Vincristine

Vincristine
Clinical data
Pronunciation	/ˈvɪnˈkrɪstiːn/
Trade names	Oncovin, Vincasar, Marqibo, 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 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]

^ "Vincristine". Dictionary.com. Random House, Inc. Archived from the original on 9 November 2014. Retrieved 9 November 2014.
^ "NCI Drug Dictionary". NCI. 2011-02-02. Archived from the original on 8 December 2015. Retrieved 28 November 2015.
^ ^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.
^ "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.
^ ^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.
^ 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.
^ ^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.
^ 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.
^ 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.

[DictionaryVincristine-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.

[MD-3] 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.

[MSR-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.

[AHFS2015-5] ^ ^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.

[ChotsampancharoenSripornsawanWongchanchailert2015-6] 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.

[Rav2011-7] 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.

[WHO21st-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.

[WHO22nd-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.

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Clinical data


Pronunciation	/ˈvɪnˈkrɪstiːn/ ^ⓘ^[1]
Trade names	Oncovin, Vincasar, Marqibo, others^[2]
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)^[3]
Protein binding	~44%^[4]
Metabolism	Liver, mostly via CYP3A4 and CYP3A5^[3]
Elimination half-life	19 to 155 hours (mean: 85 hours)^[3]
Excretion	Faeces (70–80%), urine (10–20%)^[3]
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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