CHEBI:50924 - sorafenib

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ChEBI Name sorafenib
ChEBI ID CHEBI:50924
Definition A member of the class of phenylureas that is urea in which one of the nitrogens is substituted by a 4-chloro-3-trifluorophenyl group while the other is substituted by a phenyl group which, in turn, is substituted at the para position by a [2-(methylcarbamoyl)pyridin-4-yl]oxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:47228
Supplier Information ChemicalBook:CB9319046, eMolecules:883948
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2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C3H8O2 that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer: C2H5O+ + CH3OH → C3H8O2 + H+ 2-Methoxyethanol is used as a solvent for many different purposes such as varnishes, dyes, and resins. It is also used as an additive in airplane deicing solutions. In organometallic chemistry it is commonly used for the synthesis of Vaska's complex and related compounds such as carbonylchlorohydridotris(triphenylphosphine)ruthenium (II). During these reactions the alcohol acts as a source of hydride and carbon monoxide. 2-Methoxyethanol is toxic to the bone marrow and testicles. Workers exposed to high levels are at risk for granulocytopenia, macrocytic anemia, oligospermia, and azoospermia. The methoxyethanol is converted by alcohol dehydrogenase into methoxyacetic acid which is the substance which causes the harmful effects. Both ethanol and acetate have a protecting effect. The methoxyacetate can enter the Krebs cycle where it forms methoxycitrate.
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Formula C21H16ClF3N4O3
Net Charge 0
Average Mass 464.826
Monoisotopic Mass 464.08630
InChI InChI=1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31)
InChIKey MLDQJTXFUGDVEO-UHFFFAOYSA-N
SMILES C1(=C(C=C(C=C1)NC(NC2=CC=C(C=C2)OC3=CC=NC(=C3)C(NC)=O)=O)C(F)(F)F)Cl
Roles Classification
Biological Role(s): EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of non-specific serine/threonine protein kinase (EC 2.7.11.1), a kinase enzyme involved in phosphorylation of hydroxy group of serine or threonine.
tyrosine kinase inhibitor
Any protein kinase inhibitor that interferes with the action of tyrosine kinase.
anticoronaviral agent
Any antiviral agent which inhibits the activity of coronaviruses.
ferroptosis inducer
Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
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ChEBI Ontology
Outgoing sorafenib (CHEBI:50924) has role angiogenesis inhibitor (CHEBI:48422)
sorafenib (CHEBI:50924) has role anticoronaviral agent (CHEBI:149553)
sorafenib (CHEBI:50924) has role antineoplastic agent (CHEBI:35610)
sorafenib (CHEBI:50924) has role EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor (CHEBI:50925)
sorafenib (CHEBI:50924) has role ferroptosis inducer (CHEBI:173085)
sorafenib (CHEBI:50924) has role tyrosine kinase inhibitor (CHEBI:38637)
sorafenib (CHEBI:50924) is a (trifluoromethyl)benzenes (CHEBI:83565)
sorafenib (CHEBI:50924) is a aromatic ether (CHEBI:35618)
sorafenib (CHEBI:50924) is a monochlorobenzenes (CHEBI:83403)
sorafenib (CHEBI:50924) is a phenylureas (CHEBI:134043)
sorafenib (CHEBI:50924) is a pyridinecarboxamide (CHEBI:25529)
Incoming sorafenib tosylate (CHEBI:50928) has part sorafenib (CHEBI:50924)
IUPAC Name
4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-N-methylpyridine-2-carboxamide
INNs Sources
sorafenib WHO MedNet
sorafénib WHO MedNet
sorafenib WHO MedNet
sorafenibum WHO MedNet
Synonyms Sources
4-(4-((((4-Chloro-3-(trifluoromethyl)phenyl)amino)carbonyl)amino)phenoxy)-N-methyl-2-pyridinecarboxamide ChemIDplus
N-(4-Chloro-3-(trifluoromethyl)phenyl)-N'-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea ChemIDplus
Manual Xrefs Databases
2459 DrugCentral
BAX PDBeChem
D08524 KEGG DRUG
DB00398 DrugBank
LSM-1008 LINCS
Sorafenib Wikipedia
View more database links
Registry Number Type Source
284461-73-0 CAS Registry Number ChemIDplus
Citations Types Sources
18520294 PubMed citation Europe PMC
19568496 PubMed citation Europe PMC
19633425 PubMed citation Europe PMC
19821497 PubMed citation Europe PMC
36029544 PubMed citation Europe PMC
Last Modified
05 September 2022