Vinflunine

Vinflunine

Systematic (IUPAC) name
methyl (2β,3β,4β,5α,12β,19α)- 4-(acetyloxy)- 15-[(4R,6R,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]- 3-hydroxy- 16-methoxy- 1-methyl- 6,7-didehydroaspidospermidine- 3-carboxylate
Clinical data
AHFS/Drugs.com	International Drug Names
License data	EU EMA: Javlor
Routes of administration	Intravenous
Legal status
Legal status	℞ (Prescription only)
Identifiers
CAS Number	162652-95-1
ATC code	L01CA05 (WHO)
PubChem	CID 10629256
ChemSpider	8804619
UNII	5BF646324K
ChEBI	CHEBI:90241
ChEMBL	CHEMBL510329
Chemical data
Formula	C45H54F2N4O8
Molar mass	816.92 g/mol
SMILES CC[C@@]12C=CCN3[C@@H]1[C@]4(CC3)[C@H]([C@]([C@@H]2OC(=O)C)(C(=O)OC)O)N(C5=CC(=C(C=C45)[C@]6(C[C@H]7C[C@H](CN(C7)CC8=C6NC9=CC=CC=C89)C(C)(F)F)C(=O)OC)OC)C
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 Key:NMDYYWFGPIMTKO-KLCPSUAYSA-N
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Vinflunine (INN, trade name Javlor) is a novel fluorinated Vinca alkaloid^[1] 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),^[2] 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.^[3]

References

1. Kruczynski A, Barret JM, Etiévant C, Colpaert F, Fahy J, Hill BT (March 1998). "Antimitotic and tubulin-interacting properties of vinflunine, a novel fluorinated Vinca alkaloid". Biochem. Pharmacol. 55 (5): 635–48. doi:10.1016/S0006-2952(97)00505-4. PMID 9515574.
2. Vinca Alkaloids in Superacidic Media: A Method for Creating a New Family of Antitumor Derivatives Fahy, J.; Duflos, A.; Ribet, J.-P.; Jacquesy, J.-C.; Berrier, C.; Jouannetaud, M.-P.; Zunino, F. J. Am. Chem. Soc.; (Communication); 1997; 119(36); 8576-8577.
3. "Bristol -Myers Squibb press release - Bristol-Myers Squibb and Pierre Fabre Provide Update On Vinflunine Development Status". Retrieved 2008-06-27.