An iron chelator, antifungal, and anticancer agent
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Labeled Version(s)
28698Ciclopirox-d11 (sodium salt)
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Ciclopirox

Item No. 16021

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone
CAS Number
29342-05-0
Synonyms
  • HOE 296b
Molecular Formula
C12H17NO2
Formula Weight
207.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 15 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
231, 303 nm
SMILES
O=C1C=C(C)C=C(C2CCCCC2)N1O
InChi Code
InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3
InChi Key
SCKYRAXSEDYPSA-UHFFFAOYSA-N
Shipping & Storage Information
Storage
Room temperature
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $90

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    250 mg

    $196

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    500 mg

    $349

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    1 g

    $636

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    Cayman Chemical
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    Product Description

    Ciclopirox is an iron chelator, antifungal, and anticancer agent.1,2,3,4 It inhibits the iron-dependent enzyme hypoxia-inducible factor prolyl hydroxylase 2 (HIF-PH2; IC50 = 1.58 μM), an effect that is reduced in the presence of iron.1 It stabilizes hypoxia-inducible factor-α (HIF-1α) under normoxic conditions in rat glomus cells when used at a concentration of 5 μM.5 Ciclopirox is active against clinical isolates of T. rubrum, T. mentagrophytes, and C. albicans (MICs = 0.03-0.5, 0.03-0.5, and 0.06-0.5 μg/ml, respectively) and inhibits growth of T. mentagrophytes on porcine skin ex vivo when applied topically.2,3 It inhibits proliferation of Rh30, HT-29, and MDA-MB-231 cells in a concentration-dependent manner and halts the cell cycle at the G1/G0 phase and induces apoptosis in Rh30 cells.4 Ciclopirox (25 mg/kg) reduces tumor growth in an MDA-MB-231 mouse xenograft model. Formulations containing ciclopirox have been used in the topical treatment of fungal infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Aowicki, D., and Huczynski, A. Structure and antimicrobial properties of monensin A and its derivatives: Summary of the achievements. Biomed. Res. Int. 742149 (2013).

    2. Jo Siu, W.J., Tatsumi, Y., Senda, H., et al. Comparison of in vitro antifungal activities of efinaconazole and currently available antifungal agents against a variety of pathogenic fungi associated with onychomycosis. Antimicrob. Agents Chemother. 57(4), 1610-1616 (2013).

    3. Ceschin-Roques, C.G., Hänel, H., Pruja-Bougaret, S.M., et al. Ciclopirox nail lacquer 8%: In vivo penetration into and through nails and in vitro effect on pig skin. Skin Pharmacol. 4(2), 89-94 (1991).

    4. Zhou, H., Shen, T., Luo, Y., et al. The antitumor activity of the fungicide ciclopirox. Int. J. Cancer 127(10), 2467-2477 (2010).

    5. Baby, S.M., Roy, A., Mokashi, A.M., et al. Effects of hypoxia and intracellular iron chelation on hypoxia-inducible factor-1α and -1β in the rat carotid body and glomus cells. Histochem. Cell. Biol. 120(5), 343-352 (2003).