WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100963
CAS#: 57-22-7 (free base)
Description: Vincristine is a natural alkaloid isolated from the plant Vinca rosea Linn with antimitotic and antineoplastic activities. Vincristine binds irreversibly to microtubules and spindle proteins in S phase of the cell cycle and interferes with the formation of the mitotic spindle, thereby arresting tumor cells in metaphase. This agent also depolymerizes microtubules and may also interfere with amino acid, cyclic AMP, and glutathione metabolism; calmodulin-dependent Ca++ -transport ATPase activity; cellular respiration; and nucleic acid and lipid biosynthesis. Note: Cat#100920A was changed to Cat#100963
MedKoo Cat#: 100963
Name: Vincristine free base
CAS#: 57-22-7 (free base)
Chemical Formula: C46H56N4O10
Exact Mass: 824.39964
Molecular Weight: 824.96
Elemental Analysis: C, 66.97; H, 6.84; N, 6.79; O, 19.39
Related CAS #: 57-22-7 (free base) 2068-78-2 (sulfate)
Synonym: leurocristine sulfate, Vincasar PFS, Oncovin, VCR
IUPAC/Chemical Name: (3aR,3a1R,4R,5S,5aR,10bR)-methyl 4-acetoxy-3a-ethyl-9-((3S,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.
InChi Key: OGWKCGZFUXNPDA-XQKSVPLYSA-N
InChi Code: InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1
SMILES Code: O=C([C@]1(O)[C@]2([H])N(C=O)C3=C(C=C([C@@]4(C(OC)=O)C[C@@]5([H])C[C@@](O)(CC)C[N@](C5)CCC6=C4NC7=C6C=CC=C7)C(OC)=C3)[C@]2(CCN8CC=C9)[C@]8([H])[C@]9(CC)[C@H]1OC(C)=O)OC
Appearance: White to off-white, odorless amorphous or crystalline powder
Purity: >95% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, water, slightly soluble in ethanol.
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 824.96 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Harrison TS, Lyseng-Williamson KA. Vincristine sulfate liposome injection: a guide to its use in refractory or relapsed acute lymphoblastic leukemia. BioDrugs. 2013 Feb;27(1):69-74. doi: 10.1007/s40259-012-0002-5. Review. PubMed PMID: 23329395.
2: Silverman JA, Deitcher SR. Marqibo® (vincristine sulfate liposome injection) improves the pharmacokinetics and pharmacodynamics of vincristine. Cancer Chemother Pharmacol. 2013 Mar;71(3):555-64. doi: 10.1007/s00280-012-2042-4. Epub 2012 Dec 5. Review. PubMed PMID: 23212117; PubMed Central PMCID: PMC3579462.
3: Keglevich P, Hazai L, Kalaus G, Szántay C. Modifications on the basic skeletons of vinblastine and vincristine. Molecules. 2012 May 18;17(5):5893-914. doi: 10.3390/molecules17055893. Review. PubMed PMID: 22609781.
4: Moriyama B, Henning SA, Leung J, Falade-Nwulia O, Jarosinski P, Penzak SR, Walsh TJ. Adverse interactions between antifungal azoles and vincristine: review and analysis of cases. Mycoses. 2012 Jul;55(4):290-7. doi: 10.1111/j.1439-0507.2011.02158.x. Epub 2011 Nov 29. Review. PubMed PMID: 22126626; PubMed Central PMCID: PMC3345292.
5: Addo NK, Kamaly-Asl ID, Josan VA, Kelsey AM, Estlin EJ. Preoperative vincristine for an inoperable choroid plexus papilloma: a case discussion and review of the literature. J Neurosurg Pediatr. 2011 Aug;8(2):149-53. doi: 10.3171/2011.5.PEDS1187. Review. PubMed PMID: 21806355.
6: Pongudom S, Chinthammitr Y. Inadvertent intrathecal vincristine administration: report of a fatal case despite cerebrospinal fluid lavage and a review of the literature. J Med Assoc Thai. 2011 Feb;94 Suppl 1:S258-63. Review. PubMed PMID: 21721457.
7: Pana ZD, Roilides E. Risk of azole-enhanced vincristine neurotoxicity in pediatric patients with hematological malignancies: old problem - new dilemma. Pediatr Blood Cancer. 2011 Jul 15;57(1):30-5. doi: 10.1002/pbc.22972. Epub 2011 Jan 24. Review. PubMed PMID: 21265011.
8: Latiff ZA, Kamal NA, Jahendran J, Alias H, Goh BS, Syed Zakaria SZ, Jamal R. Vincristine-induced vocal cord palsy: case report and review of the literature. J Pediatr Hematol Oncol. 2010 Jul;32(5):407-10. doi: 10.1097/MPH.0b013e3181e01584. Review. PubMed PMID: 20505534.
9: Eden T, Pieters R, Richards S; Childhood Acute Lymphoblastic Leukaemia Collaborative Group (CALLCG). Systematic review of the addition of vincristine plus steroid pulses in maintenance treatment for childhood acute lymphoblastic leukaemia - an individual patient data meta-analysis involving 5,659 children. Br J Haematol. 2010 Jun;149(5):722-33. doi: 10.1111/j.1365-2141.2010.08148.x. Epub 2010 Mar 16. Review. PubMed PMID: 20331462.
10: Hennipman B, de Vries E, Bökkerink JP, Ball LM, Veerman AJ. Intrathecal vincristine: 3 fatal cases and a review of the literature. J Pediatr Hematol Oncol. 2009 Nov;31(11):816-9. doi: 10.1097/MPH.0b013e3181b83fba. Review. PubMed PMID: 19801949.
