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Clioquinol

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Name

Clioquinol

EINECS 204-984-4
CAS No. 130-26-7 Density 2.047 g/cm3
PSA 33.12000 LogP 3.19840
Solubility water: <0.1 g/100 mL at 20 °C Melting Point 175-183 °C
Formula C9H5ClINO Boiling Point 350.424 °C at 760 mmHg
Molecular Weight 305.502 Flash Point 165.731 °C
Transport Information UN 2811 6.1/PG 3 Appearance Cream-colored to brownish-yellow powder
Safety 36/37/39-45 Risk Codes 25
Molecular Structure Molecular Structure of 130-26-7 (Clioquinol) Hazard Symbols ToxicT
Synonyms

Barquinol;Chinoform;Chloroiodoquine;Cifoform;Dioquinol;Eczecidin;Enteroquinol;Enterozol;Iodochlorhydroxyquin;Iodochloroquine;Iodochloroxyquinoline;Iodoxyquinoline;NSC 3531;Nioform;Quinambicide;Quiniodochlor;Quinoform;Rheaform;Rheaform Boluses;Vioform;5-Chloro-7-iodo-8-oxyquinoline;5-Chloro-7-iodo-8-quinolinol;7-Iodo-5-chloro-8-hydroxyquinoline;8-Hydroxy-7-iodo-5-chloroquinoline;Amebil;Bactol;Clioquinol;

Article Data 18

Clioquinol Synthetic route

130-16-5

5-Chloro-8-hydroxyquinoline

130-26-7

5-chloro-7-iodoquinolin-8-ol

Conditions
ConditionsYield
With 1-butyl-3-methyl-pyridinium dichloroiodate at 80℃; for 1h; Inert atmosphere;94%
Stage #1: With iodine; tert-butylamine In chloroform; toluene at -78℃;
Stage #2: 5-Chloro-8-hydroxyquinoline In chloroform; toluene at -78 - 20℃; for 0.75h;
7385-89-9

7-iodo-8-hydroxyquinoline

130-26-7

5-chloro-7-iodoquinolin-8-ol

Conditions
ConditionsYield
With trichloroisocyanuric acid In acetonitrile at 20℃; for 2h;65%
148-24-3

8-quinolinol

130-26-7

5-chloro-7-iodoquinolin-8-ol

Conditions
ConditionsYield
With tetrachloromethane; iodine trichloride Behandeln des Reaktionsprodukts mit Wasser;
With iodine trichloride; acetic acid Behandeln des jeweils erhalten Reaktionsprodukts mit Wasser;
With hydrogenchloride; iodine trichloride Behandeln des jeweils erhalten Reaktionsprodukts mit Wasser;
220819-20-5

1-(5-chloro-7-iodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>butandioate

A

130-26-7

5-chloro-7-iodoquinolin-8-ol

B

110-15-6

succinic acid

C

443-48-1

metronidazole

D

13182-87-1

4-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy]-4-oxobutanoic acid

Conditions
ConditionsYield
With phosphate buffer; potassium chloride In methanol at 37℃; Rate constant; var. pH; also with human plasma and rat liver homogenate;
220819-25-0

1-(5-chloro-7-iodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>phthalate

A

130-26-7

5-chloro-7-iodoquinolin-8-ol

B

88-99-3

benzene-1,2-dicarboxylic acid

C

443-48-1

metronidazole

D

126613-32-9

1,2-benzenedicarboxylic acid, mono[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]ester

Conditions
ConditionsYield
With phosphate buffer; potassium chloride In methanol at 37℃; Rate constant; var. pH; also with human plasma and rat liver homogenate;
5-chloro-quinolin-8-ol-iodo chloride-hydrochloride

5-chloro-quinolin-8-ol-iodo chloride-hydrochloride

130-26-7

5-chloro-7-iodoquinolin-8-ol

Conditions
ConditionsYield
With water
alkali salt of 5-chloro-8-oxy-quinoline

alkali salt of 5-chloro-8-oxy-quinoline

130-26-7

5-chloro-7-iodoquinolin-8-ol

Conditions
ConditionsYield
With water; iodine; potassium iodide
With sodium hypochlorite; water; potassium iodide
7647-01-0

hydrogenchloride

148-24-3

8-quinolinol

iodine trichloride

iodine trichloride

130-26-7

5-chloro-7-iodoquinolin-8-ol

Conditions
ConditionsYield
anschl. Behandeln mit Wasser;
27037-46-3

5-chloro-7-iodoquinolin-8-yl ethanoate

130-26-7

5-chloro-7-iodoquinolin-8-ol

Conditions
ConditionsYield
With sodium hydroxide Heating;
1371439-48-3

5-chloro-7-iodo-8-quinolinyl-β-D-glucopyranoside

A

492-61-5

β-D-glucose

B

130-26-7

5-chloro-7-iodoquinolin-8-ol

Conditions
ConditionsYield
With β-glucosidase from almonds; water at 37℃; for 4h; pH=7; Reagent/catalyst; Enzymatic reaction;

Clioquinol Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Clioquinol Specification

Clioquinol is an antifungal drug and antiprotozoal drug. With the CAS NO.130-26-7, Clioquinol is a quinoline compound that has antibacterial and antifungal properties. It is found in topical preparations to treat skin infections such as infected eczema, athlete's foot and other fungal infections. It is also found in combination preparations with hydrocortisone. It can be found in eye and ear preparations. Clioquinol is mainly used for intestinal amoebic dysentery and bacillary dysentery,and diarrhea caused by taking antibiotics, diarrhea and other nerve.

Physical properties about Clioquinol are: (1)ACD/LogP: 4.171; (2)ACD/LogD (pH 5.5: 3.10; (3)ACD/LogD (pH 7.4): 2.47; (4)ACD/BCF (pH 5.5): 73.89; (5)ACD/BCF (pH 7.4): 17.47; (6)ACD/KOC (pH 5.5): 375.51; (7)ACD/KOC (pH 7.4): 88.78; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.768; (12)Molar Refractivity: 61.87 cm3; (13)Molar Volume: 149.226 cm3; (14)Polarizability: 24.527 10-24cm3; (15)Surface Tension: 70.0690002441406 dyne/cm; (16)Density: 2.047 g/cm3; (17)Flash Point: 165.731 °C; (18)Enthalpy of Vaporization: 61.852 kJ/mol; (19)Boiling Point: 350.424 °C at 760 mmHg

When you are using this chemical, please be cautious about it as the following:
1. Wear suitable protective clothing, gloves and eye/face protection
2. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)

You can still convert the following datas into molecular structure:
(1)InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H;
(2)InChIKey=QCDFBFJGMNKBDO-UHFFFAOYSA-N;
(3)Smilesc12c(c(cc(c1O)I)Cl)cccn2

The toxicity data is as follows:

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.

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