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Details

Stereochemistry ACHIRAL
Molecular Formula C18H18N2O3
Molecular Weight 310.3478
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ORANTINIB

SMILES

Cc1c(CCC(=O)O)c(C)[nH]c1/C(/[H])=C\2/c3ccccc3N=C2O

InChI

InChIKey=NHFDRBXTEDBWCZ-ZROIWOOFSA-N
InChI=1S/C18H18N2O3/c1-10-12(7-8-17(21)22)11(2)19-16(10)9-14-13-5-3-4-6-15(13)20-18(14)23/h3-6,9,19H,7-8H2,1-2H3,(H,20,23)(H,21,22)/b14-9-

HIDE SMILES / InChI

Molecular Formula C18H18N2O3
Molecular Weight 310.3478
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Orantinib (SU-6668) is an orally bioavailable receptor tyrosine kinase inhibitor. Orantinib binds to and inhibits the autophosphorylation of vascular endothelial growth factor receptor 2 (VEGFR2), platelet-derived growth factor receptor (PDGFR), and fibroblast growth factor receptor (FGFR), thereby inhibiting angiogenesis and cell proliferation. Orantinib also inhibits the phosphorylation of the stem cell factor receptor tyrosine kinase c-kit, often expressed in acute myelogenous leukemia cells. Orantinib was in phase II clinical trials for the treatment of breast cancer. It was also in phase III clinical trials for the treatment of hepatocellular carcinoma. However, this research was terminated in 2014. The compound was originally developed by Sugen (subsidiary of Pfizer). In 1998, a co-development agreement took place between Sugen and Taiho for the compound.

Originator

Curator's Comment:: # Pfizer

Approval Year

PubMed

PubMed

TitleDatePubMed
In vivo assessment of antiangiogenic activity of SU6668 in an experimental colon carcinoma model.
2004 Jan 15
Combined antiangiogenic and immune therapy of prostate cancer.
2005
Combined inhibition of vascular endothelial growth factor and platelet-derived growth factor signaling: effects on the angiogenesis, microcirculation, and growth of orthotopic malignant gliomas.
2005 Feb
Vascular endothelial growth factor: a therapeutic target for tumors of the Ewing's sarcoma family.
2005 Mar 15
Inhibition of peritoneal dissemination of ovarian cancer by tyrosine kinase receptor inhibitor SU6668 (TSU-68).
2005 Mar 20
Dose-finding study of the multitargeted tyrosine kinase inhibitor SU6668 in patients with advanced malignancies.
2005 Sep 1
Potent platelet-derived growth factor-beta receptor (PDGF-betaR) inhibitors: Synthesis and structure-activity relationships of 7-[3-(cyclohexylmethyl)ureido]-3-{1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl}quinoxalin-2(1H)-one derivatives.
2007 Feb
5-Substituted pyrido[2,3-d]pyrimidine, an inhibitor against three receptor tyrosine kinases.
2009 Feb 1
Acenaphtho[1,2-b]pyrrole-based selective fibroblast growth factor receptors 1 (FGFR1) inhibitors: design, synthesis, and biological activity.
2011 Jun 9
Patents

Sample Use Guides

Orantinib at 200 mg, twice per day, or placebo was given orally until TACE failure or unacceptable toxicity.
Route of Administration: Oral
Orantinib (SU-6668) inhibited PDGF-stimulated PDGFRb tyrosine phosphorylation in NIH-3T3 cells overexpressing PDGFRb at a minimum concentration of 0.03–0.1 uM. SU-6668 inhibited acidic FGF-induced
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:26:18 UTC 2021
Edited
by admin
on Sat Jun 26 07:26:18 UTC 2021
Record UNII
9RL37ZZ665
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ORANTINIB
INN   WHO-DD  
INN  
Official Name English
1H-PYRROLE-3-PROPANOIC ACID, 5-((1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)METHYL)-2,4-DIMETHYL-
Common Name English
NSC-702827
Code English
TSU-68
Code English
5-((1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)METHYL)-2,4-DIMETHYL-1H-PYRROLE-3-PROPANOIC ACID
Systematic Name English
3-(2,4-DIMETHYL-5-(2-OXO-1,2-DIHYDROINDOL-3-YLIDENEMETHYL)-1H-PYRROL-3-YL)PROPIONIC ACID
Systematic Name English
3-(2,4-DIMETHYL-5-(((3Z)-2-OXO-1,2-DIHYDRO-3H-INDOL-3-YLIDENE)METHYL)-1H-PYRROL-3-YL)PROPANOIC ACID
Systematic Name English
3-(2,4-DIMETHYL-5-((2-OXO-1,2-DIHYDRO-3H-INDOL-3-YLIDENE)METHYL)-1H-PYRROL-3-YL)PROPIONIC ACID
Systematic Name English
ORANTINIB [INN]
Common Name English
3-(4-(2-CARBOXYETHYL)-3,5-DIMETHYLPYRROL-2-METHYLIDENYL)-2-INDOLINONE
Common Name English
ORANTINIB [WHO-DD]
Common Name English
SU-6668
Code English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Sat Jun 26 07:26:19 UTC 2021 , Edited by admin on Sat Jun 26 07:26:19 UTC 2021
Code System Code Type Description
PUBCHEM
5329099
Created by admin on Sat Jun 26 07:26:19 UTC 2021 , Edited by admin on Sat Jun 26 07:26:19 UTC 2021
PRIMARY
ChEMBL
CHEMBL274654
Created by admin on Sat Jun 26 07:26:19 UTC 2021 , Edited by admin on Sat Jun 26 07:26:19 UTC 2021
PRIMARY
CAS
252916-29-3
Created by admin on Sat Jun 26 07:26:19 UTC 2021 , Edited by admin on Sat Jun 26 07:26:19 UTC 2021
PRIMARY
EVMPD
SUB74858
Created by admin on Sat Jun 26 07:26:19 UTC 2021 , Edited by admin on Sat Jun 26 07:26:19 UTC 2021
PRIMARY
EPA CompTox
252916-29-3
Created by admin on Sat Jun 26 07:26:19 UTC 2021 , Edited by admin on Sat Jun 26 07:26:19 UTC 2021
PRIMARY
MESH
C412603
Created by admin on Sat Jun 26 07:26:19 UTC 2021 , Edited by admin on Sat Jun 26 07:26:19 UTC 2021
PRIMARY
NCI_THESAURUS
C1884
Created by admin on Sat Jun 26 07:26:19 UTC 2021 , Edited by admin on Sat Jun 26 07:26:19 UTC 2021
PRIMARY
DRUG BANK
DB12072
Created by admin on Sat Jun 26 07:26:19 UTC 2021 , Edited by admin on Sat Jun 26 07:26:19 UTC 2021
PRIMARY
INN
9267
Created by admin on Sat Jun 26 07:26:19 UTC 2021 , Edited by admin on Sat Jun 26 07:26:19 UTC 2021
PRIMARY
FDA UNII
9RL37ZZ665
Created by admin on Sat Jun 26 07:26:19 UTC 2021 , Edited by admin on Sat Jun 26 07:26:19 UTC 2021
PRIMARY
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