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Vincristine sulfate

CAS No.2068-78-2
Chemical Name:Vincristine sulfate
CBNumber:CB9479083
Molecular Formula:C46H58N4O14S
Formula Weight:923.04
MOL File:2068-78-2.mol

Vincristine sulfate Property

Melting point 300 °C
Boiling point 273-281 °C
alpha D26 +8.5° (c = 0.8)
storage temp. Sealed in dry,Store in freezer, under -20°C
solubility methanol: soluble20mg/mL
form lyophilized powder
color white to off-white
Water Solubility >=1 g/100 mL at 24 ºC
BRN 3924631
Stability Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
InChIKey AQTQHPDCURKLKT-HSMPTBRCNA-N
EWG's Food Scores 1
NCI Dictionary of Cancer Terms Oncovin; vincristine sulfate
FDA UNII T5IRO3534A
NCI Drug Dictionary vincristine sulfate
Proposition 65 List Vincristine Sulfate
IARC 3 (Vol. 26, Sup 7) 1987
EPA Substance Registry System Vincristine sulfate (2068-78-2)
UNSPSC Code 12352210
NACRES NA.77

Safety

Hazard Codes :T
Risk Statements :61-36/37/38-63-23/24/25-68-62-25
Safety Statements :22-24/25-53-45-37/39-26-36/37/39-36/37
RIDADR :UN 2811 6.1/PG 2
WGK Germany :3
RTECS :OH6340000
F :8-10
HazardClass :6.1(a)
PackingGroup :II
HS Code :29399990
Toxicity :LD50 intraperitoneal in mouse: 3mg/kg

NFPA 704:

	0
4		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H300-H341-H361fd
Precautionary statements P202-P264-P270-P280-P301+P310-P405

Vincristine sulfate Price More Price(7)

Brand: Sigma-Aldrich(India)
Product number: V8879
Product name : Vincristine sulfate salt
Purity: 95.0-105.0% (HPLC), powder or crystals
Packaging: 1MG
Price: ₹12037.4
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: V8879
Product name : Vincristine sulfate salt
Purity: 95.0-105.0% (HPLC), powder or crystals
Packaging: 5MG
Price: ₹13953.43
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: V8879
Product name : Vincristine sulfate salt
Purity: 95.0-105.0% (HPLC), powder or crystals
Packaging: 25MG
Price: ₹56874.55
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: V8388
Product name : Vincristine sulfate
Purity: meets USP testing specifications
Packaging: 1MG
Price: ₹11734.3
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: V8388
Product name : Vincristine sulfate
Purity: meets USP testing specifications
Packaging: 5MG
Price: ₹30602.28
Updated: 2022/06/14
Buy: Buy

Vincristine sulfate Chemical Properties,Usage,Production

Description Vincristine sulfate (2068-78-2) arrests cell cycle at G2/M by interfering with mitotic spindle formation. Depolymerizes microtubules and blocks binding of tubulin to microtubule proteins.1,2?Induces apoptosis.3?Vincristine sulfate is a clinically useful cancer chemotherapeutic agent.
Chemical Properties Crystalline Solid
Originator Oncovin,Lilly ,US ,1963
Uses Vincristine sulfate, is used as an anticancer agent, microtubule disrupter, Induces apoptosis in human lymphoma cells. Other applications include as a cell cycle arresting, apoptotic inducing alkaloid.
Uses Vincristin sulfate USP (Oncovin) is used to treat acute leukemia in children; lymphocytic leukemia; Hodgkin’s disease; non-Hodgkin’s lymphomas; Wilm’s tumor; neuroblastoma; rhabdomyosarcoma.
Uses H1-antihistamine
Uses An antitumor alkaloid isolated from Vinca rosea Linn. An antineoplastic.
Manufacturing Process The alkaloid mixture from the extraction of Vinca rosea plants (as in vinblastine extraction) was chromatographed to give vincristine which was then converted to the sulfate, according to US Patent 3,205,220.
Vincristine may also be prepared in a semisynthetic process starting from vinblastine. Vinblastine or a salt thereof, preferably the sulfate, is oxidized with chromic acid or with one of its salts at a low temperature, the reaction mixture is neutralized or rendered alkaline and the product is separated therefrom by extraction, the extract is evaporated to dryness, the dry residue is optionally formylated, vincristine, and optionally N-demethylvinblastine also, are isolated from the product, and the product(s) are optionally converted into their salts; preferably into the sulfates, according to US Patent 3,899,493.
brand name Oncovin (Lilly); Vincasar (Sicor).
Therapeutic Function Cancer chemotherapy
General Description Vincristine sulfate appears as an anticancer drug. White to slightly yellow, amorphous or crystalline powder. Sensitive to light. Odorless. pH (0.1% solution) 3.5 - 4.5. (NTP, 1992)
Air & Water Reactions Very hygroscopic. Water soluble.
Reactivity Profile Sensitive to hydrolysis, oxidation and heat. Incompatible with strong oxidizing agents. .
Fire Hazard Flash point data for Vincristine sulfate are not available; however, Vincristine sulfate is probably combustible.
Biological Activity Anticancer agent; microtubule disrupter. Induces apoptosis in human lymphoma cells.
Clinical Use Vincristine sulfate is available as a 1-mg/mL solution in 1-,2-, and 5-mL vials for IV administration in acute leukemiaand as part of a multidrug regime for Hodgkin’s and neuroblastoma, Ewing sarcoma, Wilms tumor, soft tissuesarcoma, testicular cancer, liver cancer, and head and neckcancers. It has also been utilized in treating pediatric cancer.
Veterinary Drugs and Treatments Vincristine is used as an antineoplastic primarily in combination drug protocols in dogs and cats in the treatment of lymphoid and hematopoietic neoplasms. In dogs, it may be used alone in the therapy of transmissible venereal neoplasms.
Because vincristine can induce thrombocytosis (at low doses) and has some immunosuppressant activity, it may also be employed in the treatment of immune-mediated thrombocytopenia.
Drug interactions Potentially hazardous interactions with other drugs
Antibacterials: possible increased risk of ventricular arrhythmias with delamanid.
Antiepileptics: phenytoin levels may be reduced.
Antifungals: metabolism possibly inhibited by itraconazole and posaconazole (increased risk of neurotoxicity).
Antimalarials: avoid with piperaquine with artenimol.
Antipsychotics: avoid concomitant use with clozapine (increased risk of agranulocytosis).
Cytotoxics: toxicity possibly increased by asparaginase, crisantaspase and pegasparagase - give at least 3-24 hours before asparaginase, crisantaspase and pegasparagase; increased risk of hepatotoxicity with dactinomycin.
Metabolism Vincristine is metabolised in the liver by the cytochrome P450 isoenzymes CYP3A4 and CYP3A5 and excreted mainly in the bile; about 70-80 % of a dose is found in faeces, as unchanged drug and metabolites (40-50 %), while 10-20 % appears in the urine.
Vincristine is highly protein bound (75%) and may also bindto platelets that contain large amounts of tubulin. Numerousmetabolites have been detected and several have been identified,one of which is the 4-O-desacetyl derivative. The metabolismthat does occur is believed to largely be mediatedby CYP3A. Elimination occurs primarily in the bile with aterminal elimination half-life of 23 to 85 hours.
storage Store at -20°C
Purification Methods The salt is recrystallised from MeOH. It has UV max at 220, 255 and 296nm (log 4.65, 4.21 and 4.18). It is a monoamine oxidase inhibitor and is used in cancer research [Son et al. J Med Chem 33 1845 1990, Horio et al. Proc Natl Acad Sci USA 85 3580 1988].
Mode of action Vincristine Sulfate is the sulfate salt of a natural alkaloid isolated from the plant Catharanthus roseus (Vinca rosea L.) 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. This agent also depolymerizes microtubules and may also interfere with amino acid, cyclic AMP, and glutathione metabolism; calmodulin-dependent Ca(2+)-activated ATPase activity; cellular respiration; and nucleic acid and lipid biosynthesis.
Toxicity evaluation The mostcommonly seen toxicity for vincristine is a dose-limitingneurotoxicity caused by effects on axonal microtubules.Symptoms are variable and include peripheral neuropathy,ataxia, seizure, bone pain, and coma. Constipation is also acommonly seen toxicity, and laxatives may be used prophylactically.Other toxicities include alopecia, skin rash, mildmyelosuppression, secretion of antidiuretic hormone,azospermia, and amenorrhea.
References 1) Jordan et al. (1998), Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle; Med. Res. Rev., 18 259 2) Lobert et al. (1996), Interaction of vinca alkaloids with tubulin: a comparison of vinblastine, vincristine, and vinorelbine; Biochemistry, 35 6806 3) Wang et al. (1999), The effect of antimicrotubule agents on signal transduction pathways of apoptosis: a review: Cancer Chemother. Pharmacol., 44 355