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Vinflunine information


Vinflunine
Clinical data
AHFS/Drugs.comInternational Drug Names
License data
  • EU EMA: by INN
Routes of
administration
Intravenous
ATC code
  • L01CA05 (WHO)
Legal status
Legal status
  • EU: Rx-only[1]
  • 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 checkY
PubChem CID
  • 10629256
DrugBank
  • DB11641 checkY
ChemSpider
  • 8804619 ☒N
UNII
  • 5BF646324K
ChEBI
  • CHEBI:90241 ☒N
ChEMBL
  • ChEMBL2110725 ☒N
CompTox Dashboard (EPA)
  • DTXSID30936722 Edit this at Wikidata
Chemical and physical data
FormulaC45H54F2N4O8
Molar mass816.944 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 ☒N
  • Key:NMDYYWFGPIMTKO-KLCPSUAYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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]

  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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Vinflunine

Last Update:

Vinflunine (INN, trade name Javlor) is a novel fluorinated vinca alkaloid derivative undergoing research for the treatment of bladder cancer. It was originally...

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Laboratoires Pierre Fabre

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an anticancer drug of the vinca alkaloid class. They also developed vinflunine, a fluorinated vinca alkaloid derivative available in Australia for "advanced...

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Mitotic inhibitor

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vinorelbine and vinblastine. Vinflunine block mitosis at the metaphase/anaphase transition, leading to apoptosis. Vinflunine is a chemotherapy drug used...

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Chemotherapy

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(used in the treatment of non-small-cell lung cancer), vindesine, and vinflunine. These drugs are cell cycle-specific. They bind to the tubulin molecules...

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Bladder cancer

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Vinflunine, a third generation vinca alkaloid (approved in Europe), Gemcitabine, Pemetrexed, Oxaliplatin, and Ifosfamide. Side effects of Vinflunine include...

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Celecoxib

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Vincristine

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Hydroxycarbamide

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Cyclophosphamide

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Tretinoin

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Vindesine

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vincristine) and semisynthetic vinca alkaloids (e.g. vinorelbine and vinflunine) derived from this plant, vindesine is an inhibitor of mitosis that is...

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Cytarabine

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Cancer immunotherapy

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Lifileucel

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Venetoclax

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Cisplatin

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Mitomycin C

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Fluorouracil

Last Update:

microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Paclitaxel

Last Update:

microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Etoposide

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

Word Count : 1052

FOLFIRI

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Nitrogen mustard

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Tebentafusp

Last Update:

microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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List of antineoplastic agents

Last Update:

and breast cancer. Myelosuppression, neurotoxicity and paralytic ileus. Vinflunine IV As above. Bladder cancer As per vinblastine. Vinorelbine IV As above...

Word Count : 708

Taxane

Last Update:

microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Mercaptopurine

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Dactinomycin

Last Update:

microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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Doxorubicin

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microtubule assembly Vinca alkaloids (Vinblastine# Vincristine# Vindesine Vinflunine§ Vinorelbine#) Block microtubule disassembly Taxanes (Cabazitaxel Docetaxel#...

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