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Details

Stereochemistry ACHIRAL
Molecular Formula C22H18N4OS
Molecular Weight 386.47
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AXITINIB

SMILES

CNC(=O)C1=CC=CC=C1SC2=CC3=C(C=C2)C(\C=C\C4=CC=CC=N4)=NN3

InChI

InChIKey=RITAVMQDGBJQJZ-FMIVXFBMSA-N
InChI=1S/C22H18N4OS/c1-23-22(27)18-7-2-3-8-21(18)28-16-10-11-17-19(25-26-20(17)14-16)12-9-15-6-4-5-13-24-15/h2-14H,1H3,(H,23,27)(H,25,26)/b12-9+

HIDE SMILES / InChI
Molecular Formula C22H18N4OS
Molecular Weight 386.47
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Axitinib (trade name Inlyta) is a small molecule tyrosine kinase inhibitor developed by Pfizer. It has been shown to significantly inhibit growth of breast cancer in animal (xenograft) models and has shown partial responses in clinical trials with renal cell carcinoma (RCC) and several other tumour types. Axitinib has been shown to inhibit receptor tyrosine kinases including vascular endothelial growth factor receptors (VEGFR)-1, VEGFR-2, and VEGFR-3 at therapeutic plasma concentrations. These receptors are implicated in pathologic angiogenesis, tumor growth, and cancer progression. VEGF-mediated endothelial cell proliferation and survival were inhibited by axitinib in vitro and in mouse models. It was approved by the U.S. Food and Drug Administration.

CNS Activity

Originator

Approval Year

2012
68
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7464
Carcinoma, Renal Cell
 0.1 nM [IC50]
Inhibitor
7464
Carcinoma, Renal Cell
 0.3 nM [IC50]
Inhibitor
7464
Carcinoma, Renal Cell
 0.2 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Vascular endothelial growth factor receptor 3
Vascular endothelial growth factor receptor 2
Vascular endothelial growth factor receptor 1
Approved
7888
INLYTA
PubMed

PubMed

TitleDatePubMed
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.
2010 Nov 24
Comprehensive analysis of kinase inhibitor selectivity.
2011 Oct 30
Evaluation of drugs with specific organ toxicities in organ-specific cell lines.
2012 Mar
The discovery of PLK4 inhibitors: (E)-3-((1H-Indazol-6-yl)methylene)indolin-2-ones as novel antiproliferative agents.
2013 Aug 8
Bridging Functional and Structural Cardiotoxicity Assays Using Human Embryonic Stem Cell-Derived Cardiomyocytes for a More Comprehensive Risk Assessment.
2015 Nov
Patents

Patents

JP2009019030A
1
JP2011528326A
12
US2004224988
1
US2006091067
1
US2008090242
1
US2008274192
1
US2009053236
1
US2009264464
1
US2010092490
1
US2010105031
1
US6891044
1

Sample Use Guides

In Vivo Use Guide
5 mg orally twice daily
Route of Administration: Oral
In Vitro Use Guide
Transfected or endogenous RTK-expressing cells were treated by axitinib with range of concentration from 0.01 nM to 10 uM. In transfected or endogenous RTK-expressing cells, axitinib potently blocked growth factor-stimulated phosphorylation of VEGFR-2 and VEGFR-3 with average IC50 values of 0.2 and 0.1 to 0.3 nmol/L, respectively. Cellular activity against VEGFR-1 was 1.2 nmol/L.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:35:21 UTC 2019
Edited
by admin
on Mon Oct 21 20:35:21 UTC 2019
Record UNII
C9LVQ0YUXG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AXITINIB
DASH   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
N-METHYL-2-(3-((E)-2-PYRIDIN-2-YL-VINYL)-1H-INDAZOL-6-YLSULFANYL)-BENZAMIDE
Systematic Name English
AXITINIB [VANDF]
Common Name English
AG-013736
Code English
AXITINIB [ORANGE BOOK]
Common Name English
AXITINIB [MI]
Common Name English
AXITINIB [INN]
Common Name English
AG-13736
Code English
AXITINIB [MART.]
Common Name English
BENZAMIDE, N-METHYL-2-((3-((1E)-2-(2-PYRIDINYL)ETHENYL)-1H-INDAZOL-6-YL)THIO)-
Systematic Name English
AXITINIB [WHO-DD]
Common Name English
AXITINIB [JAN]
Common Name English
INLYTA
Brand Name English
N-METHYL-2((3-((1E0-2-(PYRIDIN-2-YL)ETHENYL)-1H-INAZOL-6-YLSUFANYL)BENZAMIDE
Common Name English
AXITINIB [USAN]
Common Name English
Classification Tree Code System Code
WHO-ATC L01XE17
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
NCI_THESAURUS C1742
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
EMA ASSESSMENT REPORTS INLYTA (AUTHORIZED: CARCINOMA, CANCER CELL)
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
WHO-VATC QL01XE17
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
NCI_THESAURUS C93259
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
NDF-RT N0000175605
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
NCI_THESAURUS C129825
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
FDA ORPHAN DRUG 230706
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
EU-Orphan Drug EU/3/10/844
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
LIVERTOX 79
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
FDA ORPHAN DRUG 240607
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
Code System Code Type Description
RXCUI
1242999
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY RxNorm
EPA CompTox
319460-85-0
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY
MESH
C503983
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY
PUBCHEM
6450551
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY
MERCK INDEX
M2153
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY Merck Index
EVMPD
SUB25427
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY
ChEMBL
CHEMBL1289926
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY
NDF-RT
N0000020000
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY Receptor Tyrosine Kinase Inhibitors [MoA]
IUPHAR
5659
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY
INN
8720
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY
DRUG BANK
DB06626
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY
NCI_THESAURUS
C38718
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY
CAS
319460-85-0
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY
LactMed
319460-85-0
Created by admin on Mon Oct 21 20:35:21 UTC 2019 , Edited by admin on Mon Oct 21 20:35:21 UTC 2019
PRIMARY
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Related Record Type Details
Structure of PF-04621675
METABOLITE INACTIVE -> PARENT
MAJOR
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Related Record Type Details
Structure of AXITINIB
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
NIH
NCATS
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