Vinflunine

Vinflunine
Clinical data
AHFS/Drugs.com	International Drug Names
License data	EU EMA: by INN;
Routes of; administration	Intravenous
ATC code	L01CA05 (WHO) ;
Legal status
Legal status	EU: Rx-only; In general: ℞ (Prescription only);
Identifiers
	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;
CAS Number	162652-95-1 ;
PubChem CID	10629256;
DrugBank	DB11641 ;
ChemSpider	8804619 ;
UNII	5BF646324K;
ChEBI	CHEBI:90241 ;
ChEMBL	ChEMBL2110725 ;
CompTox Dashboard (EPA)	DTXSID30936722 ;
Chemical and physical data
Formula	C45H54F2N4O8
Molar mass	816.944 g·mol−1
3D model (JSmol)	Interactive image;
	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 derivative^[2] 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),^[3] 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 Medicament and Bristol-Myers Squibb announced that they were terminating their license agreement for the development of vinflunine, and that Pierre Fabre were continuing "discussions with regulatory authorities and plan to file for the registration of vinflunine for bladder cancer in the first quarter of 2008."^[4]

^ "Javlor EPAR". European Medicines Agency (EMA). Retrieved 2 January 2021.
^ 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". Biochemical Pharmacology. 55 (5): 635–48. doi:10.1016/S0006-2952(97)00505-4. PMID 9515574.
^ Fahy J, Duflos A, Ribet JP, Jacquesy JC, Berrier C, Jouannetaud MP, Zunino F (1997). "Vinca Alkaloids in Superacidic Media: A Method for Creating a New Family of Antitumor Derivatives". J. Am. Chem. Soc. 119 (36): 8576–8577. doi:10.1021/ja971864w.
^ "Bristol-Myers Squibb and Pierre Fabre Provide Update On Vinflunine Development Status" (Press release). Bristol-Myers Squibb. November 23, 2007. Archived from the original on May 28, 2008. Retrieved June 27, 2008.

[Javlor_EPAR-1] "Javlor EPAR". European Medicines Agency (EMA). Retrieved 2 January 2021.

[2] 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". Biochemical Pharmacology. 55 (5): 635–48. doi:10.1016/S0006-2952(97)00505-4. PMID 9515574.

[3] Fahy J, Duflos A, Ribet JP, Jacquesy JC, Berrier C, Jouannetaud MP, Zunino F (1997). "Vinca Alkaloids in Superacidic Media: A Method for Creating a New Family of Antitumor Derivatives". J. Am. Chem. Soc. 119 (36): 8576–8577. doi:10.1021/ja971864w.

[4] "Bristol-Myers Squibb and Pierre Fabre Provide Update On Vinflunine Development Status" (Press release). Bristol-Myers Squibb. November 23, 2007. Archived from the original on May 28, 2008. Retrieved June 27, 2008.

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