Iodoquinol (also known as Diiodohydroxyquinoline), a halogenated 8-quinolinol analog with satisfactory antibacterial properties, is widely used as an intestinal antiseptic, especially as an antiamebic agent. Iodoquinol is also used topically in other infections and may cause central nervous system and eye damage.
Physicochemical Properties
| Molecular Formula | C9H5NOI2 |
| Molecular Weight | 396.9501 |
| Exact Mass | 396.846 |
| Elemental Analysis | C, 27.23; H, 1.27; I, 63.94; N, 3.53; O, 4.03 |
| CAS # | 83-73-8 |
| Related CAS # | 53341-25-6 (sodium);83-73-8; |
| PubChem CID | 3728 |
| Appearance | Light yellow to brown crystalline solid. |
| Density | 2.5±0.1 g/cm3 |
| Boiling Point | 401.8±45.0 °C at 760 mmHg |
| Melting Point | >200 °C (dec.)(lit.) |
| Flash Point | 196.8±28.7 °C |
| Vapour Pressure | 0.0±1.0 mmHg at 25°C |
| Index of Refraction | 1.828 |
| LogP | 4.11 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Heavy Atom Count | 13 |
| Complexity | 191 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | IC1C(O)=C2C(C=CC=N2)=C(I)C=1 |
| InChi Key | UXZFQZANDVDGMM-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H |
| Chemical Name | 5,7-diiodoquinolin-8-ol |
| Synonyms | 5,7-Diiodo-8-hydroxyquinoline; 5,7-Diiodo-8-quinolinol;Diiodohydroxyquin, Diiodoquin, Diquinol, Sebaquin |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion 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. |
| References |
[1]. Flavonoids as a Natural Treatment Against Entamoeba histolytica. Front Cell Infect Microbiol. 2018 Jun 22;8:209. [2]. In vivo antimutagenic effect of ascorbic acid against mutagenicity of the common antiamebic drug diiodohydroxyquinoline. Mutat Res. 1989 Mar;222(3):219-22. [3]. Discovery of the FDA-approved drugs bexarotene, cetilistat, diiodohydroxyquinoline, and abiraterone as potential COVID-19 treatments with a robust two-tier screening system. Pharmacol Res. 2020 Sep;159:104960. [4]. Efficacy and safety of metronidazole versus a combination of metronidazole and diiodohydroxyquinoline for the treatment of patients with intestinal amebiasis: a primary care physician research group study. 1995 July, 56(7): 678-683. [5]. Cohlan SQ. Chronic nonspecific diarrhea in infants and children treated with diiodohydroxyquinoline. Pediatrics. 1956 Sep;18(3):424-32. |
| Additional Infomation |
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. Drug Indication Used in the treatment of amoebiasis. 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/ 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/ For more Therapeutic Uses (Complete) data for DIIODOHYDROXYQUIN (8 total), please visit the HSDB record page. Drug Warnings 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. |
Solubility Data
| Solubility (In Vitro) |
DMSO : 13~20.83 mg/mL ( 32.74~52.48 mM) H2O : ~0.67 mg/mL (~1.69 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (6.30 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: 2.5 mg/mL (6.30 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5192 mL | 12.5960 mL | 25.1921 mL | |
| 5 mM | 0.5038 mL | 2.5192 mL | 5.0384 mL | |
| 10 mM | 0.2519 mL | 1.2596 mL | 2.5192 mL |