vinblastine

Also known as Vincaleukoblastine, VLB, (2alpha,2'BETA,3beta,4alpha,5beta)-vincaleukoblastine, Vinblastin, Vinblastina, Vinblastinum

Vinblastine, sold under the brand name Velban among others, is a chemotherapy medication, typically used with other medications, to treat a number of types of cancer. This includes Hodgkin's lymphoma, non-small-cell lung cancer, bladder cancer, brain cancer, melanoma, and testicular cancer. It is given by injection into a vein.

Key facts

Drug.CAS_number: 865-21-4
Drug.legal_US: Rx-only
Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 460778829
Drug.image: Vinblastine2DCSD.svg
Drug.image_class: skin-invert-image
Drug.image2: Vinblastine ball-and-stick.png
Drug.image_class2: bg-transparent
Drug.tradename: Velban, Velbe, others
Drug.MedlinePlus: a682848
Drug.DailyMedID: Vinblastine
Drug.pregnancy_AU: D
Drug.routes_of_administration: intravenous
Drug.ATC_prefix: L01
Drug.ATC_suffix: CA01
Drug.legal_AU: S4
Drug.legal_CA: Rx-only

via Wikipedia infobox

Chemical data

Formula: C46H58N4O9
Molecular weight: 811 g/mol
IUPAC name: methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-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: CC[C@@]1(C[C@@H]2C[C@@](C3=C(CCN(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)O
InChIKey: JXLYSJRDGCGARV-XQKSVPLYSA-N
XLogP: 3.7
Polar surface area: 154 Å²
H-bond donors: 3
H-bond acceptors: 12
Formal charge: 0

via PubChem

Research

17,585 papers

Next Generation Antineoplastic Agents: A Review on Structurally Modified Vinblastine (VBL) Analogues.Current medicinal chemistry · 2018
Vinblastine plus vincristine.Lancet (London, England) · 1969
Effect of Laetrile Vinblastine Combination on the Proliferation of the Hela Cancer Cell Line.Asian Pacific journal of cancer prevention : APJCP · 2023
Vinblastine sulphate.IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans · 1981
[Weekly Vinblastine in Pediatric Optic Pathway/Hypothalamic Glioma:2 Cases Report].No shinkei geka. Neurological surgery · 2019

via PubMed

Wikidata facts

Has part: carbon
Mass: 810.420379
Has use: medication

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found in taxon: Catharanthus roseus
chemical formula: C₄₆H₅₈N₄O₉
subject has role: essential medicine
medical condition treated: Kaposi's sarcoma
canonical SMILES: CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
isomeric SMILES: CC[C@@]1(C[C@@H]2C[C@@](C3=C(CCN(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)O
Commons category: Vinblastine
route of administration: injection
stylized name: vinBLAStine
significant drug interaction: ritonavir

Sources (5)

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~6 min read

Encyclopedic overview

8 sections

Contents

Medical uses
Side effects
Pharmacology
Mechanism of action
Pharmacokinetics
Isolation and synthesis
History
References

Most people experience some side effects. Commonly it causes a change in sensation, constipation, weakness, loss of appetite, and headaches. Severe side effects include low blood cell counts and shortness of breath. It should not be given to people who have a current bacterial infection. Use during pregnancy will likely harm the baby. Vinblastine works by blocking cell division.

Excerpted from Wikipedia’s “vinblastine” article, available under the CC BY-SA 4.0 licence.

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