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Oncovin

HCID 5388992
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Basic information

CAS
2068-78-2
Standard SMILES
CC[C@]1(O)C[C@@H]2CN(CCc3c([nH]c4ccccc34)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C=O)[C@H]3[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]5(CC)C=CCN6CC[C@]43[C@@H]65)C2)C1.O=S(=O)(O)O
InChIKey
AQTQHPDCURKLKT-PNYVAJAMSA-N
Molecular formula
C46H58N4O14S
Average molar mass
923 g/mol
Monoisotopic mass
922.36702371

Overview

Vincristine Sulfate can cause developmental toxicity according to state or federal government labeling requirements.

Names & identifiers

Preferred name
Oncovin
IUPAC
methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate;sulfuric acid
English name
Vincristine sulfate
Molecular formula
C46H58N4O14S
Molecular weight
923.04

Names & synonyms

OncovinVincristine sulfate saltMLS000863277Vincristine (sulfate)C46H58N4O14SSMR000058540VincristinsulfatMLS000069706Vincristinsulfat [German]UNII-T5IRO3534ACCRIS 2583MFCD08706469
Show more names
VINCRISTINE SULPHATEVCRNovopharMvincristinVincristin SulfateVinorelbine SulfateLEUROCRISTINE SULFATEVINCRISTINE SULFATE USP
Vincristine sulfate; Methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-9-[(5S,7R,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-6-formyl-5-hydroxy-8-methoxy-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate sulfateEINECS 218-190-0Vincristine sulfate [USAN:USP:JAN]Vincristine Sulfate Liposomes InjectionVincristine sulfate CRSOpera_ID_836AI3-52944MLS001148250

Database identifiers

Properties

Computed structural properties

Topological polar surface area
254 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
16
Rotatable bonds
10
Heavy atoms
65
Formal charge
0
Complexity
1,830

Physicochemical properties

Melting point
300 °C · 300 °C
Boiling point
273 · 273-281 °C
alpha
26 · D26 +8.5° (c = 0.8)
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
solubility
20 mg/mL · methanol: soluble20mg/mL
form
lyophilized powder
color
white to off-white
Water Solubility
1 g/100 · >=1 g/100 mL at 24 ºC
BRN
3924631 · 3924631
Stability
2 years · Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
Major Application
pharmaceutical (small molecule)
InChIKey
AQTQHPDCURKLKT-HSMPTBRCNA-N
SMILES
OS(O)(=O)=O.CC[C@]1(O)CC2CN(CCc3c([nH]c4ccccc34)[C@@](C2)(C(=O)OC)c5cc6c(cc5OC)N(C=O)C7[C@](O)([C@H](OC(C)=O)[C@]8(CC)C=CCN9CC[C@]67C89)C(=O)OC)C1
EWG's Food Scores
1 · 1

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
8-10
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
rtecs
OH6340000
ridadr
UN 2811 6.1/PG 2
hs_code
29399990
Toxicity
LD50 intraperitoneal in mouse: 3mg/kg
risk_code
61-36/37/38-63-23/24/25-68-62-25
Signal word
Danger
Symbol(GHS)
GHS06,GHS08
hazard_code
T
safety_code
22-24/25-53-45-37/39-26-36/37/39-36/37
hazard_class
6.1(a)
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
II
Hazard statements
H300-H341-H361fd
Hazard Classifications
Acute Tox. 2 OralMuta. 2Repr. 2
Precautionary statements
P202-P264-P270-P280-P301+P310-P405

Chemistry & industry

Applications · 6 items

DescriptionVincristine 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.1,2Induces apoptosis.3Vincristine sulfate is a clinically useful cancer chemotherapeutic agent.

UsesVincristin 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.

UsesAn antitumor alkaloid isolated from Vinca rosea Linn. An antineoplastic.

UsesH1-antihistamine

UsesVincristine 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.

General DescriptionVincristine 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)

Preparation methods · 1 item

Preparation2g of vincristine sulfate was dissolved in 240ml of tetrahydrofuran, and 7.5ml of glacial acetic acid was added. Under its protection, the mixture was cooled to -65℃ with dry ice. While stirring, a prepared sodium dicadmium dicadmium solution (3g of sodium dicadmium dicadmium dissolved in 15ml of water, then 2ml of concentrated sulfuric acid was added and stirred until dissolved) was added dropwise, maintaining the reaction temperature below -50℃ during the addition. After the addition was complete, the reaction was stirred at -65℃ for 3 hours. The reaction solution was poured into a mixture of 35ml of concentrated ammonia and 200ml of water, extracted with 600ml of dichloromethane, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 2.06g of crude vincristine, with a purity of 83% as determined by HPLC. The crude vincristine was dissolved in 20 ml of isopropanol. While stirring, 16 ml of 1% isopropanol sulfate solution was added dropwise to adjust the pH to ≤ 4. The solid was filtered off, dried under vacuum, and 1.82 g of crude vincristine sulfate was obtained, with a purity of 92% as determined by HPLC. 1.8 g of crude vincristine sulfate was dissolved in 36 ml of anhydrous ethanol, cooled to -10°C, and stirred slowly. A solid precipitated, was filtered, washed with anhydrous ethanol, and dried under vacuum, yielding 1.63 g of vincristine sulfate, with a yield of 81.5% and a purity of 98.6% as determined by HPLC.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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CAS
2068-78-2
PubChem CID
5388992
ChEMBL
CHEMBL385978
UNII
T5IRO3534A
NCI Dictionary of Cancer Terms
Oncovin; vincristine sulfate
FDA UNII
5 IRO3534A · T5IRO3534A
NCI Drug Dictionary
vincristine sulfate
Proposition 65 List
Vincristine Sulfate
IARC
3 · 3 (Vol. 26, Sup 7) 1987
EPA Substance Registry System
Vincristine sulfate (2068-78-2)
UNSPSC Code
12352210 · 12352210
NACRES
77 · NA.77
Protein binding
75 % · 75%
Excreted unchanged in urine
10 · 10-20%
Volume of distribution
5 · 5-11(L/kg)
Biological half-life
15 · 15-155 / Unchanged
Symbol(GHS)
6 · GHS06,GHS08
Signal word
Danger
Hazard statements
300 · H300-H341-H361fd
Precautionary statements
202 · P202-P264-P270-P280-P301+P310-P405
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
T
Risk Statements
61 · 61-36/37/38-63-23/24/25-68-62-25
Safety Statements
22 · 22-24/25-53-45-37/39-26-36/37/39-36/37
RIDADR
2811 · UN 2811 6.1/PG 2
WGK Germany
3 · 3
RTECS
6340000 · OH6340000
F
8 · 8-10
HazardClass
6.1 · 6.1(a)
PackingGroup
II
HS Code
29399990 · 29399990
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
2 OralMuta · Acute Tox. 2 OralMuta. 2Repr. 2
Toxicity
50 intraperitoneal · LD50 intraperitoneal in mouse: 3mg/kg

Upstream & downstream products

Upstream raw materials

Sulfuric acidBenzene

Downstream products

Desacetylvinblastineamide