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
ChemSpider
28651796
ChEMBL
CHEMBL2218881
Wikipedia
Vinflunine
Predicted Properties
PropertyValueSource
Water Solubility0.00564 mg/mLALOGPS
logP4.5ALOGPS
logP4.65Chemaxon
logS-5.2ALOGPS
pKa (Strongest Acidic)10.87Chemaxon
pKa (Strongest Basic)8.66Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area133.87 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity216.53 m3·mol-1Chemaxon
Polarizability83.51 Å3Chemaxon
Number of Rings9Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon