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version 2.5
Substance Class Chemical
Record UNII
2XJX250C20
Record Status Validated (UNII)
Record Version
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Details

Stereochemistry ACHIRAL
Molecular Formula C24H25ClFN5O2
Molecular Weight 469.939
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0
Created by admin on Thu Mar 26 00:45:47 EDT 2020
Edited by admin on Thu Mar 26 00:45:47 EDT 2020
Structure of DACOMITINIB ANHYDROUS

Systematic Names:

  • None recorded
  • {{name}}

SMILES

COC1=C(NC(=O)\C=C\CN2CCCCC2)C=C3C(NC4=CC=C(F)C(Cl)=C4)=NC=NC3=C1

InChI

LVXJQMNHJWSHET-AATRIKPKSA-N
InChI=1S/C24H25ClFN5O2/c1-33-22-14-20-17(24(28-15-27-20)29-16-7-8-19(26)18(25)12-16)13-21(22)30-23(32)6-5-11-31-9-3-2-4-10-31/h5-8,12-15H,2-4,9-11H2,1H3,(H,30,32)(H,27,28,29)/b6-5+
Name Type Language Details References
DACOMITINIB ANHYDROUS
Common Name
English  
(2E)-N-(4-((3-CHLORO-4-FLUOROPHENYL)AMINO)-7-METHOXYQUINAZOLIN-6-YL)-4-PIPERIDIN-1-YLBUT-2-ENAMIDE
Systematic Name
English  
DACOMITINIB [WHO-DD]
Common Name
English  
PF-00299804
Code
English  
DACOMITINIB [INN]
Common Name
English  
Code System Code Type Description References
INN
9314
Created by admin on Thu Mar 26 00:45:47 EDT 2020 , Edited by admin on Thu Mar 26 00:45:47 EDT 2020
PRIMARY
CAS
1110813-31-4
Created by admin on Thu Mar 26 00:45:47 EDT 2020 , Edited by admin on Thu Mar 26 00:45:47 EDT 2020
PRIMARY
RXCUI
2058848
Created by admin on Thu Mar 26 00:45:47 EDT 2020 , Edited by admin on Thu Mar 26 00:45:47 EDT 2020
PRIMARY
PUBCHEM
11511120
Created by admin on Thu Mar 26 00:45:47 EDT 2020 , Edited by admin on Thu Mar 26 00:45:47 EDT 2020
PRIMARY
EPA CompTox
1110813-31-4
Created by admin on Thu Mar 26 00:45:47 EDT 2020 , Edited by admin on Thu Mar 26 00:45:47 EDT 2020
PRIMARY
Related Record Type Details References
TARGET -> INHIBITOR
Mediator Substance Details
none
IRREVERSIBLE INHIBITOR
Created by admin on Thu Mar 26 00:45:59 EDT 2020 , Edited by admin on Thu Mar 26 00:45:59 EDT 2020
TRANSPORTER -> INHIBITOR
Mediator Substance Details
none
BINDING
The reversal effect on ABCB1-overexpressing cells is more potent than that on ABCG2-overexpressing cells. Dacomitinib at 1.0€?M significantly reversed drug resistance mediated by ABCB1 and ABCG2, but not ABCC1, doing so by antagonizing the drug efflux function in ABCB1- and ABCG2-overexpressing cell lines.
MAY BE CLINICALLY SIGNIFICANT
Created by admin on Thu Mar 26 00:45:47 EDT 2020 , Edited by admin on Thu Mar 26 00:45:47 EDT 2020
TRANSPORTER -> INHIBITOR
Mediator Substance Details
none
BINDING
The reversal effect on ABCB1-overexpressing cells is more potent than that on ABCG2-overexpressing cells. Dacomitinib at 1.0€?M significantly reversed drug resistance mediated by ABCB1 and ABCG2, but not ABCC1, doing so by antagonizing the drug efflux function in ABCB1- and ABCG2-overexpressing cell lines.
MAY BE CLINICALLY SIGNIFICANT
Created by admin on Thu Mar 26 00:45:47 EDT 2020 , Edited by admin on Thu Mar 26 00:45:47 EDT 2020
METABOLIC ENZYME -> SUBSTRATE
Mediator Substance Details
none
IN-VITRO
Created by admin on Thu Mar 26 00:45:48 EDT 2020 , Edited by admin on Thu Mar 26 00:45:48 EDT 2020
METABOLIC ENZYME -> SUBSTRATE
Mediator Substance Details
none
IN-VITRO
Created by admin on Thu Mar 26 00:45:56 EDT 2020 , Edited by admin on Thu Mar 26 00:45:56 EDT 2020
SALT/SOLVATE -> PARENT
none
none
Mediator Substance Details
none
Created by admin on Thu Mar 26 00:45:59 EDT 2020 , Edited by admin on Thu Mar 26 00:45:59 EDT 2020
Related Record Type Details References
METABOLITE -> PARENT
Mediator Substance Details
none
MINOR
FECAL
Created by admin on Thu Mar 26 00:45:48 EDT 2020 , Edited by admin on Thu Mar 26 00:45:48 EDT 2020
METABOLITE -> PARENT
Mediator Substance Details
none
MAJOR
In addition, it is likely that dacomitinib underwent glutathione conjugation with subsequent hydrolysis to form the cysteine conjugate (M2).
FECAL
Created by admin on Thu Mar 26 00:45:59 EDT 2020 , Edited by admin on Thu Mar 26 00:45:59 EDT 2020
METABOLITE -> PARENT
Mediator Substance Details
none
MINOR
FECAL
Created by admin on Thu Mar 26 00:45:59 EDT 2020 , Edited by admin on Thu Mar 26 00:45:59 EDT 2020
METABOLITE ACTIVE -> PARENT
Mediator Substance Details
none
MAJOR
Concentrations of PF-05199265 peaked at 6 h post-dose.
PLASMA
Created by admin on Thu Mar 26 00:45:59 EDT 2020 , Edited by admin on Thu Mar 26 00:45:59 EDT 2020
METABOLITE ACTIVE -> PARENT
Mediator Substance Details
none
MAJOR
FECAL; PLASMA
Created by admin on Thu Mar 26 00:45:59 EDT 2020 , Edited by admin on Thu Mar 26 00:45:59 EDT 2020
METABOLITE ACTIVE -> PARENT
Mediator Substance Details
none
MAJOR
Fecal homogenate extracts indicated that metabolism of [14C] dacomitinib was similar and extensive in all the 6 subjects. The four most abundant drugrelated components were dacomitinib (20 %), PF-05199265 (20 %), a cysteine conjugate (M2; 9.5 %), and a monooxygenated metabolite (M7; 5.1 %)
FECAL
Created by admin on Thu Mar 26 00:45:59 EDT 2020 , Edited by admin on Thu Mar 26 00:45:59 EDT 2020
Related Record Type Details References
ACTIVE MOIETY
none
none
Mediator Substance Details
none
Created by admin on Thu Mar 26 00:45:59 EDT 2020 , Edited by admin on Thu Mar 26 00:45:59 EDT 2020
Note References
[Validation]WARNING:Structure has 1 possible duplicate:
[5092U85G58]DACOMITINIB
Created Thu Mar 26 00:45:47 EDT 2020
Created By admin
Last Edited Thu Mar 26 00:45:47 EDT 2020
Last Edited By admin
Index Source Text / Citation Source Type Tags Date Accessed File
1 SYSTEM
2 SRS import [2XJX250C20] SRS NOMEN Fri Apr 28 14:31:56 EDT 2017
3 Generated from relationship on:'EPIDERMAL GROWTH FACTOR RECEPTOR' SYSTEM
4 JA
5 INN 2010 SRS NOMEN
6 USAN COUN 2011 SRS NOMEN
7 SRS CODE IMPORT SRS NOMEN Fri Apr 28 14:31:56 EDT 2017
8 STN STN (SCIFINDER)
9 GSRS System-generated Validation messages VALIDATION_MESSAGE Thu Mar 26 00:45:44 EDT 2020
10 WHO-DD SRS NOMEN
11 WEBSITE WEBSITE NOMEN PUBLIC_DOMAIN_RELEASE
12 CANCER CHEMOTHERAPY AND PHARMACOLOGY \\nAUGUST 2013, VOLUME 72, ISSUE 2, PP 379-385 JOURNAL ARTICLE NOMEN
13 CANCER CHEMOTHER PHARMACOL (2013) 72:379?385 JOURNAL ARTICLE NOMEN
14 RXNORM NLM
15 GSRS System-generated Validation messages VALIDATION_MESSAGE Thu Mar 26 00:45:44 EDT 2020
16 INN SRS NOMEN PUBLIC_DOMAIN_RELEASE AUTO_SELECTED
17 CANCER CHEMOTHER PHARMACOL (2013) 72:379?385 JOURNAL ARTICLE NOMEN
18 C.-S. TAN ET AL. / LUNG CANCER 93 (2016) 59?68 JOURNAL ARTICLE NOMEN

Molecular Formula C24H25ClFN5O2
Molecular Weight 469.939
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE