apratastat

Ligand id: 6482

Name: apratastat

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 149.85
Molecular weight 414.09
XLogP 0.97
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
(3S)-N-hydroxy-4-[4-(4-hydroxybut-2-ynoxy)phenyl]sulfonyl-2,2-dimethylthiomorpholine-3-carboxamide
International Nonproprietary Names
INN number INN
8578 apratastat
Synonyms
compound 5h [PMID: 16426848] | TMI-05 | TMI005
Comments
Apratastat (TMI-005) is an orally active dual TACE (ADAM17)/MMP13 inhibitor that was developed for the potential treatment of inflammation [2]. TACE = TNF α-converting enzyme, which is a well validated therapeutic target for the treatment of rheumatoid arthritis. Inhibition of MMP13 (a peptidase that preferentially degrades type II collagen and aggrecan) is relevant since this is predicted to prevent the degradation of cartilage in rheumatoid arthritis [1,4].
Database Links
BindingDB Ligand 50181008
CAS Registry No. 287405-51-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL206815
GtoPdb PubChem SID 178103096
PubChem CID 11452716
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