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Not to be confused with vinblastine.
Systematic (IUPAC) name
(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
Clinical data
Trade names Oncovin
AHFS/ monograph
MedlinePlus a682822
  • AU: D
  • US: D (Evidence of risk)
Pharmacokinetic data
Bioavailability n/a (not reliably absorbed by the GI tract)[1]
Protein binding ~44%[2]
Metabolism Liver, mostly via CYP3A4 and CYP3A5[1]
Half-life 19 to 155 hours (mean: 85 hours)[1]
Excretion Faeces (70-80%), urine (10-20%)[1]
57-22-7 7pxY
PubChem CID 5978
DrugBank DB00541 7pxY
ChemSpider 5758 7pxY
UNII 5J49Q6B70F 7pxY
KEGG D08679 7pxY
ChEBI CHEBI:28445 7pxY
ChEMBL CHEMBL303560 7pxN
Chemical data
Formula C46H56N4O10
824.958 g/mol
 14pxN (what is this?)  (verify)

Vincristine (Listeni/ˈvɪnˈkrɪstn/[3]) (marketed under the brandname OncovinListeni/ˈɑːŋkvɪn/[4]) is a chemotherapy medication used to treat a number of types of cancer.[5] It is given intravenously and works by inhibiting mitosis (stopping cells from dividing properly), causing the cells to die.[5] The drug accomplishes this by binding to the tubulin protein, stopping the cell from separating its chromosomes during the metaphase; the cell then undergoes apoptosis.[6] Because cancer cells divide more rapidly than healthy cells, they are affected more by the drug.

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] It will likely cause harm to an infant if given during pregnancy.[5]

Vincristine is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[7] It was formerly known as leurocristine, sometimes abbreviated "VCR", and is a vinca alkaloid from the Madagascar periwinkle Catharanthus roseus (formerly named Vinca rosea).

Medical uses

Vincristine is delivered via intravenous infusion for use in various types of chemotherapy regimens.[1] Its main uses are in non-Hodgkin's lymphoma as part of the chemotherapy regimen CHOP, Hodgkin's lymphoma as part of MOPP, COPP, BEACOPP, or the less popular Stanford V chemotherapy regimen in acute lymphoblastic leukemia (ALL), and in treatment for nephroblastoma.[1] It is also used to induce remission in ALL with dexamethasone and L-Asparaginase, and in combination with prednisone to treat childhood leukemia.[1] Vincristine is occasionally used as an immunosuppressant, for example, in treating thrombotic thrombocytopenic purpura (TTP) or chronic idiopathic thrombocytopenic purpura (ITP).[1]

Side effects

The main side effects of vincristine are chemotherapy-induced peripheral neuropathy, hyponatremia, constipation, and hair loss.

Chemotherapy-induced peripheral neuropathy can be severe, and may be a reason to reduce or avoid using vincristine. The symptoms of this are progressive and enduring tingling numbness, pain and hypersensitivity to cold, beginning in the hands and feet and sometimes affecting the arms and legs.[8] One of the first symptoms of peripheral neuropathy is foot drop: A person with a family history of foot drop and/or Charcot-Marie-Tooth disease (CMT) should avoid the taking of vincristine.[9]

Accidental injection of vinca alkaloids into the spinal canal (intrathecal administration) is highly dangerous, with a mortality rate approaching 100 percent. The medical literature documents cases of ascending paralysis due to massive encephalopathy and spinal nerve demyelination, accompanied by intractable pain, almost uniformly leading to death. Several patients have survived after aggressive and immediate intervention. Rescue treatments consist of washout of the cerebrospinal fluid and administration of protective medications.[10] Children may do better following this injury. One child, who was aggressively treated at the time of the injection, recovered almost completely with only mild neurological deficits.[11] A significant series of inadvertent intrathecal vincristine administration occurred in China in 2007 when batches of cytarabine and methotrexate (both often used intrathecally) manufactured by the company Shanghai Hualian were found to be contaminated with vincristine.[12]

Mechanism of action

Vincristine binds to tubulin dimers, inhibiting assembly of microtubule structures and arresting mitosis in metaphase. Because vincristine's mechanism of action targets all rapidly dividing cell types, it not only inhibits cancerous cells but can also affect the intestinal epithelium and bone marrow.[citation needed]


Vincristine is created by the coupling of indole alkaloids vindoline and catharanthine in the vinca plant.[13]


Having been used as a folk remedy for centuries, studies in the 1950s revealed that C. roseus contained 70 alkaloids, many of which are biologically active. While initial studies for its use in diabetes mellitus were disappointing, the discovery that it caused myelosuppression (decreased activity of the bone marrow) led to its study in mice with leukemia, whose lifespan was prolonged by the use of a vinca preparation. Treatment of the ground plant with Skelly-B defatting agent and an acid benzene extract led to a fraction termed "fraction A". This fraction was further treated with aluminium oxide, chromatography, trichloromethane, benz-dichloromethane, and separation by pH to yield vincristine.[14]

Vincristine was approved by the United States Food and Drug Administration (FDA) in July 1963 as Oncovin. The drug was initially discovered by a team led by Dr. J.G. Armstrong, then marketed by Eli Lilly and Company.


Three generic drug makers supply vincristine in the United States - APP, Mayne, and Sicor (Teva).


In 2012 the FDA approved a Liposomal formulation of Vincristine.[15] A novel nano-particle bound version of Vincristine is under development.[16]


  1. ^ a b c d e f g h Brayfield, A, ed. (13 December 2013). "Vincristine". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 15 April 2014. 
  2. ^ "Oncovin, Vincasar PFS (vincristine) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 16 April 2014. 
  3. ^ "Vincristine". Random House, Inc. Retrieved 9 November 2014. 
  4. ^ "Oncovin". Merriam Webster. Retrieved 9 November 2014. 
  5. ^ a b c d e "Vincristine Sulfate". The American Society of Health-System Pharmacists. Retrieved Jan 2, 2015. 
  6. ^ Jordan, MA (January 1, 2002). "Mechanism of Action of Antitumor Drugs that Interact with Microtubules and Tubulin". Current Medicinal Chemistry - Anti-Cancer Agents. doi:10.2174/1568011023354290. Retrieved May 10, 2015. 
  7. ^ "WHO Model List of Essential Medicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014. 
  8. ^ del Pino BM. Chemotherapy-induced Peripheral Neuropathy. NCI Cancer Bulletin. Feb 23, 2010;7(4):6.
  9. ^ Graf, W. D.; Chance, P. F.; Lensch, M. W.; Eng, L. J.; Lipe, H. P.; Bird, T. D. (1996). "Severe Vincristine Neuropathy in Charcot-Marie-Tooth Disease Type 1A". Cancer 77 (7): 1356–1362. PMID 8608515. doi:10.1002/(SICI)1097-0142(19960401)77:7<1356::AID-CNCR20>3.0.CO;2-#. 
  10. ^ Qweider, M.; Gilsbach, J. M.; Rohde, V. (2007). "Inadvertent Intrathecal Vincristine Administration: A Neurosurgical Emergency. Case Report". Journal of Neurosurgery: Spine 6 (3): 280–283. PMID 17355029. doi:10.3171/spi.2007.6.3.280. 
  11. ^ Zaragosa, M.; Ritchey, M.; Walter, A. (1995). "Neurological Consequences of Accidental Intrathecal Vincristine: A Case Report.". Medial and Pediatric Oncology 24: 61–62. PMID 7968797. doi:10.1002/mpo.2950240114. 
  12. ^ Jake Hooker and Walt Bogdanich (January 31, 2008). "Tainted Drugs Tied to Maker of Abortion Pill". New York Times. 
  13. ^ "Pharmacognosy of Vinca Alkaloids". 
  14. ^ Johnson, I. S.; Armstrong, J. G.; Gorman, M.; Burnett, J. P. (1963). "The Vinca Alkaloids: A New Class of Oncolytic Agents" (PDF). Cancer Research 23 (8 Part 1): 1390–1427. PMID 14070392. 
  15. ^ FDA press release Aug 9, 2012
  16. ^ Bind Therapeutics conference call of Nov 6, 2014

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