vincristine

Also known as 22-oxovincaleukoblastine, kyocristine, leurocristine sulfate, NSC-67574, Oncovin®, leurocristine, Leurocristine, Vincristin

Vincristine, also known as leurocristine and sold under the brand name Oncovin among others, is a chemotherapy medication used to treat a number of types of cancer. This includes acute lymphocytic leukemia, acute myeloid leukemia, Hodgkin lymphoma, neuroblastoma, and small cell lung cancer among others. It is given intravenously.

Key facts

Drug.width: 240
Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 461759697
Drug.image: Vincristine.svg
Drug.image_class: skin-invert-image
Drug.bioavailability: n/a (not reliably absorbed by the GI tract)
Drug.protein_bound: ~44%
Drug.metabolism: Liver, mostly via CYP3A4 and CYP3A5
Drug.elimination_half life: 19 to 155 hours (mean: 85 hours)
Drug.excretion: Faeces (70–80%), urine (10–20%)
Drug.IUPHAR_ligand: 6785
Drug.CAS_number: 57-22-7
Drug.PubChem: 5978
Drug.DrugBank: DB00541
Drug.ChemSpiderID: 5758
Drug.UNII: 5J49Q6B70F
Drug.KEGG: D08679

via Wikipedia infobox

Chemical data

Formula: C46H56N4O10
Molecular weight: 825 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]-8-formyl-10-hydroxy-5-methoxy-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=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
InChIKey: OGWKCGZFUXNPDA-XQKSVPLYSA-N
XLogP: 2.8
Polar surface area: 171 Å²
H-bond donors: 3
H-bond acceptors: 12
Formal charge: 0

via PubChem

Research

35,867 papers

Vincristine therapy.New York state journal of medicine · 1967
Vincristine in Cancer Therapy: Mechanisms, Efficacy, and Future Perspectives.Current medicinal chemistry · 2025
Preventing vincristine sulfate medication errors.Oncology nursing forum · 2004
Vincristine neurotoxicity.The New England journal of medicine · 1972
Vincristine neurotoxicity.The Medical journal of Australia · 1986

via PubMed

Wikidata facts

Subclass of: Vinca alkaloids
Has part: carbon
Mass: 824.399644
Has use: medication

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medical condition treated: Ewing sarcoma
chemical formula: C₄₆H₅₆N₄O₁₀
significant drug interaction: itraconazole
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=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
canonical SMILES: CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
Commons category: Vincristine
NCI Thesaurus ID: C933
subject has role: mitotic inhibitor
different from: vinblastine
stylized name: vinCRIStine

Sources (7)

via Wikidata · CC0

~11 min read

Encyclopedic overview

13 sections

Contents

Medical uses
Side effects
Mechanism of action
Chemistry
History
Society and culture
Suppliers
Shortage
Controversy
Pharmaceutical bioprospecting
Vincristine and confusion with other drugs in administration
Research
References

Most people experience some side effects from vincristine treatment. Commonly it causes a change in sensation, hair loss, constipation, difficulty walking, and headaches. Serious side effects may include neuropathic pain, lung damage, or low white blood cells which increases the risk of infection. Use during pregnancy may result in birth defects. It works by stopping cells from dividing properly. It is vital that it not be given intrathecally, as this may kill.

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

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