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Vinorelbine



Vinorelbine
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

Identifiers
CAS number 71486-22-1
ATC code L01CA04
PubChem 60780
DrugBank APRD00101
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.

D(AU) D(US)

Legal status

POM(UK) ℞-only(US)

Routes intravenous, oral

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.

Contents

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.

References

  1. ^ 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.
v • d • e
Chemotherapeutic agents/Antineoplastic agents (L01)
Alkylating and alkylating-like agentsNitrogen mustards: (Chlorambucil, Chlormethine, Cyclophosphamide, Ifosfamide, Melphalan). Nitrosoureas:(Carmustine, Fotemustine, Lomustine, Streptozocin). Platinum (alkylating-like): (Carboplatin, Cisplatin, Oxaliplatin, BBR3464). Busulfan, Dacarbazine, Procarbazine, Temozolomide, ThioTEPA, Uramustine
AntimetabolitesFolic acid: (Aminopterin, Methotrexate, Pemetrexed, Raltitrexed). Purine:(Cladribine, Clofarabine, Fludarabine, Mercaptopurine, Pentostatin, Thioguanine). Pyrimidine:(Capecitabine, Cytarabine, Fluorouracil, Floxuridine, Gemcitabine)
Spindle poison/mitotic inhibitorTaxane: (Docetaxel, Paclitaxel). Vinca: (Vinblastine, Vincristine, Vindesine, Vinorelbine).
Cytotoxic/antitumor antibioticsAnthracycline family: (Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mitoxantrone, Valrubicin) - streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin) - Hydroxyurea
Topoisomerase inhibitorsCamptotheca: (Camptothecin, Topotecan, Irinotecan), Podophyllum:(Etoposide, Teniposide)
CI monoclonal antibodiesReceptor tyrosine kinase (Cetuximab, Panitumumab, Trastuzumab) - CD20 (Rituximab, Tositumomab) - other (Alemtuzumab, Bevacizumab, Gemtuzumab)
PhotosensitizersAminolevulinic acid, Methyl aminolevulinate, Porfimer sodium, Verteporfin
Tyrosine kinase inhibitorsDasatinib, Erlotinib, Gefitinib, Imatinib, Lapatinib, Nilotinib, Sorafenib, Sunitinib
Otherretinoids (Alitretinoin, Tretinoin) - Altretamine, Amsacrine, Anagrelide, Arsenic trioxide, Asparaginase (Pegaspargase), Bexarotene, Bortezomib, Denileukin diftitox, Estramustine, Ixabepilone, Masoprocol, Mitotane
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Vinorelbine". A list of authors is available in Wikipedia.
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