Vinblastine
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| Category | Antineoplastic |
| Catalog number | BBF-05883 |
| CAS | 865-21-4 |
| Molecular Weight | 810.97 |
| Molecular Formula | C46H58N4O9 |
| Purity | >98% |
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Description
Vinblastine, an inhibitor of nAChR, is a natural alkaloid isolated from the plant Vinca rosea Linn. It binds to tubulin and inhibits microtubule formation, leading to disruption of mitotic spindle assembly and arrest of tumor cells in the M-phase of the cell cycle. It may also interfere with the metabolism of amino acids, cyclic AMP, and glutathione. It is used to treat malignant lymphoma.
Specification
| Related CAS | 143-67-9 (sulfate) |
| Synonyms | [3aR-[3aa,4b,5b,5ab,9(3R*,5S*,7R*,9S*),10bR*,13aa]]-Methyl 4-(acetyloxy)-3a-ethyl-9-[5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1H-indolizino[8,1-cd]carbazole-5-carboxylate; 1H-Indolizino[8,1-cd]carbazole, vincaleukoblastine deriv.; 1H-Indolizino(8,1-cd)carbazole-5-carboxylic acid, 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-, methyl ester, (3aR-(3aα,4β,5β,5aβ,9(3R*,5S*,7R*,9S*),10bR*,13aα))-; Rozevin; (+)-Vinblastine; Vincaleukoblastine |
| Storage | Store at -20°C |
| IUPAC Name | methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate |
| Canonical SMILES | CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O |
| InChI | InChI=1S/C46H58N4O9/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/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37-,38+,39+,42-,43+,44+,45-,46-/m0/s1 |
| InChI Key | JXLYSJRDGCGARV-CFWMRBGOSA-N |
Properties
| Appearance | Yellow Solid |
| Application | antitumor |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Melting Point | 211-216°C |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in Chloroform, Dichloromethane, Dimethyl Sulfoxide, Methanol |
| LogP | 3.7 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | The antitumor activity of vinblastine is thought to be due primarily to inhibition of mitosis at metaphase through its interaction with tubulin. Vinblastine binds to the microtubular proteins of the mitotic spindle, leading to crystallization of the microtubule and mitotic arrest or cell death. |
| Toxicity | LD50 = 423 mg/kg (Oral, mouse); LD50 = 305 mg/kg (Oral,rat). |
Reference Reading
1.Post-ABVD/pre-radiotherapy 18F-FDG-PET provides additional prognostic information for early-stage Hodgkin lymphoma: a retrospective analysis on 165 patients.
Ciammella P1, Filippi AR2, Simontacchi G3, Buglione M4, Botto B5, Mangoni M3, Iotti C1, Merli F6, Marcheselli L7, Bisi G8, Ricardi U2, Versari A9. Br J Radiol. 2016 Mar 24:20150983. [Epub ahead of print]
OBJECTIVE: To evaluate the prognostic role of both interim fluorine-18 fludeoxyglucose positron emission tomography (i-18F-FDG-PET) and end-of-chemotherapy fluorine-18 fludeoxyglucose positron emission tomography (eoc-18F-FDG-PET) in patients with early-stage Hodgkin lymphoma (HL).
2.Correction: An Endophytic Fungus, Talaromyces radicus, Isolated from Catharanthus roseus, Produces Vincristine and Vinblastine, Which Induce Apoptotic Cell Death.
Palem PP, Kuriakose GC, Jayabaskaran C. PLoS One. 2016 Apr 5;11(4):e0153111. doi: 10.1371/journal.pone.0153111.
[This corrects the article DOI: 10.1371/journal.pone.0144476.].
3.Can metronomic maintenance with weekly vinblastine prevent early relapse/progression after bevacizumab-irinotecan in children with low-grade glioma?
Heng MA1, Padovani L2, Dory-Lautrec P3, Gentet JC1, Verschuur A1,4, Pasquier E4,5, Figarella-Branger D5,6, Scavarda D7, André N1,4,5. Cancer Med. 2016 Mar 31. doi: 10.1002/cam4.699. [Epub ahead of print]
The association of bevacizumab and irinotecan has been shown to display a quick efficacy in low-grade glioma (LGG), but most patients relapse within months after cessation of therapy. From October 2012 to March 2014, four patients have been treated with irinotecan-bevacizumab followed by a metronomic maintenance with weekly vinblastine to try to prevent relapses. After a median follow-up of 23 months after the end of the bevacizumab-irinotecan induction, no patient relapsed. These observations suggest that maintenance chemotherapy with weekly vinblastine after an induction by irinotecan-bevacizumab can improve progression-free survival in children with LGG.
4.Correction: An Endophytic Fungus, Talaromyces radicus, Isolated from Catharanthus roseus, Produces Vincristine and Vinblastine, Which Induce Apoptotic Cell Death.
Palem PP, Kuriakose GC, Jayabaskaran C. PLoS One. 2016 Apr 5;11(4):e0153111. doi: 10.1371/journal.pone.0153111.
[This corrects the article DOI: 10.1371/journal.pone.0144476.].
Spectrum
Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C46H58N4O9
Molecular Weight (Monoisotopic Mass): 810.4204 Da
Molecular Weight (Avergae Mass): 810.9741 Da
Derivative Type: TMS_1_1
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C46H58N4O9
Molecular Weight (Monoisotopic Mass): 810.4204 Da
Molecular Weight (Avergae Mass): 810.9741 Da
Derivative Type: TMS_1_1
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C46H58N4O9
Molecular Weight (Monoisotopic Mass): 810.4204 Da
Molecular Weight (Avergae Mass): 810.9741 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C46H58N4O9
Molecular Weight (Monoisotopic Mass): 810.4204 Da
Molecular Weight (Avergae Mass): 810.9741 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
