Erlotinib (CED0001402)

Record Information
Version1.0
Creation Date2016-05-22 05:45:11 UTC
Update Date2026-08-21 22:03:39 UTC
Accession NumberCHEM019004
Identification
Common NameErlotinib
ClassSmall Molecule
Description
Erlotinib is an organic compound with the formula C22H23N3O4 and an average molecular weight of 393.44 g/mol. Erlotinib belongs to the benzodiazines, a subclass of diazanaphthalenes within the organic compounds. It acts as an agonist/antagonist of the Nuclear receptor subfamily 1 group I member 2 (NR1I2) and the Epidermal growth factor receptor (EGFR). The compound is used as a treatment for cancer (PMC9607420), specifically lung cancer (PMC4512945), pancreatic cancer (PMC11791747), and glioblastoma (PMC6424348). Exposure to erlotinib is associated with rash (PMC13084601, PMC2935905). Erlotinib is found in or released from six recorded sources, including antineoplastic agents within healthcare, pharmaceuticals, and veterinary products. Other sources include indoor air via air, dust, and atmospheric transport; television systems within electrical and electronic equipment; the preparation of malt in food, food processing, and cookware; and consumer products and household cleaning items such as soap dispensers and non-electric simulated smoking devices. Recorded exposure routes for this compound include oral and inhalation.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
[6,7-Bis(2-methoxy-ethoxy)quinazoline-4-yl]-(3-ethynylphenyl)amineChEBI
[6,7-Bis-(2-methoxy-ethoxy)-quinazolin-4-yl]-(3-ethynyl-phenyl)-amineChEBI
ErlotinibumChEBI
OSI-774HMDB
11C ErlotinibHMDB
HCL, ErlotinibHMDB
Hydrochloride, erlotinibHMDB
N-(3-Ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amineHMDB
OSI 774HMDB
Erlotinib hydrochlorideHMDB
11C-ErlotinibHMDB
TarcevaHMDB
Erlotinib HCLHMDB
Chemical FormulaC22H23N3O4
Average Molecular Mass393.436 g/mol
Monoisotopic Mass393.169 g/mol
CAS Registry Number183321-74-6
IUPAC NameN-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine
Traditional Nameerlotinib
SMILESCOCCOC1=C(OCCOC)C=C2C(NC3=CC=CC(=C3)C#C)=NC=NC2=C1
InChI IdentifierInChI=1S/C22H23N3O4/c1-4-16-6-5-7-17(12-16)25-22-18-13-20(28-10-8-26-2)21(29-11-9-27-3)14-19(18)23-15-24-22/h1,5-7,12-15H,8-11H2,2-3H3,(H,23,24,25)
InChI KeyAAKJLRGGTJKAMG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentQuinazolinamines
Alternative Parents
Substituents
  • Quinazolinamine
  • Aniline or substituted anilines
  • Alkyl aryl ether
  • Aminopyrimidine
  • Monocyclic benzene moiety
  • Pyrimidine
  • Benzenoid
  • Imidolactam
  • Heteroaromatic compound
  • Dialkyl ether
  • Ether
  • Acetylide
  • Secondary amine
  • Azacycle
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0089 g/LALOGPS
logP3.13ALOGPS
logP3.2ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)16.14ChemAxon
pKa (Strongest Basic)4.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.73 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity107.79 m³·mol⁻¹ChemAxon
Polarizability43.48 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-002k-2129000000-90a20b25b74b231ffec1Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-0faffd4c59a79313872fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-4019000000-3b47513e20a5bfacb8f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-07fr-3092000000-09a2b2602ea3efd921bcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-0009000000-0e3a84b624af3648dfc4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0089-0049000000-7d705f21b90db0f6f3caNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1192000000-6d6a8f8831beb774d61cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f7o-0019000000-98c0248bef3527a16545Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fkc-0095000000-b346f0645c009b0dbd23Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uk9-2098000000-c15ff6cb37269237da44Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-cab9b4eadff55f06446dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-0009000000-576d45602f85d8bf2186Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1079000000-e0507c536b38d89e26b1Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1384.0Log mg/kg[780:2500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
lung canceris_treatment_forNot AvailablePMC4512945
canceris_treatment_forNot AvailablePMC9607420
glioblastomais_treatment_forNot AvailablePMC6424348
rashassociated_withNot AvailablePMC13084601 , PMC2935905
pancreatic canceris_treatment_forNot AvailablePMC11791747
head and neck canceris_treatment_forNot AvailablePMC9910008
cholangiocarcinomais_treatment_forNot AvailablePMC6394015
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
Pathways
3 pathways
Erlotinib Action Pathway
Erlotinib Action Pathway
Erlotinib Action Pathway (New)
Erlotinib Action Pathway (New)
Erlotinib Drug Metabolism Action Pathway
Erlotinib Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)0.0778492
Receptor tyrosine-protein kinase erbB-2 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-2P04626HumansPredicted (SEA)0.622794
Cyclin-G-associated kinase structureClick to view 3D structureCyclin-G-associated kinaseO14976HumansPredicted (SEA)0.0778492
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)12.3002
Proto-oncogene tyrosine-protein kinase receptor Ret structureClick to view 3D structureProto-oncogene tyrosine-protein kinase receptor RetP07949HumansPredicted (SEA)3.03612
Receptor-interacting serine/threonine-protein kinase 2 structureClick to view 3D structureReceptor-interacting serine/threonine-protein kinase 2O43353HumansPredicted (SEA)0.389246
Tyrosine-protein kinase ABL1 structureClick to view 3D structureTyrosine-protein kinase ABL1P00519HumansPredicted (SEA)9.03051
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)17.4382
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)12.7673
Broad substrate specificity ATP-binding cassette transporter ABCG2 structureClick to view 3D structureBroad substrate specificity ATP-binding cassette transporter ABCG2Q9UNQ0HumansPredicted (SEA)0.778492
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)22.6541
Dual specificity protein kinase CLK1 structureClick to view 3D structureDual specificity protein kinase CLK1P49759HumansPredicted (SEA)2.25763
Mitogen-activated protein kinase kinase kinase 1 structureClick to view 3D structureMitogen-activated protein kinase kinase kinase 1Q13233HumansPredicted (SEA)0.155698
MAP kinase-interacting serine/threonine-protein kinase 1 structureClick to view 3D structureMAP kinase-interacting serine/threonine-protein kinase 1Q9BUB5HumansPredicted (SEA)1.40129
Vascular endothelial growth factor receptor 1 structureClick to view 3D structureVascular endothelial growth factor receptor 1P17948HumansPredicted (SEA)12.2223
Ephrin type-B receptor 2 structureClick to view 3D structureEphrin type-B receptor 2P29323HumansPredicted (SEA)0.778492
STE20-like serine/threonine-protein kinase structureClick to view 3D structureSTE20-like serine/threonine-protein kinaseQ9H2G2HumansPredicted (SEA)4.98235
Tyrosine-protein kinase Lyn structureClick to view 3D structureTyrosine-protein kinase LynP07948HumansPredicted (SEA)13.5458
Click to view 3D structureFructose-1,6-bisphosphatase 1P19112Rattus norvegicusPredicted (SEA)1.16774
Click to view 3D structureFructose-1,6-bisphosphatase 1P00636Sus scrofaPredicted (SEA)1.01204
Fructose-1,6-bisphosphatase 1 structureClick to view 3D structureFructose-1,6-bisphosphatase 1P09467HumansPredicted (SEA)1.16774
Leucine-rich repeat serine/threonine-protein kinase 2 structureClick to view 3D structureLeucine-rich repeat serine/threonine-protein kinase 2Q5S007HumansPredicted (SEA)4.51525
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)14.3243
Serine/threonine-protein kinase 10 structureClick to view 3D structureSerine/threonine-protein kinase 10O94804HumansPredicted (SEA)1.63483
Tyrosine-protein kinase JAK3 structureClick to view 3D structureTyrosine-protein kinase JAK3P52333HumansPredicted (SEA)22.187
Concentrations
Not Available
External Links
DrugBank IDDB00530
HMDB IDHMDB0014671
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDAQ4
Wikipedia LinkErlotinib
Chemspider ID154044
ChEBI ID114785
PubChem Compound ID176870
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Blum G, Gazit A, Levitzki A: Substrate competitive inhibitors of IGF-1 receptor kinase. Biochemistry. 2000 Dec 26;39(51):15705-12.
2. Raymond E, Faivre S, Armand JP: Epidermal growth factor receptor tyrosine kinase as a target for anticancer therapy. Drugs. 2000;60 Suppl 1:15-23; discussion 41-2.
3. Jones HE, Goddard L, Gee JM, Hiscox S, Rubini M, Barrow D, Knowlden JM, Williams S, Wakeling AE, Nicholson RI: Insulin-like growth factor-I receptor signalling and acquired resistance to gefitinib (ZD1839; Iressa) in human breast and prostate cancer cells. Endocr Relat Cancer. 2004 Dec;11(4):793-814.
4. Dudek AZ, Kmak KL, Koopmeiners J, Keshtgarpour M: Skin rash and bronchoalveolar histology correlates with clinical benefit in patients treated with gefitinib as a therapy for previously treated advanced or metastatic non-small cell lung cancer. Lung Cancer. 2006 Jan;51(1):89-96. Epub 2005 Nov 14.
5. Li Z, Xu M, Xing S, Ho WT, Ishii T, Li Q, Fu X, Zhao ZJ: Erlotinib effectively inhibits JAK2V617F activity and polycythemia vera cell growth. J Biol Chem. 2007 Feb 9;282(6):3428-32. Epub 2006 Dec 18.
6. Lansiaux A, Bailly C: [Perspectives on the oncologist pharmacopoeia]. Bull Cancer. 2003 Jan;90(1):25-30.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=12270171
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=14684309
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15711537
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16014882
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16014883
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=16236747
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=16240471
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=16240472
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=16480284
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=17889528
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=17983745
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=21675909
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=21793762
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=29448920
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=29579331
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=29687154
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=30039303
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=30071517
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=30150014
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=30158288