancer.
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[edit] 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.
[edit] 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.
[edit] 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.
[edit] References
- ^ Marty M, Fumoleau P, Adenis A, Rousseau Y, Merrouche Y, Robinet G, Senac I, Puozzo C (2001). "Oral vinorelbine pharmacokinetics and absolute bioavailability study in patients with solid tumors". Ann Oncol 12 (11): 1643-9. PMID 11822766.
