Details of the Drug

General Information of Drug (ID: DM6BIHE)

Drug Name

RWJ-56423

Synonyms

RWJ-56423; CHEMBL256892; CHEMBL124571; (2S,4R)-1-ACETYL-N-[(1S)-4-[(AMINOIMINOMETHYL)AMINO]-1-(2-BENZOTHIAZOLYLCARBONYL)BUTYL]-4-HYDROXY-2-PYRROLIDINECARBOXAMIDE; (2S,4R)-1-acetyl-N-[(2S)-1-(1,3-benzothiazol-2-yl)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-4-hydroxypyrrolidine-2-carboxamide; AC1NR9Y0; SCHEMBL4314345; GTPL9333; VXDAVYUFYPFGDX-SNPRPXQTSA-N; BDBM50228764; BDBM50131977; DB02812; (2S)-6; (4R)-1-acetyl-N-[(1S)-1-(1,3-benzothiazol-2-ylcarbonyl)-4-carbamimidamidobutyl]-4-hydroxy-L-prolinamide

Indication

Disease Entry	ICD 11	Status	REF
Asthma	CA23	Discontinued in Phase 1	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

446.5

Logarithm of the Partition Coefficient (xlogp)

0

Rotatable Bond Count (rotbonds)

8

Hydrogen Bond Donor Count (hbonddonor)

4

Hydrogen Bond Acceptor Count (hbondacc)

7

Chemical Identifiers

Formula: C20H26N6O4S
IUPAC Name: (2S,4R)-1-acetyl-N-[(2S)-1-(1,3-benzothiazol-2-yl)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-4-hydroxypyrrolidine-2-carboxamide
Canonical SMILES: CC(=O)N1C[C@@H](C[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)C2=NC3=CC=CC=C3S2)O
InChI: InChI=1S/C20H26N6O4S/c1-11(27)26-10-12(28)9-15(26)18(30)24-14(6-4-8-23-20(21)22)17(29)19-25-13-5-2-3-7-16(13)31-19/h2-3,5,7,12,14-15,28H,4,6,8-10H2,1H3,(H,24,30)(H4,21,22,23)/t12-,14+,15+/m1/s1
InChIKey: VXDAVYUFYPFGDX-SNPRPXQTSA-N

Cross-matching ID

PubChem CID: 5287596
DrugBank ID: DB02812
TTD ID: D05QMJ

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Cationic trypsinogen (PRSS1)	TT2WR1T	TRY1_HUMAN	Inhibitor	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Potent, small-molecule inhibitors of human mast cell tryptase. Antiasthmatic action of a dipeptide-based transition-state analogue containing a benzothiazole ketone. J Med Chem. 2003 Aug 28;46(18):3865-76.
2	Inhibitors of serine proteases as potential therapeutic agents: the road from thrombin to tryptase to cathepsin G. J Med Chem. 2004 Feb 12;47(4):769-87.