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
| 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 |
| Molecular Formula | C45H54F2N4O8 |
| Molecular Weight | 816.9291 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 9 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|||
| 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 |
|---|---|---|
| Markedly diminished drug resistance-inducing properties of vinflunine (20',20'-difluoro-3',4'-dihydrovinorelbine) relative to vinorelbine, identified in murine and human tumour cells in vivo and in vitro. | 2001 Jul |
|
| Mechanism of mitotic block and inhibition of cell proliferation by the semisynthetic Vinca alkaloids vinorelbine and its newer derivative vinflunine. | 2001 Jul |
|
| Vinflunine, a second generation novel Vinca Alkaloid with a distinctive pharmacological profile, now in clinical development and prospects for future mitotic blockers. | 2001 Sep |
|
| Model of chemotherapy-induced myelosuppression with parameter consistency across drugs. | 2002 Dec 15 |
|
| Gateways to clinical trials. | 2004 Jun |
|
| HIV-1 Tat protein enhances microtubule polymerization. | 2005 Feb 3 |
|
| [Vinflunine: a new anti-cancer fluorinated agent derived from Vinca-alkaloids]. | 2005 Jan |
|
| Cell cycle effects of vinflunine, the most recent promising Vinca alkaloid, and its interaction with radiation, in vitro. | 2006 Aug |
|
| Antiangiogenic concentrations of vinflunine increase the interphase microtubule dynamics and decrease the motility of endothelial cells. | 2006 Mar 15 |
|
| Phase II study of vinflunine in patients with metastatic renal cell carcinoma. | 2006 Sep |
|
| Development of a sensitive liquid chromatography method coupled with a tandem mass spectrometric detection for the clinical analysis of vinflunine and 4-O-deacetyl vinflunine in blood, urine and faeces. | 2007 Jun 15 |
|
| Upregulation of bfl-1 is a potential mechanism of chemoresistance in B-cell chronic lymphocytic leukaemia. | 2007 Sep 17 |
|
| 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 Jan 15 |
|
| Pharmacokinetics, metabolites, and preclinical safety of 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 |
|
| Progress in the development of early diagnosis and a drug with unique pharmacology to improve cancer therapy. | 2008 Oct 13 |
|
| 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 Mar |
|
| Anti-angiogenic effects of pterogynidine alkaloid isolated from Alchornea glandulosa. | 2009 May 22 |
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
| Substance Class |
Chemical
Created
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| Record UNII |
33MG53C7XW
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Validated (UNII)
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C67422
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EMA ASSESSMENT REPORTS |
JAVLOR (AUTHORIZED: UROLOGIC NEOPLASMS)
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C76266
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