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57-22-7

Basic Information
CAS No.: 57-22-7
Name: Vincristine
Article Data: 3
Molecular Structure:
Molecular Structure of 57-22-7 (Vincristine)
Formula: C46H56N4O10
Molecular Weight: 824.971
Synonyms: (+)-Vincristine;22-Oxovincaleukoblastine;Leucristine;OncoTCS;VCR;Vincristin;Vinkristin;Leurocristine(7CI,8CI);
EINECS: 200-318-1
Density: 1.406 g/cm3
Melting Point: 211-216 °C
Boiling Point: 761.92°C (rough estimate)
Appearance: a white crystalline solid
PSA: 171.17000
LogP: 4.09420
Synthetic route
2068-78-2

vincristine sulfate

57-22-7

Vincristine

Conditions
ConditionsYield
With sodium carbonate In methanol; chloroform; water98%
101156-38-1

cyclovincristine

57-22-7

Vincristine

Conditions
ConditionsYield
With sodium tetrahydroborate In dichloromethane; acetic acid for 2h; Ambient temperature;79%

A

57-22-7

Vincristine

B

catharine

D

23360-92-1

vinleurosine

Conditions
ConditionsYield
With cell-free extracts from Catharanthus roseus Product distribution; Mechanism; Ambient temperature; biosynthesis of the products were studied; experiment was performed with 3',4'-anhydrovinblastine and the incorporation of the radiolabel into the products were investigated;
57-22-7

Vincristine

3704-01-6

desacetylvincristine

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; for 48h;70%

bromomethyl 4-hydroxy-3-methoxystyryl ketone

57-22-7

Vincristine

C57H67N4O13(1+)*Br(1-)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 3h;68%
57-22-7

Vincristine

vincristine N'b-oxide

Conditions
ConditionsYield
Stage #1: Vincristine With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 0.0333333h;
Stage #2: With sodium carbonate In dichloromethane; water
67%

C14H11BrO

57-22-7

Vincristine

C60H67N4O11(1+)*Br(1-)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 3h;67%
1392239-32-5

C10H8BrClO

57-22-7

Vincristine

C56H66ClN4O11(1+)*Br(1-)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 3h;65%
358-23-6

trifluoromethylsulfonic anhydride

C13H17N3O3

57-22-7

Vincristine

C59H72N7O12(1+)*CF3O3S(1-)

Conditions
ConditionsYield
Stage #1: trifluoromethylsulfonic anhydride; C13H17N3O3 With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 0.833333h; Inert atmosphere;
Stage #2: Vincristine In tetrahydrofuran at -78℃; for 1.33333h; Inert atmosphere;
57%
57-22-7

Vincristine

101156-38-1

cyclovincristine

Conditions
ConditionsYield
With chromium(VI) oxide; acetic anhydride In methanol; dichloromethane; acetic acid at -20℃; for 17h;46%
Raw Materials
2068-78-2
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  • Casno:

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    57-22-7 CAS NO.57-22-7

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Consensus Reports

NCI Carcinogenesis Studies (ipr); No Evidence: mouse, rat CANCAR    Cancer. 40 (1977),1935. . EPA Genetic Toxicology Program.

Specification

The Vincristine, with the CAS registry number 57-22-7, is also known as Vincaleukoblastine, 22-oxo-, (3β,4'β)-. It belongs to the classification codes of Antimitotic Agents; Antineoplastic Agents; AntineoplasticAagents, Phytogenic; Drug / Therapeutic Agent; Human Data; Mitosis Modulators; Mutation Data; Natural Product; Reproductive Effect; Skin / Eye Irritant; Tubulin Modulators; Tumor Data. Its EINECS registry number is 200-318-1. This chemical's molecular formula is C46H56N4O10 and molecular weight is 824.96. What's more, its IUPAC name is called (2α,2'β,3α,4α,5β,19β)-22-Oxovincaleukoblastine. It is a mitotic inhibitor, and is used in cancer chemotherapy. Vincristine is created by the coupling of indole alkaloids vindoline and catharanthine in the vinca plant.

Physical properties about Vincristine are: (1)ACD/LogP: 5.749; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 3.15; (4)ACD/LogD (pH 7.4): 5.20; (5)ACD/BCF (pH 5.5): 34.56; (6)ACD/BCF (pH 7.4): 3920.85; (7)ACD/KOC (pH 5.5): 80.12; (8)ACD/KOC (pH 7.4): 9090.30; (9)#H bond acceptors: 14; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 171.17 Å2; (13)Index of Refraction: 1.677; (14)Molar Refractivity: 221.088 cm3; (15)Molar Volume: 586.859 cm3; (16)Polarizability: 87.646×10-24cm3; (17)Surface Tension: 74.056 dyne/cm; (18)Density: 1.406 g/cm3.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(OC)[C@]4(c2c(c1ccccc1n2)CCN3C[C@](O)(CC)C[C@@H](C3)C4)c5c(OC)cc6c(c5)[C@@]89[C@@H](N6C=O)[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@@]7(/C=C\CN([C@@H]78)CC9)CC
(2) InChI: InChI=1S/C46H56N4O10/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/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1
(3) InChIKey: OGWKCGZFUXNPDA-XQKSVPLYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo parenteral 8290ug/kg (8.29mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION

BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)
Archives of Disease in Childhood. Vol. 51, Pg. 289, 1976.
child TDLo intravenous 500ug/kg (.5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ANOREXIA (HUMAN

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pediatrics. Vol. 81, Pg. 90, 1972.
hamster LD10 parenteral 350ug/kg (.35mg/kg)   Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980.
human TDLo intravenous 120ug/kg/8W (.12mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
British Medical Journal. Vol. 1, Pg. 1251, 1977.
mouse LD50 intraperitoneal 1300ug/kg (1.3mg/kg)   Cancer Treatment Reports. Vol. 65, Pg. 1049, 1981.
mouse LD50 intravenous 3mg/kg (3mg/kg)   United States Patent Document. Vol. #4279915,
mouse LD50 unreported 5800ug/kg (5.8mg/kg)   Cancer Research. Vol. 46, Pg. 2703, 1986.
mouse LDLo intratracheal 1200ug/kg (1.2mg/kg)   Toxicology Letters. Vol. 30, Pg. 63, 1986.
rat LD50 intraperitoneal 1250ug/kg (1.25mg/kg)   Advances in Teratology. Vol. 3, Pg. 181, 1968.
rat LD50 intravenous 1mg/kg (1mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Journal of Medicinal Chemistry. Vol. 28, Pg. 1079, 1985.
women TDLo intravenous 40ug/kg (.04mg/kg) BEHAVIORAL: MUSCLE WEAKNESS Medical Journal of Australia. Vol. 143, Pg. 305, 1985.