Vinblastine sulfate
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MedKoo CAT#: 100911

CAS#: 143-67-9

Description: Vinblastine is a natural alkaloid isolated from the plant Vinca rosea Linn. Vinblastine binds to tubulin and inhibits microtubule formation, resulting in disruption of mitotic spindle assembly and arrest of tumor cells in the M phase of the cell cycle. This agent may also interfere with amino acid, cyclic AMP, and glutathione metabolism; calmodulin-dependent Ca++ -transport ATPase activity; cellular respiration; and nucleic acid and lipid biosynthesis.


Price and Availability

Size
Price

50mg
USD 150
500mg
USD 450
5g
USD 1850
Size
Price

100mg
USD 250
1g
USD 650
10g
USD 3250
Size
Price

200mg
USD 350
2g
USD 950
20g
USD 5950

Vinblastine sulfate, purity > 98%, is in stock. Same day shipping after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100911
Name: Vinblastine sulfate
CAS#: 143-67-9
Chemical Formula: C46H60N4O13S
Exact Mass: 908.38776
Molecular Weight: 909.05
Elemental Analysis: C, 60.78; H, 6.65; N, 6.16; O, 22.88; S, 3.53


Related CAS #: 143-67-9 (sulfate)   865-21-4 (free)  

Synonym: Vincaleucoblastine, Velban, Velsar, VLB

IUPAC/Chemical Name: (3aR,3a1R,4R,5S,5aR,10bR)-methyl 4-acetoxy-3a-ethyl-9-((5S,7R,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-2,4,5,6,7,8,9,10-octahydro-1H-3,7-methano[1]azacycloundecino[5,4-b]indol-9-yl)-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate sulfate

InChi Key: KDQAABAKXDWYSZ-PNYVAJAMSA-N

InChi Code: InChI=1S/C46H58N4O9.H2O4S/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7;1-5(2,3)4/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3;(H2,1,2,3,4)/t28-,37-,38+,39+,42-,43+,44+,45-,46-;/m0./s1

SMILES Code: O=C([C@]1(O)[C@]2([H])N(C)C3=C(C=C([C@@]4(C(OC)=O)C[C@]5([H])C[C@@](O)(CC)CN(C5)CCC6=C4NC7=C6C=CC=C7)C(OC)=C3)[C@]2(CCN8CC=C9)[C@]8([H])[C@]9(CC)[C@H]1OC(C)=O)OC.O=S(O)(O)=O


Technical Data

Appearance:
White to slight yellow 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:
Stock solution storage:

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

History
Vinblastine was first isolated by Robert Noble and Charles Thomas Beer from the Madagascar periwinkle plant. Vinblastine's utility as a chemotherapeutic agent was first discovered when it was crushed into a tea. Consumption of the tea led to a decreased number of white blood cells; therefore, it was hypothesized that vinblastine might be effective against cancers of the white blood cells such as lymphoma. From http://en.wikipedia.org/wiki/Vinblastine.
 
Pharmacology
Vinblastine is a vinca alkaloid and a chemical analogue of vincristine. It binds tubulin, thereby inhibiting the assembly of microtubules. It is M phase cell cycle specific since microtubules are a component of the mitotic spindle and the kinetochore which are necessary for the separation of chromosomes during anaphase of mitosis. Toxicities include bone marrow suppression (which is dose-limiting), gastrointestinal toxicity, potent vesicant (blister-forming) activity, and extravasation injury (forms deep ulcers). Vinblastine paracrystals may be composed of tightly-packed unpolymerized tubulin or microtubules.
 


References

1: Hay AE, Meyer RM. Balancing risks and benefits of therapy for patients with favorable-risk limited-stage Hodgkin lymphoma: the role of doxorubicin, bleomycin, vinblastine, and dacarbazine chemotherapy alone. Hematol Oncol Clin North Am. 2014 Feb;28(1):49-63. doi: 10.1016/j.hoc.2013.10.001. Review. PubMed PMID: 24287067; PubMed Central PMCID: PMC3859248.

2: Keglevich P, Hazai L, Kalaus G, Szántay C. Modifications on the basic skeletons of vinblastine and vincristine. Molecules. 2012 May 18;17(5):5893-914. doi: 10.3390/molecules17055893. Review. PubMed PMID: 22609781.

3: Gobbi PG, Federico M. What has happened to VBM (vinblastine, bleomycin, and methotrexate) chemotherapy for early-stage Hodgkin lymphoma? Crit Rev Oncol Hematol. 2012 Apr;82(1):18-24. doi: 10.1016/j.critrevonc.2011.04.003. Epub 2011 May 17. Review. PubMed PMID: 21592816.

4: Yokoshima S, Tokuyama H, Fukuyama T. Total synthesis of (+)-vinblastine: control of the stereochemistry at C18'. Chem Rec. 2010 Apr;10(2):101-18. doi: 10.1002/tcr.201090001. Review. PubMed PMID: 20394103.

5: Martinelli G, Cocorocchio E, Saletti PC, Orecchia R, Bernier J, Tradati N, Santoro P, Robertson C, Peccatori FA, Zucca E, Cavalli F. Efficacy of vinblastine, bleomycin, methotrexate (VBM) combination chemotherapy with involved field radiotherapy in early stage (I-IIA) Hodgkin disease patients. Leuk Lymphoma. 2003 Nov;44(11):1919-23. Review. PubMed PMID: 14738143.

6: Ramírez-Amador V, Esquivel-Pedraza L, Lozada-Nur F, De la Rosa-García E, Volkow-Fernández P, Súchil-Bernal L, Mohar A. Intralesional vinblastine vs. 3% sodium tetradecyl sulfate for the treatment of oral Kaposi's sarcoma. A double blind, randomized clinical trial. Oral Oncol. 2002 Jul;38(5):460-7. Review. PubMed PMID: 12110340.

7: Anderson CM, Walters RS, Hortobagyi GN. Mediastinitis related to probable central vinblastine extravasation in a woman undergoing adjuvant chemotherapy for early breast cancer. Am J Clin Oncol. 1996 Dec;19(6):566-8. Review. PubMed PMID: 8931672.

8: Roth BJ, Bajorin DF. Advanced bladder cancer: the need to identify new agents in the post-M-VAC (methotrexate, vinblastine, doxorubicin and cisplatin) world. J Urol. 1995 Mar;153(3 Pt 2):894-900. Review. PubMed PMID: 7853569.

9: Akaza H, Kotake T, Miyanaga N, Koiso K. Effect of recombinant human granulocyte colony-stimulating factor in patients receiving methotrexate/vinblastine/doxorubicin/cisplatin therapy for the treatment of transitional cell carcinoma of the urinary tract. Semin Oncol. 1994 Feb;21(1 Suppl 1):70-4. Review. PubMed PMID: 7512280.

10: Kuebler JP, Whitehead RP, Ward DL, Hemstreet GP 3rd, Bradley EC. Treatment of metastatic renal cell carcinoma with recombinant interleukin-2 in combination with vinblastine or lymphokine-activated killer cells. J Urol. 1993 Sep;150(3):814-20. Review. PubMed PMID: 8345590.