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
• ATC Code:
  D08AH30: CLIOQUINOL
  D08AH: Quinoline derivatives
  D08A: ANTISEPTICS AND DISINFECTANTS
  D08: ANTISEPTICS AND DISINFECTANTS
  D: DERMATOLOGICALS
  D09AA10: CLIOQUINOL
  D09AA: Medicated dressings with antiinfectives
  D09A: MEDICATED DRESSINGS
  D09: MEDICATED DRESSINGS
  D: DERMATOLOGICALS
  G01AC02: CLIOQUINOL
  G01AC: Quinoline derivatives
  G01A: ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
  G01: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
  G: GENITO URINARY SYSTEM AND SEX HORMONES
  P01AA02: CLIOQUINOL
  P01AA: Hydroxyquinoline derivatives
  P01A: AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
  P01: ANTIPROTOZOALS
  P: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
  S02AA05: CLIOQUINOL
  S02AA: Antiinfectives
  S02A: ANTIINFECTIVES
  S02: OTOLOGICALS
  S: SENSORY ORGANS
• 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: CHEMBL497
  CAS Number: 130-26-7
  UNII: 7BHQ856EJ5
  DrugBank ID: DB04815
  TTD ID: D06ABW
  INTEDE ID: DR0341
• Drug-Molecule Activity Atlas (DMA)NEW: Click to Jump to the Detailed DMA Information of This Drug
• Drug Pharmacogenomic Perturbation (DPP)NEW: Click to Jump to the Detailed DPP Information of This Drug
• Drug ADMET Endpoint Profile (DAE)NEW: Click to Jump to the Detailed DAE Information of This Drug

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]
COMM domain-containing protein 1 (COMMD1)	OT7WUD5R	COMD1_HUMAN	Drug Response	[5]
Copper transport protein ATOX1 (ATOX1)	OT05LF59	ATOX1_HUMAN	Post-Translational Modifications	[6]
Cyclin-dependent kinase inhibitor 1 (CDKN1A)	OTQWHCZE	CDN1A_HUMAN	Gene/Protein Processing	[7]
DNA damage-inducible transcript 3 protein (DDIT3)	OTI8YKKE	DDIT3_HUMAN	Gene/Protein Processing	[8]
Egl nine homolog 1 (EGLN1)	OT5QODDK	EGLN1_HUMAN	Gene/Protein Processing	[4]
Endothelial transcription factor GATA-2 (GATA2)	OTBP2QQ2	GATA2_HUMAN	Gene/Protein Processing	[9]
Growth arrest and DNA damage-inducible protein GADD45 alpha (GADD45A)	OTDRV63V	GA45A_HUMAN	Gene/Protein Processing	[7]
Histone H2AX (H2AX)	OT18UX57	H2AX_HUMAN	Post-Translational Modifications	[7]

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] 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.
• [6] 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.
• [7] 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.
• [8] 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.
• [9] Clioquinol increases the expression of interleukin-8 by down-regulating GATA-2 and GATA-3. Neurotoxicology. 2018 Jul;67:296-304. doi: 10.1016/j.neuro.2018.06.014. Epub 2018 Jun 30.