apratastat   Click here for help

GtoPdb Ligand ID: 6482

Synonyms: compound 5h [PMID: 16426848] | TMI-05 | TMI005
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: 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].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 149.85
Molecular weight 414.09
XLogP 0.93
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC#CCOc1ccc(cc1)S(=O)(=O)N1CCSC(C1C(=O)NO)(C)C
Isomeric SMILES OCC#CCOc1ccc(cc1)S(=O)(=O)N1CCSC([C@@H]1C(=O)NO)(C)C
InChI InChI=1S/C17H22N2O6S2/c1-17(2)15(16(21)18-22)19(9-12-26-17)27(23,24)14-7-5-13(6-8-14)25-11-4-3-10-20/h5-8,15,20,22H,9-12H2,1-2H3,(H,18,21)/t15-/m0/s1
InChI Key MAVDNGWEBZTACC-HNNXBMFYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(3S)-N-hydroxy-4-[4-(4-hydroxybut-2-ynoxy)phenyl]sulfonyl-2,2-dimethylthiomorpholine-3-carboxamide
International Nonproprietary Names Click here for help
INN number INN
8578 apratastat
Synonyms Click here for help
compound 5h [PMID: 16426848] | TMI-05 | TMI005
Database Links Click here for help
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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