An antimitotic inhibitor of tubulin polymerization
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Labeled Version(s)
34512Vincristine-d3
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Vincristine (sulfate)

Item No. 11764

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
22-oxo-vincaleukoblastine sulfate
CAS Number
2068-78-2
Synonyms
  • Kyocristine
  • Lilly 37231
  • Leurocristine
  • Novopharm
  • NSC 67574
  • Oncovin
  • VCR
Molecular Formula
C46H56N4O10 • H2SO4
Formula Weight
923.0
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 5 mg/mlPBS (pH 7.2): 2 mg/ml
λmax
221, 259, 296 nm
SMILES
CC[C@]1(O)C[C@@](C[N@@](CC2)C1)([H])C[C@](C(OC)=O)(C3=C(OC)C=C(N(C)[C@]4([H])[C@@]56[C@](N7CC6)([H])[C@](C=CC7)(CC)[C@@H](OC(C)=O)[C@]4(O)C(OC)=O)C5=C3)C8=C2C(C=CC=C9)=C9N8.O=S(O)(O)=O
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
InChi Key
AQTQHPDCURKLKT-PNYVAJAMSA-N
Origin
Plant/Vinca rosea
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $44

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    10 mg

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    25 mg

    $195

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    Cayman Chemical
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    Product Description

    Vincristine is an antimitotic vinca alkaloid, isolated from the plant V. rosea. It irreversibly blocks mitosis by binding to tubulin (Ki = 85 nM) and inhibiting tubulin polymerization.1,2 Vincristine is exported from cells via the ATP-binding cassette transporter P-glycoprotein, but not by multidrug resistance-associated protein.3 Its effectiveness in blocking the proliferation of cancer cells is affected by overexpression of P-glycoprotein.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jordan, M.A., Himes, R.H., and Wilson, L. Comparison of the effects of vinblastine, vincristine, vindesine, and vinepidine on microtubule dynamics and cell proliferation in vitro. Cancer Res. 45(6), 2741-2747 (1985).

    2. Towle, M.J., Salvato, K.A., Wels, B.F., et al. Eribulin induces irreversible mitotic blockade: Implications of cell-based pharmacodynamics for in vivo efficacy under intermittent dosing conditions. Cancer Res. 71(2), 496-505 (2011).

    3. van Tellingen, O., Buckle, T., Jonker, J.W., et al. P-glycoprotein and Mrp1 collectively protect the bone marrow from vincristine-induced toxicity in vivo. Br. J. Cancer 89(9), 1776-1782 (2003).

    4. Chan, H.S.L., Haddad, G., Thorner, P.S., et al. P-glycoprotein expression as a predictor of the outcome of therapy for neuroblastoma. New Engl. J. Med. 325(23), 1608-1614 (1991).

    Product Citations

    Pearson, J.M., Tan, S.-F., Sharma, A., et al. Ceramide analogue SACLAC modulates sphingolipid levels and MCL-1 splicing to induce apoptosis in acute myeloid leukemia. Mol. Cancer Res. 18(3), 352-363 (2020).