Structure via PubChem · Public domain (PubChem)
vinorelbine
Sign in to saveAlso known as 5'-Noranhydrovinblastine, Nor-5'-anhydrovinblastine
Vinorelbine, sold under the brand name Navelbine among others, is a chemotherapy medication used to treat a number of types of cancer. This includes breast cancer and non-small cell lung cancer. It is given by injection into a vein or by mouth.
Chemical data
- Formula
- C45H54N4O8
- Molecular weight
- 778.9 g/mol
- IUPAC name
- methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(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]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
- SMILES
- CCC1=C[C@H]2C[C@@](C3=C(CN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC
- InChIKey
- GBABOYUKABKIAF-IELIFDKJSA-N
- XLogP
- 3.6
- Polar surface area
- 134 Ų
- H-bond donors
- 2
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Research
4,723 papers- Randomized Phase III Study of Pemetrexed Plus Cisplatin Versus Vinorelbine Plus Cisplatin for Completely Resected Stage II to IIIA Nonsquamous Non-Small-Cell Lung Cancer.Journal of clinical oncology : official journal of the American Society of Clinical Oncology · 2020
- Vinorelbine in cancer therapy.Current drug targets · 2012
- Vinorelbine: a novel vinca alkaloid.American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists · 1995
- Vinorelbine for non-small cell lung cancer.Expert opinion on drug safety · 2010
- Oral vinorelbine-based concomitant chemoradiotherapy in unresectable stage III non-small cell lung cancer: a systematic review.Expert review of anticancer therapy · 2018
via PubMed
Wikidata facts
- Mass
- 778.3941646879999
Show 4 more facts
- isomeric SMILES
- CCC1=C[C@@H]2CN(C1)Cc1c([nH]c3ccccc13)[C@@](C(=O)OC)(c1cc3c(cc1OC)N(C)[C@H]1[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]4(CC)C=CCN5CC[C@]31[C@@H]54)C2
- chemical formula
- C₄₅H₅₄N₄O₈
- Commons category
- Vinorelbine
- canonical SMILES
- CCC1=CC2CN(C1)Cc1c([nH]c3ccccc13)C(C(=O)OC)(c1cc3c(cc1OC)N(C)C1C(O)(C(=O)OC)C(OC(C)=O)C4(CC)C=CCN5CCC31C54)C2
Sources (6)
via Wikidata · CC0
~4 min read
Article
8 sectionsContents
- Medical uses
- Side effects
- Pharmacology
- History
- Sources
- Oral formulation
- References
- External links
Vinorelbine, sold under the brand name Navelbine among others, is a chemotherapy medication used to treat a number of types of cancer. This includes breast cancer and non-small cell lung cancer. It is given by injection into a vein or by mouth.
Common side effects include bone marrow suppression, pain at the site of injection, vomiting, feeling tired, numbness, and diarrhea. Other serious side effects include shortness of breath. Use during pregnancy may harm the baby. Vinorelbine is in the vinca alkaloid family of medications. It is believed to work by disrupting the normal function of microtubules and thereby stopping cell division.