vincristine   Click here for help

GtoPdb Ligand ID: 6785

Synonyms: 22-oxovincaleukoblastine | kyocristine | leurocristine sulfate | NSC-67574 | Oncovin®
Approved drug
vincristine is an approved drug (FDA (1963))
Comment: A pan tubulin inhibitor, isolated from Catharanthus roseus (the Madagascar periwinkle, formerly Vinca rosea). Marketed formulations contain vincristine sulfate (PubChem CID 249332).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 171.17
Molecular weight 824.4
XLogP 3.56
No. Lipinski's rules broken 1
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Canonical SMILES O=CN1c2cc(OC)c(cc2C23C1C(O)(C(=O)OC)C(OC(=O)C)C1(C3N(CC2)CC=C1)CC)C1(CC2CN(CCc3c1[nH]c1c3cccc1)CC(C2)(O)CC)C(=O)OC
Isomeric SMILES O=CN1c2cc(OC)c(cc2[C@]23[C@@H]1[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@]1([C@@H]3N(CC2)CC=C1)CC)[C@]1(C[C@@H]2CN(CCc3c1[nH]c1c3cccc1)C[C@](C2)(O)CC)C(=O)OC
InChI 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
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Summary of Clinical Use Click here for help
Used as an anti-neoplastic agent in the treatment of leukemia, Hodgkin disease, non-Hodgkin lymphomas, rhabdomyosarcoma, neuroblastoma, Wilms' tumor. Has orphan drug designation by EMA for use to treat acute lymphoblastic leukemia (July 2008).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Causes cell cycle arrest by inhibiting microtubule assembly.
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