sulfuric acid 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]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

• ChemBase ID: 72588
• Molecular Formular: C46H58N4O14S
• Molecular Mass: 923.03612
• Monoisotopic Mass: 922.36702356
• SMILES: c1(cc2c(cc1[C@@]1(c3c(c4c([nH]3)cccc4)CCN3C[C@H](C1)C[C@@](C3)(O)CC)C(=O)OC)[C@@]13[C@@H](N2C=O)[C@]([C@@H]([C@]2([C@@H]1N(CC3)CC=C2)CC)OC(=O)C)(C(=O)OC)O)OC.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.O=CN1c2cc(OC)c(cc2[C@]23[C@@H]1[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@]1([C@@H]3N(CC2)CC=C1)CC)[C@]1(C[C@H]2CN(CCc3c1[nH]c1c3cccc1)C[C@](C2)(O)CC)C(=O)OC
• InChI: 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
• InChIKey: AQTQHPDCURKLKT-FCIBFBFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2,4,6,13-tetraene-10-carboxylate; sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate; sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
• IUPAC Traditional name: sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2,4,6,13-tetraene-10-carboxylate; sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate; sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
• Synonyms: Vincristine sulfate salt; 22-Oxovincaleukoblastine sulfate salt; Leurocristine sulfate salt; Vincrex; Vincristine Sulfate; leurocristine; Oncovin; Vincasar PFS; VCR; Vincristine sulfate; 长春新碱 硫酸盐; 醛基长春碱 硫酸盐; 长春新碱 硫酸盐; 长春醛碱 硫酸盐; 长春新碱 硫酸酯

Database IDs

• CAS Number: 2068-78-2
• EC Number: 218-190-0
• MDL Number: MFCD00084729
• Beilstein Number: 3924631
• PubChem SID: 162037513; 24278774; 24900771
• PubChem CID: 5388992

CALCULATED PROPERTIES

• Acid pKa: 10.849017
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -2.3829613
• LogD (pH = 7.4): 1.1448158
• Log P: 3.128179
• Molar Refractivity: 221.4804 cm^3
• Polarizability: 87.836975 Å^3
• Polar Surface Area: 171.17 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; methanol: soluble20 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: -20°C
• RTECS: OH6340000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 63-25-62-68
• Safety Statements: 22-24/25; 36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H341-H361fd
• GHS Precautionary statements: P264-P281-P301 + P310
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Target: Microtubule Formation

Product Information

• Purity: ≥95.0% (HPLC); 95.0-105.0% (HPLC)
• Salt Data: H2SO4; Sulfate
• Suitability: meets USP testing specifications
• Impurities: ≤10% water; ≤12% ethanol(actual content given on label)
• Empirical Formula (Hill Notation): C46H56N4O10 · H2SO4
• Classification: Genuine Natural Compounds

DETAILS

Selleck Chemicals - S1241

Research Area: Cancer
Biological Activity:
Vincristine Sulfate is a kind of microtubule function inhibitor with IC50 of 10.4±1.1, 28.1±3.4, 22.4±2.1 µM for HL-60, Bel7402, HO-8910, respectively. It is the sulfate salt of a natural alkaloid isolated from the plant Vinca rosea Linn with antimitotic and antineoplastic activities. Vincristine binds irreversibly to microtubules and spindle proteins in S phase of the cell cycle and interferes with the formation of the mitotic spindle, thereby arresting tumor cells in metaphase. The IC50 and IC90 of vincristine for the 4 vaccine-associated feline sarcoma (VAFS) cell lines were between 0.005 to 0.039 µg/ml and 0.045 to 1.027 µg/ml, respectively .This agent also depolymerizes microtubules and may also interfere with amino acid, cyclic AMP, and glutathione metabolism. [1][2][3]

Sigma Aldrich - V8879

Application
Vincristine is an antitumor alkaloid isolated from Vinca Rosea. It is used to treat acute leukaemia, malignant lymphoma, Hodgkin′s disease, acute erythraemia, acute panmyelosis, breast cancer, Kaposi’s sarcoma and testicular cancer. Vincristine is widely used in cancer research. It is used to study multi-drug resistance. It is used to inhibit cell cycle progression at M-phase and to inhibit monoamine oxidase (MAO) 1.
Biochem/physiol Actions
Vincristine is a plant alkaloid that inhibits microtubule assembly by binding tubulin and inducing coiled spiral aggregate formation. It arrests cell cycle in G2/M-phase by blocking mitotic spindle formation2. Vincristine triggers Raf-1 activation, phosphorylation of bcl-2-family proteins, induction of p53 expression, and apoptosis in several tumor cell lines. It inhibits VEGF production in leukemia cell lines. It is a substrate for Pgp and CYP3A4. MRP1 transports vincristine in an ATP- and GSH-dependent manner. Vincristine has some immunosuppressant effect. Vincristine may also interfere with amino acid, cyclic AMP, and glutathione metabolism, calmodulin-dependent Ca2+-transport, cellular respiration, and nucleic acid and lipid biosynthesis1.

Sigma Aldrich - V8388

Application
Widely used in cancer research. In studies on multi-drug resistance. Used to inhibit cell cycle progression at M-phase. Used to inhibit monoamine oxidase (MAO).

REFERENCES

• Banerji N et al. Am J Vet Res. 2002;63(5):728-32