Structure of Clioquinol
CAS No.: 130-26-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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Batch number can be found on the product's label following the word 'Batch'.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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| 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 |
| 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 |
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 << |
| 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 |
|
Tags: Clioquinol | Iodochlorohydroxyquinoline | Fungal | Autophagy | Mitophagy | Antibiotic | Parasite | Mitochondrial Autophagy | 130-26-7
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| H305 | May be harmful if swallowed and enters airways |
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| H311 | Toxic in contact with skin |
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| H315 | Causes skin irritation |
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| H318 | Causes serious eye damage |
| H319 | Causes serious eye irritation |
| H320 | Causes eye irritation |
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| H372 | Causes damage to organs through prolonged or repeated exposure |
| H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
| Code | Phrase |
| H400 | Very toxic to aquatic life |
| H401 | Toxic to aquatic life |
| H402 | Harmful to aquatic life |
| H410 | Very toxic to aquatic life with long-lasting effects |
| H411 | Toxic to aquatic life with long-lasting effects |
| H412 | Harmful to aquatic life with long-lasting effects |
| H413 | May cause long-lasting harmful effects to aquatic life |
| H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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