WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100911
CAS#: 143-67-9 (sulfate)
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.
MedKoo Cat#: 100911
Name: Vinblastine sulfate
CAS#: 143-67-9 (sulfate)
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-methanoazacycloundecino[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
Appearance: White to slight yellow solid powder
Purity: >98% (or refer to the Certificate of Analysis)
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).
HS Tariff Code: 2934.99.9001
|Biological target:||Vinblastine sulfate (NSC49842, Vincaleukoblastine sulfate salt, 29060-LE, Exal, Velban, Velbe) inhibits microtubule formation and suppresses nAChR activity with IC50 of 8.9 μM in a cell-free assay, used to treat certain kinds of cancer.|
|In vitro activity:||In NB4 cells, vinblastine produces alteration of p53 and DNA fragmentation. Vinblastine treatment had an antiproliferative effect via the induction of apoptosis producing Bax/Bcl-2 imbalance. Vinblastine treatment suppressed NFκB expression and depressed NFκB-DNA binding activity while maintaining JNK activation that subsequently resulted in apoptotic response through caspase-dependent pathway. This provides a possible anti-cancer mechanism of vinblastine action on NB4 cells by deregulation of the intracellular signalling cascade affecting to JNK activation and NFκB expression. Moreover, JNK activation and NFκB depression can be very significant factors in apoptosis induction by vinblastine. Reference: Cell Biochem Funct. 2015 Jun;33(4):211-9. https://onlinelibrary.wiley.com/doi/abs/10.1002/cbf.3105|
|In vivo activity:||Male Sprague Dawley rats were treated for twenty-eight consecutive days with vinblastine dose levels from 0.0156 to 0.125 mg/kg/day. Micronucleated reticulocyte frequencies in peripheral blood were determined at Days 4 and 29, and mutant cell frequencies were determined at Days -4, 15, 29, and 46. Vinblastine affected reticulocyte frequencies, with reductions noted during the treatment phase and increases observed following cessation of treatment. Micronucleated reticulocyte frequencies were significantly elevated at Day 4 in the high dose group. Although a statistically significant increase in mutant reticulocyte frequencies were found for one dose group at a single time point (Day 46), it was not deemed biologically relevant because there was no analogous finding in mutant RBCs, it occurred at the lowest dose tested, and only 1 rat exceeded an upper bound tolerance interval established with historical negative control rats. Therefore, whereas micronucleus induction reflects vinblastine's well-established aneugenic effect on hematopoietic cells, the lack of a Pig-a response indicates that this tubulin-binding agent does not cause appreciable mutagenicity in this same cell type. Reference: Environ Mol Mutagen. 2018 Jan;59(1):30-37. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/28833575/|
|Solvent||Max Conc. mg/mL||Max Conc. mM|
The following data is based on the product molecular weight 909.05 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
|In vitro protocol:||1. Calviño E, Tejedor MC, Sancho P, Herráez A, Diez JC. JNK and NFκB dependence of apoptosis induced by vinblastine in human acute promyelocytic leukaemia cells. Cell Biochem Funct. 2015 Jun;33(4):211-9. doi: 10.1002/cbf.3105. Epub 2015 Apr 23. PMID: 25914345.|
|In vivo protocol:||1. Avlasevich SL, Labash C, Torous DK, Bemis JC, MacGregor JT, Dertinger SD. In vivo pig-a and micronucleus study of the prototypical aneugen vinblastine sulfate. Environ Mol Mutagen. 2018 Jan;59(1):30-37. doi: 10.1002/em.22122. Epub 2017 Aug 19. PMID: 28833575; PMCID: PMC5773054.|
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, SzÃ¡ntay 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: RamÃrez-Amador V, Esquivel-Pedraza L, Lozada-Nur F, De la Rosa-GarcÃa E, Volkow-FernÃ¡ndez P, SÃºchil-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.
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.
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.