Vinflunine

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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
Licence data	EMA:Link
Legal status	℞ Prescription only
Routes	Intravenous
Identifiers
CAS number	162652-95-1^Y
ATC code	L01CA05
PubChem	CID 6918295
UNII	5BF646324K^Y
ChEMBL	CHEMBL510329^N
Chemical data
Formula	C₄₅H₅₄F₂N₄O₈
Mol. 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
N (what is this?) (verify)

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

↑ 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.
↑ 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.
↑ "Bristol -Myers Squibb press release - Bristol-Myers Squibb and Pierre Fabre Provide Update On Vinflunine Development Status". Retrieved 2008-06-27.

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly	Vinca alkaloids (Vinblastine^# Vincristine^# Vinflunine^§ Vindesine Vinorelbine)

Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel^# Larotaxel Ortataxel^† Paclitaxel^# Tesetaxel) Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Raltitrexed Pemetrexed)

Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Thioguanine^# Mercaptopurine^#)

Pyrimidine	Thymidylate synthase inhibitor (Fluorouracil^# Capecitabine Tegafur (+gimeracil/oteracil) Carmofur Floxuridine) DNA polymerase inhibitor (Cytarabine^#) Ribonucleotide reductase inhibitor (Gemcitabine) Hypomethylating agent (Azacitidine Decitabine)

Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Camptothecin Topotecan Irinotecan Rubitecan^‡ Belotecan)

II	Podophyllum (Etoposide^# Teniposide)

II+Intercalation	Anthracyclines (Aclarubicin Daunorubicin^# Doxorubicin^# Epirubicin Idarubicin Amrubicin^† Pirarubicin Valrubicin Zorubicin) Anthracenediones (Mitoxantrone Pixantrone)

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards: Mechlorethamine Cyclophosphamide^# (Ifosfamide Trofosfamide) Chlorambucil^# (Melphalan Prednimustine) Bendamustine Uramustine Estramustine Nitrosoureas: Carmustine Lomustine (Semustine) Fotemustine Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone ThioTEPA Triaziquone Triethylenemelamine

Platinum-based	Carboplatin Cisplatin Nedaplatin Oxaliplatin Satraplatin

Nonclassical	Hydrazines (Procarbazine^#) Triazenes (Dacarbazine^# Temozolomide) Altretamine Mitobronitol Pipobroman

Intercalation	Streptomyces (Actinomycin^# Bleomycin^# Mitomycin Plicamycin)

Photosensitizers/PDT

Aminolevulinic acid / Methyl aminolevulinate
Efaproxiral
Porphyrin derivatives (Porfimer sodium
Talaporfin
Temoporfin
Verteporfin)

Other

Enzyme inhibitors	FI (Tipifarnib) CDK inhibitors (Alvocidib^† Seliciclib^†) PrI (Bortezomib Carfilzomib) PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Olaparib^§) HDAC (Panobinostat Vorinostat Romidepsin)

Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)

Other/ungrouped	Amsacrine Trabectedin Retinoids (Alitretinoin Tretinoin) Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Celecoxib Demecolcine Elesclomol^§ Elsamitrucin Etoglucid Lonidamine Lucanthone Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Eribulin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: NEO

tsoc, mrkr

tumr, epon, para

drug (L1i/1e/V03)

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