Vincristine

Not to be confused with vinblastine.
Vincristine
Clinical data
Pronunciation/ˈvɪnˈkrɪstiːn/ ⓘ[1]
Trade namesOncovin, Vincasar, Marqibo, others[2]
Other namesleurocristine ki
AHFS/Drugs.comMonograph
MedlinePlusa682822
License data
Pregnancy
category
  • AU: D
Routes of
administration		intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityn/a (not reliably absorbed by the GI tract)[3]
Protein binding~44%[4]
MetabolismLiver, mostly via CYP3A4 and CYP3A5[3]
Elimination half-life19 to 155 hours (mean: 85 hours)[3]
ExcretionFaeces (70–80%), urine (10–20%)[3]
Identifiers
  • (3aR,3a1R,4R,5S,5aR,10bR)-Methyl 4-acetoxy-3a-ethyl-9-((5S,7S,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-2,4,5,6,7,8,9,10-octahydro-1H-3,7-methano[1]azacycloundecino[5,4-b]indol-9-yl)-6-formyl-5-hydroxy-8-methoxy-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.289 Edit this at Wikidata
Chemical and physical data
FormulaC46H56N4O10
Molar mass824.972 g·mol−1
3D model (JSmol)
  • 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
  • InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28) ☒N
  • Key:OGWKCGZFUXNPDA-XQKSVPLYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Vincristine, also known as leurocristine and marketed under the brand name Oncovin among others, is a chemotherapy medication used to treat a number of types of cancer.[5] This includes acute lymphocytic leukemia, acute myeloid leukemia, Hodgkin's disease, neuroblastoma, and small cell lung cancer among others.[5] It is given intravenously.[5]

Most people experience some side effects from vincristine treatment.[5] Commonly it causes a change in sensation, hair loss, constipation, difficulty walking, and headaches.[5] Serious side effects may include neuropathic pain, lung damage, or low white blood cells which increases the risk of infection.[5] Use during pregnancy may result in birth defects.[5] It works by stopping cells from dividing properly.[5] It is vital that it not be given intrathecally, as this may kill.[6]

Vincristine was first isolated in 1961.[7] It is on the World Health Organization's List of Essential Medicines.[8][9] It is a vinca alkaloid that can be obtained from the Madagascar periwinkle Catharanthus roseus.[7]

  1. ^ "Vincristine". Dictionary.com. Random House, Inc. Archived from the original on 9 November 2014. Retrieved 9 November 2014.
  2. ^ "NCI Drug Dictionary". NCI. 2011-02-02. Archived from the original on 8 December 2015. Retrieved 28 November 2015.
  3. ^ a b c d Brayfield A, ed. (13 December 2013). "Vincristine". Martindale: The Complete Drug Reference. Pharmaceutical Press. Archived from the original on 8 April 2020. Retrieved 15 April 2014.
  4. ^ "Oncovin, Vincasar PFS (vincristine) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 16 April 2014. Retrieved 16 April 2014.
  5. ^ a b c d e f g h "Vincristine Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 2015-01-02. Retrieved Jan 2, 2015.
  6. ^ Chotsampancharoen T, Sripornsawan P, Wongchanchailert M (5 December 2015). "Two Fatal Cases of Accidental Intrathecal Vincristine Administration: Learning from Death Events". Chemotherapy. 61 (2): 108–110. doi:10.1159/000441380. eISSN 1421-9794. PMID 26636546. S2CID 22376877.
  7. ^ a b Ravina E (2011). The evolution of drug discovery : from traditional medicines to modern drugs (1. Aufl. ed.). Weinheim: Wiley-VCH. pp. 157–159. ISBN 9783527326693. Archived from the original on 2017-08-01.
  8. ^ 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.
  9. ^ 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.