Vinflunine
Vinflunine is a third-generation semisynthetic fluorinated vinca alkaloid that binds to tubulin at the vinca binding site, inhibiting microtubule polymerization and disrupting mitotic spindle formation, thereby arresting cells in metaphase and inducing apoptosis. It is approved in Europe for second-line treatment of advanced or metastatic urothelial carcinoma (bladder cancer) after failure of platinum-based chemotherapy. Its fluorine substitutions alter pharmacokinetic and pharmacodynamic properties compared to first-generation vinca alkaloids.
Peso molecular
816,9000 g/mol
LogP
4,40
TPSA
134,00 Ų
Regla de cinco de Lipinski
No cumple
Áreas terapéuticas
Mecanismo de acción
Disrupts microtubule dynamics by binding to tubulin, preventing the formation of the mitotic spindle and arresting cell division at metaphase. This induces apoptosis in rapidly dividing cells.
Pharmacokinetics (PK)
Pharmacodynamics (PD)
Disrupts microtubule dynamics by binding to tubulin, preventing the formation of the mitotic spindle and arresting cell division at metaphase. This induces apoptosis in rapidly dividing cells.
Estructura 2D
Cite this structure
Embed this structure
SMILES
CC[C@]12C=CCN3CC[C@@]4(c5cc([C@@]6(C(=O)OC)C[C@@H]7C[C@@H](C(C)(F)F)CN(Cc8c6[nH]c6ccccc86)C7)c(OC)cc5N(C)[C@H]4[C@@](O)(C(=O)OC)[C@@H]1OC(C)=O)[C@@H]32
InChI
InChI=1S/C45H54F2N4O8/c1-8-42-14-11-16-51-17-15-43(36(42)51)30-19-31(34(56-5)20-33(30)49(4)37(43)45(55,40(54)58-7)38(42)59-25(2)52)44(39(53)57-6)21-26-18-27(41(3,46)47)23-50(22-26)24-29-28-12-9-10-13-32(28)48-35(29)44/h9-14,19-20,26-27,36-38,48,55H,8,15-18,21-24H2,1-7H3/t26-,27+,36-,37+,38+,42+,43+,44-,45-/m0/s1
Molecular Formula
C45H54F2N4O8
HBD / HBA
2 / 13
Enlaces Rotables
10
Átomos Pesados
59
No targets recorded
Target interaction data is not yet available for this drug.
No interactions recorded
Drug interaction data is not yet available for this compound.
No side effects recorded
Side effect data is not yet available for this drug.
Preguntas frecuentes
Vinflunine is a third-generation semisynthetic fluorinated vinca alkaloid that binds to tubulin at the vinca binding site, inhibiting microtubule polymerization and disrupting mitotic spindle formation, thereby arresting cells in metaphase and inducing apoptosis. It is approved in Europe for second-line treatment of advanced or metastatic urothelial carcinoma (bladder cancer) after failure of platinum-based chemotherapy. Its fluorine substitutions alter pharmacokinetic and pharmacodynamic properties compared to first-generation vinca alkaloids.
Disrupts microtubule dynamics by binding to tubulin, preventing the formation of the mitotic spindle and arresting cell division at metaphase. This induces apoptosis in rapidly dividing cells.
Yes, Vinflunine is an approved drug. It has reached clinical phase 4. It is classified as a Small molecule.
References & Data Sources
- ChEMBL — European Bioinformatics Institute (EBI). CHEMBL2110725. Open-access bioactivity database.
- PubChem — National Center for Biotechnology Information (NCBI). CID 10629256. Chemical information database.
Data aggregated from publicly available pharmacological databases. Last updated 2026-03-28.
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