Clioquinol

Names

[ CAS No. ]:
130-26-7

[ Name ]:
Clioquinol

[Synonym ]:
5-Chloro-8-hydroxy-7-iodoquinoline
Emaform
Bactol
5-21-03-00294 (Beilstein Handbook Reference)
5-chloro-7-iodo-8-hydroxy-quinoline
EINECS 204-984-4
Clioqinol
Vioform
cortin
T66 BNJ GG II JQ
Amebil
8-Quinolinol, 5-chloro-7-iodo-
Rometin
MFCD00006787
5-Chloro-7-iodo-8-quinolinol
5-chloro-7-iodoquinolin-8-ol
oralcer
Nioform
Cliochinolo [DCIT]
Amoenol
Clioquinol
Cliquinol
hysone
5-Cl-7-I-8-HQ
iodochlorohydroxyquinoline
iodochlorohydroxyquin
corque

Biological Activity

[Description]:

Clioquinol(Iodochlorhydroxyquin) is an antifungal drug and antiprotozoal compound that shows effectivity for Alzheimer's disease treatment and induce cancer cell death.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Autophagy >> Mitophagy

Research Areas >> Infection

[References]

[1]. Nguyen T, et al. Clioquinol down-regulates mutant huntingtin expression in vitro and mitigates pathology in a Huntington's disease mouse model. Proc Natl Acad Sci U S A. 2005 Aug 16;102(33):11840-5.

[2]. Cao B, et al. Clioquinol induces pro-death autophagy in leukemia and myeloma cells by disrupting the mTOR signaling pathway. Sci Rep. 2014 Jul 18;4:5749.

[3]. Katsuyama M, et al. Clioquinol increases the expression of VGF, a neuropeptide precursor, through induction of c-Fos expression. J Pharmacol Sci. 2014;124(4):427-32.

[4]. Matlack KE, et al. Clioquinol promotes the degradation of metal-dependent amyloid-β (Aβ) oligomers to restore endocytosis and ameliorate Aβ toxicity. Proc Natl Acad Sci U S A. 2014 Mar 18;111(11):4013-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Boiling Point ]:
350.4±37.0 °C at 760 mmHg

[ Melting Point ]:
175-183 °C

[ Molecular Formula ]:
C₉H₅ClINO

[ Molecular Weight ]:
305.500

[ Flash Point ]:
165.7±26.5 °C

[ Exact Mass ]:
304.910431

[ PSA ]:
33.12000

[ LogP ]:
3.86

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.768

[ Water Solubility ]:
<0.1 g/100 mL at 20 ºC

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VC5075000

CHEMICAL NAME :: 8-Quinolinol, 5-chloro-7-iodo-

CAS REGISTRY NUMBER :: 130-26-7

BEILSTEIN REFERENCE NO. :: 0153637

LAST UPDATED :: 199710

DATA ITEMS CITED :: 29

MOLECULAR FORMULA :: C9-H5-Cl-I-N-O

MOLECULAR WEIGHT :: 305.50

WISWESSER LINE NOTATION :: T66 BNJ GG II JQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 11 gm/kg/36W

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - optic nerve neuropathy Sense Organs and Special Senses (Eye) - visual field changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 1400 mg/kg/20D-I

TOXIC EFFECTS :: Brain and Coverings - recordings from specific areas of CNS

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 69 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 590 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Liver - other changes

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Liver - fatty liver degeneration Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 175 mg/kg

TOXIC EFFECTS :: Liver - other changes

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 15600 mg/kg/26W-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in bladder weight Blood - pigmented or nucleated red blood cells Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 20 gm/kg/14W-I

TOXIC EFFECTS :: Spinal Cord - demyelination Spinal Cord - other degenerative changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 44 gm/kg/25W-I

TOXIC EFFECTS :: Liver - changes in liver weight Musculoskeletal - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 36600 mg/kg/17W-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - acute pulmonary edema Lungs, Thorax, or Respiration - dyspnea Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 7 gm/kg/7D-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - acute pulmonary edema Lungs, Thorax, or Respiration - dyspnea Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 9000 mg/kg

SEX/DURATION :: female 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1320 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4) Reproductive - Effects on Newborn - physical

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 528 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - rat Cells - not otherwise specified

DOSE/DURATION :: 10 umol/L

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 12,97,1987 *** REVIEWS *** TOXICOLOGY REVIEW PRTODI "Progress in Toxicology," Zbinden, G., New York, Springer-Verlag, 1973 Volume(issue)/page/year: 1,68,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4788 No. of Facilities: 152 (estimated) No. of Industries: 2 No. of Occupations: 5 No. of Employees: 13895 (estimated) No. of Female Employees: 11269 (estimated)

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
Missing Phrase - N15.00950417

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
S36/37/39-S45

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
VC5075000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2933499090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933499090

[ Summary ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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