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Chemical Structure| 41621-49-2 Chemical Structure| 41621-49-2

Structure of Ciclopirox olamine
CAS No.: 41621-49-2

Chemical Structure| 41621-49-2

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Ciclopirox Olamine is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses.

Synonyms: Ciclopirox ethanolamine; HOE 296

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Product Details of Ciclopirox olamine

CAS No. :41621-49-2
Formula : C14H24N2O3
M.W : 268.35
SMILES Code : O=C1C=C(C)C=C(C2CCCCC2)N1O.NCCO
Synonyms :
Ciclopirox ethanolamine; HOE 296
MDL No. :MFCD00078997
InChI Key :MBRHNTMUYWQHMR-UHFFFAOYSA-N
Pubchem ID :38911

Safety of Ciclopirox olamine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

Target
  • ATPase

In Vitro:

Cell Line
Concentration Treated Time Description References
HeLa-NP-GFP 1, 5, 10 μM 48 h To screen small-molecule compounds that promote NP degradation, results showed that ciclopirox significantly decreased GFP signal. Acta Pharm Sin B. 2024 Jun;14(6):2505-2519.
U118 cells 5, 10, 20, 40, 80, 160, 320 μM 48 h To evaluate the cytotoxicity of CPX on GBM cells, results showed that CPX significantly inhibited GBM cell growth. Cell Death Dis. 2021 Mar 5;12(3):251.
A172 cells 5, 10, 20, 40, 80, 160, 320 μM 48 h To evaluate the cytotoxicity of CPX on GBM cells, results showed that CPX significantly inhibited GBM cell growth. Cell Death Dis. 2021 Mar 5;12(3):251.
SF126 cells 5, 10, 20, 40, 80, 160, 320 μM 48 h To evaluate the cytotoxicity of CPX on GBM cells, results showed that CPX significantly inhibited GBM cell growth. Cell Death Dis. 2021 Mar 5;12(3):251.
U251 cells 5, 10, 20, 40, 80, 160, 320 μM 48 h To evaluate the cytotoxicity of CPX on GBM cells, results showed that CPX significantly inhibited GBM cell growth. Cell Death Dis. 2021 Mar 5;12(3):251.
SGC cells 0, 20, 40, 80 μM 24 h To evaluate the antitumor activity of CPX in vitro, CPX markedly inhibited the proliferation of all tested cell lines and reduced their viability in a dose-dependent manner. Cell Death Dis. 2022 Nov 28;13(11):1007.
AGS cells 0, 5, 10, 20 μM 24 h To evaluate the antitumor activity of CPX in vitro, CPX markedly inhibited the proliferation of all tested cell lines and reduced their viability in a dose-dependent manner. Cell Death Dis. 2022 Nov 28;13(11):1007.
MGC cells 0, 5, 10, 20 μM 24 h To evaluate the antitumor activity of CPX in vitro, CPX markedly inhibited the proliferation of all tested cell lines and reduced their viability in a dose-dependent manner. Cell Death Dis. 2022 Nov 28;13(11):1007.
Huh-7 cells 1μM 36 h Evaluating the effect of ciclopirox on intracellular HBV capsid assembly, it inhibited HBV capsid assembly Nat Commun. 2019 May 16;10(1):2184.
HepG2.2.15 cells 1μM 3 days Screening compounds for HBV replication inhibition, ciclopirox strongly inhibited HBV DNA secretion Nat Commun. 2019 May 16;10(1):2184.
DLD-1 5, 10, 20 μM 48 h To evaluate the anticancer activity of CPX in CRC cells, the results showed that CPX markedly suppressed CRC viability and proliferation in vitro. Cell Death Dis. 2020 Jul 27;11(7):582.
HCT-8/5-FU 10, 20, 40 μM 7 days To evaluate the antiproliferative activity of CPX, the results showed that CPX significantly reduced the colony-forming ability of CRC cells in a dose-dependent manner. Cell Death Dis. 2020 Jul 27;11(7):582.
HCT-8 5, 10, 20, 40, 80 μM 48 h To evaluate the anticancer activity of CPX in CRC cells, the results showed that CPX markedly suppressed CRC viability and proliferation in vitro. Cell Death Dis. 2020 Jul 27;11(7):582.
Murine lymphatic endothelial cells (LECs) 5 μM 0-24 h CPX inhibited LEC tube formation in a time-dependent manner, significantly blocking tube formation by ~20% after 4 h and ~90% after 24 h. Oncogene. 2011 May 5;30(18):2098-107.
Murine lymphatic endothelial cells (LECs) 0-5 μM 24 h CPX inhibited LEC tube formation in a concentration-dependent manner, with approximately 70% and 90% inhibition at 2.5 and 5 μM, respectively. Oncogene. 2011 May 5;30(18):2098-107.
adenocarcinoma SK-HEP-1 cells 10 μM 12 h CPX completely blocked H2O2-stimulated release of lactate dehydrogenase (a marker of cell death) and decrease in MTT reduction (a marker of mitochondrial function). Br J Pharmacol. 2005 Jun;145(4):469-76.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
BALB/C mice SARS-CoV-2 infection model Intraperitoneal injection 20 mg/kg 5 consecutive days To evaluate the inhibitory effect of ciclopirox on SARS-CoV-2 replication in vivo, results showed that ciclopirox significantly reduced viral titers and lung pathology. Acta Pharm Sin B. 2024 Jun;14(6):2505-2519.
SD rats Middle cerebral artery occlusion (MCAO) model Intravenous injection 3 mg/kg Single dose or continuous administration every 24 hours for 7 days To evaluate the alleviative effect of CPX on brain infarction, neurological deficits, and brain edema in MCAO rats, results showed CPX significantly reduced brain infarction, neurological deficits, and brain edema, and improved long-term motor function recovery. Acta Pharm Sin B. 2020 Mar;10(3):434-446
BALB/c nude mice GBM xenograft model Intraperitoneal injection 20 mg/kg, 15 mg/kg Once daily for 12 days To evaluate the inhibitory effect of CPX on GBM tumor growth, results showed that CPX significantly suppressed tumor growth. Cell Death Dis. 2021 Mar 5;12(3):251.
BALB/c nude mice GC xenograft model Intraperitoneal injection 20 mg/kg Once daily for 12 days To evaluate the antitumor tumor growth potential of CPX in vivo, CPX significantly suppressed GC tumor growth when compared to the control group. Cell Death Dis. 2022 Nov 28;13(11):1007.
BALB/c male mice Humanized liver mouse model Oral 5 mg/kg Daily for 4 weeks Assessing the antiviral effect of ciclopirox on HBV replication in vivo, it significantly reduced serum HBV DNA levels Nat Commun. 2019 May 16;10(1):2184.
Balb/c nude mice CRC xenograft model Intraperitoneal injection 20 mg/kg Once a day for 12 days To evaluate the antitumor activity of CPX in vivo, the results showed that CPX significantly inhibited CRC xenograft growth. Cell Death Dis. 2020 Jul 27;11(7):582.

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.73mL

0.75mL

0.37mL

18.63mL

3.73mL

1.86mL

37.26mL

7.45mL

3.73mL

References

[1]Zarember KA, Cruz AR, et al. Antifungal activities of natural and synthetic iron chelators alone and in combination with azole and polyene antibiotics against Aspergillus fumigatus. Antimicrob Agents Chemother. 2009 Jun;53(6):2654-6.

[2]Niewerth M, Kunze D, et al. Ciclopirox olamine treatment affects the expression pattern of Candida albicans genes encoding virulence factors, iron metabolism proteins, and drug resistance factors. Antimicrob Agents Chemother. 2003 Jun;47(6):1805-17.

[3]Bernier KM, Morrison LA, et al. Antifungal drug ciclopirox olamine reduces HSV-1 replication and disease in mice. Antiviral Res. 2018 Aug;156:102-106.

[4]Mihailidou C, Papakotoulas P, et al. Superior efficacy of the antifungal agent ciclopirox olamine over gemcitabine in pancreatic cancer models. Oncotarget. 2017 Dec 8;9(12):10360-10374.

[5]Weir SJ, Wood R, et al. Preclinical Pharmacokinetics of Fosciclopirox, a Novel Treatment of Urothelial Cancers, in Rats and Dogs. J Pharmacol Exp Ther. 2019 Aug;370(2):148-159.

[6]Lim SH, Kim C, Aref AR, Kamm RD, Raghunath M. Complementary effects of ciclopirox olamine, a prolyl hydroxylase inhibitor and sphingosine 1-phosphate on fibroblasts and endothelial cells in driving capillary sprouting. Integr Biol (Camb). 2013 Dec;5(12):1474-84.

[7]Kremer A, Wußmann M, Herrmann M, Raghunath M, Walles H. Ciclopirox olamine promotes the angiogenic response of endothelial cells and mesenchymal stem cells. Clin Hemorheol Microcirc. 2019;73(2):317-328.

[8]Kang JA, Kim S, Park M, Park HJ, Kim JH, Park S, Hwang JR, Kim YC, Jun Kim Y, Cho Y, Sun Jin M, Park SG. Ciclopirox inhibits Hepatitis B Virus secretion by blocking capsid assembly. Nat Commun. 2019 May 16;10(1):2184.

[10]Shen T, Huang S. Repositioning the Old Fungicide Ciclopirox for New Medical Uses. Curr Pharm Des. 2016;22(28):4443-50.

 

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