Details of the Drug

General Information of Drug (ID: DM5QSKN)

• Drug Name: INDOPROFEN
• Synonyms: Dexindoprofen; UNII-004T8726AU; 53086-13-8; 004T8726AU; (+)-indoprofen; Dexindoprofenum; Dexindoprofene; Dexindoprofeno; Dexindoprofen [INN]; Dexindoprofenum [INN-Latin]; Dexindoprofene [INN-French]; Dexindoprofeno [INN-Spanish]; Indoprofen (+)-; EINECS 258-351-2; AC1Q5QZO; AC1L2A9M; ZINC391; SCHEMBL286896; (+)-(S)-4-(1-Oxo-2-isoindolinyl)hydratropasaeure; CHEMBL2106252; AJ-07888; (+)-(S)-p-(1-Oxo-2-isoindolinyl)hydratropic acid; UNII-CPE46ZU14N component RJMIEHBSYVWVIN-NSHDSACASA-N

Indication

Disease Entry	ICD 11	Status	REF
Gout	FA25	Withdrawn from market	[1]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 281.3
  Logarithm of the Partition Coefficient (xlogp); 2.8
  Rotatable Bond Count (rotbonds); 3
  Hydrogen Bond Donor Count (hbonddonor); 1
  Hydrogen Bond Acceptor Count (hbondacc); 3
• ADMET Property:
  Clearance: The drug is cleared by the renal []
  Half-life: The concentration or amount of drug in body reduced by one-half in 2.3 hours [2]
  Metabolism: The drug is metabolized via the glucuronidation []
  Unbound Fraction: The unbound fraction of drug in plasma is 0.01% [2]
  Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.12 L/kg [2]
• Chemical Identifiers:
  Formula: C17H15NO3
  IUPAC Name: 2-[4-(3-oxo-1H-isoindol-2-yl)phenyl]propanoic acid
  Canonical SMILES: CC(C1=CC=C(C=C1)N2CC3=CC=CC=C3C2=O)C(=O)O
  InChI: InChI=1S/C17H15NO3/c1-11(17(20)21)12-6-8-14(9-7-12)18-10-13-4-2-3-5-15(13)16(18)19/h2-9,11H,10H2,1H3,(H,20,21)
  InChIKey: RJMIEHBSYVWVIN-UHFFFAOYSA-N
• Cross-matching ID:
  PubChem CID: 3718
  ChEBI ID: CHEBI:76162
  CAS Number: 31842-01-0
  DrugBank ID: DB08951
  TTD ID: D0Q5PL

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
C-X-C chemokine receptor type 1 (CXCR1)	TTMWT8Z	CXCR1_HUMAN	Inhibitor	[3]
C-X-C chemokine receptor type 2 (CXCR2)	TT30C9G	CXCR2_HUMAN	Inhibitor	[3]
Fatty acid-binding protein 1 (FABP1)	TTIV96N	FABPL_HUMAN	Inhibitor	[4]
Prostaglandin G/H synthase 1 (COX-1)	TT8NGED	PGH1_HUMAN	Inhibitor	[3]
Prostaglandin G/H synthase 2 (COX-2)	TTVKILB	PGH2_HUMAN	Inhibitor	[3]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Nuclear receptor subfamily 1 group I member 2 (NR1I2)	OTC5U0N5	NR1I2_HUMAN	Gene/Protein Processing	[5]
UDP-glucuronosyltransferase 1A10	OTOTZVEY	UD110_HUMAN	Biotransformations	[6]
UDP-glucuronosyltransferase 1A3	OTUEOER3	UD13_HUMAN	Biotransformations	[6]
UDP-glucuronosyltransferase 1A7	OTY4JJ32	UD17_HUMAN	Biotransformations	[6]
UDP-glucuronosyltransferase 1A8	OTTMABBG	UD18_HUMAN	Biotransformations	[6]

Molecular Expression Atlas of This Drug

• The Studied Disease: Gout
• ICD Disease Classification: FA25

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Prostaglandin G/H synthase 2 (COX-2)	DTT	PTGS2	7.93E-04	-0.29	-0.34
Prostaglandin G/H synthase 1 (COX-1)	DTT	PTGS1	3.97E-03	0.16	0.43

References

• [1] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
• [2] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [3] 2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors. J Med Chem. 2005 Jun 30;48(13):4312-31.
• [4] Characterization of the drug binding specificity of rat liver fatty acid binding protein. J Med Chem. 2008 Jul 10;51(13):3755-64.
• [5] Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. Toxicol Lett. 2015 Jan 5;232(1):193-202. doi: 10.1016/j.toxlet.2014.10.009. Epub 2014 Oct 16.
• [6] Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. J Biol Chem. 2004 Jul 2;279(27):28320-9. doi: 10.1074/jbc.M401396200. Epub 2004 Apr 26.