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MedKoo Cat#: 100911 | Name: Vinblastine sulfate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Vinblastine sulfate
Vinblastine sulfate
CAS#143-67-9 (sulfate)

Theoretical Analysis

MedKoo Cat#: 100911

Name: Vinblastine sulfate

CAS#: 143-67-9 (sulfate)

Chemical Formula: C46H60N4O13S

Exact Mass: 908.3878

Molecular Weight: 909.05

Elemental Analysis: C, 60.78; H, 6.65; N, 6.16; O, 22.88; S, 3.53

Price and Availability

Size Price Availability Quantity
10mg USD 90.00 Ready to ship
25mg USD 150.00 Ready to ship
50mg USD 225.00 Ready to ship
100mg USD 350.00 Ready to ship
200mg USD 550.00 Ready to ship
500mg USD 950.00 Ready to ship
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Related CAS #
865-21-4 (free base) 143-67-9 (sulfate)
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
Appearance
White to slight yellow solid powder
Purity
>90% (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
More Info
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.  
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 mg/mL mM
Solubility
DMSO 44.0 48.40
Water 50.0 55.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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
Formulation protocol:
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: Lee HJ, Ramchandren R, Friedman J, Melear J, Flinn IW, Burke JM, Linhares Y, Gonzales P, Peterson M, Raval M, Chintapatla R, Feldman TA, Yimer H, Islas- Ohlmayer M, Patel A, Metheny L, Dean A, Rana V, Gandhi MD, Renshaw J, Ho L, Fanale MA, Guo W, Yasenchak CA. Brentuximab vedotin, nivolumab, doxorubicin, and dacarbazine for advanced-stage classical Hodgkin lymphoma. Blood. 2025 Jan 16;145(3):290-299. doi: 10.1182/blood.2024024681. PMID: 39622165. 2: Pavlovsky A, Altuve JIG, Cerutti A, Fiad L, Kurgansky N, Warley F, Negri Aranguren F. Benefits of BV-AVD (Brentuximab vedotin, doxorubicin, vinblastine, and dacarbazine) versus ABVD (doxorubicin hydrochloride, bleomycin sulfate, vinblastine sulfate, dacarbazine) in patients with advanced-stage Hodgkin's lymphoma: an analysis of the ECHELON 1 trial by the GATLA group using the Delphi Method. Hematol Transfus Cell Ther. 2024 Dec;46 Suppl 6(Suppl 6):S250-S256. doi: 10.1016/j.htct.2024.07.007. Epub 2024 Sep 25. PMID: 39366886; PMCID: PMC11726065. 3: Dulley LH, Braga AGO, Rodrigues GG, Fortier SC, Chiattone CS, da Silveira TMB. Lower doses of dacarbazine (modified BEACODD) as a safer strategy with equal effectiveness in an intensive treatment protocol of Hodgkin's lymphoma: a preliminary retrospective analysis of a single public center in Brazil. Hematol Transfus Cell Ther. 2024 Sep 7:S2531-1379(24)00306-7. doi: 10.1016/j.htct.2024.06.003. Epub ahead of print. PMID: 39261149. 4: Sookai S, Akerman MP, Munro OQ. Chiral Au(III) chelates exhibit unique NCI-60 cytotoxicity profiles and interactions with human serum albumin. Dalton Trans. 2024 Mar 12;53(11):5089-5104. doi: 10.1039/d3dt04024k. PMID: 38375922. 5: Coelho YNB, Soldi LR, da Silva PHR, Mesquita CM, Paranhos LR, Dos Santos TR, Silva MJB. Tyrosine kinase inhibitors as an alternative treatment in canine mast cell tumor. Front Vet Sci. 2023 Jun 8;10:1188795. doi: 10.3389/fvets.2023.1188795. PMID: 37360406; PMCID: PMC10285312. 6: Alelyani RH, Alghamdi AH, Almughamisi TA, Alshareef AM, Kadasa AN, Alrajhi AM, Alburayk AK, Barefah AS, Radhwi OO, Almohammadi AT, Bahashawan SM, AlAhwal HM. Incidence and Risk Factors of Infections Among Diffuse Large B-cell Lymphoma and Classical Hodgkin's Lymphoma Patients in a Tertiary Care Center in Saudi Arabia: A Retrospective Cohort Study. Cureus. 2023 Mar 9;15(3):e35922. doi: 10.7759/cureus.35922. PMID: 36911585; PMCID: PMC9996399. 7: Simba K, Mohamed Z, Opie JJ, Andera LF, Brown K, Oosthuizen J, Antel K, Dawood T, Van der Vyfer L, Du Toit C, Louw VJ, Verburgh E. The International Prognostic Score and HIV status predict red cell concentrate transfusion needs in Hodgkin lymphoma. Leuk Lymphoma. 2023 Mar;64(3):613-620. doi: 10.1080/10428194.2022.2157214. Epub 2022 Dec 23. PMID: 36562564; PMCID: PMC10200008. 8: El-Atawy MA, Alshaye NA, Elrubi N, Hamed EA, Omar AZ. Pyrimidines-Based Heterocyclic Compounds: Synthesis, Cytoxicity Evaluation and Molecular Docking. Molecules. 2022 Aug 1;27(15):4912. doi: 10.3390/molecules27154912. PMID: 35956864; PMCID: PMC9370056. 9: Chew K, Lee B, van Haren SD, Nanishi E, O'Meara T, Splaine JB, DeLeon M, Soni D, Seo HS, Dhe-Paganon S, Ozonoff A, Smith JA, Levy O, Dowling DJ. Adjuvant Discovery via a High Throughput Screen using Human Primary Mononuclear Cells. bioRxiv [Preprint]. 2022 Jul 11:2022.06.17.496630. doi: 10.1101/2022.06.17.496630. PMID: 35860217; PMCID: PMC9298130. 10: Cannavà C, De Gaetano F, Stancanelli R, Venuti V, Paladini G, Caridi F, Ghica C, Crupi V, Majolino D, Ferlazzo G, Tommasini S, Ventura CA. Chitosan- Hyaluronan Nanoparticles for Vinblastine Sulfate Delivery: Characterization and Internalization Studies on K-562 Cells. Pharmaceutics. 2022 Apr 26;14(5):942. doi: 10.3390/pharmaceutics14050942. PMID: 35631528; PMCID: PMC9143110. 11: Okada E, Fujiishi Y, Narumi K, Ohyama W. Evaluation of a 4-day repeated-dose micronucleus test in rat glandular stomach and colon using aneugens and non- genotoxic non-carcinogens. Genes Environ. 2022 Apr 11;44(1):12. doi: 10.1186/s41021-022-00241-6. PMID: 35410395; PMCID: PMC9004010. 12: Chu C, Zang Y, Yang F, Zou Y, Li J, Liu EH, Yi T, Yan J, Tong S. A simple and sensitive preconcentration strategy by coupling salting-out assisted liquid- liquid extraction with online three-step stacking for the determination of potent anti-tumour compound vinblastine and its precursor in biological samples by capillary electrophoresis. J Chromatogr A. 2022 Feb 8;1664:462794. doi: 10.1016/j.chroma.2021.462794. Epub 2021 Dec 30. PMID: 34998026. 13: Cairns LV, Lappin KM, Mutch A, Ali A, Matchett KB, Mills KI. Multiplex Screening for Interacting Compounds in Paediatric Acute Myeloid Leukaemia. Int J Mol Sci. 2021 Sep 21;22(18):10163. doi: 10.3390/ijms221810163. PMID: 34576326; PMCID: PMC8468645. 14: Tlili G, Ammar H, Majdoub W, Dziri S, Farhat W, Acacha E, Gupta R, Jalleli N, Azzabi A, Jaidane M. Paraplegia due to medullary compression caused by a large cell neuroendocrine carcinoma of the urinary bladder: A case report. Ann Med Surg (Lond). 2021 Jun 6;67:102475. doi: 10.1016/j.amsu.2021.102475. PMID: 34188905; PMCID: PMC8220165. 15: Juszczak AM, Czarnomysy R, Strawa JW, Zovko Končić M, Bielawski K, Tomczyk M. In Vitro Anticancer Potential of Jasione montana and Its Main Components against Human Amelanotic Melanoma Cells. Int J Mol Sci. 2021 Mar 25;22(7):3345. doi: 10.3390/ijms22073345. PMID: 33805898; PMCID: PMC8036727. 16: Smart DJ, Helbling FR, Verardo M, Huber A, McHugh D, Vanscheeuwijck P. Development of an integrated assay in human TK6 cells to permit comprehensive genotoxicity analysis in vitro. Mutat Res Genet Toxicol Environ Mutagen. 2020 Jan;849:503129. doi: 10.1016/j.mrgentox.2019.503129. Epub 2019 Dec 27. PMID: 32087850. 17: Al-Enazi NM, Awaad AS, Alqasoumi SI, Alwethairi MF. Biological activities of the red algae Galaxaura rugosa and Liagora hawaiiana butters. Saudi Pharm J. 2018 Jan;26(1):25-32. doi: 10.1016/j.jsps.2017.11.003. Epub 2017 Nov 13. PMID: 29379330; PMCID: PMC5783822. 18: 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. 19: Zhu Y, Yang L, Huang D, Zhu Q. Molecularly imprinted nanoparticles and their releasing properties, bio-distribution as drug carriers. Asian J Pharm Sci. 2017 Mar;12(2):172-178. doi: 10.1016/j.ajps.2016.08.008. Epub 2016 Sep 20. PMID: 32104327; PMCID: PMC7032076. 20: Theerawatanasirikul S, Phecharat N, Prawettongsopon C, Chaicumpa W, Lekcharoensuk P. Dynein light chain DYNLL1 subunit facilitates porcine circovirus type 2 intracellular transports along microtubules. Arch Virol. 2017 Mar;162(3):677-686. doi: 10.1007/s00705-016-3140-0. Epub 2016 Nov 17. PMID: 27858289.

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