Details of the Drug

General Information of Drug (ID: DM8W4N9)

Drug Name
Apratastat
Synonyms
TMI-005; TMI-05; UNII-C6BZ5263BJ; 287405-51-0; C6BZ5263BJ; CHEMBL206815; TMI 005; Apratastat [USAN:INN]; Apratastat (USAN/INN); MLS006010301; SCHEMBL2834310; GTPL6482; TMI005; Apratastat, > MolPort-021-805-014; BCPP000041; ZINC28571311; BDBM50181008; DB13020; API0013699; compound 5h [PMID: 16426848]; SMR004701369; 4CA-0170; D08859; 3-Thiomorpholinecarboxamide,N-hydroxy-4-[[4-[(4-hydroxy-2-butyn-1-yl)oxy]phenyl]sulfonyl]-2,2-dimethyl-,(3S)-; TMI-1; Dual TACE/MMP-13 inhibitors (inflammation), Wyeth; Dual TACE/MMP-13 inhibitors (rheumatoid arthritis), Wyeth; Dual TACE/MMP-13 inhibitors, Wyeth-Ayerst
Indication
Disease Entry ICD 11 Status REF
Rheumatoid arthritis FA20 Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 414.5
Logarithm of the Partition Coefficient (xlogp) 0.3
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C17H22N2O6S2
IUPAC Name
(3S)-N-hydroxy-4-[4-(4-hydroxybut-2-ynoxy)phenyl]sulfonyl-2,2-dimethylthiomorpholine-3-carboxamide
Canonical SMILES
CC1([C@@H](N(CCS1)S(=O)(=O)C2=CC=C(C=C2)OCC#CCO)C(=O)NO)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
InChIKey
MAVDNGWEBZTACC-HNNXBMFYSA-N
Cross-matching ID
PubChem CID
11452716
ChEBI ID
CHEMBL206815
CAS Number
287405-51-0
UNII
C6BZ5263BJ
DrugBank ID
DB13020
TTD ID
D0HG5M
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Matrix metalloproteinase-1 (MMP-1) TTMX39J MMP1_HUMAN Inhibitor [2]
Matrix metalloproteinase-13 (MMP-13) TTHY57M MMP13_HUMAN Modulator [2]
TNF alpha converting enzyme (ADAM17) TT6AZXG ADA17_HUMAN Modulator [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Syndecan-4 (SDC4) OTKUVUGZ SDC4_HUMAN Protein Interaction/Cellular Processes [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6482).
2 Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. Bioorg Med Chem Lett. 2006 Mar 15;16(6):1605-9.
3 A disintegrin and metalloproteinase 17 (ADAM17) mediates inflammation-induced shedding of syndecan-1 and -4 by lung epithelial cells. J Biol Chem. 2010 Jan 1;285(1):555-64. doi: 10.1074/jbc.M109.059394. Epub 2009 Oct 29.