An internal standard for the quantification of ciclopirox
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Unlabeled Version(s)
16021Ciclopirox
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Ciclopirox-d11 (sodium salt)

Item No. 28698

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-(cyclohexyl-d11)-1-hydroxy-4-methyl-2(1H)-pyridinone, monosodium salt
Synonyms
  • HOE 296b-d11
Molecular Formula
C12H5D11NO2 • Na
Formula Weight
240.3
Purity
≥99% deuterated forms (d1-d11)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
O=C1C=C(C)C=C(C2([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C2([2H])[2H])N1[O-].[Na+]
InChi Code
InChI=1S/C12H16NO2.Na/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10;/h7-8,10H,2-6H2,1H3;/q-1;+1/i2D2,3D2,4D2,5D2,6D2,10D;
InChi Key
YHRJBSLTTUNMMI-ZBARUEKKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $281

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    Product Description

    Ciclopirox-d11 (sodium salt) is intended for use as an internal standard for the quantification of ciclopirox (Item No. 16021) by GC- or LC-MS. Ciclopirox is an iron chelator, antifungal, and anticancer agent.1,2,3,4 It inhibits the iron-dependent enzyme prolyl hydroxylase 2 (PHD2; 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).