Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C45H54F2N4O8.2C4H6O6 |
| Molecular Weight | 1117.1027 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 14 / 14 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O.O[C@H]([C@@H](O)C(O)=O)C(O)=O.[H][C@@]12N3CC[C@@]14C5=C(C=C(OC)C(=C5)[C@]6(C[C@@H]7C[C@H](C[N@@](C7)CC8=C6NC9=C8C=CC=C9)C(C)(F)F)C(=O)OC)N(C)[C@@]4([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC
InChI
InChIKey=YIHUEPHBPPAAHH-IIQAEXPMSA-N
InChI=1S/C45H54F2N4O8.2C4H6O6/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;2*5-1(3(7)8)2(6)4(9)10/h9-14,19-20,26-27,36-38,48,55H,8,15-18,21-24H2,1-7H3;2*1-2,5-6H,(H,7,8)(H,9,10)/t26-,27+,36-,37+,38+,42+,43+,44-,45-;2*1-,2-/m011/s1
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18347163 | http://adisinsight.springer.com/drugs/800010899
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095182 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Javlor Approved UseJavlor (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 Date2009 |
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| Primary | Javlor Approved UseJavlor (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 Date2009 |
|||
| Primary | Javlor Approved UseJavlor (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 Date2009 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Characterization of cell death induced by vinflunine, the most recent Vinca alkaloid in clinical development. | 2002 Jan 7 |
|
| Phase I and pharmacokinetic study of the new vinca alkaloid vinflunine administered as a 10-min infusion every 3 weeks in patients with advanced solid tumours. | 2003 Apr |
|
| Modelling and simulation in the development and use of anti-cancer agents: an underused tool? | 2004 Dec |
|
| Gateways to clinical trials. | 2004 Jan-Feb |
|
| Head and neck carcinoma cell lines are sensitive to vinflunine in vitro. | 2005 Nov-Dec |
|
| Gateways to clinical trials. | 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 |
|
| Evolving nonendocrine therapeutic options for metastatic breast cancer: how adjuvant chemotherapy influences treatment. | 2007 Dec |
|
| Gateways to clinical trials. | 2007 Jan-Feb |
|
| The novel microtubule-interfering agent TZT-1027 enhances the anticancer effect of radiation in vitro and in vivo. | 2007 May 21 |
|
| Gateways to clinical trials. | 2007 Oct |
|
| Phase II study of vinflunine in malignant pleural mesothelioma. | 2007 Oct 20 |
|
| Further mechanistic unravelling of the influence of the cell cycle effects on the radiosensitising mechanism of vinflunine, in vitro. | 2008 Jul |
|
| Systemic treatments for mesothelioma: standard and novel. | 2008 Jun |
|
| Exploring the mechanisms of action of the novel microtubule inhibitor vinflunine. | 2008 Jun |
|
| Clinical activity of vinflunine in transitional cell carcinoma of the urothelium and other solid tumors. | 2008 Jun |
|
| Vinflunine: a new microtubule inhibitor agent. | 2008 Mar 15 |
|
| Progress in the development of early diagnosis and a drug with unique pharmacology to improve cancer therapy. | 2008 Oct 13 |
|
| Gateways to clinical trials. | 2009 Mar |
|
| Gateways to clinical trials. | 2009 May |
|
| Anti-angiogenic effects of pterogynidine alkaloid isolated from Alchornea glandulosa. | 2009 May 22 |
|
| Second-line therapy in bladder cancer. | 2009 Sep |
|
| Vinflunine in platinum-pretreated patients with locally advanced or metastatic urothelial carcinoma: results of a large phase 2 study. | 2009 Sep 15 |
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
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NCI_THESAURUS |
C67422
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EMA ASSESSMENT REPORTS |
JAVLOR (AUTHORIZED: UROLOGIC NEOPLASMS)
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TT-79
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194468-36-5
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SUB28421
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90241
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DTXSID80870081
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33MG53C7XW
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m11456
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DBSALT002672
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C76266
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
