. . Vinorelbine tartrate | CAS#125317-39-7 | CAS#71486-22-1 | MedKoo Biosciences

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 Vinorelbine tartrate

  

Description of Vinorelbine: Vinorelbine tartrate is the ditartrate salt of a semisynthetic vinca alkaloid derived from the leaves of the periwinkle plant (Vinca rosea) with antineoplastic activity. Vinorelbine binds to tubulin, thereby inhibiting tubulin polymerization into microtubules and spindle formation and resulting in apoptosis of susceptible cancer cells. Inhibition of mitotic microtubules correlates with antitumor activity, whereas inhibition of axonal microtubules seems to correlate with vinorelbine's neurotoxicity. Compared to related vinca alkaloids, vinorelbine is more selective against mitotic than axonal microtubules in vitro, which may account for its decreased neurotoxicity. This agent is also a radiation-sensitizing agent. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus) (last updated: 2/16/2015).

   

MedKoo Cat#: 100930

Name: Vinorelbine tartrate

CAS#: 125317-39-7 (Vinorelbine tartrate); 71486-22-1 (Vinorelbine).

Synonym:  KW-2307; KW2307; KW 2307; Vinorelbine Bitartrate, Vinorelbine ditartrate Nor-5'-anhydrovinblastine ditartrate; 3',4'-didehydro-4'-deoxy-C'-norvincaleukoblastine; US brand name: Navelbine.  Foreign brand names: Biovelbin; Eunades.

IUPAC/Chemical name:

(3aR,3a1R,4R,5S,5aR,10bR)-methyl 4-acetoxy-3a-ethyl-9-((2R,8S)-4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl)-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate bis((2R,3R)-2,3-dihydroxysuccinate)

Chemical structure:

Theoretical analysis :

Vinorelbine structure

MedKoo Cat#: 100930
Name: Vinorelbine tartrate
CAS#: 125317-39-7

Chemical Formula: C53H66N4O20

Molecular Weight: 1079.10

Vinorelbine

Chemical Formula: C45H54N4O8

Exact Mass: 778.39416 , Molecular Weight: 778.93  

  

Availability and price:

Vinorelbine tartrate, purity > 98%, is in stock. Price update 2/16/2015. Current shipping out time is about 10days after order is received. Delivery time; overnight (USA/Canada) or 3-5 days (international). Same day shipping from Chapel Hill, USA. Shipping fee from $30.00 (USA),from $45.00 (Canada); from $70.00 (international).  

10mg / $50.00

25mg / $80.00

50mg / $120.00

100mg / $190.00

200mg / $350.00

500mg / $550.00

1.0g / $950.00 

2.0g / $1,650.00

5.0g / $2,950.00

10.0g / Ask price 

20.0g / Ask price

500g / Ask price

 Bulk available at discount price.

    

 

Technical data 

Appearance:

Solid powder

Purity:

>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

View CoA: current batch, Lot#  (will be available for download when it's in stock)

QC data:

View QC data: current batch, Lot#  (will be available for download when it's in stock)

Safety Data Sheet (MSDS):

View Material Safety Data Sheet (MSDS)  (will be available for download when it's in stock)

Shipping condition:

Shipped under ambient temperature as non-hazardous chemical.  This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage condition:

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:

Soluble in DMSO, not in water

Shelf life:

>2 years if stored properly

Drug formulation:

This drug may be formulated in DMSO

Stock solution storage:

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Note: The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis. 

 

 

Information about this agent

 

DRUG DESCRIPTION

NAVELBINE (vinorelbine tartrate) Injection is for intravenous administration. Each vial contains vinorelbine tartrate equivalent to 10 mg (1-mL vial) or 50 mg (5-mL vial) vinorelbine in Water for Injection. No preservatives or other additives are present. The aqueous solution is sterile and nonpyrogenic. Vinorelbine tartrate is a semi-synthetic vinca alkaloid with antitumor activity. The chemical name is 3',4'-didehydro-4'-deoxy-C'-norvincaleukoblastine [R-(R*,R*)-2, 3-dihydroxybutanedioate (1:2)(salt)]. vinorelbine tartrate is a white to yellow or light brown amorphous powder with the molecular formula C45H54N4O8•2C4H6O6 and molecular weight of 1079.12. The aqueous solubility is > 1,000 mg/mL in distilled water. The pH of NAVELBINE Injection is approximately 3.5.

 

Oral formulation

An oral formulation has been marketed and registered in most European coutries for the same settings. It has similar efficacy as the intravenous formulation, avoids venous toxicities of an infusion and is easier to take. from: http://en.wikipedia.org/wiki/Vinorelbine.

 

CLINICAL PHARMACOLOGY

Vinorelbine is a vinca alkaloid that interferes with microtubule assembly. The vinca alkaloids are structurally similar compounds comprised of 2 multiringed units, vindoline and catharanthine. Unlike other vinca alkaloids, the catharanthine unit is the site of structural modification for vinorelbine. The antitumor activity of vinorelbine is thought to be due primarily to inhibition of mitosis at metaphase through its interaction with tubulin. Like other vinca alkaloids, vinorelbine may also interfere with: 1) amino acid, cyclic AMP, and glutathione metabolism, 2) calmodulin-dependent Ca++-transport ATPase activity, 3) cellular respiration, and 4) nucleic acid and lipid biosynthesis. In intact tectal plates from mouse embryos, vinorelbine, vincristine and vinblastine inhibited mitotic microtubule formation at the same concentration (2 µM), inducing a blockade of cells at metaphase. Vincristine produced depolymerization of axonal microtubules at 5 µM, but vinblastine and vinorelbine did not have this effect until concentrations of 30 µM and 40 µM, respectively. These data suggest relative selectivity of vinorelbine for mitotic microtubules.

 

History

Vinorelbine was invented by the pharmacist Pierre Potier and his team from the CNRS in France in the 1980s and was licensed to the oncology department of the Pierre Fabre Group. The drug was approved in France in 1989 under the brand name Navelbine for the treatment of non-small cell lung cancer. It gained approval to treat metastatic breast cancer in 1991. Vinorelbine received approval by the United States Food and Drug Administration (FDA) in December 1994 sponsored by Burroughs Wellcome Company. Pierre Fabre Group now markets Navelbine in the U.S. where the drug went generic in February 2003. In most European countries, it is approved to treat non-small cell lung cancer and breast cancer. from: http://en.wikipedia.org/wiki/Vinorelbine.

 

References

1: Barletta G, Genova C, Rijavec E, Burrafato G, Biello F, Sini C, Dal Bello MG, Coco S, Truini A, Vanni I, Alama A, Beltramini S, Grassi MA, Boccardo F, Grossi F. Oral vinorelbine in the treatment of non-small-cell lung cancer. Expert Opin Pharmacother. 2014 Aug;15(11):1585-99. doi: 10.1517/14656566.2014.934224. Epub 2014 Jun 27. Review. PubMed PMID: 24972635.

2: Caffo O, Dipasquale M, Murgia V, Veccia A, Galligioni E. An evaluation of the pharmacokinetics and clinical use of vinorelbine for NSCLC treatment. Expert Opin Drug Metab Toxicol. 2013 Aug;9(8):1037-51. doi: 10.1517/17425255.2013.804065. Epub 2013 May 27. Review. PubMed PMID: 23705788.

3: Xu YC, Wang HX, Tang L, Ma Y, Zhang FC. A systematic review of vinorelbine for the treatment of breast cancer. Breast J. 2013 Mar-Apr;19(2):180-8. doi: 10.1111/tbj.12071. Epub 2013 Jan 16. Review. PubMed PMID: 23320984.

4: Capasso A. Vinorelbine in cancer therapy. Curr Drug Targets. 2012 Jul;13(8):1065-71. Review. PubMed PMID: 22594474.

5: Galano G, Caputo M, Tecce MF, Capasso A. Efficacy and tolerability of vinorelbine in the cancer therapy. Curr Drug Saf. 2011 Jul;6(3):185-93. Review. PubMed PMID: 22122393.

6: Aapro M, Finek J. Oral vinorelbine in metastatic breast cancer: a review of current clinical trial results. Cancer Treat Rev. 2012 Apr;38(2):120-6. doi: 10.1016/j.ctrv.2011.05.005. Epub 2011 Jul 13. Review. PubMed PMID: 21742438.

7: Liu X, Ma L, Yang K, Tian J. [Vinorelbine plus oxaliplatin versus vinorelbine plus cisplatin for advanced non-small cell lung cancer: a systematic review]. Zhongguo Fei Ai Za Zhi. 2010 Feb;13(2):112-7. doi: 10.3779/j.issn.1009-3419.2010.02.06. Review. Chinese. PubMed PMID: 20673502.

8: June RR, Dougherty DW, Reese CT, Harpster LE, Hoffman SL, Drabick JJ. Significant activity of single agent vinorelbine against small-cell cancer of the bladder as second line chemotherapy: a case series and review of the literature. Urol Oncol. 2012 Mar-Apr;30(2):192-5. doi: 10.1016/j.urolonc.2009.12.017. Epub 2010 Apr 3. Review. PubMed PMID: 20363163.

9: Piccirillo MC, Daniele G, Di Maio M, Bryce J, De Feo G, Del Giudice A, Perrone F, Morabito A. Vinorelbine for non-small cell lung cancer. Expert Opin Drug Saf. 2010 May;9(3):493-510. doi: 10.1517/14740331003774078. Review. PubMed PMID: 20350282.

10: Zhu ZF, Fan M, Fu XL. Radiation recall with vinorelbine and cisplatin. Onkologie. 2010;33(3):107-9. doi: 10.1159/000277672. Epub 2010 Feb 22. Review. PubMed PMID: 20215801.

11: Chan A, Verrill M. Capecitabine and vinorelbine in metastatic breast cancer. Eur J Cancer. 2009 Sep;45(13):2253-65. doi: 10.1016/j.ejca.2009.04.031. Epub 2009 May 20. Review. PubMed PMID: 19464166.

12: Gralla RJ, Gatzemeier U, Gebbia V, Huber R, O'Brien M, Puozzo C. Oral vinorelbine in the treatment of non-small cell lung cancer: rationale and implications for patient management. Drugs. 2007;67(10):1403-10. Review. PubMed PMID: 17600389.

13: Devlin JG, Langer CJ. Salvage therapy with vinorelbine in advanced non-small-cell lung cancer: a retrospective review of the Fox Chase Cancer Center experience and a review of the literature. Clin Lung Cancer. 2007 Mar;8(5):319-26. Review. PubMed PMID: 17562231.

14: Aapro MS, Conte P, Esteban González E, Trillet-Lenoir V. Oral vinorelbine: role in the management of metastatic breast cancer. Drugs. 2007;67(5):657-67. Review. PubMed PMID: 17385939.

15: Chan A. A review of the use of trastuzumab (Herceptin) plus vinorelbine in metastatic breast cancer. Ann Oncol. 2007 Jul;18(7):1152-8. Epub 2007 Jan 29. Review. PubMed PMID: 17264064.

16: Bartsch V. [Oral vinorelbine: pharmacology and treatment outcome in non-small cell bronchial carcinoma and breast carcinoma]. Onkologie. 2006 Mar;29 Suppl 1:1-28. Epub 2006 Mar 3. Review. German. PubMed PMID: 16534241.

17: Mano M. Vinorelbine in the management of breast cancer: New perspectives, revived role in the era of targeted therapy. Cancer Treat Rev. 2006 Apr;32(2):106-18. Epub 2006 Feb 13. Review. PubMed PMID: 16473470.

18: de Lemos ML. Vinorelbine and venous irritation: optimal parenteral administration. J Oncol Pharm Pract. 2005 Jun;11(2):79-81. Review. PubMed PMID: 16460608.

19: Gebbia V, Puozzo C. Oral versus intravenous vinorelbine: clinical safety profile. Expert Opin Drug Saf. 2005 Sep;4(5):915-28. Review. PubMed PMID: 16111453.

20: Rossi A, Gridelli C, Gebbia V, Rosati G, Tortoriello A, Maione P, Borsellino N, Rossi N, Pisano A, Colantuoni G, Iaffaioli RV, Castaldo V, Manzione L. Single agent vinorelbine as first-line chemotherapy in elderly patients with advanced breast cancer. Anticancer Res. 2003 Mar-Apr;23(2C):1657-64. Review. PubMed PMID: 12820437.
 

 

 

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