WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 414296
CAS#: 865-21-4 (free base)
Description: Vinblastine Free Base is an antitumor alkaloid isolated from Vinca rosea.
MedKoo Cat#: 414296
Name: Vinblastine Free Base
CAS#: 865-21-4 (free base)
Chemical Formula: C46H58N4O9
Exact Mass: 810.4204
Molecular Weight: 810.98
Elemental Analysis: C, 68.13; H, 7.21; N, 6.91; O, 17.75
Related CAS #: 865-21-4 (free base) 143-67-9 (sulfate)
Synonym: Vinblastine Free Base; HSDB3263; HSDB 3263; HSDB-3263; NSC49842; NSC-49842; NSC 49842
IUPAC/Chemical Name: methyl (3aR,3a1R,4R,5S,5aR,10bR)-4-acetoxy-3a-ethyl-9-((5S,7R,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-2H-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
InChi Key: JXLYSJRDGCGARV-CFWMRBGOSA-N
InChi Code: 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
SMILES Code: CC[C@@]1(C[C@@H]2CN(C1)CCc(c([C@@](C(OC)=O)(c3c(OC)cc(N([C@H]4[C@]([C@@H]([C@@]5(C=CCN6CC[C@]74[C@H]56)CC)OC(C)=O)(C(OC)=O)O)C)c7c3)C2)[nH]8)c9c8cccc9)O
Appearance: 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: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
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
The following data is based on the product molecular weight 810.98 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 |
1: Haque A, Rahman MA, Faizi MSH, Khan MS. Next Generation Antineoplastic Agents: A Review on Structurally Modified Vinblastine (VBL) Analogues. Curr Med Chem. 2018;25(14):1650-1662. doi: 10.2174/0929867324666170502123639. PMID: 28464783.
2: Radakovic A, Boger DL. Ultra-potent vinblastine analogues improve on-target activity of the parent microtubulin-targeting compound. Bioorg Med Chem Lett. 2019 Jun 1;29(11):1370-1374. doi: 10.1016/j.bmcl.2019.03.036. Epub 2019 Mar 26. PMID: 30952593; PMCID: PMC6487230.
3: Parthasarathy R, Shanmuganathan R, Pugazhendhi A. Vinblastine production by the endophytic fungus Curvularia verruculosa from the leaves of Catharanthus roseus and its in vitro cytotoxicity against HeLa cell line. Anal Biochem. 2020 Mar 15;593:113530. doi: 10.1016/j.ab.2019.113530. Epub 2019 Nov 30. PMID: 31794703.
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. PMID: 20394103.
5: 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. PMID: 22609781; PMCID: PMC6268133.
6: Sears JE, Boger DL. Total synthesis of vinblastine, related natural products, and key analogues and development of inspired methodology suitable for the systematic study of their structure-function properties. Acc Chem Res. 2015 Mar 17;48(3):653-62. doi: 10.1021/ar500400w. Epub 2015 Jan 14. PMID: 25586069; PMCID: PMC4363169.
7: Meimetis LG, Giedt RJ, Mikula H, Carlson JC, Kohler RH, Pirovich DB, Weissleder R. Fluorescent vinblastine probes for live cell imaging. Chem Commun (Camb). 2016 Aug 2;52(64):9953-6. doi: 10.1039/c6cc04129a. PMID: 27439765; PMCID: PMC4970878.
8: Miyazaki T, Yokoshima S, Simizu S, Osada H, Tokuyama H, Fukuyama T. Synthesis of (+)-vinblastine and its analogues. Org Lett. 2007 Nov 8;9(23):4737-40. doi: 10.1021/ol702040y. Epub 2007 Oct 13. PMID: 17935340.
9: Cosgriff TM. The metabolic effects of the periwinkle alkaloid vinblastine. Minn Med. 1968 Jul;51(7):977-82. PMID: 4873497.
10: Frampton JE, Moen MD. Vinflunine. Drugs. 2010 Jul 9;70(10):1283-93. doi: 10.2165/11204970-000000000-00000. PMID: 20568834.
