WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 203150
CAS#: 194468-36-5 (ditartrate)
Description: Vinflunine is a bi-fluorinated derivative of the semi-synthetic vinca alkaloid vinorelbine with antitubulin, antineoplastic, and antiangiogenic activities. Vinflunine inhibits tubulin assembly without any stablization of assembled microtubules at concentrations comparable to those of other vinca alkaloids such as vincristine, vinblastine and vinorelbine; this effect on microtubule dynamics results in cell cycle arrest in mitosis and apoptosis. Compared to other vinca alkaloids, this agent binds weakly to the vinca-binding site, indicating that vinflunine may exhibit reduced neurotoxicity.
MedKoo Cat#: 203150
Name: Vinflunine ditartrate
CAS#: 194468-36-5 (ditartrate)
Chemical Formula: C53H66F2N4O20
Exact Mass: 1078.42704
Molecular Weight: 1079.10594
Elemental Analysis: C, 66.16; H, 6.66; F, 4.65; N, 6.86; O, 15.67
Related CAS #: 194468-36-5 (ditartrate) 162652-95-1 (free base)
Synonym: BMS 710485, BMS710485, BMS-710485, F 12158, F12158, F12158, Vinflunine, vinflunine ditartrate, Javlor
IUPAC/Chemical Name: methyl (3aR,3a1R,4R,5S,5aR,10bR)-4-acetoxy-9-((4S,6S,8S)-4-(1,1-difluoroethyl)-8-(methoxycarbonyl)-1,3,4,5,6,7,8,9-octahydro-2,6-methanoazecino[4,3-b]indol-8-yl)-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate bis(2,3-dihydroxysuccinate).
InChi Key: YIHUEPHBPPAAHH-DMHAPLPBSA-N
InChi Code: InChI=1S/C45H54F2N4O8.2C4H6O6/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;2*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;2*1-2,5-6H,(H,7,8)(H,9,10)/t26-,27-,36-,37+,38+,42+,43+,44-,45-;;/m0../s1
SMILES Code: O=C([C@]1(O)[C@]2([H])N(C)C3=C(C=C([C@]4(C[C@]5(CN(CC6=C4NC7=C6C=CC=C7)C[C@H](C5)C(F)(C)F)[H])C(OC)=O)C(OC)=C3)[C@]2(CCN8CC=C9)[C@]8([H])[C@]9(CC)[C@H]1OC(C)=O)OC.OC(C(C(O)=O)O)C(O)=O.OC(C(C(O)=O)O)C(O)=O
Appearance: White to off-white solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 1079.10594 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Aparicio LM, Pulido EG, Gallego GA. Vinflunine: a new vision that may translate into antiangiogenic and antimetastatic activity. Anticancer Drugs. 2012 Jan;23(1):1-11. doi: 10.1097/CAD.0b013e32834d237b. Review. PubMed PMID: 22027536.
2: Schutz FA, Bellmunt J, Rosenberg JE, Choueiri TK. Vinflunine: drug safety evaluation of this novel synthetic vinca alkaloid. Expert Opin Drug Saf. 2011 Jul;10(4):645-53. doi: 10.1517/14740338.2011.581660. Epub 2011 Apr 28. Review. PubMed PMID: 21524237.
3: Vinflunine. Prescrire Int. 2011 Jan;20(112):11-3. Review. PubMed PMID: 21462785.
4: Gerullis H. Vinflunine: a fluorinated vinca alkaloid for bladder cancer therapy. Drugs Today (Barc). 2011 Jan;47(1):17-25. doi: 10.1358/dot.2011.47.1.1576693. Review. PubMed PMID: 21373647.
5: Mamtani R, Vaughn DJ. Vinflunine in the treatment of advanced bladder cancer. Expert Rev Anticancer Ther. 2011 Jan;11(1):13-20. doi: 10.1586/era.10.196. Review. PubMed PMID: 21166506.
6: Gerullis H, Ecke T, Eimer C, Wishahi M, Otto T. Vinflunine as second-line treatment in platin-resistant metastatic urothelial carcinoma: a review. Anticancer Drugs. 2011 Jan;22(1):9-17. doi: 10.1097/CAD.0b013e3283404db0. Review. PubMed PMID: 20948429.
7: Ng JS. Vinflunine: review of a new vinca alkaloid and its potential role in oncology. J Oncol Pharm Pract. 2011 Sep;17(3):209-24. doi: 10.1177/1078155210373525. Epub 2010 Jun 28. Review. PubMed PMID: 20584744.
8: Frampton JE, Moen MD. Vinflunine. Drugs. 2010 Jul 9;70(10):1283-93. doi: 10.2165/11204970-000000000-00000. Review. PubMed PMID: 20568834.
9: Jordan MA, Horwitz SB, Lobert S, Correia JJ. Exploring the mechanisms of action of the novel microtubule inhibitor vinflunine. Semin Oncol. 2008 Jun;35(3 Suppl 3):S6-S12. doi: 10.1053/j.seminoncol.2008.01.009. Review. PubMed PMID: 18538179.
10: Bellmunt J, Delgado FM, George C. Clinical activity of vinflunine in transitional cell carcinoma of the urothelium and other solid tumors. Semin Oncol. 2008 Jun;35(3 Suppl 3):S34-43. doi: 10.1053/j.seminoncol.2008.01.008. Review. PubMed PMID: 18538178.
According to http://en.wikipedia.org/wiki/Vinflunine; Vinflunine (INN, trade name Javlor) is a novel fluorinated Vinca alkaloid undergoing research for the treatment of bladder cancer. It was originally discovered by the team of the Professor Jean-Claude Jacquesy (UMR CNRS 6514 - Poitiers University), developed by Laboratoires Pierre Fabre and was licensed to Bristol-Myers Squibb for development in certain countries, including the United States. On November 23, 2007, Pierre Fabre and BMS announced that they are terminating their license agreement for the development of vinflunine.
