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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H54F2N4O8
Molecular Weight 816.9291
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VINFLUNINE

SMILES

CC[C@@]12C=CCN3CC[C@@]4([C@H]13)[C@@H](N(C)C5=CC(OC)=C(C=C45)[C@]6(C[C@@H]7C[C@H](C[N@@](C7)CC8=C6NC9=C8C=CC=C9)C(C)(F)F)C(=O)OC)[C@](O)([C@@H]2OC(C)=O)C(=O)OC

InChI

InChIKey=NMDYYWFGPIMTKO-KLCPSUAYSA-N
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

HIDE SMILES / InChI

Molecular Formula C45H54F2N4O8
Molecular Weight 816.9291
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18347163 | http://adisinsight.springer.com/drugs/800010899

Vinflunine (Javlor) is the first fluorinated microtubule inhibitor belonging to the Vinca alkaloids family. Vinflunine, at the lowest effective concentrations, interacts with the Vinca alkaloid binding site on tubulin, suppresses microtubule dynamics (switching at microtubule ends between phases of slow growth and rapid shortening) and microtubule treadmilling (growth at the plus end and shortening at the minus end of the microtubule), causes cell cycle arrest which appears on fluorescence-activated cell sorting analysis as a G2 + M phase arrest, and is associated with an accumulation of cells in mitosis leading to cell death via apoptosis. Vinflunine has been been approved for advanced or metastatic transitional cell carcinoma of the urothelial tract. Pierre Fabre submitted an extension to the EU authorisation to add treatment of advanced breast cancer.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Javlor

Approved Use

Javlor (vinflunine ditartrate) is indicated in monotherapy for the treatment of adult patients with advanced or metastatic transitional cell carcinoma of the urothelial tract after failure of a prior platinum-containing regimen

Launch Date

2009
Primary
Javlor

Approved Use

Javlor (vinflunine ditartrate) is indicated in monotherapy for the treatment of adult patients with advanced or metastatic transitional cell carcinoma of the urothelial tract after failure of a prior platinum-containing regimen

Launch Date

2009
Primary
Javlor

Approved Use

Javlor (vinflunine ditartrate) is indicated in monotherapy for the treatment of adult patients with advanced or metastatic transitional cell carcinoma of the urothelial tract after failure of a prior platinum-containing regimen

Launch Date

2009
PubMed

PubMed

TitleDatePubMed
Anti-vascular effects of vinflunine in the MAC 15A transplantable adenocarcinoma model.
2001 Jan
Gemcitabine, paclitaxel, pemetrexed and other newer agents in urothelial and kidney cancers.
2003 Jun 27
Gateways to clinical trials.
2003 Nov
Vinflunine potentiates the activity of cisplatin but not 5-fluorouracil in a transplantable murine adenocarcinoma model.
2003 Nov-Dec
Gateways to clinical trials.
2004 Apr
Modelling and simulation in the development and use of anti-cancer agents: an underused tool?
2004 Dec
Highlights from the International Conference on Molecular Targets and Cancer Therapeutics: Discovery, Biology, And Clinical Applications, Philadelphia, PA, November 2005; ECCO 13--The European Cancer Conference, Paris, France, October 30-November 3, 2005.
2005 Dec
[Vinflunine: a new anti-cancer fluorinated agent derived from Vinca-alkaloids].
2005 Jan
Gateways to clinical trials.
2005 Oct
Vinflunine: a novel antitubulin agent in solid malignancies.
2005 Oct
Pharmacokinetics, tissue distribution and excretion of vinflunine.
2006 Apr-Jun
Gateways to clinical trials.
2006 Mar
Update on tubulin-binding agents.
2006 Mar
Phase I study of vinflunine administered as a 10-minute infusion on days 1 and 8 every 3 weeks.
2006 May
Vinflunine -- an active chemotherapy for treatment of advanced non-small-cell lung cancer previously treated with a platinum-based regimen: results of a phase II study.
2006 May 22
Bcl-2 down-regulation and tubulin subtype composition are involved in resistance of ovarian cancer cells to vinflunine.
2006 Nov
Phase II study of vinflunine in patients with metastatic renal cell carcinoma.
2006 Sep
Vinflunine, a novel microtubule inhibitor, suppresses calmodulin interaction with the microtubule-associated protein STOP.
2007 Dec 25
Gateways to clinical trials.
2007 Jan-Feb
Gateways to clinical trials.
2007 Oct
Systemic treatment for advanced (stage IIIb/IV) non-small cell lung cancer: more treatment options; more things to consider. Conclusion.
2008
Emerging agents in the treatment of anthracycline- and taxane-refractory metastatic breast cancer.
2008 Apr
Novel therapies in genitourinary cancer: an update.
2008 Aug 11
Synthesis and biological evaluation of C-12' substituted vinflunine derivatives.
2008 Aug 15
Vinflunine in the treatment of bladder cancer.
2008 Dec
Comparative study of the radiosensitizing and cell cycle effects of vinflunine and vinorelbine, in vitro.
2008 Feb 29
Gateways to clinical trials.
2008 Jan-Feb
Gateways to clinical trials. July-August 2008.
2008 Jul-Aug
Neuropathy associated with microtubule inhibitors: diagnosis, incidence, and management.
2008 Jun
Clinical activity of vinflunine in transitional cell carcinoma of the urothelium and other solid tumors.
2008 Jun
Antitumor activity of vinflunine: effector pathways and potential for synergies.
2008 Jun
Introduction. The novel microtubule inhibitor vinflunine.
2008 Jun
Options for the treatment of patients with taxane-refractory metastatic breast cancer.
2008 Mar
Vinflunine: a new microtubule inhibitor agent.
2008 Mar 15
Advanced bladder cancer: status of first-line chemotherapy and the search for active agents in the second-line setting.
2008 Sep 15
Gateways to clinical trials.
2009 Jan-Feb
Gateways to clinical trials.
2009 May
Second-line therapy in bladder cancer.
2009 Sep
Patents

Patents

Sample Use Guides

The recommended dose is 320 mg/m² vinflunine as a 20 minute intravenous infusion every 3 weeks
Route of Administration: Intravenous
IC50 values for inhibition of HeLa cell proliferation for vinflunine were 18 nM, similar to the concentrations that induced mitotic block at the metaphase/anaphase transition (38 nM)
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:26:11 GMT 2025
Edited
by admin
on Wed Apr 02 09:26:11 GMT 2025
Record UNII
5BF646324K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VINFLUNINE [EMA EPAR]
Preferred Name English
VINFLUNINE
EMA EPAR   INN   MART.   MI   WHO-DD  
INN  
Official Name English
VINFLUNINE [MI]
Common Name English
4'-DEOXY-20',20'-DIFLUORO-8'-NORVINCALEUCOBLASTINE
Common Name English
vinflunine [INN]
Common Name English
VINFLUNINE [MART.]
Common Name English
Vinflunine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QL01CA05
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
NCI_THESAURUS C932
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
EMA ASSESSMENT REPORTS JAVLOR (AUTHORIZED: CARCINOMA, TRANSITIONAL CELL, UROLOGIC NEOPLASM)
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
WHO-ATC L01CA05
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
NCI_THESAURUS C67422
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID30936722
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
MERCK INDEX
m11456
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY Merck Index
SMS_ID
100000079091
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
EVMPD
SUB00063MIG
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
CAS
162652-95-1
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
ChEMBL
CHEMBL2110725
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
DRUG CENTRAL
3644
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
DRUG BANK
DB11641
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
WIKIPEDIA
Vinflunine
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
INN
7499
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
PUBCHEM
10629256
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
FDA UNII
5BF646324K
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
MESH
C111217
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
CHEBI
90241
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
NCI_THESAURUS
C61564
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY