SynCED: Vincristine

Record Information

Version

1.0

Creation Date

2014-08-29 04:49:14 UTC

Update Date

2026-08-22 14:58:02 UTC

Accession Number

CHEM002976

Identification

Common Name

Vincristine

Class

Small Molecule

Description

Vincristine is only found in individuals that have used or taken this drug. It is an antitumor alkaloid isolated from Vinca Rosea. (Merck, 11th ed.) The antitumor activity of Vincristine is thought to be due primarily to inhibition of mitosis at metaphase through its interaction with tubulin. Like other vinca alkaloids, Vincristine may also interfere with: 1) amino acid, cyclic AMP, and glutathione metabolism, 2) calmodulin-dependent Ca²⁺-transport ATPase activity, 3) cellular respiration, and 4) nucleic acid and lipid biosynthesis. Vincristine is indicated for the treatment of acute leukaemia, malignant lymphoma, Hodgkin's disease, acute erythraemia, and acute panmyelosis. Vincristine sulfate is often chosen as part of polychemotherapy because of lack of significant bone marrow suppression (at recommended doses) and of unique clinical toxicity (neuropathy).

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Antineoplastic Agent, Phytogenic
Drug
Ester
Ether
Human Neurotoxin
Metabolite
Organic Compound
PFAS
Phytotoxin
Synthetic Compound
Tubulin Modulator

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Vincristine	ChEBI
22-oxo-Vincaleukoblastine	ChEBI
22-Oxovincaleukoblastine	ChEBI
Leucristine	ChEBI
Leurocristine	ChEBI
Oncovin	ChEBI
Vincristin	ChEBI
Vinkristin	ChEBI
Tecnocris	Kegg
Indole alkaloid	HMDB
LCR	HMDB
VCR	HMDB
VIN	HMDB
Vincristina	HMDB
Vincristine sulfate	HMDB
Vincrstine	HMDB
Vincrystine	HMDB
Z-D-Val-lys(Z)-OH	HMDB
Citomid	HMDB
Oncovine	HMDB
Sulfate, vincristine	HMDB
Vincasar PFS	HMDB
Vincrisul	HMDB
Onkocristin	HMDB
Vincasar	HMDB
Farmistin	HMDB
PFS, Vincasar	HMDB
Vincristin bristol	HMDB
Vincristin medac	HMDB
Vintec	HMDB
Cellcristin	HMDB

Chemical Formula

C₄₆H₅₆N₄O₁₀

Average Molecular Mass

824.958 g/mol

Monoisotopic Mass

824.400 g/mol

CAS Registry Number

57-22-7

IUPAC Name

methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,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

Traditional Name

vincristine

SMILES

[H][C@@]12N3CC[C@@]11C4=CC(=C(OC)C=C4N(C=O)[C@@]1([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC)[C@]1(C[C@]2([H])CN(C[C@](O)(CC)C2)CCC2=C1NC1=CC=CC=C21)C(=O)OC

InChI Identifier

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

InChI Key

OGWKCGZFUXNPDA-XQKSVPLYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Alpha-amino acid ester
Benzazepine
Alpha-amino acid or derivatives
Azepine
Fatty acid ester
Aralkylamine
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Tertiary carboxylic acid amide
Carboxylic acid ester
Amino acid or derivatives
Amino acid
Lactam
Carboxamide group
Carboxylic acid
Secondary aliphatic amine
Azacycle
Secondary amine
Organoheterocyclic compound
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dicarboxylic acid monoester (CHEBI:3011 )
ethyl ester (CHEBI:3011 )
benzazepine (CHEBI:3011 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Vincristine Pathway	Not Available	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	220°C
Boiling Point	Not Available
Solubility	3.00e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	3.36	ALOGPS
logP	3.13	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	10.85	ChemAxon
pKa (Strongest Basic)	8.66	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	171.17 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	221.48 m³·mol⁻¹	ChemAxon
Polarizability	88.59 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

The antitumor activity of Vincristine is thought to be due primarily to inhibition of mitosis at metaphase through its interaction with tubulin. Like other vinca alkaloids, Vincristine may also interfere with: 1) amino acid, cyclic AMP, and glutathione metabolism, 2) calmodulin-dependent Ca²⁺-transport ATPase activity, 3) cellular respiration, and 4) nucleic acid and lipid biosynthesis.

Metabolism

Hepatic. Cytochrome P450 isoenzymes of the CYP3A subfamily facilitate the metabolism of vincristine. Route of Elimination: The liver is the major excretory organ in humans and animals. 80% of an injected dose of vincristine sulfate is excreted via feces. 10 - 20% is excreted via urine. Half Life: When intravenously injected into cancer patients, a triphasic serum decay patten was observed. The initial, middle, and terminal half-lives are 5 minutes, 2.3 hours, 85 hours respectively. The range of the terminal half-life is humans is 19 - 155 hours.

Toxicity Values

IVN-RAT LD₅₀ 1300 mg/kg; IPR-MUS LD₅₀ 5.2 mg/kg.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Vincristine sulfate is not classifiable as to its carcinogenicity to humans (Group 3). Vincristine is part of MOPP, a combination chemotherapy regimen that is carcinogenic to humans (Group 1). (5)

Uses/Sources

Treatment of acute lymphocytic leukemia (ALL), Hodgkin lymphoma, non-Hodgkin lymphomas, Wilms' tumor, neuroblastoma, rhabdomyosarcoma. Liposomal vincristine is indicated for the treatment of relapsed Philadelphia chromosome-negative (Ph-) acute lymphoblastic leukemia (ALL).

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID