Vinorelbine

Vinorelbine
Clinical data
Trade namesNavelbine
AHFS/Drugs.comMonograph
MedlinePlusa695013
Pregnancy
category
  • AU: D
Routes of
administration		intravenous, by mouth[1]
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability43 ± 14% (oral)[3]
Protein binding79 to 91%
Metabolismliver (CYP3A4-mediated)
Elimination half-life27.7 to 43.6 hours
ExcretionFecal (46%) and kidney (18%)
Identifiers
  • Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC45H54N4O8
Molar mass778.947 g·mol−1
3D model (JSmol)
  • [H][C@]89C=C(CC)CN(Cc1c([nH]c2ccccc12)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C)[C@@]5([H])[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]7(CC)C=CCN6CC[C@]45[C@@]67[H])C8)C9
  • InChI=1S/C45H54N4O8/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3/t28-,37-,38+,39+,42+,43+,44-,45-/m0/s1 checkY
  • Key:GBABOYUKABKIAF-IELIFDKJSA-N checkY
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Vinorelbine (NVB), sold under the brand name Navelbine among others, is a chemotherapy medication used to treat a number of types of cancer.[4] This includes breast cancer and non-small cell lung cancer.[4] It is given by injection into a vein or by mouth.[4][1]

Common side effects include bone marrow suppression, pain at the site of injection, vomiting, feeling tired, numbness, and diarrhea.[4] Other serious side effects include shortness of breath.[4] Use during pregnancy may harm the baby.[4] Vinorelbine is in the vinca alkaloid family of medications.[1] It is believed to work by disrupting the normal function of microtubules and thereby stopping cell division.[4]

Vinorelbine was approved for medical use in the United States in 1994.[4] It is on the World Health Organization's List of Essential Medicines.[5][6]

  1. ^ a b c British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 594. ISBN 9780857111562.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  3. ^ Marty M, Fumoleau P, Adenis A, Rousseau Y, Merrouche Y, Robinet G, et al. (November 2001). "Oral vinorelbine pharmacokinetics and absolute bioavailability study in patients with solid tumors". Annals of Oncology. 12 (11): 1643–1649. doi:10.1023/A:1013180903805. PMID 11822766.
  4. ^ a b c d e f g h "Vinorelbine Tartrate". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  5. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  6. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.