Axitinib (CED0002775)

Record Information

Version

1.0

Creation Date

2016-05-22 06:57:35 UTC

Update Date

2026-08-21 21:13:26 UTC

Accession Number

CHEM020259

Identification

Common Name

Axitinib

Class

Small Molecule

Description

Axitinib is an organic compound with the chemical formula C22H18N4OS and an average molecular weight of 386.47 g/mol. Axitinib belongs to the aryl thioethers, a subclass of thioethers within the organic compounds. This substance is associated with two recorded sources: electrical and electronic equipment, specifically antennas, and healthcare, pharmaceuticals, and veterinary products, where it is categorized as an antineoplastic agent. The recorded route of exposure for this compound is oral. At the molecular level, axitinib acts upon four recorded protein targets. It functions as an inhibitor of tyrosine-protein kinase ABL1, as well as the vascular endothelial growth factor receptors 1 (FLT1), 2 (KDR), and 3 (FLT4).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
AG-013736	ChEBI
Axitinibum	ChEBI
Inlyta	ChEBI
N-Methyl-2-({3-[(e)-2-(pyridin-2-yl)vinyl]-1H-indazol-6-yl}sulfanyl)benzamide	ChEBI
N-Methyl-2-({3-[(e)-2-(pyridin-2-yl)vinyl]-1H-indazol-6-yl}sulphanyl)benzamide	Generator

Chemical Formula

C₂₂H₁₈N₄OS

Average Molecular Mass

386.470 g/mol

Monoisotopic Mass

386.120 g/mol

CAS Registry Number

319460-85-0

IUPAC Name

N-methyl-2-({3-[(E)-2-(pyridin-2-yl)ethenyl]-2H-indazol-6-yl}sulfanyl)benzene-1-carboximidic acid

Traditional Name

axitinib

SMILES

[H]\C(=C(\[H])C1=CC=CC=N1)C1=C2C=CC(SC3=CC=CC=C3C(O)=NC)=CC2=NN1

InChI Identifier

InChI=1S/C22H18N4OS/c1-23-22(27)18-7-2-3-8-21(18)28-16-10-11-17-19(25-26-20(17)14-16)12-9-15-6-4-5-13-24-15/h2-14H,1H3,(H,23,27)(H,25,26)/b12-9+

InChI Key

RITAVMQDGBJQJZ-FMIVXFBMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Aryl thioethers

Direct Parent

Diarylthioethers

Alternative Parents

Substituents

Diarylthioether
O-sulfanylbenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzopyrazole
Indazole
Benzoyl
Thiophenol ether
Monocyclic benzene moiety
Pyridine
Benzenoid
Vinylogous thioester
Azole
Pyrazole
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aryl sulfide (CHEBI:66910 )
benzamides (CHEBI:66910 )
pyridines (CHEBI:66910 )
indazoles (CHEBI:66910 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00051 g/L	ALOGPS
logP	4.56	ALOGPS
logP	5.01	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	7.73	ChemAxon
pKa (Strongest Basic)	5.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.16 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.73 m³·mol⁻¹	ChemAxon
Polarizability	42.71 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum	splash10-052r-0129000000-7dcde0f91b9466cce9b4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0119000000-67322847bfa9d499acae	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4r-0029000000-82c0cd274af66f6f3f23	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ab9-0930000000-953c194c8196ffb70e4a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-9b4a9f82b6743f6cfeb9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05p9-1229000000-b54e607fb399c575cb1c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fw9-6971000000-4424644dc84a5b708cac	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
960.0	Log mg/kg	[540:1700]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
358	Antineoplastic agents	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available

Pathways

3 pathways

Axitinib Action Pathway

Axitinib Drug Metabolism

Axitinib Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Fibroblast growth factor receptor 1	P11362	Humans	Predicted (SEA)	235.883
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	385.431
Click to view 3D structure	Platelet-derived growth factor receptor beta	P09619	Humans	Predicted (SEA)	195.557
Click to view 3D structure	Macrophage colony-stimulating factor 1 receptor	P07333	Humans	Predicted (SEA)	242.5
Click to view 3D structure	Platelet-derived growth factor receptor alpha	P16234	Humans	Predicted (SEA)	168.466
Click to view 3D structure	Mast/stem cell growth factor receptor Kit	P10721	Humans	Predicted (SEA)	278.778
Click to view 3D structure	High affinity nerve growth factor receptor	P04629	Humans	Predicted (SEA)	253.711
Click to view 3D structure	BDNF/NT-3 growth factors receptor	Q16620	Humans	Predicted (SEA)	205.366
Click to view 3D structure	NT-3 growth factor receptor	Q16288	Humans	Predicted (SEA)	160.836
Click to view 3D structure	Serine/threonine-protein kinase Chk1	O14757	Humans	Predicted (SEA)	215.876
Click to view 3D structure	Tyrosine-protein kinase Lck	P06239	Humans	Predicted (SEA)	364.646
Click to view 3D structure	Casein kinase I isoform alpha	P48729	Humans	Predicted (SEA)	190.419
Click to view 3D structure	Focal adhesion kinase 1	Q05397	Humans	Predicted (SEA)	226.93
Click to view 3D structure	Tyrosine-protein kinase JAK3	P52333	Humans	Predicted (SEA)	364.412
Click to view 3D structure	Vascular endothelial growth factor receptor 1	P17948	Humans	Predicted (SEA)	245.147
Click to view 3D structure	ALK tyrosine kinase receptor	Q9UM73	Humans	Predicted (SEA)	251.92
Click to view 3D structure	Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	Humans	Predicted (SEA)	295.983
Click to view 3D structure	Receptor-type tyrosine-protein kinase FLT3	P36888	Humans	Predicted (SEA)	406.84
Click to view 3D structure	Tyrosine-protein kinase JAK2	O60674	Humans	Predicted (SEA)	372.82
Click to view 3D structure	Vascular endothelial growth factor receptor 3	P35916	Humans	Predicted (SEA)	212.451
Click to view 3D structure	Tyrosine-protein kinase ABL1	P00519	Humans	Predicted (SEA)	337.866
Click to view 3D structure	Activated CDC42 kinase 1	Q07912	Humans	Predicted (SEA)	163.795
Click to view 3D structure	Dual specificity mitogen-activated protein kinase kinase 1	Q02750	Humans	Predicted (SEA)	179.053
Click to view 3D structure	RAC-alpha serine/threonine-protein kinase	P31749	Humans	Predicted (SEA)	276.365
Click to view 3D structure	Ribosomal protein S6 kinase beta-1	P23443	Humans	Predicted (SEA)	223.894