Ciclopirox

Ciclopirox is an iron chelator, antifungal, and anticancer agent. 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. It stabilizes hypoxia-inducible factor-alpha (HIF-1alpha) under normoxic conditions in rat glomus cells when used at a concentration of 5 µM. 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. 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. 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.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: DMF: 15 mg/ml, DMSO: 15 mg/ml, Ethanol: 30 mg/ml, PBS (pH 7.2): 1 mg/ml. lambdamax: 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.