Vinflunine ditartrateProduct ingredient for Vinflunine
- Name
- Vinflunine ditartrate
- Drug Entry
- Vinflunine
Vinflunine is a third-generation member of the vinca alkaloid family with anti-tumour actions. It was first described in 1998 at the Pierre Fabre research center in France. Like other vinca agents, vinflunine is an anti-mitotic agent that induces a cell cycle arrest at the G2/M phase and promotes cell death via apoptosis 6. Vinflunine is a microtubule inhibitor that binds to tubulin at or near to the vinca binding sites to inhibits its polymerization into microtubules during cell proliferation 6. In murine tumors and human tumor xenografts, vinflunine exhibits an antitumor efficacy than Vinorelbine, Vinblastine, and Vincristine 5.
Having an incidence of 429,700 new cases per year worldwide, urothelial carcinoma of the bladder is one of the most common malignancies that mostly affects individuals aged 50–79 years 3. Some patients with advanced urothelial carcinoma experience inadequate therapeutic response from a prior platinum-containing regimen. While these patients have a median survival of approximately 4 months and a poor prognosis 6, there is currently no standard therapy in patients with advanced urothelial carcinoma 3. In 2009, vinflunine was approved by the European Medicines Agency (EMA) as a second-line therapy of metastatic and advanced urothelial cancer after failure of platinum-based treatment 3. Vinflunine ditartrate is an active ingredient in the EMA-authorised product Javlor for intravenous infusion. Efficacy and safety of vinflunine has not been studied in patients with performance status of 2 or less. The clinical use of vinflunine in other urologic malignancies, such as inoperable cancer of the penis, are currently have been investigated 3.
- Accession Number
- DBSALT002672
- Structure
- Synonyms
- Not Available
- External IDs
- BMS-710485 / F-12158
- UNII
- 33MG53C7XW
- CAS Number
- 194468-36-5
- Weight
- Average: 967.03
Monoisotopic: 966.407408954 - Chemical Formula
- C49H60F2N4O14
- InChI Key
- TXONSEMUKVZUON-WVJCOWEJSA-N
- InChI
- InChI=1S/C45H54F2N4O8.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h9-14,19-20,26-27,36-38,48,55H,8,15-18,21-24H2,1-7H3;1-2,5-6H,(H,7,8)(H,9,10)/t26-,27+,36-,37+,38+,42+,43+,44-,45-;/m0./s1
- IUPAC Name
- 2,3-dihydroxybutanedioic acid; methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-4-[(12S,14S,16R)-16-(1,1-difluoroethyl)-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4(9),5,7-tetraen-12-yl]-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
- SMILES
- OC(C(O)C(O)=O)C(O)=O.[H][C@@]12N3CC[C@@]11C4=C(C=C(OC)C(=C4)[C@]4(C[C@]5([H])C[C@H](CN(C5)CC5=C4NC4=C5C=CC=C4)C(C)(F)F)C(=O)OC)N(C)[C@@]1([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC
- External Links
- ChemSpider
- 28651796
- ChEMBL
- CHEMBL2218881
- Wikipedia
- Vinflunine
- Predicted Properties
Property Value Source Water Solubility 0.00564 mg/mL ALOGPS logP 4.5 ALOGPS logP 4.65 Chemaxon logS -5.2 ALOGPS pKa (Strongest Acidic) 10.87 Chemaxon pKa (Strongest Basic) 8.66 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 133.87 Å2 Chemaxon Rotatable Bond Count 13 Chemaxon Refractivity 216.53 m3·mol-1 Chemaxon Polarizability 83.51 Å3 Chemaxon Number of Rings 9 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon