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Home > Encyclopedia > 5,7-Diiodo-8-hydroxyquinoline

5,7-Diiodo-8-hydroxyquinoline

5,7-Diiodo-8-hydroxyquinoline structure

5,7-Diiodo-8-hydroxyquinoline 

structure
  • CAS No:

    83-73-8

  • Formula:

    C9H5I2NO

  • Chemical Name:

    5,7-Diiodo-8-hydroxyquinoline

  • Synonyms:

    8-Quinolinol,5,7-diiodo-;5,7-Diiodo-8-quinolinol;Diiodohydroxyquin;Diiodohydroxyquinoline;5,7-Diiodooxine;Diiodoquin;5,7-Diiodo-8-hydroxyquinoline;Dinoleine;Diodohydroxyquin;Diodoquin;Diodoxylin;Di-Quinol;Direxiode;Disoquin;Dyodin;Embequin;Enterosept;Floraquin;8-Hydroxy-5,7-diiodoquinoline;Lanodoxin;Moebiquin;Quinadome;Searlequin;Sebaquin;Zoaquin;Yodoxin;Enterodiamoebin;Diamoebin;Iodoquinol;Diiodoquinol;SS 578;Rafamebin;Ioquin;Searlewuin;Stanquinate;NSC 74939;NSC 8704;Iodoquin

  • Categories:

    Active Pharmaceutical Ingredients  >  Antiparasitic Drugs

Description

Diiodohydroxyquinoline is a topical therapeutic agent, with satisfactory antibacterial properties.


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 antiseptic drug and an antiprotozoal drug. It is a monohydroxyquinoline and an organoiodine compound.|Diiodohydroxyquinoline, also known as uidoquinol and iodoquinol, is a quinoline derivative that can be used in the treatment of amoebiasis. The exact mechanism of action is unknown. Iodoquinol is not currently available in any FDA-approved products.|One of the halogenated 8-quinolinols widely used as an intestinal antiseptic, especially as an antiamebic agent. It is also used topically in other infections and may cause CNS and eye damage. It is known by very many similar trade names world-wide.

5,7-Diiodo-8-hydroxyquinoline Basic Attributes

396.95

396.95

201-497-9

63W7IE88K8

757077|8704

DTXSID6023155

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

G - Genito urinary system and sex hormones

2933499090

Characteristics

33.1

3.1

2.5±0.1 g/cm3

210 °C

402ºC

196.8±28.7 °C

1.828

ALMOST INSOL IN WATER; SPARINGLY SOL IN ALCOHOL, ETHER, ACETONE; SOL IN HOT PYRIDINE & HOT DIOXANE

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.

LD50 intravenous in mouse: 56mg/kg

ODORLESS OR NEARLY SO

143.7 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

III

6.1(b)

3249

3

22-41

26-36/37/39

VC5775000

Xn

STABLE IN AIR

P280-P305 + P351 + P338

H302-H318

|Danger|H302 (98.46%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 66 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Used in the treatment of amoebiasis.

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/|For more Therapeutic Uses (Complete) data for DIIODOHYDROXYQUIN (8 total), please visit the HSDB record page.

WHILE...EFFECTIVE IN CYST-PASSING PT, THEY ARE MUCH LESS EFFECTIVE IN TREATMENT OF ACUTE AMEBIC DYSENTERY.|USE OF THESE AGENTS TO TREAT "TRAVELER'S DIARRHEA" & CHRONIC NONSPECIFIC DIARRHEA IN CHILDREN /PRC: OR ADULTS/ CANNOT BE CONDONED, SINCE SUCH CONDITIONS ARE SELF-LIMITED & ANY POSSIBLE THERAPEUTIC BENEFIT DOES NOT JUSTIFY RISK OF SERIOUS NEUROTOXICITY. /8-HYDROXYQUINOLINES/|THESE DRUGS ARE CONTRAINDICATED IN PT WITH HEPATIC DAMAGE OR IODINE INTOLERANCE. ...THESE AGENTS INTERFERE WITH CERTAIN THYROID FUNCTION TESTS FOR MO BECAUSE OF THEIR CONTENT OF IODINE. /8-HYDROXYQUINOLINES/|...IT NOW APPEARS THAT GI-NEUROLOGIC SYNDROME OF OBSCURE ETIOLOGY, COMMON IN REGIONS WHERE DIIODOHYDROXYQUIN IS USED, IS CAUSED BY DRUG... FOR THIS REASON, JAPAN WITHDREW SUCH DRUGS FROM MARKET.|VET: COMMERCIAL PREPN MAY CAUSE YELLOW-BROWN STAINING OF WHITE HAIR. USE MAY ALTER SERUM PROTEIN-BOUND IODINE TEST.

4(?). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB). ...ITS TOXICITY IS UNPREDICTABLE.

Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal. (See all compounds classified as Amebicides.)

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.

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/

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.

Diiodohydroxyquin

5,7-Diiodo-8-hydroxyquinoline Use and Manufacturing

Methods of Manufacturing

From 8-hydroxyquinoline by iodination.

Uses

It acts as an amoebicidal and so used in the treatment of amoebiasis, balantidiasis (an infection caused by protozoa).

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.

8-Quinolinol, 5,7-diiodo-: ACTIVE

THIN-LAYER CHROMATOGRAPHY METHOD WAS DEVELOPED FOR ISOLATION OF 5-CHLORO-7-IODO-8-HYDROXYQUINOLINE & ITS HOMOLOGS.

Computed Properties

Molecular Weight:396.95
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:396.84606
Monoisotopic Mass:396.84606
Topological Polar Surface Area:33.1
Heavy Atom Count:13
Complexity:191
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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