Vinblastine sulfate

Vinblastine sulfate Basic information
Product Name:Vinblastine sulfate
Synonyms:29060le;exal;nsc49842;rozevinsulfate;velban;velbe;vincaleukoblastine,sulfate(1:1)(salt);Vinblastine, sulphate salt
CAS:143-67-9
MF:C46H60N4O13S
MW:909.05
EINECS:205-606-0
Product Categories:APIs;Antineoplastic;chemical reagent;pharmaceutical intermediate;phytochemical;Anti-cancer & immunity;VINBLASTINE SULPHATE;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents;Heterocycles;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;VELBAN;Active Pharmaceutical Ingredients;Caspases/Apoptosis;Inhibitors;API
Mol File:143-67-9.mol
Vinblastine sulfate Structure
Vinblastine sulfate Chemical Properties
Melting point 267 °C (dec.)(lit.)
alpha -21.7 º (c=2, CH3OH 21 ºC)
storage temp. 2-8°C
solubility H2O: 10 mg/mL
form powder
color white
PH3.5~5.0 (1g/l, 25℃)
Water Solubility >=1 g/100 mL at 24.5 ºC
Merck 13,10044
BRN 3659812
InChIKeyKDQAABAKXDWYSZ-PNYVAJAMSA-N
CAS DataBase Reference143-67-9(CAS DataBase Reference)
IARC3 (Vol. 26, Sup 7) 1987
EPA Substance Registry SystemVinblastine sulfate (143-67-9)
Safety Information
Hazard Codes Xn,T
Risk Statements 22-37/38-41-61-36/37/38-63-23/24/25
Safety Statements 26-36/39-53-45-37/39-36/37/39
RIDADR 1544
WGK Germany 3
RTECS YY8400000
8-10
HazardClass 6.1(a)
PackingGroup II
HS Code 29399990
ToxicityLD50 i.v. in mice: 9.5 mg/kg (Lu, Meistrich)
MSDS Information
ProviderLanguage
Vinblastine sulfate English
SigmaAldrich English
ACROS English
Vinblastine sulfate Usage And Synthesis
DescriptionVinblastine sulfate is the salt of an alkaloid extracted from Vinca rosea Linn., a common flowering herb known as the periwinkle (more properly known as Catharanthus roseus G. Don). Previously, the generic name was vincaleukoblastine, abbreviated VLB. It is a stathmokinetic oncolytic agent. When treated in vitro with this preparation, growing cells are arrested in metaphase. Chemical and physical evidence indicate that vinblastine sulfate is a dimeric alkaloid containing both indole and dihydroindole moieties.
Chemical PropertiesVinblastine sulfate is a white to off-white crystalline powder that is freely soluble in water, soluble in methane, and slightly soluble in ethanol. Its empiric formula is C46H58N4O9.H2SO4 , and it has a molecular weight of 909.07.
OriginatorVelban ,Lilly ,US ,1961
UsesAnticancer agent; microtubule disrupter; Induces apoptosis.Vinblastine sulfate is therapeutically used as an antineoplastic. It is also used in the treatment of Hodgkin disease, choriocarcinoma, acute and chronic leukemias.
UsesVinblastin sulfate USP (Velban) is used to treat Hodgkin’s disease; lymphosarcoma; reticulum cell sarcoma; neuroblastoma; choriocarcinoma; carcinoma of breast, lung, oral cavity, testis, bladder; acute and chronic leukemia; histiocytosis; mycosis fungoides.
DefinitionChEBI: Vincaleukoblastine sulfate is an alkaloid sulfate salt. It is functionally related to a vincaleukoblastine.
Brand nameVelban (Lilly).
Therapeutic FunctionCancer chemotherapy
General DescriptionVinblastine Sulfate is the sulfate salt of vinblastine, a natural alkaloid isolated from the plant Catharanthus roseus (Madagascar periwinkle) with antineoplastic properties. Vinblastine disrupts microtubule formation and function during mitosis and interferes with glutamic acid metabolism. (NCI04)
Air & Water ReactionsWater soluble..Rapidly hydrolyzes.
Reactivity ProfileVinblastine sulfate is sensitive to light, hydrolysis, oxidation, and heat. Vinblastine sulfate is very hygroscopic. .
Health HazardSYMPTOMS: Symptoms of exposure to Vinblastine sulfate include temporary mental depression, paresthesias, loss of deep-tendon reflexes, headache, convulsions, psychoses; dysfunction of the autonomic nervous system, with marked constipation, paralytic ileus, urinary retention, bilateral pain and tenderness of the parotid glands associated with dryness of the mouth, sinus tachycardia; nausea, vomiting, anorexia, diarrhea; loss of hair, vesicular mucositis of the mouth, and dermatitis.
Biological ActivityAnticancer agent; microtubule disrupter. Induces apoptosis in cultured hepatocytes and human lymphoma cells.
Biochem/physiol ActionsPrimary TargetInteraction of tubulin with microtubule-associated proteins, specifically Tau and MAP2
Clinical UseVinblastine sulfate is available as a powder in 10-mg vials and as a solution in 10- and 25-mL vials for IV administrationin the treatment of various cancers including Hodgkin’sdisease, lymphocytic lymphoma, histiocytic lymphoma, advancedmycosis fungoides, advanced testicular carcinoma,and Kaposi sarcoma. It has also been used in treating choriocarcinomaand breast cancer when other therapies havefailed.
Side effectsThe major toxic effect of vinblastine is a dose-related bone marrow depression. This is more frequent and severe than with the close structural analog, vincristine. Dose-related leukopenia occurs with a nadir of 4 to 10 days and with recovery occurring over another 7 to 14 days. Because of the relatively predictable nadir, it may be possible to administer vinblastine cautiously as often as every 7 to 10 days. Thrombocytopenia typically occurs; however, with standard dosing regimens, serious platelet depressions are infrequent. Erythrocytes are usually only slightly depressed.
Safety ProfilePoison by ingestion, intraperitoneal, and intravenous routes. An experimental teratogen. Human systemic effects by intravenous route: blood leukopenia and hair changes. Experimental reproductive effects. Questionable carcinogen. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also VINCALEUKOBLASTINE and SULFATES.
Veterinary Drugs and TreatmentsVinblastine may be employed in the treatment of lymphomas, carcinomas, mastocytomas, and splenic tumors in small animals. It is more effective than vincristine in the treatment of canine mast cell tumors.
Drug interactionsPotentially hazardous interactions with other drugs
Aldesleukin: avoid concomitant use.
Antibacterials: toxicity increased by erythromycin - avoid; possible increased risk of ventricular arrhythmias with delamanid.
Antiepileptics: phenytoin levels may be reduced.
Antifungals: possible increased risk of toxicity with itraconazole; metabolism possibly inhibited by posaconazole (increased risk of neurotoxicity).
Antimalarials: avoid with piperaquine with artenimol.
Antipsychotics: avoid with clozapine (increased risk of agranulocytosis).





MetabolismVinblastine is extensively metabolised mainly in the liver by the CYP3A group of isoenzymes to desacetylvinblastine, which is more active than the parent compound. 33
% of the drug is slowly excreted in the urine and 21
% in the faeces within 72 hours.

storageStore at -20°C
Purification MethodsCrystallise the sulfate from MeOH or EtOH and dry it in vacuo over conc H2SO4. The free base crystallises from EtOH or MeOH m 211-216o (+ 2MeOH .1 H2O) and forms a stable etherate from Et2O with m 201-211o, and [] D +42o (CHCl3), and UV max at 214 and 259nm (log  4.73 and 4.21). The dihydrochloride has m 244-246o(dec)(MeOH). It is a monoamine oxidase B inhibitor and induces microtubule aggregation. It is an antineoplastic drug for Hodgkin’s lymphoma. [Neuss et al. J Am Chem Soc 81 4754 1959, Jong-KeunSon et al. J Med Chem 33 1845 1990, Warfield & Bouck Science 186 1219 1974, Beilstein 26 III/IV 3167.]
Mode of actionVinblastine binds to tubulin and inhibits microtubule assembly. This inhibition prevents mitotic spindle formation and results in an accumulation of cells in metaphase.
Vinblastine is considered cell cycle phase specic for mitosis; however, the cytotoxic effect probably occurs in S phase and is expressed only in M phase. At high doses, direct effects may be expressed in S and G1 phases. Vinblastine is assumed to have stathmokinetic (cell cycle arrest) effects similar to vincristine.
Vinblastine sulfate Preparation Products And Raw materials
Raw materialsSulfuric acid-->Benzene-->Vindoline
Preparation ProductsDESACETYLVINBLASTINEAMIDE
Vincristine sulfate 4-Desacetyl Vinblastine Sodium dodecyl sulfate Kanamycin sulfate sulfate Sodium thiosulfate 5-Amino-2-methylphenol sulfate n-Dodecyl alcohol, sulfated Vinblastine sulfate Copper(II) sulfate Aluminum sulfate GOLD COAST SOLUTION NO 1 Magnesium sulfate Ferrous sulfate heptahydrate Ammonium sulfate Magnesium sulfate heptahydrate Barium sulfate Dimethyl sulfate

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