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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
Vinflunine in platinum-pretreated patients with locally advanced or metastatic urothelial carcinoma: results of a large phase 2 study.
2009-09-15
Second-line therapy in bladder cancer.
2009-09
Phase 2 study of single-agent IV vinflunine as third-line treatment of metastatic breast cancer after failure of anthracycline-/taxane-based chemotherapy.
2009-08
Systemic therapy of advanced urothelial cancer.
2009-08
What does the structure-function relationship of the HIV-1 Tat protein teach us about developing an AIDS vaccine?
2009-05-25
Anti-angiogenic effects of pterogynidine alkaloid isolated from Alchornea glandulosa.
2009-05-22
Gateways to clinical trials.
2009-05
Gateways to clinical trials.
2009-04-10
Gateways to clinical trials.
2009-03
Novel anti-tubulin cytotoxic agents for breast cancer.
2009-02
Tubulin-targeted drug action: functional significance of class ii and class IVb beta-tubulin in vinca alkaloid sensitivity.
2008-12-01
Vinflunine in the treatment of bladder cancer.
2008-12
Gateways to clinical trials. July-August 2008.
2008-10-14
Progress in the development of early diagnosis and a drug with unique pharmacology to improve cancer therapy.
2008-10-13
Advanced bladder cancer: status of first-line chemotherapy and the search for active agents in the second-line setting.
2008-09-15
Synthesis and biological evaluation of C-12' substituted vinflunine derivatives.
2008-08-15
Novel therapies in genitourinary cancer: an update.
2008-08-11
Murine leukemia P388 vinorelbine-resistant cell lines are sensitive to vinflunine.
2008-08
Antiangiogenic vinflunine affects EB1 localization and microtubule targeting to adhesion sites.
2008-07
Further mechanistic unravelling of the influence of the cell cycle effects on the radiosensitising mechanism of vinflunine, in vitro.
2008-07
Systemic treatments for mesothelioma: standard and novel.
2008-06
Neuropathy associated with microtubule inhibitors: diagnosis, incidence, and management.
2008-06
Exploring the mechanisms of action of the novel microtubule inhibitor vinflunine.
2008-06
Clinical activity of vinflunine in transitional cell carcinoma of the urothelium and other solid tumors.
2008-06
Vinflunine: discovery and synthesis of a novel microtubule inhibitor.
2008-06
Pharmacokinetics, metabolites, and preclinical safety of vinflunine.
2008-06
Potential mechanisms of resistance to microtubule inhibitors.
2008-06
Antitumor activity of vinflunine: effector pathways and potential for synergies.
2008-06
Introduction. The novel microtubule inhibitor vinflunine.
2008-06
Gateways to clinical trials.
2008-04-05
Emerging agents in the treatment of anthracycline- and taxane-refractory metastatic breast cancer.
2008-04
Vinflunine: clinical perspectives of an emerging anticancer agent.
2008-04
Vinflunine: a new microtubule inhibitor agent.
2008-03-15
Newer cytotoxic agents: attacking cancer broadly.
2008-03-15
Options for the treatment of patients with taxane-refractory metastatic breast cancer.
2008-03
Comparative study of the radiosensitizing and cell cycle effects of vinflunine and vinorelbine, in vitro.
2008-02-29
Methotrexate, vinblastine, doxorubicin and cisplatin combination regimen as salvage chemotherapy for patients with advanced or metastatic transitional cell carcinoma after failure of gemcitabine and cisplatin chemotherapy.
2008-01-15
Systemic treatment for advanced (stage IIIb/IV) non-small cell lung cancer: more treatment options; more things to consider. Conclusion.
2008
Vinflunine, a novel microtubule inhibitor, suppresses calmodulin interaction with the microtubule-associated protein STOP.
2007-12-25
Evolving nonendocrine therapeutic options for metastatic breast cancer: how adjuvant chemotherapy influences treatment.
2007-12
Phase II study of vinflunine in malignant pleural mesothelioma.
2007-10-20
The evolving role of chemotherapy in advanced urothelial cancer.
2007-10
Gateways to clinical trials.
2007-10
Upregulation of bfl-1 is a potential mechanism of chemoresistance in B-cell chronic lymphocytic leukaemia.
2007-09-17
New developments in first- and second-line chemotherapy for transitional cell, squamous cell and adenocarcinoma of the bladder.
2007-09
American Society of Clinical Oncology--43rd annual meeting. Research into therapeutics: Part 2.
2007-08
Phase II study of IV vinflunine in patients with chemotherapy naive metastatic malignant melanoma.
2007-08
Therapy of metastatic bladder carcinoma.
2007-06
The novel microtubule-interfering agent TZT-1027 enhances the anticancer effect of radiation in vitro and in vivo.
2007-05-21
[NSCLC: update on second line therapy following ASCO 2007].
2007
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
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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