erlotinib (CHEBI:114785)

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CHEBI:114785 - erlotinib

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ChEBI Name	erlotinib

ChEBI ID	CHEBI:114785

Definition	A quinazoline compound having a (3-ethynylphenyl)amino group at the 4-position and two 2-methoxyethoxy groups at the 6- and 7-positions.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:40877

Supplier Information	ChemicalBook:CB22566418, Selleckchem:pf299804, ZINC000072266312

Download	Molfile XML SDF

more structures >>

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Marvin 09130717253D

52 54 0 0 0 0 999 V2000

-1.8080 -1.7250 -7.3140 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0440 -1.0880 -6.6910 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1110 -0.3110 -5.9320 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1600 -0.3250 -4.5380 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7410 0.4340 -3.8100 C 0 0 0 0 0 0 0 0 0 0 0 0

0.6920 0.4290 -2.4120 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.5190 0.2940 -1.7650 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5800 0.1680 -0.3570 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5710 0.1760 0.4380 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4580 0.0580 1.7940 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5780 0.0650 2.5650 O 0 0 0 0 0 0 0 0 0 0 0 0

2.6890 0.2070 1.6780 C 0 0 0 0 0 0 0 0 0 0 0 0

3.9880 0.2220 2.4870 C 0 0 0 0 0 0 0 0 0 0 0 0

4.1120 -1.0010 3.2130 O 0 0 0 0 0 0 0 0 0 0 0 0

5.3380 -0.9260 3.9430 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7980 -0.0820 2.3980 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.8840 -0.2030 3.7490 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.2730 -0.3210 4.0650 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.4410 -0.4620 5.5790 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9010 0.6900 6.2270 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.0880 0.4990 7.6310 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9470 -0.0920 1.6380 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8550 0.0330 0.2470 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.9430 0.0300 -0.5370 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.8260 0.1490 -1.8380 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.6570 0.2780 -2.4460 N 0 0 0 0 0 0 0 0 0 0 0 0

1.6980 1.1980 -4.4690 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7500 1.2070 -5.8490 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8530 0.4580 -6.5840 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.4920 -2.2950 -7.8710 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9040 -0.9190 -4.0280 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5090 0.5200 -1.8980 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5450 0.2780 -0.0180 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5950 1.1410 1.1240 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7060 -0.6290 0.9800 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9720 1.0590 3.1850 H 0 0 0 0 0 0 0 0 0 0 0 0

4.8360 0.3310 1.8100 H 0 0 0 0 0 0 0 0 0 0 0 0

5.4760 -1.8430 4.5160 H 0 0 0 0 0 0 0 0 0 0 0 0

6.1680 -0.8030 3.2480 H 0 0 0 0 0 0 0 0 0 0 0 0

5.3040 -0.0750 4.6230 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6850 -1.2010 3.5700 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8010 0.5680 3.7220 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9140 -1.3520 5.9220 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5000 -0.5520 5.8200 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6890 1.3590 8.1710 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1510 0.3970 7.8460 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5650 -0.4020 7.9480 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9110 -0.1960 2.1120 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7220 0.1420 -2.4400 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4030 1.7860 -3.8990 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4960 1.8010 -6.3560 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8960 0.4680 -7.6630 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 3 0 0 0 0

1 30 1 0 0 0 0

2 3 1 0 0 0 0

3 4 4 0 0 0 0

3 29 4 0 0 0 0

4 5 4 0 0 0 0

4 31 1 0 0 0 0

5 6 1 0 0 0 0

5 27 4 0 0 0 0

6 7 1 0 0 0 0

6 32 1 0 0 0 0

7 8 4 0 0 0 0

7 26 4 0 0 0 0

8 9 4 0 0 0 0

8 23 4 0 0 0 0

9 10 4 0 0 0 0

9 33 1 0 0 0 0

10 11 1 0 0 0 0

10 16 4 0 0 0 0

11 12 1 0 0 0 0

12 13 1 0 0 0 0

12 34 1 0 0 0 0

12 35 1 0 0 0 0

13 14 1 0 0 0 0

13 36 1 0 0 0 0

13 37 1 0 0 0 0

14 15 1 0 0 0 0

15 38 1 0 0 0 0

15 39 1 0 0 0 0

15 40 1 0 0 0 0

16 17 1 0 0 0 0

16 22 4 0 0 0 0

17 18 1 0 0 0 0

18 19 1 0 0 0 0

18 41 1 0 0 0 0

18 42 1 0 0 0 0

19 20 1 0 0 0 0

19 43 1 0 0 0 0

19 44 1 0 0 0 0

20 21 1 0 0 0 0

21 45 1 0 0 0 0

21 46 1 0 0 0 0

21 47 1 0 0 0 0

22 23 4 0 0 0 0

22 48 1 0 0 0 0

23 24 4 0 0 0 0

24 25 4 0 0 0 0

25 26 4 0 0 0 0

25 49 1 0 0 0 0

27 28 4 0 0 0 0

27 50 1 0 0 0 0

28 29 4 0 0 0 0

28 51 1 0 0 0 0

29 52 1 0 0 0 0

M END): 26 ms

reading 52 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

52 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Dacomitinib, sold under the brand name Vizimpro, is a medication for the treatment of non-small-cell lung carcinoma (NSCLC). It is a selective and irreversible inhibitor of EGFR. Dacomitinib has advanced to several Phase III clinical trials. In January 2014, results of the first trials were disappointing, with a failure to meet the study goals, but additional Phase III trials continued. In 2017, results of a trial comparing dacomitinib to gefitinib for NSCLC (driven by mutated EGFR) were announced. Dacomitinib was approved for medical use in the United States in September 2018, in Japan in 2019, and in the European Union in 2019; for the treatment of non-small cell lung cancer with epidermal growth factor receptor (EGFR) gene mutation.
Read full article at Wikipedia

Formula

C22H23N3O4

Net Charge

Average Mass

393.43570

Monoisotopic Mass

393.16886

InChI

InChI=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)

InChIKey

AAKJLRGGTJKAMG-UHFFFAOYSA-N

SMILES

COCCOc1cc2ncnc(Nc3cccc(c3)C#C)c2cc1OCCOC

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	protein kinase inhibitor An EC 2.7.* (P-containing group transferase) inhibitor that interferes with the action of protein kinases. epidermal growth factor receptor antagonist An antagonist at the epidermal growth factor receptor.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	erlotinib (CHEBI:114785) has role antineoplastic agent (CHEBI:35610) erlotinib (CHEBI:114785) has role epidermal growth factor receptor antagonist (CHEBI:74440) erlotinib (CHEBI:114785) has role protein kinase inhibitor (CHEBI:37699) erlotinib (CHEBI:114785) is a aromatic ether (CHEBI:35618) erlotinib (CHEBI:114785) is a quinazolines (CHEBI:38530) erlotinib (CHEBI:114785) is a secondary amino compound (CHEBI:50995) erlotinib (CHEBI:114785) is a terminal acetylenic compound (CHEBI:73477)

Incoming	erlotinib hydrochloride (CHEBI:53509) has part erlotinib (CHEBI:114785)

IUPAC Name

N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine

INNs	Sources
erlotinib	WHO MedNet
erlotinib	WHO MedNet
erlotinibum	WHO MedNet

Synonyms	Sources
[6,7-bis(2-methoxy-ethoxy)quinazoline-4-yl]-(3-ethynylphenyl)amine	PDBeChem
[6,7-bis-(2-methoxy-ethoxy)-quinazolin-4-yl]-(3-ethynyl-phenyl)-amine	DrugBank

Manual Xrefs	Databases
1045	DrugCentral
AQ4	PDBeChem
D07907	KEGG DRUG
DB00530	DrugBank
Erlotinib	Wikipedia
HMDB0014671	HMDB
LSM-1097	LINCS
US2010094004	Patent
View more database links

Registry Numbers	Types	Sources
183321-74-6	CAS Registry Number	ChemIDplus
183321-74-6	CAS Registry Number	DrugBank
183321-74-6	CAS Registry Number	KEGG DRUG
8798958	Reaxys Registry Number	Reaxys

Citations	Types	Sources
12270171	PubMed citation	ChEMBL
14684309	PubMed citation	ChEMBL
15711537	PubMed citation	ChEMBL
16014882	PubMed citation	Europe PMC
16014883	PubMed citation	Europe PMC
16236747	PubMed citation	Europe PMC
16240471	PubMed citation	Europe PMC
16240472	PubMed citation	Europe PMC
16480284	PubMed citation	ChEMBL
17889528	PubMed citation	ChEMBL
17983745	PubMed citation	ChEMBL
21675909	PubMed citation	Europe PMC
21793762	PubMed citation	Europe PMC
29448920	PubMed citation	Europe PMC
29579331	PubMed citation	Europe PMC
29687154	PubMed citation	Europe PMC
30039303	PubMed citation	Europe PMC
30071517	PubMed citation	Europe PMC
30150014	PubMed citation	Europe PMC
30158288	PubMed citation	Europe PMC

Last Modified

28 September 2018

CHEBI:114785 - erlotinib

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