Details of the Drug

General Information of Drug (ID: DM746BZ)

• Drug Name: CLIOQUINOL
• Synonyms: clioquinol; 130-26-7; 5-Chloro-7-iodoquinolin-8-ol; Iodochlorhydroxyquin; Chinoform; Chloroiodoquin; Chloroiodoquine; 5-Chloro-8-hydroxy-7-iodoquinoline; Iodochloroxyquinoline; Cliquinol; Vioform; Iodochlorohydroxyquinoline; Chlorojodochin; Iodochloroxine; Iodochloroquine; Enteroquinol; Iodoenterol; 7-Iodo-5-chloroxine; Entero-Vioform; 5-Chloro-7-iodo-8-quinolinol; Iodochlorhydroxyquinoline; Iodoxyquinoline; Rheaform; Quinoform; Quinambicide; Lekosept; Dioquinol; Dermaform; Iodenterol; Entrokin; Enteroseptol; Domeform; Barquinol
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 305.5
  Logarithm of the Partition Coefficient (xlogp); 3.5
  Rotatable Bond Count (rotbonds); 0
  Hydrogen Bond Donor Count (hbonddonor); 1
  Hydrogen Bond Acceptor Count (hbondacc); 2
• Chemical Identifiers:
  Formula: C9H5ClINO
  IUPAC Name: 5-chloro-7-iodoquinolin-8-ol
  Canonical SMILES: C1=CC2=C(C(=C(C=C2Cl)I)O)N=C1
  InChI: InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
  InChIKey: QCDFBFJGMNKBDO-UHFFFAOYSA-N
• Cross-matching ID:
  PubChem CID: 2788
  ChEBI ID: CHEBI:74460
  CAS Number: 130-26-7
  DrugBank ID: DB04815
  TTD ID: D06ABW
  INTEDE ID: DR0341

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Carbonic anhydrase (CA)	TTUNARX	NOUNIPROTAC	Inhibitor	[1]
Opioid receptor kappa (OPRK1)	TTQW87Y	OPRK_HUMAN	Inhibitor	[2]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Sulfotransferase 1A1 (SULT1A1) Main DME	DEYWLRK	ST1A1_HUMAN	Substrate	[3]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Adenylate kinase isoenzyme 1 (AK1)	OT614AR3	KAD1_HUMAN	Gene/Protein Processing	[4]
BCL2/adenovirus E1B 19 kDa protein-interacting protein 3-like (BNIP3L)	OTJKOMXE	BNI3L_HUMAN	Gene/Protein Processing	[4]
Beclin-1 (BECN1)	OT4X293M	BECN1_HUMAN	Gene/Protein Processing	[5]
Calreticulin (CALR)	OTYD2TR1	CALR_HUMAN	Gene/Protein Processing	[5]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Post-Translational Modifications	[6]
COMM domain-containing protein 1 (COMMD1)	OT7WUD5R	COMD1_HUMAN	Drug Response	[7]
Copper transport protein ATOX1 (ATOX1)	OT05LF59	ATOX1_HUMAN	Post-Translational Modifications	[8]
Cyclic AMP-dependent transcription factor ATF-3 (ATF3)	OTC1UOHP	ATF3_HUMAN	Gene/Protein Processing	[9]
Cyclin-dependent kinase inhibitor 1 (CDKN1A)	OTQWHCZE	CDN1A_HUMAN	Gene/Protein Processing	[6]
DNA damage-inducible transcript 3 protein (DDIT3)	OTI8YKKE	DDIT3_HUMAN	Gene/Protein Processing	[5]

Molecular Expression Atlas of This Drug

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Opioid receptor kappa (OPRK1)	DTT	OPRK1	9.17E-01	0.04	0.1
Sulfotransferase 1A1 (SULT1A1)	DME	SULT1A1	8.90E-01	-2.90E-02	-1.34E-01

References

• [1] Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Bioorg Med Chem Lett. 2008 Jun 15;18(12):3593-6.
• [2] In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
• [3] Clioquinol is sulfated by human jejunum cytosol and SULT1A3, a human-specific dopamine sulfotransferase. Toxicol Lett. 2011 Oct 10;206(2):229-33.
• [4] Identification of chemical compounds that induce HIF-1alpha activity. Toxicol Sci. 2009 Nov;112(1):153-63.
• [5] Clioquinol induces autophagy by down-regulation of calreticulin in human neurotypic SH-SY5Y cells. Chem Biol Interact. 2023 Jan 5;369:110268. doi: 10.1016/j.cbi.2022.110268. Epub 2022 Nov 15.
• [6] Clioquinol induces DNA double-strand breaks, activation of ATM, and subsequent activation of p53 signaling. Toxicology. 2012 Sep 4;299(1):55-9. doi: 10.1016/j.tox.2012.05.013. Epub 2012 May 22.
• [7] Population-based in vitro hazard and concentration-response assessment of chemicals: the 1000 genomes high-throughput screening study. Environ Health Perspect. 2015 May;123(5):458-66. doi: 10.1289/ehp.1408775. Epub 2015 Jan 13.
• [8] Clioquinol inhibits dopamine--hydroxylase secretion and noradrenaline synthesis by affecting the redox status of ATOX1 and copper transport in human neuroblastoma SH-SY5Y cells. Arch Toxicol. 2021 Jan;95(1):135-148. doi: 10.1007/s00204-020-02894-0. Epub 2020 Oct 9.
• [9] Identification of novel activators of the metal responsive transcription factor (MTF-1) using a gene expression biomarker in a microarray compendium. Metallomics. 2020 Sep 23;12(9):1400-1415. doi: 10.1039/d0mt00071j.