Vinorelbine tartrate
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MedKoo CAT#: 100930

CAS#: 125317-39-7

Description: Vinorelbine is 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.


Price and Availability

Size
Price

50mg
USD 90
500mg
USD 450
5g
USD 1950
Size
Price

100mg
USD 150
1g
USD 750
10g
USD 2950
Size
Price

200mg
USD 250
2g
USD 1250
20g
USD 4650

Vinorelbine tartrate, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 5g may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100930
Name: Vinorelbine tartrate
CAS#: 125317-39-7
Chemical Formula: C53H66N4O20
Exact Mass: 1078.42704
Molecular Weight: 1079.1
Elemental Analysis: C, 58.99; H, 6.16; N, 5.19; O, 29.65


Related CAS #: 125317-39-7 (tartrate)   105661-07-2 (tartrate 1:1)   71486-22-1 (free)  

Synonym: KW2307, KW-2307, KW 2307, vinorelbine tartrate, Navelbine, Biovelbin, Eunades

IUPAC/Chemical Name: methyl (3aR,3a1R,4R,5S,5aR,10bR)-4-acetoxy-3a-ethyl-9-((6R,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)

InChi Key: CILBMBUYJCWATM-PYGJLNRPSA-N

InChi Code: InChI=1S/C45H54N4O8.2C4H6O6/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7;2*5-1(3(7)8)2(6)4(9)10/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3;2*1-2,5-6H,(H,7,8)(H,9,10)/t28-,37-,38+,39+,42+,43+,44-,45-;2*1-,2-/m011/s1

SMILES Code: O=C(OC)[C@@]1([C@@]2(N(C3=C([C@@]24CCN5CC=C[C@@](CC)([C@H]1OC(C)=O)[C@@]45[H])C=C(C(OC)=C3)[C@]6(C[C@]7([H])C=C(CN(CC8=C6NC9=C8C=CC=C9)C7)CC)C(OC)=O)C)[H])O.O=C([C@@H]([C@H](C(O)=O)O)O)O.O=C([C@@H]([C@H](C(O)=O)O)O)O


Technical Data

Appearance:
White to off-white solid powder

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

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


Additional Information

 


References

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2: Kolek V, Grygárková I, Koubková L, Skřičková J, Švecová J, Sixtová D, Bartoš J, Tichopád A. Carboplatin with intravenous and subsequent oral administration of vinorelbine in resected non-small-cell-lung cancer in real-world set-up. PLoS One. 2017 Jul 21;12(7):e0181803. doi: 10.1371/journal.pone.0181803. eCollection 2017. PubMed PMID: 28732018.

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4: Sathyamoorthy N, Magharla DD, Vankayalu SD. Effect of Surface Modification on the In vitro Protein Adsorption and Cell Cytotoxicity of Vinorelbine Nanoparticles. J Pharm Bioallied Sci. 2017 Apr-Jun;9(2):135-143. doi: 10.4103/jpbs.JPBS_258_16. PubMed PMID: 28717337; PubMed Central PMCID: PMC5508415.

5: Mamesaya N, Nakashima K, Naito T, Nakajima T, Endo M, Takahashi T. ALK-rearranged lung squamous cell carcinoma responding to alectinib: a case report and review of the literature. BMC Cancer. 2017 Jul 6;17(1):471. doi: 10.1186/s12885-017-3468-1. PubMed PMID: 28683775; PubMed Central PMCID: PMC5501098.

6: Bilir C, Durak S, Kızılkaya B, Hacıbekiroglu I, Nayır E, Engin H. Efficacy of metronomic vinorelbine in elderly patients with advanced non-small-cell lung cancer and poor performance status. Curr Oncol. 2017 Jun;24(3):e199-e204. doi: 10.3747/co.24.3486. Epub 2017 Jun 27. PubMed PMID: 28680287; PubMed Central PMCID: PMC5486392.

7: Yamamoto N, Kenmotsu H, Yamanaka T, Nakamura S, Tsuboi M. Randomized Phase III Study of Cisplatin With Pemetrexed and Cisplatin With Vinorelbine for Completely Resected Nonsquamous Non-Small-Cell Lung Cancer: The JIPANG Study Protocol. Clin Lung Cancer. 2017 Jun 8. pii: S1525-7304(17)30169-9. doi: 10.1016/j.cllc.2017.05.020. [Epub ahead of print] PubMed PMID: 28668204.

8: Steger GG, Dominguez A, Dobrovolskaya N, Giotta F, Tubiana-Mathieu N, Pecherstorfer M, Ardizzoia A, Blasinska-Morawiec M, Espinosa E, Villanova G. Single-Agent Oral Vinorelbine as First-Line Chemotherapy for Endocrine-Pretreated Breast Cancer With Bone Metastases and No Visceral Involvement: NORBREAST-228 Phase II Study. Clin Breast Cancer. 2017 Jun 27. pii: S1526-8209(16)30562-6. doi: 10.1016/j.clbc.2017.05.012. [Epub ahead of print] PubMed PMID: 28666812.

9: Cortés J, Rugo HS, Awada A, Twelves C, Perez EA, Im SA, Gómez-Pardo P, Schwartzberg LS, Diéras V, Yardley DA, Potter DA, Mailliez A, Moreno-Aspitia A, Ahn JS, Zhao C, Hoch U, Tagliaferri M, Hannah AL, O'Shaughnessy J. Prolonged survival in patients with breast cancer and a history of brain metastases: results of a preplanned subgroup analysis from the randomized phase III BEACON trial. Breast Cancer Res Treat. 2017 Jun 13. doi: 10.1007/s10549-017-4304-7. [Epub ahead of print] PubMed PMID: 28612225.

10: Yamamura J, Masuda N, Yamamoto D, Tsuyuki S, Yamaguchi M, Tanaka S, Tsurutani J, Tokunaga S, Yoshidome K, Mizutani M, Aono T, Ooe A, Tanino H, Matsunami N, Yasojima H, Nakayama T, Nishida Y. Gemcitabine and Vinorelbine Combination Chemotherapy in Taxane-Pretreated Patients with Metastatic Breast Cancer: A Phase II Study of the Kinki Multidisciplinary Breast Oncology Group (KMBOG) 1015. Chemotherapy. 2017 Jun 13;62(5):307-313. doi: 10.1159/000475879. [Epub ahead of print] PubMed PMID: 28605730.

11: Guohua H, Hongyang L, Zhiming J, Danhua Z, Haifang W. Study of small-cell lung cancer cell-based sensor and its applications in chemotherapy effects rapid evaluation for anticancer drugs. Biosens Bioelectron. 2017 Nov 15;97:184-195. doi: 10.1016/j.bios.2017.05.050. Epub 2017 May 31. PubMed PMID: 28599178.

12: Passardi A, Fanini F, Turci L, Foca F, Rosetti P, Ruscelli S, Casadei Gardini A, Valgiusti M, Dazzi C, Marangolo M. Prolonged Pemetrexed Infusion Plus Gemcitabine in Refractory Metastatic Colorectal Cancer: Preclinical Rationale and Phase II Study Results. Oncologist. 2017 Jun 7. pii: theoncologist.2017-0206. doi: 10.1634/theoncologist.2017-0206. [Epub ahead of print] PubMed PMID: 28592624.

13: Andersson M, López-Vega JM, Petit T, Zamagni C, Easton V, Kamber J, Restuccia E, Perez EA. Efficacy and Safety of Pertuzumab and Trastuzumab Administered in a Single Infusion Bag, Followed by Vinorelbine: VELVET Cohort 2 Final Results. Oncologist. 2017 Jun 7. pii: theoncologist.2017-0079. doi: 10.1634/theoncologist.2017-0079. [Epub ahead of print] PubMed PMID: 28592618.

14: Weiss GJ, Waypa J, Blaydorn L, Coats J, McGahey K, Sangal A, Niu J, Lynch CA, Farley JH, Khemka V. A phase Ib study of pembrolizumab plus chemotherapy in patients with advanced cancer (PembroPlus). Br J Cancer. 2017 Jun 27;117(1):33-40. doi: 10.1038/bjc.2017.145. Epub 2017 Jun 6. PubMed PMID: 28588322; PubMed Central PMCID: PMC5520208.

15: Robson M, Im SA, Senkus E, Xu B, Domchek SM, Masuda N, Delaloge S, Li W, Tung N, Armstrong A, Wu W, Goessl C, Runswick S, Conte P. Olaparib for Metastatic Breast Cancer in Patients with a Germline BRCA Mutation. N Engl J Med. 2017 Jun 4. doi: 10.1056/NEJMoa1706450. [Epub ahead of print] PubMed PMID: 28578601.

16: Suda K, Rozeboom L, Rivard CJ, Yu H, Ellison K, Melnick MAC, Hinz TK, Chan D, Heasley LE, Politi K, Mitsudomi T, Hirsch FR. Therapy-induced E-cadherin downregulation alters expression of programmed death ligand-1 in lung cancer cells. Lung Cancer. 2017 Jul;109:1-8. doi: 10.1016/j.lungcan.2017.04.010. Epub 2017 Apr 19. PubMed PMID: 28577937.

17: Derks JL, van Suylen RJ, Thunnissen E, den Bakker MA, Groen HJ, Smit EF, Damhuis RA, van den Broek EC, Speel EM, Dingemans AC; PALGA group. Chemotherapy for pulmonary large cell neuroendocrine carcinomas: does the regimen matter? Eur Respir J. 2017 Jun 1;49(6). pii: 1601838. doi: 10.1183/13993003.01838-2016. Print 2017 Jun. PubMed PMID: 28572122.

18: Gadgeel SM. Role of Chemotherapy and Targeted Therapy in Early-Stage Non-Small Cell Lung Cancer. Am Soc Clin Oncol Educ Book. 2017;37:630-639. doi: 10.14694/EDBK_175188. PubMed PMID: 28561669.

19: Mencoboni M, Filiberti RA, Taveggia P, Del Corso L, Del Conte A, Covesnon MG, Puccetti C, Donati S, Auriati L, Amoroso D, Camerini A. Safety of First-line Chemotherapy with Metronomic Single-agent Oral Vinorelbine in Elderly Patients with NSCLC. Anticancer Res. 2017 Jun;37(6):3189-3194. PubMed PMID: 28551663.

20: Montagna E, Vingiani A, Maisonneuve P, Cancello G, Contaldo F, Pruneri G, Colleoni M. Unfavorable prognostic role of tumor-infiltrating lymphocytes in hormone-receptor positive, HER2 negative metastatic breast cancer treated with metronomic chemotherapy. Breast. 2017 Aug;34:83-88. doi: 10.1016/j.breast.2017.05.009. Epub 2017 May 23. PubMed PMID: 28544923.