clioquinol indications/contra

Stem definitionDrug idCAS RN
quinoline derivatives 681 130-26-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • clioquinol
  • chloroiodoquin
  • chloroiodoquine
  • cliquinol
A potentially neurotoxic 8-hydroxyquinoline derivative long used as a topical anti-infective, intestinal antiamebic, and vaginal trichomonacide. The oral preparation has been shown to cause subacute myelo-optic neuropathy and has been banned worldwide.
  • Molecular weight: 305.50
  • Formula: C9H5ClINO
  • CLOGP: 3.73
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 33.12
  • ALOGS: -3.06
  • ROTB: 0

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
None FDA

FDA Adverse Event Reporting System

None

Pharmacologic Action:

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SourceCodeDescription
ATC D08AH30 DERMATOLOGICALS
ANTISEPTICS AND DISINFECTANTS
ANTISEPTICS AND DISINFECTANTS
Quinoline derivatives
ATC D09AA10 DERMATOLOGICALS
MEDICATED DRESSINGS
MEDICATED DRESSINGS
Medicated dressings with antiinfectives
ATC G01AC02 GENITO URINARY SYSTEM AND SEX HORMONES
GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
Quinoline derivatives
ATC P01AA02 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
Hydroxyquinoline derivatives
ATC S02AA05 SENSORY ORGANS
OTOLOGICALS
ANTIINFECTIVES
Antiinfectives
ATC P01AA52 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
Hydroxyquinoline derivatives
FDA EPC N0000185508 Standardized Chemical Allergen
FDA PE N0000175629 Increased Histamine Release
FDA PE N0000184306 Cell-mediated Immunity
FDA Chemical/Ingredient N0000171131 Allergens
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35820 antiprotozoal drug

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Tinea pedis indication 6020002 DOID:12403
Tinea corporis indication 84849002 DOID:12179
Tinea cruris indication 399029005
Open wound contraindication 125643001
Telangiectasia disorder contraindication 247479008 DOID:1272
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Atrophoderma contraindication 399979006 DOID:2733
Peripheral vascular disease contraindication 400047006

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.63 acidic
pKa2 2.39 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Amyloid beta A4 protein Unclassified IC50 4 CHEMBL
Catechol O-methyltransferase Enzyme IC50 5.32 CHEMBL
Botulinum neurotoxin type A Enzyme IC50 4.69 CHEMBL
Carbonic anhydrase 15 Enzyme Ki 5.63 CHEMBL

External reference:

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IDSource
4018572 VUID
N0000146888 NUI
C0021978 UMLSCUI
D03538 KEGG_DRUG
CHEMBL497 ChEMBL_ID
7BHQ856EJ5 UNII
2116 INN_ID
6683 MMSL
5942 RXNORM
387291001 SNOMEDCT_US
52896000 SNOMEDCT_US
4470 MMSL
4018572 VANDF
N0000007232 NDFRT
N0000146888 NDFRT
002874 NDDF
2788 PUBCHEM_CID
CHEBI:74460 CHEBI
DB04815 DRUGBANK_ID
D007464 MESH_DESCRIPTOR_UI
CQL PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Ala Quin HUMAN PRESCRIPTION DRUG LABEL 2 0316-0123 CREAM 30 mg TOPICAL unapproved drug other 18 sections
DERMOSCRIBE ICHYBUM HUMAN OTC DRUG LABEL 2 69683-101 CREAM 1 g TOPICAL OTC monograph not final 8 sections