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Vinblastine sulfate

Product Name
Vinblastine sulfate
CAS No.
143-67-9
Chemical Name
Vinblastine sulfate
Synonyms
VLB;exal;velban;VINCALEUKOBLASTINE;VINBLASTINE SULFATE SALT;velbe;Velsar;29060le;nsc49842;Periblastine
CBNumber
CB7407655
Molecular Formula
C46H60N4O13S
Formula Weight
909.05
MOL File
143-67-9.mol
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Vinblastine sulfate Property

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
PH
3.5～5.0 (1g/l, 25℃)
Water Solubility 
>=1 g/100 mL at 24.5 ºC
Merck 
13,10044
BRN 
3659812
InChI
InChI=1/C46H58N4O9.H2O4S/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;1-5(2,3)4/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3;(H2,1,2,3,4)/t28-,37+,38-,39-,42+,43-,44-,45+,46+;/s3
InChIKey
KDQAABAKXDWYSZ-PNYVAJAMSA-N
SMILES
[C@]1(C(OC)=O)(C2C(OC)=CC3=C(C=2)[C@@]24[C@]5(N(CC2)CC=C[C@]5([C@@H](OC(C)=O)[C@](C(OC)=O)([C@@]4(N3C)[H])O)CC)[H])C2NC3C=CC=CC=3C=2CC[N@@]2C[C@@](CC)(O)C[C@@]([H])(C2)C1.S(=O)(=O)(O)O |&1:0,13,14,21,22,27,32,51,53,58,r|
CAS DataBase Reference
143-67-9(CAS DataBase Reference)
IARC
3 (Vol. 26, Sup 7) 1987
EPA Substance Registry System
Vinblastine sulfate (143-67-9)
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Safety

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
F 
8-10
HazardClass 
6.1(a)
PackingGroup 
II
HS Code 
29399990
Toxicity
LD50 i.v. in mice: 9.5 mg/kg (Lu, Meistrich)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H341Suspected of causing genetic defects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2698
Product name
Vinblastine Sulfate
Purity
Pharmaceutical Secondary Standard; Certified Reference Material, certified reference material, pharmaceutical secondary standard, pkg of 100?mg
Packaging
100MG
Price
$365
Updated
2024/03/01
Sigma-Aldrich
Product number
1713004
Product name
Vinblastine sulfate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
50mg
Price
$993
Updated
2024/03/01
Alfa Aesar
Product number
J63598
Product name
Vinblastine sulfate
Purity
98%
Packaging
10mg
Price
$114
Updated
2023/06/20
Alfa Aesar
Product number
J63598
Product name
Vinblastine sulfate
Purity
98%
Packaging
50mg
Price
$417
Updated
2023/06/20
Cayman Chemical
Product number
11762
Product name
Vinblastine (sulfate)
Purity
≥95%
Packaging
5mg
Price
$57
Updated
2024/03/01
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Vinblastine sulfate Chemical Properties,Usage,Production

Description

Vinblastine 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 Properties

Vinblastine 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.

Originator

Velban ,Lilly ,US ,1961

Uses

Anticancer 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.

Uses

Vinblastin 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.

Definition

ChEBI: Vincaleukoblastine sulfate is an alkaloid sulfate salt. It is functionally related to a vincaleukoblastine.

brand name

Velban (Lilly).

Therapeutic Function

Cancer chemotherapy

General Description

Vinblastine 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 Reactions

Water soluble..Rapidly hydrolyzes.

Reactivity Profile

Vinblastine sulfate is sensitive to light, hydrolysis, oxidation, and heat. Vinblastine sulfate is very hygroscopic. .

Health Hazard

SYMPTOMS: 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 Activity

Anticancer agent; microtubule disrupter. Induces apoptosis in cultured hepatocytes and human lymphoma cells.

Biochem/physiol Actions

Primary TargetInteraction of tubulin with microtubule-associated proteins, specifically Tau and MAP2

Clinical Use

Vinblastine 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 effects

The 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 Profile

Poison 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 Treatments

Vinblastine 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 interactions

Potentially 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).

Metabolism

Vinblastine 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.

storage

Store at -20°C

Purification Methods

Crystallise 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 action

Vinblastine 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 materials

Preparation Products

DESACETYLVINBLASTINEAMIDE
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Vinblastine sulfate Suppliers

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View Lastest Price from Vinblastine sulfate manufacturers

S&Y Biochem Co.,Ltd
Product
Vinblastine sulfate 143-67-9
Price
US $1.00/g
Min. Order
1g
Purity
99
Supply Ability
100
Release date
2024-08-01
Wuhan Boyuan Import & Export Co., LTD
Product
Vinblastine Sulfate 143-67-9
Price
US $9.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000tons
Release date
2023-05-30
Shaanxi Haibo Biotechnology Co., Ltd
Product
Vinblastine sulfate 143-67-9
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000ton
Release date
2023-09-07

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