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8-Quinolinol,5,7-diiodo-(CAS No. 83-73-8)

8-Quinolinol,5,7-diiodo- C9H5I2NO (cas 83-73-8) Molecular Structure

83-73-8 Structure

Identification and Related Records

【Name】
8-Quinolinol,5,7-diiodo-
【Iupac name】
5,7-diiodoquinolin-8-ol
【CAS Registry number】
83-73-8
【Synonyms】
Rafamebin
SS578
Searlequin
Searlewuin
Sebaquin
Stanquinate
Yodoxin
Zoaquin
5,7-Diiodo-8-hydroxyquinoline
5,7-Diiodooxine
8-Hydroxy-5,7-diiodoquinoline
Di-Quinol
Diamoebin
Diiodohydroxyquin
Diiodohydroxyquinoline
Diiodoquin
Diiodoquinol
Dinoleine
Diodohydroxyquin
Diodoquin
Diodoxylin
Direxiode
Disoquin
【EINECS(EC#)】
201-497-9
【Molecular Formula】
C9H5I2NO (Products with the same molecular formula)
【Molecular Weight】
396.95
【Inchi】
InChI=1/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
【InChIKey】
UXZFQZANDVDGMM-UHFFFAOYSA-N
【Canonical SMILES】
C1=CC2=C(C(=C(C=C2I)I)O)N=C1
【MOL File】
83-73-8.mol

Chemical and Physical Properties

【Density】
2.491g/cm3
【Melting Point】
200℃
【Boiling Point】
402
【Refractive Index】
1.828
【Flash Point】
197
【Solubilities】
Insoluble
【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
【Stability】
No data.
【Storage temp】
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
【Spectral properties】
IR: 8496 (Sadtler Research Laboratories IR Grating Collection)
UV: 8-109 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
【Computed Properties】
Molecular Weight:396.95104 [g/mol]
Molecular Formula:C9H5I2NO
XLogP3-AA:3.1
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:0
Tautomer Count:2
Exact Mass:396.84605
MonoIsotopic Mass:396.84605
Topological Polar Surface Area:33.1
Heavy Atom Count:13
Formal Charge:0
Complexity:191
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:2
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
Xn: Harmful;
【Risk Statements】
R22
【Safety Statements 】
26-36/37/39
【HazardClass】
6.1(b)
【Safety】
Poison by ingestion and intravenous routes. Human systemic effects by ingestion: eye effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of I− and NOx.
【PackingGroup 】
III
【Transport】
3249
【Formulations/Preparations】
DIIODOHYDROXYQUIN...DIHALOGENATED DERIVATIVES OF 8-HYDROXYQUINOLINE... DIIODOHYDROXYQUIN, USP (DIODOQUIN, YODOXIN), IS AVAIL AS TABLETS CONTAINING 210 OR 650 MG OF DRUG.
...TOPICAL, AS 0.5-1% CREAM OR 100-MG VAGINAL INSERT.

Use and Manufacturing

【Use and Manufacturing】
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...
【Usage】
Medication (vet).

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal.
【Therapeutic Uses】
Amebicides; Anti-Infective Agents, Local
...MAY BE USED IN LOCAL & SYSTEMIC TREATMENT OF TRICHOMONAS VAGINALIS VAGINITIS & INFECTIONS CAUSED BY TRICHOMONAS HOMINIS (INTESTINALIS). IT IS USED IN TOPICAL TREATMENT OF CERTAIN FUNGAL CUTANEOUS INFECTIONS & IN ECZEMA IN WHICH FUNGAL INFECTION IS COMPLICATION.
...HAVE BEEN USED FOR TREATMENT OF VARIOUS DERMATOLOGICAL DISORDERS, & LARGE DOSES HAVE BEEN EMPLOYED ORALLY IN TREATMENT OF ACRODERMATITIS ENTEROPATHICA, RARE, POTENTIALLY FATAL PEDIATRIC CONDITION.
...EFFECTIVE FOR INTESTINAL AMEBIASIS &...FOR TREATMENT OF ASYMPTOMATIC PASSERS OF CYSTS. ...USEFUL FOR AMBULATORY & MASS TREATMENT. THEY ARE INEXPENSIVE. ...OF VALUE IN CASES OF LAMBLIASIS RESISTANT TO QUINACRINE THERAPY, IN BALANTIDIAL DYSENTERY, & IN INTESTINAL INFECTIONS DUE TO DIENTAMEBA FRAGILIS. /8-HYDROXYQUINOLINES/
DAILY DOSE ... MAY BE ADEQUATE IN ASYMPTOMATIC CARRIERS. IN TREATMENT OF SYMPTOMATIC INTESTINAL AMEBIASIS...COMMON PRACTICE TO ADMIN DIIODOHYDROXYQUIN EITHER CONCURRENTLY WITH ANOTHER EFFECTIVE INTESTINAL AMEBICIDE OR TO GIVE TWO DRUGS IN ALTERNATING COURSES.
INITIAL COURSE SHOULD NOT BE REPEATED WITHOUT INTERVENING REST PERIOD OF 2-3 WK.
MEDICATION (VET): ORALLY, ALONE OR WITH ANTIBIOTICS, AS AMEBICIDE & TO CONTROL BALANTIDIUM DYSENTERIES IN PRIMATES.
MEDICATION (VET): ...AS PRESUMED SOLE ACTIVE INGREDIENT IN ANTISEBORRHEIC SHAMPOOS (AVG 5% WT/VOL) FOR DOGS WHERE ITS ACTION IS PRIMARILY ANTIMICROBIAL. ANTISEBORRHEIC EFFECTS REPORTED MAY ALSO BE DUE TO SURFACTANTS & COMPD CHELATING ABILITY. ...INCL ECZEMAS, ALLERGIC DERMATITIS, FUNGAL INFECTIONS, COW POX, & TEAT LESIONS.
【Biomedical Effects and Toxicity】
AFTER 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.

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