Vincristine

Vincristine

Clinical data
Pronunciation	i/ˈvɪnˈkrɪstiːn/
Trade names	Oncovin, Vincasar, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682822
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	intravenous
ATC code	L01CA02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	n/a (not reliably absorbed by the GI tract)
Protein binding	~44%
Metabolism	Liver, mostly via CYP3A4 and CYP3A5
Biological half-life	19 to 155 hours (mean: 85 hours)
Excretion	Faeces (70-80%), urine (10-20%)
Identifiers
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
CAS Number	57-22-7 Y
PubChem (CID)	5978
IUPHAR/BPS	6785
DrugBank	DB00541 Y
ChemSpider	5758 Y
UNII	5J49Q6B70F Y
KEGG	D08679 Y
ChEBI	CHEBI:28445 Y
ChEMBL	CHEMBL303560 N
ECHA InfoCard	100.000.289
Chemical and physical data
Formula	C46H56N4O10
Molar mass	824.958 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(OC)[C@]4(c2c(c1ccccc1n2)CCN3C[C@](O)(CC)C[C@@H](C3)C4)c5c(OC)cc6c(c5)[C@@]89[C@@H](N6C=O)[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@@]7(/C=C\CN([C@@H]78)CC9)CC
InChI 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 Y
NY (what is this?)

Vincristine, also known as leurocristine and marketed under the brandname 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's disease, neuroblastoma, and small cell lung cancer among others. It is given intravenously.

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 blood white cells. It will likely cause harm to the baby if given during pregnancy. It works by stopping cells from dividing properly.

Vincristine was first isolated in 1961. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is between 1.80 and 42.60 USD per dose. It is a vinca alkaloid that can be obtained from the Madagascar periwinkle Catharanthus roseus.

Vincristine is delivered via intravenous infusion for use in various types of chemotherapy regimens. 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. It is also used to induce remission in ALL with dexamethasone and L-Asparaginase, and in combination with prednisone to treat childhood leukemia. Vincristine is occasionally used as an immunosuppressant, for example, in treating thrombotic thrombocytopenic purpura (TTP) or chronic idiopathic thrombocytopenic purpura (ITP).