Vincristine sulfate
- Product Name
- Vincristine sulfate
- CAS No.
- 2068-78-2
- Chemical Name
- Vincristine sulfate
- Synonyms
- oncovin;VCR;NovopharM;VINCRISTINE SULPHATE;LEUROCRISTINE SULFATE;VINCRISTINE SULFATE USP;VINCRISTINE SULFATE SALT;onkovin;nsc67574;Vincrisul
- 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.
- InChI
- InChI=1/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-;/s3
- InChIKey
- AQTQHPDCURKLKT-HSMPTBRCNA-N
- SMILES
- [C@]123CCN4CC=C[C@@](CC)([C@@H](OC(=O)C)[C@](O)(C(=O)OC)[C@@]1(N(C1C=C(OC)C([C@@]5(C(=O)OC)C[C@]6([H])C[C@@](CC)(CN(CCC7C8=C(C=CC=C8)NC5=7)C6)O)=CC2=1)C=O)[H])[C@@]34[H].S(=O)(=O)(O)O |&1:0,7,10,15,21,29,35,38,61,r|
- IARC
- 3 (Vol. 26, Sup 7) 1987
- EPA Substance Registry System
- Vincristine sulfate (2068-78-2)
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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H300Fatal 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+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 1714007
- Product name
- Vincristine sulfate
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 50mg
- Price
- $1340
- Updated
- 2024/03/01
- Product number
- J60907
- Product name
- Vincristine sulfate
- Purity
- 97+%
- Packaging
- 10mg
- Price
- $180
- Updated
- 2024/03/01
- Product number
- J60907
- Product name
- Vincristine sulfate
- Purity
- 97+%
- Packaging
- 25mg
- Price
- $304.65
- Updated
- 2024/03/01
- Product number
- 11764
- Product name
- Vincristine (sulfate)
- Purity
- ≥95%
- Packaging
- 5mg
- Price
- $40
- Updated
- 2024/03/01
- Product number
- 11764
- Product name
- Vincristine (sulfate)
- Purity
- ≥95%
- Packaging
- 10mg
- Price
- $76
- Updated
- 2024/03/01
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
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
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
An antitumor alkaloid isolated from Vinca rosea Linn. An antineoplastic.
Uses
H1-antihistamine
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
Vincristine sulfate Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Vincristine sulfate manufacturers
- Product
- Vincristine sulfate 2068-78-2
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10000 tons
- Release date
- 2024-04-15
- Product
- Vincristine Sulfate 2068-78-2
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 2000ton
- Release date
- 2023-09-08
- Product
- Vincristine Sulfate 2068-78-2
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99
- Supply Ability
- 2000ton
- Release date
- 2024-03-15