ChemicalBook > CAS DataBase List > Vincristine sulfate

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
More
Less

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)
More
Less

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
More
Less

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.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
1714007
Product name
Vincristine sulfate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
50mg
Price
$1340
Updated
2024/03/01
Alfa Aesar
Product number
J60907
Product name
Vincristine sulfate
Purity
97+%
Packaging
10mg
Price
$180
Updated
2024/03/01
Alfa Aesar
Product number
J60907
Product name
Vincristine sulfate
Purity
97+%
Packaging
25mg
Price
$304.65
Updated
2024/03/01
Cayman Chemical
Product number
11764
Product name
Vincristine (sulfate)
Purity
≥95%
Packaging
5mg
Price
$40
Updated
2024/03/01
Cayman Chemical
Product number
11764
Product name
Vincristine (sulfate)
Purity
≥95%
Packaging
10mg
Price
$76
Updated
2024/03/01
More
Less

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

DESACETYLVINBLASTINEAMIDE
More
Less

Vincristine sulfate Suppliers

Belgium 2 Canada 1 China 397 Europe 2 France 2 Germany 3 Hungary 1 India 11 Ireland 1 Japan 4 Switzerland 3 United Kingdom 18 United States 61 Global 506
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
AdooQ BioScience, LLC
Tel
+1 (866) 930-6790
Fax
+1 (866) 333-9607
Email
info@adooq.com
Country
United States
ProdList
2782
Advantage
58
ALB Technology Limited
Tel
702-983-3769
Fax
702-983-3769
Email
sales@albtechnology.com
Country
United States
ProdList
2993
Advantage
55
EMMX Biotechnology LLC
Tel
888-539-0666
Fax
888-539-0666
Email
info@emmx.com
Country
United States
ProdList
8447
Advantage
60
Target molecule Corp.
Tel
857-239-0968
Fax
857-239-8801
Email
service1@targetmol.com
Country
United States
ProdList
2559
Advantage
60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32165
Advantage
58
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6391
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38632
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
ApexBio Technology
Tel
--
Fax
--
Email
sales@apexbt.com
Country
United States
ProdList
6251
Advantage
58
CarboMer, Inc.
Tel
--
Fax
--
Email
sales@carbomer.com
Country
United States
ProdList
4026
Advantage
67
Focus Biomolecules
Tel
--
Fax
--
Email
sales@focusbiomolecules.com
Country
United States
ProdList
1284
Advantage
58
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
LC Laboratories
Tel
--
Fax
--
Email
custserv@lclabs.com
Country
United States
ProdList
503
Advantage
50
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
Creative Enzymes
Tel
--
Fax
--
Email
info@creative-enzymes.com
Country
United States
ProdList
6057
Advantage
58
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
Frontier Scientific, Inc.
Tel
--
Fax
--
Email
sales@frontiersci.com
Country
United States
ProdList
6222
Advantage
86
Olinax Inc.
Tel
--
Fax
--
Email
info@olinax.com
Country
United States
ProdList
404
Advantage
50
Selleck Chemicals LLC
Tel
--
Fax
--
Email
info@selleckchem.com
Country
United States
ProdList
824
Advantage
60
Altan Corporation
Tel
--
Fax
--
Email
OrderingService@AltanBiochemicals.com
Country
United States
ProdList
1161
Advantage
30
Santa Cruz Biotechnology, Inc.
Tel
--
Fax
--
Email
scbt@scbt.com
Country
United States
ProdList
3597
Advantage
60
Pure Chemistry Scientific Inc
Tel
--
Fax
--
Email
sales@purechems.com
Country
United States
ProdList
2321
Advantage
50
Tecoland Corporation
Tel
--
Fax
--
Email
info@tecoland.com
Country
United States
ProdList
275
Advantage
50
Tinib-Tools
Tel
--
Fax
--
Country
United States
ProdList
164
Advantage
0
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6962
Advantage
56
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
AlliChem, LLC
Tel
--
Fax
--
Email
sales@allichemllc.com
Country
United States
ProdList
6516
Advantage
60
HONEST JOY HOLDINGS LIMITED
Tel
--
Fax
--
Email
sales@honestjoy.cn
Country
United States
ProdList
6675
Advantage
54
Advance Scientific & Chemical
Tel
--
Fax
--
Email
sales@advance-scientific.com
Country
United States
ProdList
6419
Advantage
71
2A PharmaChem USA
Tel
--
Fax
--
Email
sales@2apharmachem.com
Country
United States
ProdList
6137
Advantage
39
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
AK Scientific, Inc.
Tel
--
Fax
--
Email
sales@aksci.com
Country
United States
ProdList
6347
Advantage
65
Biochemicals.net
Tel
--
Fax
--
Country
United States
ProdList
40
Advantage
47
Acros Organics USA
Tel
--
Fax
--
Email
eveleth@fisherchem.com
Country
United States
ProdList
3846
Advantage
81
Fine Chem Trading LTD
Tel
--
Fax
--
Email
chemfinder@chemfinder.co.uk
Country
United States
ProdList
1609
Advantage
64
Kainic.com
Tel
--
Fax
--
Email
info@Kainic.com
Country
United States
ProdList
330
Advantage
38
VARDA Biotech (P) Ltd.
Tel
--
Fax
--
Email
vijay@vardabiotech.com
Country
United States
ProdList
208
Advantage
66
NetQem
Tel
--
Fax
--
Email
sales@netqem.us
Country
United States
ProdList
1641
Advantage
38
Sciencelab.com, Inc.
Tel
--
Fax
--
Email
accounting@sciencelab.com
Country
United States
ProdList
4159
Advantage
82
Lab Express
Tel
--
Fax
--
Email
sales@labexpress.com
Country
United States
ProdList
1577
Advantage
67
Chem-Impex International, Inc.
Tel
--
Fax
--
Country
United States
ProdList
6730
Advantage
64
Beta Pharma, Inc.
Tel
--
Fax
--
Email
sales@betapharma.com
Country
United States
ProdList
6226
Advantage
60
QVENTAS INC.
Tel
--
Fax
--
Email
mike@qventas.com
Country
United States
ProdList
383
Advantage
47
American Custom Chemicals Corporation
Tel
--
Fax
--
Email
sales@acccorporation.com
Country
United States
ProdList
6820
Advantage
51
CGeneTech, Inc.
Tel
--
Fax
--
Email
qyu@cgenetech.com
Country
United States
ProdList
959
Advantage
30
BOSCHE SCIENTIFIC, LLC
Tel
--
Fax
--
Email
Sales@BoscheSci.com
Country
United States
ProdList
6477
Advantage
55
More
Less

View Lastest Price from Vincristine sulfate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Vincristine sulfate 2068-78-2
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
98%min
Supply Ability
100kgs
Release date
2021-11-16
S&Y Biochem Co.,Ltd
Product
Vincristine Sulphate 2068-78-2
Price
US $1.00/g
Min. Order
1g
Purity
99
Supply Ability
100
Release date
2024-08-01
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Vincristine Sulfate 2068-78-2
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
50kg/Month
Release date
2024-10-14

2068-78-2, Vincristine sulfateRelated Search:

Aluminum sulfate Ammonium sulfate Zinc sulfate heptahydrate Sodium sulfate Sodium dodecyl sulfate Magnesium sulfate heptahydrate Ammonium lauryl sulfate Dimethyl sulfate calcium sulfate Ferrous sulfate heptahydrate BERBERINE ACID SULFATE Vindesine sulfate VINBLASTINE Zinc sulphate Copper(II) sulfate Vinblastine sulfate Sodium thiosulfate Vinorelbine tartrate

  • VINCRISTINE SULFATE
  • VINCRISTINE SULFATE, APOCYNACEAE SPECIES
  • VINCRISTINE SULFATE SALT
  • VINCRISTINE SULPHATE
  • VCR
  • VCR, LEUKOCRISTINE SULFATE
  • VCR SULFATE
  • Vincristine，Leurocristine，Oncovin，Vinblastine
  • Vincristin Sulfate
  • Vincristine sulfate,95%
  • Vincaleukoblastine, 22-oxo-, sulfate (1:1)
  • Vincaleukoblastine, 22-oxo-, sulfate (1:1) (salt)
  • 22-Oxovinacleukoblastine sulfate
  • Vincristine Sulfate (50 mg)
  • Vincristine Sulfate (50 mg/ampule)
  • Vincristine sulfate salt,22-Oxovincaleukoblastine sulfate salt, Leurocristine sulfate salt, VCR
  • Vincristine Sulfate (Assay) (29.8 mg/vial)
  • leurocristinesulfate(1:1)
  • leurocristinesulfate(1:1)(salt)
  • lilly37231
  • nsc67574
  • oncovin
  • onkovin
  • vincristinsulfat
  • Vincrisul
  • LEUROCRISTINESULPHATE
  • vincristin
  • vinorelbine，NVB
  • VINCRISTINE, VCR
  • VCR, LCR, Kyocristine, Oncovin, Vincrex
  • Vincristine sulfate, 98%, from Catharanthus roseus (L.) G. Don
  • NovopharM
  • 22-Oxovinacleukoblastine
  • LEUROCRISTINE
  • LEUROCRISTINE SULFATE
  • NSC-67574 sulfate
  • Vincristine Sufate
  • Vinorelbine Impurity 4
  • Vincristine sulfate, 98%, from Vinca rosea L.
  • Vincristine Sulfate, Apocynaceae sp. - CAS 2068-78-2 - Calbiochem
  • (3aR,3a1R,4R,5S,5aR,10bR)
  • Vinorelbine Impurity
  • 22-oxo-vincaleukoblastinsulfate(1:1)(salt)
  • kyocristine
  • LEUROCRISTINE SULFATE SALT
  • 22-OXOVINCALEUKOBLASTINE
  • 22-OXOVINCALEUKO-BLASTINE SULFATE
  • 22-OXOVINCALEUKOBLASTINE SULFATE SALT
  • Vincristine sulphate USP25
  • V5 PEPTIDE
  • VINCRISTINE SULFATE USP
  • VINCRISTINE SULFATE, USP STANDARD
  • VINCRISTINE SULFATE, EP STANDARD
  • VINCRISTINE SULFATE, USP 95-101%
  • VINCRISTINE SULFATE, REFERENCE SPECTRUM EP STANDARD
  • VINCRISTINE SULFATE, WHO STANDARD
  • Vincristine Sulfate, Apocynaceae sp.
  • VincristineSulphateUsp28/Bp2003