Erlotinib (CHEM019004)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:45:11 UTC
Update Date2026-03-27 00:37:58 UTC
Accession NumberCHEM019004
Identification
Common NameErlotinib
ClassSmall Molecule
DescriptionErlotinib is an inhibitor of the epidermal growth factor receptor (EGFR) tyrosine kinase that is used in the treatment of non-small cell lung cancer, pancreatic cancer and several other types of cancer. It is typically marketed under the trade name Tarceva. Erlotinib binds to the epidermal growth factor receptor (EGFR) tyrosine kinase in a reversible fashion at the adenosine triphosphate (ATP) binding site of the receptor. Recent studies demonstrate that erlotinib is also a potent inhibitor of JAK2V617F, which is a mutant form of tyrosine kinase JAK2 found in most patients with polycythemia vera (PV) and a substantial proportion of patients with idiopathic myelofibrosis or essential thrombocythemia. This finding introduces the potential use of erlotinib in the treatment of JAK2V617F-positive PV and other myeloproliferative disorders.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002k-2129000000-90a20b25b74b231ffec1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-0faffd4c59a79313872fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-4019000000-3b47513e20a5bfacb8f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07fr-3092000000-09a2b2602ea3efd921bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-0009000000-0e3a84b624af3648dfc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-0049000000-7d705f21b90db0f6f3caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1192000000-6d6a8f8831beb774d61cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f7o-0019000000-98c0248bef3527a16545Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fkc-0095000000-b346f0645c009b0dbd23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-2098000000-c15ff6cb37269237da44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-cab9b4eadff55f06446dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0009000000-576d45602f85d8bf2186Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1079000000-e0507c536b38d89e26b1Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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