Vincristine sulfate
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MedKoo CAT#: 100920

CAS#: 2068-78-2 (sulfate)

Description: Vincristine sulfate is the sulfate salt of a natural alkaloid isolated from the periwinkle plant of the oleander family 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.


Chemical Structure

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Vincristine sulfate
CAS# 2068-78-2 (sulfate)

Theoretical Analysis

MedKoo Cat#: 100920
Name: Vincristine sulfate
CAS#: 2068-78-2 (sulfate)
Chemical Formula: C46H56N4O10
Exact Mass:
Molecular Weight: 824.96
Elemental Analysis: C, 66.97; H, 6.84; N, 6.79; O, 19.39

Price and Availability

Size Price Availability Quantity
10.0mg USD 90.0 Ready to ship
25.0mg USD 150.0 Ready to ship
50.0mg USD 250.0 Ready to ship
100.0mg USD 450.0 Ready to ship
200.0mg USD 750.0 Ready to ship
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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 sulfate.

InChi Key: AQTQHPDCURKLKT-JKDPCDLQSA-N

InChi Code: InChI=1S/C46H56N4O10.H2O4S/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;1-5(2,3)4/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3;(H2,1,2,3,4)/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.O=S(O)(O)=O

Appearance: White to off-white, odorless amorphous or crystalline powder

Purity: >99% (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

Biological target: Vincristine sulfate is an antitumor vinca alkaloid which inhibits microtubule formation in mitotic spindle and binds to microtubules with a Ki of 85 nM.
In vitro activity: The microtubule-depolymerizing agent vincristine is widely used in the treatment of acute leukemia. In order to decrease toxicity and chemoresistance of vincristine, the effects of combination vincristine and vorinostat (suberoylanilide hydroxamic acid (SAHA)), a pan-histone deacetylase inhibitor, on human acute T cell lymphoblastic leukemia cells were investigated. Cell viability showed that the combination of vincristine and SAHA exhibited greater cytotoxicity with an IC50 value of 0.88 nM, compared to each drug alone, 3.3 and 840 nM. This combination synergically induced G2/M arrest, followed by an increase in cell number at the sub-G1 phase and caspase activation. These findings indicate that the combination of vincristine and SAHA on T cell leukemic cells resulted in a change in microtubule dynamics contributing to M phase arrest followed by induction of the apoptotic pathway. Reference: J Hematol Oncol. 2015 Jul 10;8:82. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4504084/
In vivo activity: Whisker hair follicles are tactile organs in non-primate mammals which are functionally equivalent to human fingertips. Mouse whisker hair follicles were used as a model system and the pressure-clamped single-fiber recording technique was applied in order to explore how vincristine treatment affect mechanoreceptors in whisker hair follicles. In vivo treatment of mice with vincristine impaired whisker tactile behavioral responses. The pressure-clamped single-fiber recordings made from whisker hair follicle afferent nerves showed that mechanical stimulations evoked three types of mechanical responses, rapidly adapting response (RA), slowly adapting type 1 response (SA1) and slowly adapting type 2 response (SA2). Vincristine treatment significantly reduced SA1 responses but did not significantly affect RA and SA2 responses. These findings suggest that SA1 mechanoreceptors were selectively impaired by vincristine leading to the impairment of in vivo whisker tactile behavioral responses. Reference: Neurosci Lett. 2020 Nov 1;738:135355. https://www.sciencedirect.com/science/article/abs/pii/S030439402030625X?via%3Dihub

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 62.5 75.76
Water 83.33 101.01
DMF 3.0 3.64
PBS (pH 7.2) 2.0 2.42

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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
Formulation protocol: 1. Chao MW, Lai MJ, Liou JP, Chang YL, Wang JC, Pan SL, Teng CM. The synergic effect of vincristine and vorinostat in leukemia in vitro and in vivo. J Hematol Oncol. 2015 Jul 10;8:82. doi: 10.1186/s13045-015-0176-7. PMID: 26156322; PMCID: PMC4504084. 2. Sonekatsu M, Kanno S, Yamada H, Gu JG. Selective impairment of slowly adapting type 1 mechanoreceptors in mice following vincristine treatment. Neurosci Lett. 2020 Nov 1;738:135355. doi: 10.1016/j.neulet.2020.135355. Epub 2020 Sep 6. PMID: 32905836; PMCID: PMC7584766.
In vitro protocol: 1. Chao MW, Lai MJ, Liou JP, Chang YL, Wang JC, Pan SL, Teng CM. The synergic effect of vincristine and vorinostat in leukemia in vitro and in vivo. J Hematol Oncol. 2015 Jul 10;8:82. doi: 10.1186/s13045-015-0176-7. PMID: 26156322; PMCID: PMC4504084.
In vivo protocol: 1. Sonekatsu M, Kanno S, Yamada H, Gu JG. Selective impairment of slowly adapting type 1 mechanoreceptors in mice following vincristine treatment. Neurosci Lett. 2020 Nov 1;738:135355. doi: 10.1016/j.neulet.2020.135355. Epub 2020 Sep 6. PMID: 32905836; PMCID: PMC7584766.

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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.