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Substance Name: Clioquinol [USP:INN:BAN]
RN: 130-26-7
UNII: 7BHQ856EJ5
InChIKey: QCDFBFJGMNKBDO-UHFFFAOYSA-N

Note

  • 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 Formula

  • C9-H5-Cl-I-N-O

Molecular Weight

  • 305.4975
 

Classification Codes

  • Anti-Amebic
  • Anti-Infective, Topical
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Clioquinol
  • Clioquinol [USP:INN:BAN]

MeSH Heading

  • Clioquinol

Synonyms

  • 5-21-03-00294 (Beilstein Handbook Reference)
  • 5-Chlor-7-jod-8-hydroxy-chinolin
  • 5-Chlor-7-jod-8-hydroxy-chinolin [German]
  • 5-Chloro-7-iodo-8-hydroxyquinoline
  • 5-Chloro-7-iodo-8-quinolinol
  • 5-Chloro-8-hydroxy-7-iodoquinoline
  • 7-Iodo-5-chloro-8-hydroxyquinoline
  • 7-Iodo-5-chloroxine
  • AI3-16451
  • Ala-Quin
  • Alchloquin
  • Alioform
  • Amebil
  • Amoenol
  • Bactol
  • Barquinol
  • BRN 0153637
  • Budoform
  • Caswell No. 193
  • CCRIS 6050
  • Chinoform
  • Chinoformum
  • Chloro-8-hydroxyiodoquinoline
  • Chloroiodoquin
  • Chloroiodoquine
  • Chlorojodochin
  • Cifoform
  • Cliochinolo
  • Cliochinolo [DCIT]
  • Cliochinolum
  • Clioquinol
  • Clioquinolum
  • Clioquinolum [INN-Latin]
  • Cliquinol
  • Corque
  • Cort-Quin
  • Cortin
  • Cremo-quin
  • Dermaform
  • Dioquinol
  • Domeform
  • Domeform-HC
  • EC 204-984-4
  • Eczecidin
  • EINECS 204-984-4
  • Emaform
  • Enteritan
  • Entero-bio form
  • Entero-Bioform
  • Entero-vioform
  • Entero-Vioformio
  • Enteroquinol
  • Enteroseptol
  • Enterovalodon
  • Enterozol
  • Enterseptol
  • Enterum locorten
  • Entrokin
  • EPA Pesticide Chemical Code 024001
  • HI-Enterol
  • HSDB 6843
  • Hydriodide-enterol
  • Hysone
  • Iodenterol
  • Iodochlorhydroxyquin
  • Iodochlorhydroxyquin Cream
  • Iodochlorhydroxyquinol
  • Iodochlorhydroxyquinoline
  • Iodochlorohydroxyquin
  • Iodochlorohydroxyquinoline
  • Iodochloroquine
  • Iodochloroxine
  • Iodochloroxychinolinum
  • Iodochloroxyquinoline
  • Iodoenterol
  • Iodoxyquinoline
  • Jodchloroxychinolinum
  • Lekosept
  • Mycoquin
  • Nioform
  • NSC 3531
  • NSC 74938
  • Oralcer
  • Quin-O-Creme
  • Quinambicide
  • Quinoform
  • Quinoform (antiseptic)
  • Quinoform (VAN)
  • Quinoline, chloro-8-hydroxyiodo-
  • Rheaform
  • Rheaform Boluses
  • Rheaform Boluses (Veterinary)
  • Rometin
  • UAD Lotion
  • UNII-7BHQ856EJ5
  • Vioform
  • Vioform N.N.R.
  • Vioform-Hydrocortisone
  • Vioform-Hydrocortisone Mild

Systematic Names

  • 8-Quinolinol, 5-chloro-7-iodo-
  • Clioquinol
  • Iodochlorohydroxyquinoline

Mixture Names

  • Formtone-HC
  • Lidaform-HC
  • Nystaform
  • Nystaform-HC
  • Racet
  • Vioform-Hydrocortisone

Registry Numbers

CAS Registry Number

  • 130-26-7

FDA UNII

  • 7BHQ856EJ5

Other Registry Numbers

  • 22112-03-4
  • 736176-41-3

System Generated Number

  • 0000130267

Structure Descriptors

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

Smiles

c1cc2c(cc(c(c2nc1)O)I)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 400mg/kg (400mg/kg) LIVER: OTHER CHANGES American Journal of Tropical Medicine. Vol. 24, Pg. 29, 1944.
chicken LDLo oral 5gm/kg (5000mg/kg)   Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989.
dog LD oral > 1gm/kg (1000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1566, 1973.
guinea pig LDLo oral 175mg/kg (175mg/kg) LIVER: OTHER CHANGES American Journal of Tropical Medicine. Vol. 24, Pg. 29, 1944.
guinea pig LDLo subcutaneous 200mg/kg (200mg/kg) BEHAVIORAL: ATAXIA Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989.
human TDLo oral 1400mg/kg/20D (1400mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS Japanese Journal of Medical Science and Biology. Vol. 24, Pg. 195, 1971.
mouse LD50 intraperitoneal 590mg/kg (590mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 75, 1977.
mouse LD50 oral 69mg/kg (69mg/kg)   Archives of Toxicology, Supplement. Vol. 2, Pg. 371, 1979.
mouse LD50 subcutaneous 5gm/kg (5000mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 75, 1977.
rabbit LDLo oral 250mg/kg (250mg/kg) LIVER: FATTY LIVER DEGERATION

LIVER: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
JAMA, Journal of the American Medical Association. Vol. 100, Pg. 1658, 1933.
rat LD50 intraperitoneal 3400mg/kg (3400mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 75, 1977.
rat LD50 oral > 5gm/kg (5000mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 75, 1977.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 75, 1977.
women TDLo oral 11gm/kg/36W (11000mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

SENSE ORGANS AND SPECIAL SENSES: OPTIC NERVE NEUROPATHY: EYE
Lancet. Vol. 1, Pg. 1015, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 178.5 deg C   EXP
log P (octanol-water) 3.470 (none)   EST
Atmospheric OH Rate Constant 1.06E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.