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Details

Stereochemistry ACHIRAL
Molecular Formula C24H18ClFN4O2
Molecular Weight 448.8776
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALLITINIB

SMILES

C=CC(=Nc1ccc2c(c1)c(ncn2)Nc3ccc(c(c3)Cl)OCc4cccc(c4)F)O

InChI

InChIKey=MVZGYPSXNDCANY-UHFFFAOYSA-N
InChI=1S/C24H18ClFN4O2/c1-2-23(31)29-17-6-8-21-19(11-17)24(28-14-27-21)30-18-7-9-22(20(25)12-18)32-13-15-4-3-5-16(26)10-15/h2-12,14H,1,13H2,(H,29,31)(H,27,28,30)

HIDE SMILES / InChI

Molecular Formula C24H18ClFN4O2
Molecular Weight 448.8776
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/24612546 | http://adisinsight.springer.com/drugs/800032292

AST-1306, also known as Allitinib, is an orally active potent, selective, irreversible inhibitor of the HER family of receptor tyrosine kinases. AST-1306 inhibits the enzymatic activities of wild-type epidermal growth factor receptor (EGFR) and ErbB2 as well as EGFR resistant mutant in both cell-free and cell-based systems. AST1306 potently suppressed tumor growth in ErbB2-overexpressing adenocarcinoma xenograft and FVB-2/N(neu) transgenic breast cancer mouse models. Allitinib is in Phase I clinical trial for the treatment of advanced solid tumors. Serious adverse effects detected were: diarrhea, dehydration and hyperbilirubinemia.

Originator

Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/21789172

Approval Year

PubMed

PubMed

TitleDatePubMed
AST1306, a potent EGFR inhibitor, antagonizes ATP-binding cassette subfamily G member 2-mediated multidrug resistance.
2014 Aug 1
Repositioning of Tyrosine Kinase Inhibitors as Antagonists of ATP-Binding Cassette Transporters in Anticancer Drug Resistance.
2014 Sep 29
Cytotoxicity of allitinib, an irreversible anti-EGFR agent, in a large panel of human cancer-derived cell lines: KRAS mutation status as a predictive biomarker.
2016 Jun
Patents

Sample Use Guides

1000 mg three times daily
Route of Administration: Oral
The Calu-3 lung adenocarcinoma and BT474 breast cancer cell line, containing high levels of ErbB2, were more sensitive to AST1306, with IC50 values of 0.23 and 0.97 uM/L, respectively.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:50:39 UTC 2021
Edited
by admin
on Fri Jun 25 20:50:39 UTC 2021
Record UNII
CX0M5RO7CY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALLITINIB
Common Name English
AST1306
Common Name English
N-(4-((3-CHLORO-4-((3-FLUOROBENZYL)OXY)PHENYL)AMINO)QUINAZOLIN-6-YL)ACRYLAMIDE
Systematic Name English
ALS 1306
Common Name English
AST 1306
Common Name English
2-PROPENAMIDE, N-(4-((3-CHLORO-4-((3-FLUOROPHENYL)METHOXY)PHENYL)AMINO)-6-QUINAZOLINYL)-
Systematic Name English
N-(4-((3-CHLORO-4-((3-FLUOROPHENYL)METHOXY)PHENYL)AMINO)-6-QUINAZOLINYL)-2-PROPENAMIDE
Systematic Name English
Code System Code Type Description
FDA UNII
CX0M5RO7CY
Created by admin on Fri Jun 25 20:50:39 UTC 2021 , Edited by admin on Fri Jun 25 20:50:39 UTC 2021
PRIMARY
PUBCHEM
24739943
Created by admin on Fri Jun 25 20:50:39 UTC 2021 , Edited by admin on Fri Jun 25 20:50:39 UTC 2021
PRIMARY
NCI_THESAURUS
C179280
Created by admin on Fri Jun 25 20:50:39 UTC 2021 , Edited by admin on Fri Jun 25 20:50:39 UTC 2021
PRIMARY
CAS
897383-62-9
Created by admin on Fri Jun 25 20:50:39 UTC 2021 , Edited by admin on Fri Jun 25 20:50:39 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
irreversible selective inhibitor
IRREVERSIBLE INHIBITOR
IC50
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TARGET -> INHIBITOR
irreversible selective inhibitor
IRREVERSIBLE INHIBITOR
IC50
EXCRETED UNCHANGED
FECAL
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC AT DAY 1

IN CANCER PATIENTS

THREE TIMES A DAY

ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC IN CANCER PATIENTS

AT DAY 24

THREE TIMES A DAY FOR 21 DAYS

ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC THREE TIMES A DAY

IN CANCER PATIENTS

AT DAY 1

ORAL ADMINISTRATION

Tmax PHARMACOKINETIC IN CANCER PATIENTS

AT DAY 24

THREE TIMES A DAY FOR 21 DAYS

ORAL ADMINISTRATION