Vincristine

Vincristine
Clinical data
Pronunciation	/ˈvɪnˈkrɪstiːn/ ⓘ
Trade names	Oncovin, others
Other names	leurocristine ki
AHFS/Drugs.com	Monograph
MedlinePlus	a682822
License data	US DailyMed: Vincristine;
Pregnancy; category	AU: D;
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
Elimination 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 ;
PubChem CID	5978;
IUPHAR/BPS	6785;
DrugBank	DB00541 ;
ChemSpider	5758 ;
UNII	5J49Q6B70F;
KEGG	D08679 ;
ChEBI	CHEBI:28445 ;
ChEMBL	ChEMBL303560 ;
CompTox Dashboard (EPA)	DTXSID1032278 ;
ECHA InfoCard	100.000.289
Chemical and physical data
Formula	C46H56N4O10
Molar mass	824.972 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28) ; Key:OGWKCGZFUXNPDA-XQKSVPLYSA-N ;
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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.

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.

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

Clinical data


Pronunciation	/ˈvɪnˈkrɪstiːn/ ^ⓘ
Trade names	Oncovin, others
Other names	leurocristine ki
AHFS/Drugs.com	Monograph
MedlinePlus	a682822
License data	US DailyMed: Vincristine
Pregnancy category	AU: D
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
Elimination 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
KEGG	D08679^Y
ChEBI	CHEBI:28445^Y
ChEMBL	ChEMBL303560^N
CompTox Dashboard (EPA)	DTXSID1032278
ECHA InfoCard	100.000.289
Chemical and physical data
Formula	C₄₆H₅₆N₄O₁₀
Molar mass	824.972 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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
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