Grundinformationen
- CAS
83-73-8- Standard-SMILES
Oc1c(I)cc(I)c2cccnc12- InChIKey
UXZFQZANDVDGMM-UHFFFAOYSA-N- Summenformel
- C9H5I2NO
- Durchschnittliche Molmasse
- 396,95 g/mol
- Monoisotopische Masse
- 396,84606
Überblick
Iodoquinol is a monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 are replaced by iodine. It is considered the drug of choice for treating asymptomatic or moderate forms of amoebiasis. It has a role as an antiamoebic agent, an antibacterial agent, an antiprotozoal drug and an antiseptic drug. It is an organoiodine compound and a monohydroxyquinoline.
Namen und Bezeichner
- Bevorzugter Name
- 5,7-Diiodo-8-hydroxyquinoline
- IUPAC
- 5,7-diiodoquinolin-8-ol
- Lokaler Name
- Diiodhydroxychinolin
- Englischer Name
- 5,7-Diiodo-8-quinolinol
- Summenformel
- C9H5I2NO
- Molmasse
- 396.95
Namen und Synonyme
iodoquinol83-73-8Diiodohydroxyquinoline5,7-diiodoquinolin-8-ol5,7-Diiodo-8-hydroxyquinolineDiodoquinSearlequinIoquinZoaquinLanodoxinQuinadomeDiodohydroxyquin
Weitere Namen anzeigen
Lodoquinol5,7-DIIODOOXINEDIIODOHYDROXYQUINss578DyodinSS 578
DinoleineDiodoxylinDirexiodeEnteroseptFloraquinMoebiquinDisoquinEmbequin
Datenbank-Bezeichner
- CAS
83-73-8- PubChem CID
- 3728
- DTXSID
DTXSID6023155- ChEMBL
CHEMBL86754- ChEBI
CHEBI:5950- UNII
- 63W7IE88K8
- EC Number
- 201-497-9
- Nikkaji
- J4.643D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,1
- Polarare Oberfläche (TPSA)
- 33,1 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 190
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesBoiling point
LogP2.49
OdorODORLESS OR NEARLY SO
Color/Form
CRYSTALS FROM XYLENE; MEDICINAL GRADE IS YELLOWISH-BROWN POWDER
ABOVE 150 DEG, SUBLIMATES OF NEEDLES, PRISMS & RODS; ABOVE 200 DEG BROWN DROPS; MELT TURNS DARK-BROWN
LIGHT YELLOWISH TO TAN, MICROCRYSTALLINE POWDER
SolubilityALMOST INSOL IN WATER; SPARINGLY SOL IN ALCOHOL, ETHER, ACETONE; SOL IN HOT PYRIDINE & HOT DIOXANE
Melting PointMP 200-215 °C WITH EXTENSIVE DECOMP
Stability/Shelf LifeSTABLE IN AIR
Collision Cross Section
146.4 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID6023155]
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H302 (98.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 67 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationREACH registered substance: Diiodohydroxyquinoline (EC: 201-497-9)
Other Safety InformationIMAP assessments - 8-Quinolinol, 5,7-diiodo-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (98.5%)
Toxikologische Informationen
Human Toxicity Excerpts
MOST IMPORTANT TOXIC REACTION...IS SUBACUTE MYELO-OPTIC NEUROPATHY, INCIDENCE OF WHICH HAS PECULIAR GEOGRAPHIC DISTRIBUTION. /IODOCHLORHYDROXYQUIN/
/SUBACUTE MYELO-OPTIC NEUROPATHY/...SLIGHT INVOLVEMENT OF UPPER LIMBS. LESS COMMON ARE BLURRED VISION & BLINDNESS, DISTURBANCES OF AUTONOMIC NERVOUS SYSTEM, PSYCHOLOGICAL CHANGES, & GREENISH DISCOLORATION OF TONGUE. /IODOCHLORHYDROXYQUIN/
/SUBACUTE MYELO-OPTIC NEUROPATHY/...IS USUALLY PRECEDED BY ABDOMINAL PAIN & PERSISTENT DIARRHEA, & IT PROCEEDS TO BILATERAL SENSORY DISTURBANCES- PARESTHESIAS & DYSESTHESIAS, PREFERENTIALLY IN DISTAL PARTS OF LOWER LIMBS. ... DEEP SENSORY DISTURBANCES, MUSCLE WEAKNESS IN LEGS, PYRAMIDAL SIGNS... /IODOCHLORHYDROXYQUIN/
SYSTEMIC TOXICITY CAN RESULT FROM TOPICAL, ESP INTRAVAGINAL, APPLICATION.
For more Human Toxicity Excerpts (Complete) data for DIIODOHYDROXYQUIN (9 total), please visit the HSDB record page.
Chemie und Industrie
Pharmakologische Informationen
ATC Code
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Mechanism of Action
Unknown.
...IT IS NOT KNOWN IF THEY ARE EFFECTIVE IN INTESTINAL AMEBIASIS SOLELY BY VIRTUE OF THEIR PRESENCE IN LUMEN OF BOWEL OR ALSO IN PART BY THEIR PRESENCE IN CIRCULATION. /8-HYDROXYQUINOLINES/
...8-HYDROXYQUINOLINES ARE DIRECTLY AMEBICIDAL. THEY ARE ACTIVE AGAINST BOTH MOTILE & CYSTIC FORMS, BUT THEIR EFFICACY IN ELIMINATING CYSTS IS PROBABLY BASED ON THEIR ABILITY TO DESTROY TROPHOZOITES. THEY ACT ONLY ON AMEBAE IN INTESTINAL TRACT & ARE INEFFECTIVE IN AMEBIC ABSCESS & HEPATITIS. /8-HYDROXYQUINOLINES/
MeSH Pharmacological ClassificationAgents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal.
Absorption, Distribution and ExcretionAFTER ORAL ADMIN, VARIABLE BUT SIGNIFICANT PORTION OF INGESTED DOSE IS ABSORBED. ... DIIODOHYDROXYQUIN WAS LEAST WELL ABSORBED--ONLY 1/3 AS MUCH AS IODOCHLORHYDROXYQUIN. BULK OF THESE DRUGS IS PASSED IN FECES.
Verwendung und Herstellung
Uses
MEDICATION (VET)
MEDICATION
Methods of Manufacturing
PREPD BY ACTION OF IODINE MONOCHLORIDE ON 8-HYDROXYQUINOLINE: PAPESCH, BURTNER, J AM CHEM SOC 58, 1314 (1936): BY ACTION OF KIO3 ON 8-HYDROXYQUINOLINE: ZIEFMAN, CA 34, 3745. ELECTROLYTIC PREPN: BROWN, BERKOWITZ, TRANS ELECTROCHEM SOC 75, 385 (1939) SEE ALSO CLAUS GER PAT 78,880; PASSEK, GER PAT 411,050...
Formulations/Preparations
DIIODOHYDROXYQUIN...DIHALOGENATED DERIVATIVES OF 8-HYDROXYQUINOLINE... DIIODOHYDROXYQUIN, USP (DIODOQUIN, YODOXIN), IS AVAIL AS TABLETS CONTAINING 210 OR 650 MG OF DRUG.
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