U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H27FN4O4
Molecular Weight 442.4842
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SU-14813

SMILES

Cc1c(/C(/[H])=C\2/c3cc(ccc3N=C2O)F)[nH]c(C)c1C(=NC[C@@]([H])(CN4CCOCC4)O)O

InChI

InChIKey=CTNPALGJUAXMMC-PMFHANACSA-N
InChI=1S/C23H27FN4O4/c1-13-20(10-18-17-9-15(24)3-4-19(17)27-22(18)30)26-14(2)21(13)23(31)25-11-16(29)12-28-5-7-32-8-6-28/h3-4,9-10,16,26,29H,5-8,11-12H2,1-2H3,(H,25,31)(H,27,30)/b18-10-/t16-/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H27FN4O4
Molecular Weight 442.4842
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800021861

SU-14813 is an oral, multitargeted tyrosine kinase inhibitor (TKI) targeting vascular endothelial growth factor receptors (VEGFR), platelet-derived growth factor receptors (PDGFR), KIT, and fms-like tyrosine kinase 3 (FLT-3). SU-14813 was developed as a next-generation TKI agent following sunitinib (SU-11248) designed to demonstrate optimized pharmacokinetic (PK) and tolerability profiles. SU14813 demonstrated broad and potent antitumor activity equivalent to that of sunitinib, which resulted in tumor regression, growth arrest, growth delay, and prolonged survival in established xenograft cancer models in mice. A phase II trial of SU-14813 in patients with breast cancer was completed. However, according to the Pfizer pipeline development has been discontinued.

Originator

Curator's Comment:: # Pfizer

Approval Year

PubMed

PubMed

TitleDatePubMed
Pharmacologic inhibition of CDK4/6: mechanistic evidence for selective activity or acquired resistance in acute myeloid leukemia.
2007 Sep 15
Patents

Sample Use Guides

Escalating doses of SU-14813 from 50 to 250mg/day . Capsules administered daily either as continuous dosing or in cycles of 4 weeks on 1 week off
Route of Administration: Oral
SU-14813 inhibited VEGFR-2, PDGFR-h, and KIT phosphorylation in porcine aorta endothelial cells overexpressing these targets, with cellular IC50 values of 5.2, 9.9, and 11.2 nmol/L, respectively. SU-14813 inhibited the growth of U-118MG with an IC50 of 50 to 100 nmol/L.
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:44:15 UTC 2021
Edited
by admin
on Sat Jun 26 14:44:15 UTC 2021
Record UNII
ZZ6VH5MZ17
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SU-14813
Common Name English
1H-PYRROLE-3-CARBOXAMIDE, 5-((Z)-(5-FLUORO-1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)METHYL)-N-(2-HYDROXY-3-(4-MORPHOLINYL)PROPYL)-2,4-DIMETHYL-
Systematic Name English
5-((Z)-(5-FLUORO-2-OXO-1,2-DIHYDRO-3H-INDOL-3-YLIDENE)METHYL)-N-(2-HYDROXY-3-MORPHOLIN-4-YLPROPYL)-2,4-DIMETHYL-1H-PYRROLE-3-CARBOXAMIDE
Systematic Name English
1H-PYRROLE-3-CARBOXAMIDE, 5-((5-FLUORO-1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)METHYL)-N-((2S)-2-HYDROXY-3-(4-MORPHOLINYL)PROPYL)-2,4-DIMETHYL-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Sat Jun 26 14:44:15 UTC 2021 , Edited by admin on Sat Jun 26 14:44:15 UTC 2021
Code System Code Type Description
PUBCHEM
10138259
Created by admin on Sat Jun 26 14:44:15 UTC 2021 , Edited by admin on Sat Jun 26 14:44:15 UTC 2021
PRIMARY
ChEMBL
CHEMBL1721885
Created by admin on Sat Jun 26 14:44:15 UTC 2021 , Edited by admin on Sat Jun 26 14:44:15 UTC 2021
PRIMARY
FDA UNII
ZZ6VH5MZ17
Created by admin on Sat Jun 26 14:44:15 UTC 2021 , Edited by admin on Sat Jun 26 14:44:15 UTC 2021
PRIMARY
ChEMBL
CHEMBL3545160
Created by admin on Sat Jun 26 14:44:15 UTC 2021 , Edited by admin on Sat Jun 26 14:44:15 UTC 2021
PRIMARY
CAS
452105-23-6
Created by admin on Sat Jun 26 14:44:15 UTC 2021 , Edited by admin on Sat Jun 26 14:44:15 UTC 2021
PRIMARY
CAS
627908-92-3
Created by admin on Sat Jun 26 14:44:15 UTC 2021 , Edited by admin on Sat Jun 26 14:44:15 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
NCI_THESAURUS
C61507
Created by admin on Sat Jun 26 14:44:15 UTC 2021 , Edited by admin on Sat Jun 26 14:44:15 UTC 2021
PRIMARY NCIT
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY