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.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=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
| 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 |
| Molecular Formula | C4H6O6 |
| Molecular Weight | 150.0868 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000983/WC500039604.pdfCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18347163 | http://adisinsight.springer.com/drugs/800010899
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000983/WC500039604.pdf
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 |
|||
| 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 |
|---|---|---|
| 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
Sample Use Guides
The recommended dose is 320 mg/m² vinflunine as a 20 minute intravenous infusion every 3 weeks
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11408618
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
Edited
Mon Mar 31 18:07:44 GMT 2025
by
admin
on
Mon Mar 31 18:07:44 GMT 2025
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| Record UNII |
33MG53C7XW
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| Record Status |
Validated (UNII)
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C67422
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EMA ASSESSMENT REPORTS |
JAVLOR (AUTHORIZED: UROLOGIC NEOPLASMS)
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m11456
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C76266
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