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Chemical Structure| 130-26-7 Chemical Structure| 130-26-7

Structure of Clioquinol
CAS No.: 130-26-7

Chemical Structure| 130-26-7

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

Synonyms: Iodochlorohydroxyquinoline; Iodochlorohydroxyquin; NSC 74938

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Product Details of Clioquinol

CAS No. :130-26-7
Formula : C9H5ClINO
M.W : 305.50
SMILES Code : OC1=C(I)C=C(Cl)C2=C1N=CC=C2
Synonyms :
Iodochlorohydroxyquinoline; Iodochlorohydroxyquin; NSC 74938
MDL No. :MFCD00006787
InChI Key :QCDFBFJGMNKBDO-UHFFFAOYSA-N
Pubchem ID :2788

Safety of Clioquinol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H361-H317
Precautionary Statements:P501-P261-P270-P202-P201-P264-P280-P272-P308+P313-P337+P313-P305+P351+P338-P302+P352-P333+P313-P362-P301+P312+P330-P405

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
OPM2 20 µM 24 hours Induced LC3-II expression, indicating autophagosome formation Sci Rep. 2014 Jul 18;4:5749.
RPMI-8226 20 µM 24 hours Induced LC3-II expression, indicating autophagosome formation Sci Rep. 2014 Jul 18;4:5749.
K562 20 µM 24 hours Induced LC3-II expression, indicating autophagosome formation Sci Rep. 2014 Jul 18;4:5749.
LP1 10, 20, 30 µM 24 hours Induced LC3-II expression, indicating autophagosome formation Sci Rep. 2014 Jul 18;4:5749.
THP-1 20 µM 24 hours Induced LC3-II expression, indicating autophagosome formation Sci Rep. 2014 Jul 18;4:5749.
OCI-AML2 20 µM 24 hours Induced LC3-II expression, indicating autophagosome formation Sci Rep. 2014 Jul 18;4:5749.
Human cervical cancer (HeLa) cells 50 µM 16 hours CQ treatment increased total H3K4me3, H3K9me3, and H3K27me3 iScience. 2022 Jun 3;25(7):104517.
Human adipocyte-derived stem cells (hADSCs) 25 µM and 50 µM 16 hours CQ treatment increased total H3K4me3, H3K9me3, and H3K27me3 iScience. 2022 Jun 3;25(7):104517.
Yeast cells 0.6 µM 16 hours Clioquinol significantly reduced the accumulation of Aβ, and this effect was dependent on metal binding. Proc Natl Acad Sci U S A. 2014 Mar 18;111(11):4013-8.
DRG neurons 3 µM 20 seconds To investigate the effect of CQ in DRG neurons, results showed that CQ activated Ca2+ influx via TRPA1. Proc Natl Acad Sci U S A. 2009 May 19;106(20):8374-9.
MCF10A 20 µM 24 hours To test the proteasome inhibition and apoptosis induction effects of Clioquinol mixed with copper on normal and malignant breast cells. Results showed that Clioquinol mixed with copper had significant inhibitory effects on malignant cells but no effect on normal cells. Breast Cancer Res. 2005;7(6):R897-908.
MDA-MB-231 20 µM 24 hours To test the proteasome inhibition and apoptosis induction effects of Clioquinol mixed with copper on breast cancer cells. Results showed that Clioquinol mixed with copper significantly inhibited proteasome activity and induced apoptosis. Breast Cancer Res. 2005;7(6):R897-908.
HUVECs 2.5, 5, 10 µM 24 hours Assessed cell proliferation, showing dose-dependent inhibition Angiogenesis. 2025 Feb 3;28(2):13.
M1C cells 5 µM 24 hours To evaluate the effect of CQ on tau protein levels. Results showed that 5 µM CQ significantly reduced tau protein levels detected by non-phospho dependent Tau5 Int J Mol Sci. 2021 Nov 8;22(21):12063.
M1C cells 1 µM 24 hours To evaluate the effect of CQ on intracellular Cu+ levels. Results showed that 1 µM CQ significantly reduced intracellular Cu+ levels Int J Mol Sci. 2021 Nov 8;22(21):12063.
M1C cells 0.1 to 10 µM 24 hours To evaluate the effect of CQ on cell viability. Morphological analysis and ATP assay showed that CQ up to 10 µM had no effect on cell viability, but 100 µM CQ was cytotoxic Int J Mol Sci. 2021 Nov 8;22(21):12063.
HL-1 cardiomyocytes 80 μg/ml 24 hours Evaluate the inhibitory effect of Clioquinol on ISO-induced ferroptosis in HL-1 cardiomyocytes. Results showed that Clioquinol significantly inhibited ISO-induced ferroptosis in HL-1 cardiomyocytes. Front Pharmacol. 2022 Jul 22;13:918292.
HL-1 cardiomyocytes 0, 10, 20, 40, 60, 80, 100 μg/ml 24 hours Evaluate the cytotoxicity of Clioquinol on HL-1 cardiomyocytes. Results showed that when the concentration of Clioquinol was 60–100 μg/ml, HL-1 cells exhibited significant cytotoxicity. Front Pharmacol. 2022 Jul 22;13:918292.
HEK293 cells 0, 1, 5, 6, 8, 10 µM 24 hours To evaluate the effect of CQ on lipid peroxidation. CQ increased lipid peroxidation in HEK293 cells, while the antioxidants NAC and Trolox significantly reduced CQ-induced lipid peroxidation. Front Pharmacol. 2022 Oct 4;13:1000278.
HepG2 cells 0, 1, 2, 3, 4, 5, 10 µM 24 hours To evaluate the effect of CQ on ATP levels. Only at the highest concentrations, a small but significant reduction of ATP was detected in both media. Front Pharmacol. 2022 Oct 4;13:1000278.
SK-N-SH cells 5 µM 24 hours Clioquinol at low dose increased cell viability and reversed cell death caused by MPP+ or H2O2, reducing apoptosis and ROS levels. Aging (Albany NY). 2020 May 18;12(10):9515-9533.
HEK293 cells 0.5–8 µM 30 minutes Reduced mutant protein expression and cell death Proc Natl Acad Sci U S A. 2005 Aug 16;102(33):11840-5.
PC12 cells 4 µM 48 hours Reduced mutant protein accumulation and cell death Proc Natl Acad Sci U S A. 2005 Aug 16;102(33):11840-5.
HDMECs 10 µM 48 hours Assessed cell viability, showing selective and significant reduction Angiogenesis. 2025 Feb 3;28(2):13.
HUVECs 10 µM 48 hours Assessed cell viability, showing selective and significant reduction Angiogenesis. 2025 Feb 3;28(2):13.
CNE-2s cells 1 µM 6 hours Enhanced radiosensitivity of CNE-2s cells through autophagy inhibition, activation of the caspase system and impairment of DNA damage repair Int J Biol Sci. 2020 Jan 14;16(5):777-789.
Yeast cells 0.8 µM 7 hours Clioquinol promotes Aβ degradation through a metal-dependent mechanism, reducing Aβ levels and restoring functional vesicle trafficking ACS Chem Neurosci. 2017 Sep 20;8(9):2039-2055.
A2780 cells 13.00±2.1 µM (IC50) 72 hours Compare the cytotoxicity of clioquinol and its analogues, IC50 value was 13.00±2.1 μM Cancer Lett. 2011 Dec 15;312(1):11-7.
Panc-1 cells 5.89±0.28 µM (IC50) 72 hours Compare the cytotoxicity of clioquinol and its analogues, IC50 value was 5.89±0.28 μM Cancer Lett. 2011 Dec 15;312(1):11-7.
DHL-4 cells 2.71±0.18 µM (IC50) 72 hours Compare the cytotoxicity of clioquinol and its analogues, IC50 value was 2.71±0.18 μM Cancer Lett. 2011 Dec 15;312(1):11-7.
HL-60 cells 12.90±0.16 µM (IC50) 72 hours Compare the cytotoxicity of clioquinol and its analogues, IC50 value was 12.90±0.16 μM Cancer Lett. 2011 Dec 15;312(1):11-7.
Raji cells 5.09±0.20 µM (IC50) 72 hours Compare the cytotoxicity of clioquinol and its analogues, IC50 value was 5.09±0.20 μM Cancer Lett. 2011 Dec 15;312(1):11-7.
CHO cells 10 µM To investigate whether CQ directly activates TRPA1, results showed that CQ evoked currents in CHO cells via TRPA1 activation. Proc Natl Acad Sci U S A. 2009 May 19;106(20):8374-9.
Human glioblastoma (U87) 50 µM CQ treatment increased total H3K4me3, H3K9me3, and H3K27me3 iScience. 2022 Jun 3;25(7):104517.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Caenorhabditis elegans Glutamatergic neuron-specific Aβ expression model Soaking administration 0.125-0.25 μM 24-hour treatment followed by 4-day observation Clioquinol synergizes with DHPM-thiones to significantly protect Aβ-expressing glutamatergic neurons from toxicity ACS Chem Neurosci. 2017 Sep 20;8(9):2039-2055.
Caenorhabditis elegans Glutamatergic neuron model expressing Aβ Acute administration 0.5 μM, 1 μM, 2 μM Single dose, transferred to normal media after 24 hours Clioquinol significantly reduced Aβ-induced neuronal loss and improved the survival rate of the worms. Proc Natl Acad Sci U S A. 2014 Mar 18;111(11):4013-8.
BALB/c mice Matrigel plug assay Subcutaneous injection 10 µM 7 days Assessed blood vessel formation, showing a 43% reduction in microvessel density Angiogenesis. 2025 Feb 3;28(2):13.
BALB/C nu/nu mice CNE-2s cell xenograft model Intraperitoneal injection 10 mg/kg Once every other day for one week CQ combined with zinc significantly enhanced the radiosensitivity of CNE-2s cells and inhibited tumor growth Int J Biol Sci. 2020 Jan 14;16(5):777-789.
Rhesus monkeys (Macaca mulatta lasiotis) MPTP-induced Parkinson’s disease model Oral 10 mg/kg Twice daily for four weeks Clioquinol significantly improved motor and non-motor deficits induced by MPTP, reduced iron content and ROS levels in the SN, improved pathology, and activated the AKT/mTOR pathway. Aging (Albany NY). 2020 May 18;12(10):9515-9533.
Mice Wild-type and TRPA1-deficient mice Intraplantar injection 2.5 nmoles Single injection, observed for 4 hours To investigate the acute nociceptive effects of CQ in mice, results showed that CQ caused mechanical hyperalgesia and cold hypersensitivity via TRPA1. Proc Natl Acad Sci U S A. 2009 May 19;106(20):8374-9.
C57BL/6 mice Diabetic wound model Local injection 4 μg/wound Dressing changed on postoperative days 3 and 6 To evaluate the efficacy of EXOsiFDX1-PDA@CQ in diabetic wound models. Results showed that EXOsiFDX1-PDA@CQ significantly promoted wound healing, reduced Cu content, and inhibited FDX1 expression. Adv Sci (Weinh). 2025 Jan;12(4):e2413408
C57BL/6 mice MSU-induced acute peritonitis Intraperitoneal injection 5 mg/kg or 10 mg/kg Every 12 hours for 24 hours To evaluate the therapeutic effect of CQ on MSU-induced acute peritonitis, results showed that CQ significantly reduced the frequency and number of white blood cells, neutrophils, and monocytes, and decreased the release of IL-1β, IL-6, and TNF-α. J Pharm Anal. 2025 Jan;15(1):101069

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT00943748 Parkinson's Disease Phase 2 Phase 3 Completed - France ... More >> Service de Neurologie, Clinique Neurologique, EA 2683, IFR 114 Lille, France, 59037 Less <<
NCT01429701 Eczema Phase 3 Completed - -
NCT00963495 Acute Myeloid Leukemia|Acute L... More >>ymphocytic Leukemia|Chronic Lymphocytic Leukemia|Myelodysplasia|Lymphoma, Non-Hodgkin|Hodgkin's Lymphoma|Multiple Myeloma Less << PHASE1 TERMINATED 2025-09-13 Princess Margaret Hospital, To... More >>ronto, Ontario, M5G 2M9, Canada Less <<
NCT05727943 Epilepsy Intractable PHASE2 UNKNOWN 2023-12-31 University Hospitals UZ Leuven... More >>, Leuven, 3000, Belgium Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.27mL

0.65mL

0.33mL

16.37mL

3.27mL

1.64mL

32.73mL

6.55mL

3.27mL

References

 

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