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Details

Stereochemistry ACHIRAL
Molecular Formula C18H13N7S
Molecular Weight 359.4095
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SGX-523

SMILES

Cn1cc(cn1)-c2ccc3nnc(n3n2)Sc4ccc5c(cccn5)c4

InChI

InChIKey=BCZUAADEACICHN-UHFFFAOYSA-N
InChI=1S/C18H13N7S/c1-24-11-13(10-20-24)16-6-7-17-21-22-18(25(17)23-16)26-14-4-5-15-12(9-14)3-2-8-19-15/h2-11H,1H3

HIDE SMILES / InChI

Molecular Formula C18H13N7S
Molecular Weight 359.4095
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/22547164

SGX523 is a selective, ATP-competitive inhibitor of the MET receptor tyrosine kinase. SGX523 was able to inhibit HGF-induced cell migration and cell scatter. SGX523 inhibition of MET in vivo was associated with the dose-dependent inhibition of growth of tumor xenografts derived from human glioblastoma and lung and gastric cancers. The clinical development of SGX523, however, was discontinued at Phase I due to renal toxicity manifested by an early rise of serum blood urea nitrogen and creatinine.

CNS Activity

Curator's Comment:: Systemic delivery of SGX523 via oral gavage to mice bearing orthotopic human glioblastoma xenografts led to a significant decrease of in vivo tumor growth

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P08581
Gene ID: 4233
Gene Symbol: MET
Target Organism: Homo sapiens (Human)
2.70000000000000018 nM [Ki]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
An orally bioavailable c-Met kinase inhibitor potently inhibits brain tumor malignancy and growth.
2010 Jan
Patents

Sample Use Guides

In a phase I clinical trials SGX523 was administered on an intermittent schedule at a starting dose of 60 mg PO BID for 14 days followed by 7 days of rest. The second protocol explored a continuous 28-day dosing schedule with SGX523 administered at a starting dose of 20 mg PO BID for 28 days without rest.
Route of Administration: Oral
To investigate cell migration, A549 cells were plated in 12-well plates (6 × 104 per well) and incubated to confluence. A channel was introduced into the monolayers by scratching with a pipette tip. Various dilutions of the compound were added in starve medium in the presence and absence of HGF (90 ng/mL). Twenty-four hours later, wells were checked for cell migration. Cells were stained and visualized. SGX523 was active in prevention cells migration at concentrations above 50 nM
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:51:53 UTC 2021
Edited
by admin
on Sat Jun 26 15:51:53 UTC 2021
Record UNII
WH8SQN09KJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SGX-523
Code English
QUINOLINE, 6-((6-(1-METHYL-1H-PYRAZOL-4-YL)-1,2,4-TRIAZOLO(4,3-B)PYRIDAZIN-3-YL)THIO)-
Systematic Name English
SGX523
Code English
Code System Code Type Description
CAS
1022150-57-7
Created by admin on Sat Jun 26 15:51:53 UTC 2021 , Edited by admin on Sat Jun 26 15:51:53 UTC 2021
PRIMARY
FDA UNII
WH8SQN09KJ
Created by admin on Sat Jun 26 15:51:53 UTC 2021 , Edited by admin on Sat Jun 26 15:51:53 UTC 2021
PRIMARY
ChEMBL
CHEMBL1236107
Created by admin on Sat Jun 26 15:51:53 UTC 2021 , Edited by admin on Sat Jun 26 15:51:53 UTC 2021
PRIMARY
EPA CompTox
1022150-57-7
Created by admin on Sat Jun 26 15:51:53 UTC 2021 , Edited by admin on Sat Jun 26 15:51:53 UTC 2021
PRIMARY
DRUG BANK
DB06314
Created by admin on Sat Jun 26 15:51:53 UTC 2021 , Edited by admin on Sat Jun 26 15:51:53 UTC 2021
PRIMARY
PUBCHEM
24779724
Created by admin on Sat Jun 26 15:51:53 UTC 2021 , Edited by admin on Sat Jun 26 15:51:53 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY