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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
CAS Number: 287405-51-0
DrugBank ID: DB13020
TTD ID: D0HG5M

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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Syndecan-1 (SDC1)	OTWKRVZC	SDC1_HUMAN	Protein Interaction/Cellular Processes	[3]
Syndecan-4 (SDC4)	OTKUVUGZ	SDC4_HUMAN	Protein Interaction/Cellular Processes	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.