clioquinol 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

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

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • clioquinol
  • chloroiodoquin
  • chloroiodoquine
  • cliquinol
  • iodochlorhydroxyquin
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
  • Status: OFM
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BA (Bioavailability) 22 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 3.611 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.243 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 27.733 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 129.718 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 0.270 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 0.500 % High 1
herg hERG pIC50 4.653 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 85.310 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 24.946 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 0.410 % High 1
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AKT3,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK1,CDK2,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,IKBKB,ITK,JAK1,JAK2,KDR,KIT,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAP4K1,MAPK1,MAPK10,MAPK12,MAPK7,MAPK8,MAPK9,MAPKAPK2,MARK4,MET,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM1,PIM2,PLK1,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ULK2,ZAP70 70
kinase-selectivity-class ACVR2B,AXL,BRAF,CDK9,DYRK1B,EIF2AK3,GRK2,MAP2K6,MAPK1,MAPK12,MAPK7,PIK3CB,STK33,SYK,TEK,TTK 16
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.366 High 1
mh-clint Mouse hepatocyte intrinsic clearance 494.311 High 1
mppb Mouse plasma protein binding (% unbound) 0.580 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.132 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 0.370 % High 1
rh-clint Rat hepatocyte intrinsic clearance 274.789 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 11.860 % High 1
rppb Rat plasma protein binding (% unbound) 0.220 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 1.629 uM High 1

Approvals:

DateAgencyCompanyOrphan
None FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Porphyria acute 130.30 45.31 54 9252 17921 90601220
Frequent bowel movements 114.86 45.31 72 9234 56863 90562278
Dislocation of vertebra 110.96 45.31 70 9236 55898 90563243
C-reactive protein abnormal 87.42 45.31 85 9221 127344 90491797
Colitis ulcerative 82.65 45.31 60 9246 60206 90558935
Oedema 82.26 45.31 102 9204 200193 90418948
Peripheral venous disease 81.28 45.31 68 9238 83853 90535288
X-ray abnormal 73.38 45.31 50 9256 45374 90573767
Feeling hot 71.00 45.31 61 9245 77947 90541194
Injury 70.79 45.31 94 9212 197255 90421886
Prescribed overdose 70.48 45.31 67 9239 97558 90521583
Lip dry 63.02 45.31 64 9242 100891 90518250
Joint range of motion decreased 62.04 45.31 73 9233 135570 90483571
Medication error 60.91 45.31 58 9248 84594 90534547
Breast cancer stage III 57.25 45.31 56 9250 84391 90534750
Adjustment disorder with depressed mood 57.03 45.31 47 9259 56706 90562435
Wound infection 56.70 45.31 62 9244 106340 90512801
Retinitis 56.64 45.31 40 9266 38418 90580723
Rectal haemorrhage 56.34 45.31 55 9251 82689 90536452
Facet joint syndrome 53.59 45.31 58 9248 98331 90520810
Night sweats 53.49 45.31 66 9240 128700 90490441
Delirium 52.48 45.31 59 9247 104300 90514841
Bursitis 52.32 45.31 66 9240 131588 90487553
Psoriatic arthropathy 52.06 45.31 88 9218 228247 90390894
Insomnia 51.76 45.31 109 9197 333365 90285776
Obesity 50.27 45.31 58 9248 105449 90513692
Musculoskeletal pain 47.24 45.31 72 9234 171179 90447962
Type 2 diabetes mellitus 47.21 45.31 79 9227 203165 90415976
Liver disorder 46.92 45.31 60 9246 121209 90497932
Lung disorder 45.62 45.31 66 9240 149817 90469324

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Porphyria acute 149.88 51.22 58 9727 18722 110560792
Dislocation of vertebra 142.62 51.22 72 9713 43649 110535865
Frequent bowel movements 117.13 51.22 75 9710 71315 110508199
C-reactive protein abnormal 103.04 51.22 88 9697 129607 110449907
Peripheral venous disease 99.06 51.22 72 9713 84045 110495469
X-ray abnormal 96.49 51.22 53 9732 38064 110541450
Prescribed overdose 85.46 51.22 67 9718 87514 110492000
Joint range of motion decreased 83.43 51.22 76 9709 121756 110457758
Colitis ulcerative 79.42 51.22 61 9724 77302 110502212
Adjustment disorder with depressed mood 79.22 51.22 49 9736 43834 110535680
Wound infection 77.70 51.22 66 9719 96399 110483115
Lip dry 77.61 51.22 67 9718 100016 110479498
Retinitis 76.48 51.22 43 9742 32284 110547230
Feeling hot 74.75 51.22 63 9722 91043 110488471
Breast cancer stage III 73.90 51.22 59 9726 79058 110500456
Night sweats 68.12 51.22 71 9714 133912 110445602
Liver disorder 68.10 51.22 73 9712 142170 110437344
Facet joint syndrome 67.45 51.22 61 9724 96767 110482747
Lung disorder 65.24 51.22 80 9705 179967 110399547
Bursitis 64.53 51.22 68 9717 129850 110449664
Medication error 61.17 51.22 60 9725 105306 110474208
Nausea 61.13 51.22 17 9768 1235673 109343841
Obesity 61.11 51.22 62 9723 113289 110466225
Musculoskeletal pain 59.44 51.22 77 9708 182946 110396568
Contusion 59.01 51.22 87 9698 233274 110346240
Fibromyalgia 58.81 51.22 74 9711 170835 110408679
Anti-cyclic citrullinated peptide antibody positive 58.22 51.22 76 9709 181908 110397606
Rheumatic fever 57.07 51.22 62 9723 122517 110456997
Sleep disorder due to general medical condition, insomnia type 55.52 51.22 57 9728 105586 110473928
Psoriatic arthropathy 55.07 51.22 77 9708 196684 110382830
Rheumatoid factor positive 53.44 51.22 62 9723 131578 110447936
Rectal haemorrhage 52.99 51.22 59 9726 119774 110459740
Discomfort 52.77 51.22 79 9706 214628 110364886

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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 P01AA52 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
Hydroxyquinoline derivatives
ATC S02AA05 SENSORY ORGANS
OTOLOGICALS
ANTIINFECTIVES
Antiinfectives
FDA CS M0000728 Allergens
FDA PE N0000175629 Increased Histamine Release
FDA PE N0000184306 Cell-mediated Immunity
FDA EPC N0000185508 Standardized Chemical Allergen
CHEBI has role CHEBI:33281 antibiotics
CHEBI has role CHEBI:33282 bactericides
CHEBI has role CHEBI:35610 antineoplastic agents
CHEBI has role CHEBI:35718 antifungal agents
CHEBI has role CHEBI:35820 antiprotozoal drugs
CHEBI has role CHEBI:38161 Chelating agent
CHEBI has role CHEBI:166831 copper chelator

Related Drugs by ATC class:

D08AH Quinoline derivatives 3 drugs
chlorquinaldoldequaliniumoxyquinoline
D09AA Medicated dressings with antiinfectives 11 drugs
aluminium chlorohydratebenzalkoniumcetylpyridiniumchlorhexidineframycetinfusidic acidiodoformnitrofurazonephenylmercuric nitratepovidone-iodinetriclosan
G01AC Quinoline derivatives 5 drugs
broxyquinolinechlorquinaldoldequaliniumdiiodohydroxyquinolineoxyquinoline
P01AA Hydroxyquinoline derivatives 4 drugs
broxyquinolinechlorquinaldoltilbroquinoltiliquinol
S02AA Antiinfectives 17 drugs
acetic acidaluminium acetotartrateboric acidcefmenoximechloramphenicolchlorhexidineciprofloxacinfosfomycingentamicinhydrogen peroxidemiconazoleneomycin show all 17 →

Drug Use | Suggest Off label Use Form| |View source of the data|

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




🐶 Veterinary Drug Use

SpeciesUseRelation
Horses Diarrhea Indication

🐶 Veterinary products

ProductApplicantIngredients
Rheaform Bolus Zoetis Inc. 1

Acid dissociation constants calculated using MoKa v3.0.0

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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Matrix metalloproteinase-14 Enzyme Kd 5.92 CHEMBL
Methionine aminopeptidase 2 Enzyme IC50 4.09 CHEMBL
Methionine aminopeptidase 1 Enzyme IC50 4.07 CHEMBL
Amyloid beta A4 protein Membrane other 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
Beta-lactamase NDM-1 Enzyme IC50 5.52 CHEMBL
Spike glycoprotein Glycoprotein IC50 5.25 CHEMBL

External reference:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
DERMOSCRIBE ICHYBUM HUMAN OTC DRUG LABEL 2 69683-101 CREAM 1 g TOPICAL OTC Monograph Drug 10 sections
DERMOSCRIBE ICHYBUM HUMAN OTC DRUG LABEL 2 69683-101 CREAM 1 g TOPICAL OTC Monograph Drug 10 sections
DERMOSCRIBE DIAPER HUMAN OTC DRUG LABEL 2 69683-102 OINTMENT 1 g TOPICAL OTC monograph not final 9 sections