CAS Number2068-78-2
Synonymsoncovin; VCR; Vincrisul; (2'b)-22-oxovincaleukoblastine sulfate (1:1); NovopharM; V5 PEPTIDE; kyocristine; (2'β)-22-Oxovincaleukoblastine sulfate (1:1); 22-Oxovincaleukoblastine Sulfate (1:1) (salt); 22-oxovincaleukoblastine sulfate; Vincristine sulfate salt; onkovin; MFCD00084729; vincaleukoblastine, 22-oxo-, (2'b)-, sulfate (1:1); vincristin; Vincristine sulfate; Vincaleukoblastine, 22-oxo-, (2'β)-, sulfate (1:1); EINECS 218-190-0; Vincristine (sulfate); Vincristine; vincaleukoblastine, 22-oxo-, (3β,4'β)-, sulfate (1:1); 22-Oxovincaleukoblastine sulfate salt,Leurocristine sulfate salt,VCR
Molecular FormulaC46H58N4O14S
Molecular Weight923.04
Purity98%
Boiling Point273-281 °C
Melting Point300 °C
AppearanceWhite crystalline powder
EINECS218-190-0
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 2068-78-2 |
| Catalog No. | 2A-9012934 |
| Chinese Name | 硫酸长春新碱 |
| Synonyms | oncovin; VCR; Vincrisul; (2'b)-22-oxovincaleukoblastine sulfate (1:1); NovopharM; V5 PEPTIDE; kyocristine; (2'β)-22-Oxovincaleukoblastine sulfate (1:1); 22-Oxovincaleukoblastine Sulfate (1:1) (salt); 22-oxovincaleukoblastine sulfate; Vincristine sulfate salt; onkovin; MFCD00084729; vincaleukoblastine, 22-oxo-, (2'b)-, sulfate (1:1); vincristin; Vincristine sulfate; Vincaleukoblastine, 22-oxo-, (2'β)-, sulfate (1:1); EINECS 218-190-0; Vincristine (sulfate); Vincristine; vincaleukoblastine, 22-oxo-, (3β,4'β)-, sulfate (1:1); 22-Oxovincaleukoblastine sulfate salt,Leurocristine sulfate salt,VCR |
| Molecular Formula | C46H58N4O14S |
| Molecular Weight | 923.04 |
| Purity | 98 |
| Boiling Point | 273-281 °C |
| Melting Point | 300 °C |
| Appearance | White crystalline powder |
| Water Solubility | ≥1 G/100 ML AT 24 ºC |
| Storage Condition | Sealed with argon and stored in a dry and dark pla |
| Packaging | II |
| Application | Vincristine sulfate is an anti-tumor vinca alkaloid that inhibits microtubule formation in the mitotic spindle, leading to arrest of dividing cells during metaphase. It binds to microtubule with a Ki |
| EINECS | 218-190-0 |
| HTC | 2942000000 |
| PubChem ID | 24900771 |
| MDL Number | MFCD00084729 |
| SMILES | OS(O)(=O)=O.CC[C@]1(O)CC2CN(CCc3c([nH]c4ccccc34)[C@@](C2)(C(=O)OC)c5cc6c(cc5OC)N(C=O)C7[C@](O)([C@H](OC(C)=O)[C@]8(CC)C=CCN9CC[C@]67C89)C(=O)OC)C1 |
| InChI | 1S/C46H56N4O10.H2O4S/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6;1-5(2,3)4/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3;(H2,1,2,3,4)/t28-,37-,38+,39+,42-,43+,44+,45-,46-;/m0./s1 |
| InChI Key | AQTQHPDCURKLKT-PNYVAJAMSA-N |
| Beilstein/REAXYS | 3924631 |
| NACRES Code | NA.21 |
| UNSPSC | 12352210 |
| Hazard Symbols | 6.1(a) |
| MSDS | msds/12934_1_2068_78_2.pdf |
| Bioactivity | Vincristine sulfate is an antitumor vinca alkaloid which inhibits microtubule formation in mitotic spindle, resulting in an arrest of dividing cells at the metaphase stage. It binds to microtubule with a Ki of 85 nM. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin Natural Products >> Alkaloid Research Areas >> Cancer In Vitro Vincristine inhibits net addition of tubulin dimers at assembly ends of steady-state microtubules with Ki of 85 nM[1]. Vincristine stabilizes the spindle apparatus resulting in failure of the chromosomes to segregate leading to metaphase arrest and inhibition of mitosis at low concentrations. At higher concentrations, Vincristine may disrupt and induce total depolymerization of microtubules[2]. Vincristine induces apoptosis in tumor cells and inhibits SH-SY5Y cell proliferation with IC50 of 0.1 μM. Vincristine induces mitotic arrest and promots the expression of caspase-3 and -9 and cyclin B, while decreasing the expression of cyclin D[3]. Vincristine induced neurotoxicity is caused by interference with microtubule function, which results in blockage of axonal transport and thus in axonal degeneration[4]. In Vivo Vincristine (3 mg/kg, i.p.) induces mean growth delay of > 120 and > 52 day, and repopulates fractions of 0.06% and 5%, administrated in mice bearing bilateral subcutaneous xenografts Rh12 or Rh18, respectively[5]. Cell Assay Cells are plated in 2 mL of medium in 35 mm plates at a concentration of about 5×104 cells/mL and grow for 24 h at 37°C in an atmosphere of 5% CO2 and 95% air. Then medium is replaced with fresh medium lacking or containing 4 nM drug and proliferation is continued for 3 days. Cell counts are done each day in a Coulter Counter after detaching the cells with trypsin and EDTA. References [1]. Jordan, M.A., et al. Comparison of the effects of vinblastine, vincristine, vindesine, and vinepidine on microtubule dynamics and cell proliferation in vitro. Cancer Res, 1985. 45(6): p. 2741-7. [2]. Gidding, C.E., et al, Vincristine revisited. Crit Rev Oncol Hematol, 1999. 29(3): p. 267-87. [3]. Donoso, J.A., et al, Action of the vinca alkaloids vincristine, vinblastine, and desacetyl vinblastine amide on axonal fibrillar organelles in vitro. Cancer Res, 1977. 37(5): p. 1401-7. [4]. Horton, J.K., et al. Relationships between tumor responsiveness, vincristine pharmacokinetics and arrest of mitosis in human tumor xenografts. Biochem Pharmacol, 1988. 37(20): p. 3995-4000. [5]. Baguley, B.C., et al, Inhibition of growth of colon 38 adenocarcinoma by vinblastine and colchicine: evidence for a vascular mechanism. Eur J Cancer, 1991. 27(4): p. 482-7. [6]. Zhang D, et al. Co-delivery nanoparticles with characteristics of intracellular precision release drugs for overcoming multidrug resistance. Int J Nanomedicine. 2017 Mar 16;12:2081-2108. Chemical & Physical Properties Boiling Point 273-281 °C Melting Point 300 °C Molecular Formula C46H58N4O14S Molecular Weight 923.036 Exact Mass 922.367004 PSA 254.15000 LogP 4.52220 InChIKey AQTQHPDCURKLKT-JKDPCDLQSA-N SMILES CCC1(O)CC2CN(CCc3c([nH]c4ccccc34)C(C(=O)OC)(c3cc4c(cc3OC)N(C=O)C3C(O)(C(=O)OC)C(OC(C)=O)C5(CC)C=CCN6CCC43C65)C2)C1.O=S(=O)(O)O Storage condition 2-8°C Water Solubility ≥1 G/100 ML AT 24 ºC |
| Use of | Vincristine sulfate is an antitumor vinca alkaloid which inhibits microtubule formation in mitotic spindle, resulting in an arrest of dividing cells at the metaphase stage. It binds to microtubule with a Ki of 85 nM. Properties Articles199 Name Vincristine Sulfate Synonym More Synonyms Vincristine Sulfate Biological Activity Description Vincristine sulfate is an antitumor vinca alkaloid which inhibits microtubule formation in mitotic spindle, resulting in an arrest of dividing cells at the metaphase stage. It binds to microtubule with a Ki of 85 nM. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin Natural Products >> Alkaloid Research Areas >> Cancer In Vitro Vincristine inhibits net addition of tubulin dimers at assembly ends of steady-state microtubules with Ki of 85 nM[1]. Vincristine stabilizes the spindle apparatus resulting in failure of the chromosomes to segregate leading to metaphase arrest and inhibition of mitosis at low concentrations. At higher concentrations, Vincristine may disrupt and induce total depolymerization of microtubules[2]. Vincristine induces apoptosis in tumor cells and inhibits SH-SY5Y cell proliferation with IC50 of 0.1 μM. Vincristine induces mitotic arrest and promots the expression of caspase-3 and -9 and cyclin B, while decreasing the expression of cyclin D[3]. Vincristine induced neurotoxicity is caused by interference with microtubule function, which results in blockage of axonal transport and thus in axonal degeneration[4]. References [1]. Jordan, M.A., et al. Comparison of the effects of vinblastine, vincristine, vindesine, and vinepidine on microtubule dynamics and cell proliferation in vitro. Cancer Res, 1985. 45(6): p. 2741-7. [2]. Gidding, C.E., et al, Vincristine revisited. Crit Rev Oncol Hematol, 1999. 29(3): p. 267-87. [3]. Donoso, J.A., et al, Action of the vinca alkaloids vincristine, vinblastine, and desacetyl vinblastine amide on axonal fibrillar organelles in vitro. Cancer Res, 1977. 37(5): p. 1401-7. [4]. Horton, J.K., et al. Relationships between tumor responsiveness, vincristine pharmacokinetics and arrest of mitosis in human tumor xenografts. Biochem Pharmacol, 1988. 37(20): p. 3995-4000. [5]. Baguley, B.C., et al, Inhibition of growth of colon 38 adenocarcinoma by vinblastine and colchicine: evidence for a vascular mechanism. Eur J Cancer, 1991. 27(4): p. 482-7. [6]. Zhang D, et al. Co-delivery nanoparticles with characteristics of intracellular precision release drugs for overcoming multidrug resistance. Int J Nanomedicine. 2017 Mar 16;12:2081-2108. Chemical & Physical Properties Molecular Formula C46H58N4O14S Exact Mass 922.367004 PSA 254.15000 LogP 4.52220 InChIKey AQTQHPDCURKLKT-JKDPCDLQSA-N Water Solubility ≥1 G/100 ML AT 24 ºC |
| Transport Info | Product name: Vincristine sulfate |
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