Ciclopirox

Ciclopirox (Penlac) is a synthetic antifungal agent.Target: AntifungalCiclopirox is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor. The mechanism of action of ciclopirox is poorly understood [1]. However, loss of function of certain catalase and peroxidase enzymes has been implicated as the mechanism of action, as well as various other components of cellular metabolism. In a study conducted to further elu

Solid

Ciclopirox is a cyclic hydroxamic acid that is 1-hydroxypyridin-2(1H)-one in which the hydrogens at positions 4 and 6 are substituted by methyl and cyclohexyl groups, repectively. A broad spectrum antigfungal agent, it also exhibits antibacterial activity against many Gram-positive and Gram-negative bacteria, and has anti-inflammatory properties. It is used a a topical treatment of fungal skin and nail infections. It has a role as an antibacterial agent and an antiseborrheic. It is a pyridone, a cyclic hydroxamic acid and a hydroxypyridone antifungal drug.|Ciclopirox olamine (used in preparations called Batrafen, Loprox, Mycoster, Penlac and Stieprox) is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. In particular, the agent is especially effective in treating Tinea versicolor.|The mechanism of action of ciclopirox is as a Protein Synthesis Inhibitor. The physiologic effect of ciclopirox is by means of Decreased DNA Replication, and Decreased Protein Synthesis, and Decreased RNA Replication.|Ciclopirox is a synthetic, broad-spectrum antifungal agent with additional antibacterial and anti-inflammatory activities. Ciclopirox exerts its action by binding to and chelating trivalent cations, such as Fe3+ and Al3+, thereby inhibiting the availability of essential co-factors for enzymes. This may lead to a loss of activity of enzymes that are essential for cellular metabolism, organization of cell wall structure and other crucial cell functions. In addition, ciclopirox exerts its anti-inflammatory activity by inhibiting 5-lipoxygenase and cyclooxygenase (COX).|A cyclohexane and pyridinone derivative that is used for the treatment of fungal infections of the skin and nails, and for treatment of VAGINAL YEAST INFECTIONS.

The reaction of Scheme 1 prepares a ciclopirox from a olamine salt thereof. [094] In one embodiment, the present invention provides a method of preparing 6- cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one, which method can include reactionScheme 1 as shown in Figure 1. The reaction of Scheme 1 prepares a ciclopirox from anolamine salt thereof. Briefly, ciclopirox olamine (5 g, 18.6 mmol) can be dissolved in 2 NHC1, extracted with EtOAc, and precipitated with hexane in order to obtain ciclopirox(about an 84percent yield).30g of aluminum trichloride dissolved in 50ml of dichloromethane, dropwise under stirring into the mixed solution, and HBTA-2 HBTA-02, the control is completed in 20min dropwise, slowly and stirring was continued at reflux for 3 hours on a water bath, until no evolution of hydrogen chloride gas, cooled, slowly poured into ice water 100ml and a mixture of 100ml of concentrated hydrochloric acid, the organic layer was separated, the aqueous phase was extracted with dichloromethane, the combined organic phases were washed with sodium bicarbonate solution and then with water until neutral, dried over anhydrous magnesium sulfate, and evaporated dichloro methane, distillation under reduced pressure collecting 179 / 266Pa distillate, the product 5-oxo-3-methyl-5-cyclohexyl-3-pentenoate 16.7g, 75percent yield. In step (4), a mixture of 11.2g of HBTA-3A and the HBTA-3B, 4.1g of hydroxylamine hydrochloride, dubbed 8ml methanol solution at room temperature with stirring, was added 15ml water and 4.5g of sodium acetate dubbed aqueous solution, vigorously stirred at 30 20 hours and then added to 8ml of 4g of sodium hydroxide aqueous solution under cooling dubbed stirred at room temperature for 1 hour, extracted with benzene, the aqueous solution was acidified to pH 6, a precipitate was filtered, the aqueous phase continue was acidified to pH 3, and extracted with methylene chloride, methylene chloride recovered, concentrated hydrochloric acid was added to the residue, a precipitate was filtered and the precipitate washed twice was recrystallized from ethanol and washed with an aqueous solution to give the product 5g, 34percent yield.Good results are obtained when using a solution which contains one or more of the compounds and/or their salts from the group ... 2-hydroxy-3-methoxy-benzohydroxamic acid 2-hydroxy-5-methoxy-benzohydroxamic acid 2-hydroxy-3-methyl-isocarbostyril 4-chloro-N-methyl-benzohydroxamic acid 6-cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone.Solution according to one of the previous claims, which contains one or more of the compounds and/or their salts from the group ... 2-hydroxy-3-methoxy-benzohydroxamic acid 2-hydroxy-5-methoxy-benzohydroxamic acid 2-hydroxy-3-methyl-isocarbostyril 4-chloro-N-methyl-benzohydroxamic acid 6-cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone.12. Isopropyl alcohol: 27.0% Ethyl acetate: 27.0% 50% solution of a copolymer of methyl vinyl ether and monobutyl maleate in isopropyl alcohol: 34.0% 1-Hydroxy-4-methyl-6-cyclohexyl-2-pyridone: 12.0%Compounds that can be prepared by the process of the invention are, for example, the following: ... 1-hydroxy-3, 4, 6-trimethyl-2-pyridone, 1-hydroxy-4-methyl-6-ethyl-2-pyridone, 1-hydroxy-4, 6-dimethyl-5-ethyl-2-pyridone, 1-hydroxy-3-ethyl-4-methyl-6-isobutyl-2l -pyridone, 1-hydroxy-4-methyl-6-cyclohexyl-2-pyridone, 1-hydroxy-4-methyl-6-cyclohexylmethyl-2-pyridone, 1-hydroxy-4-methyl-6-(beta-cyclohexylethyl)-2-pyridone, 1-hydroxy-3, 4-dimethyl-6-cyclopentyl-2-pyridone, ...Benzene sulfonyl chloride (699 muL, 5.30 mmol) was added dropwise to a solution of 23 ciclopirox (1.03 g, 4.97 mmol) in 24 pyridine (5 mL). After stirring at room temperature for 1 day, the mixture was concentrated under vacuum. The residue was dissolved in 25 dichloromethane (60 mL) and washed with water (2×30 mL). The organic layer was dried over magnesium sulfate and then passed through silica gel, eluting with dichloromethane. The organic solution was evaporated under vacuum, and the crude product was triturated sequentially with hexanes and ether to afford 26 6-cyclohexyl-4-methyl-2-oxopyridin-1(2H)-yl benzenesulfonate A1 as a white solid (0.330 g, 19% yield). 1H NMR (CDCl3) delta 8.13 (d, J=0.015, 2H), 7.74 (dd, J=0.015, 0.015, 1H), 7.61 (dd, J=0.016, 0.016, 2H), 6.24 (s, 1H), 5.83 (d, J=0.004, 1H), 2.98 (m, 1H), 2.16 (s, 3H), 2.03 (m, 2H), 1.85 (m, 2H), 1.76 (m, 1H), 1.41 (m, 2H), 1.38 (m, 3H); MS m/z calcd. for C18H22NO4S (M+H)+, 348; found, 348N, N-Dimethyl(p-(chlorosulfonyl)phenyl)amine (0.701 g, 3.19 mmol) was added to a solution of 23 ciclopirox (0.661 g, 3.19 mmol) in 24 pyridine (5 mL). After stirring at room temperature for 1 day, the mixture was concentrated under vacuum. The residue was dissolved in 29 ethyl acetate (60 mL) and washed with water (2×30 mL). The organic layer was dried over magnesium sulfate and then evaporated under vacuum. The crude product was triturated sequentially with hexanes and ether to afford 30 6-cyclohexyl-4-methyl-2-oxopyridin-1(2H)-yl 4-(dimethylamino)benzenesulfonate A2 as a light beige solid (0.840 g, 67% yield). 1H NMR (DMSO-d6) delta 7.75 (d, J=0.018, 2H), 6.85 (d, J=0.019, 2H), 6.22 (s, 1H), 5.97 (d, J=0.004, 1H), 3.07 (s, 6H), 2.58 (m, 1H), 2.12 (s, 3H), 1.76 (m, 4H), 1.61 (m, 1H), 1.19 (m, 2H), 1.12 (m, 3H); MS m/z calcd. for C20H26N2O4SNa (M+Na)+, 413; found, 413The HBTA-4 1- hydroxy-4-methyl-6-cyclohexyl -2 (1H) - pyridone was dissolved in 35ml of ethyl acetate, then 2-aminoethanol was added, and vigorous stirring at 50 deg.] C to precipitate quickly crystals, stirring was continued for 30min, cooled to room temperature, filtered off with suction, washed with ethyl acetate, and dried 45 deg.] C, as a white powdery product ciclopirox.

Ciclopirox (Penlac) is a synthetic antifungal agent. Ciclopirox (Penlac) is used for topical dermatologic treatment of superficial mycoses. Ciclopirox (Penlac) is most useful against Tinea versicolor. [1] In a study conducted to further elucidate ciclopir

Molecular Weight:207.27
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:207.125928785
Monoisotopic Mass:207.125928785
Topological Polar Surface Area:40.5
Heavy Atom Count:15
Complexity:325
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes