| Identification | More | [Name]
Ciclopirox | [CAS]
29342-05-0 | [Synonyms]
6-CYCLOHEXYL-1-HYDROXY-4-METHYL-1H-PYRIDIN-2-ONE
CICLOPIROX
CIELOPIROX
6-Cyclohexyl-1-hydroxy-4-methyl-2[1H]-pyridinone
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone
Brumixol
Ciciopirox
Cidochem
Dafnegin
geprox
gopmx
Micoxolamina
Mycoster
2(1H)-Pyridinone, 6-cyclohexyl-1-hydroxy-4-methyl-
2(1H)-Pyridone, 6-cyclohexyl-1-hydroxy-4-methyl-
6-Cyclohexyl-1-hydroxy-4-methylpyridin-2-one
Loprox
Penlac
6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one | [EINECS(EC#)]
249-577-2 | [Molecular Formula]
C12H17NO2 | [MDL Number]
MFCD00599441 | [Molecular Weight]
207.27 | [MOL File]
29342-05-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White or Light-Yellow Powder | [Melting point ]
1440C | [Boiling point ]
350.0±25.0 °C(Predicted) | [density ]
1.193±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Slightly soluble in water, freely soluble in anhydrous ethanol and in methylene chloride | [form ]
Solid | [pka]
6.25±0.58(Predicted) | [color ]
Off-White | [Usage]
Broad spectrum antimycotic agent with some antibacterial activity | [CAS DataBase Reference]
29342-05-0(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Originator]
Fungirox Esmalte, UCI-Farma | [Definition]
ChEBI: 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 acti
ity 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. | [Manufacturing Process]
A mixture of 5-oxo-3-methyl-5-cyclohexylpentene-2 acid 1-methyl ester and
5-oxo-3-methyl-5-cyclohexylpentene-3 acid 1-methyl ester was obtained by
condensation of hexahydrobenzoyl chloride with β,β-dimethylacrylic acid
methyl ester. 11.2 g of this mixture and a solution of 4.6 g of sodium acetate
and 4 g of hydroxylamine hydrochloride were shaken for 20 hours at 25°C
with a mixture of 8 ml of water and 15 ml methanol. Subsequently, a solution
of 4 g of sodium hydroxide in 8 ml of water was then added, while cooling,
shaken for 1 hour at room temperature. The mixture was extracted by means
of benzene and the aqueous phase was acidified to reach a pH of 6. 3.5 g of
1-hydroxy-4-methyl-6-cyclohexyl-2-pyridone were obtained; melting point
144°C.
For preparation of cyclopirox from 1-hydroxy-4-methyl-6-cyclohexyl-2-
pyridone was added 2-aminoethanol (1:1).Merck Index, Monograph number: 2325, Twelfth edition, 1996, Editor: S.
Budavari; Merck and Co., Inc.
Greene L.A.; US Patent No. 5,846,984; Dec. 8, 1998; Assigned to The
Trustees of Columbia University in the City of New York (New York, NY)
Lohaus G. et al.; US Patent No. 3,883,545; May 13, 1975; Assigned to
Hoechst Aktiengesellschaft, Frankfurt am Main, Germany | [Brand name]
Loprox(Medicis); Penlac (Sanofi Aventis). | [Therapeutic Function]
Antifungal | [Mechanism of action]
Ciclopirox has a unique mechanism of action through chelation of polyvalent cations, such as Fe3+, which causes inhibition of a number of metal-dependent enzymes within the fungal cell. | [Clinical Use]
Ciclopirox is a hydroxylated pyridinone that is employed for superficial dermatophytic infections, principally onychomycosis. | [storage]
Store at +4°C |
| Questions And Answer | Back Directory | [Topical antifungal]
Ciclopirox is a novel broad-spectrum topical antifungal agent,it is successfully developed by pharmaceutical companies of the Federal Republic of Germany , the mechanism is by changing the integrity of the fungal cell membrane, causing intracellular material outflow, and blocking intake of protein precursors, resulting in fungal cell death, it has a strong bactericidal effect against dermatophytes, yeasts, molds, etc. And it has strong permeability . At higher concentrations,it can also have a certain extent inhibiting effect on a variety of actinomycetes, Gram-positive and Gram-negative bacteria and mycoplasma, chlamydia, trichomonas, Trichomonas vaginalis and Pseudomonas aeruginosa.
Compared with imidazole antifungal, ciclopirox has strong penetration ability in cuticle where skin fungus survive, so it has a significant inhibition effect on the cuticle deep fungi, such as onychomycosis.
Mainly it is used in clinical for superficial skin fungal infections, such as ringworm, athlete's foot, jock itch, tinea manus and pedis(especially keratosis thickening), tinea versicolor, skin candidiasis, Candida albicans and onychomycosis treatment.
The above information is edited by the chemicalbook of Tian Ye.
| [Chemical Properties]
Solid, m.p. 144 ℃.
Ciclopirox Olamine: [41621-49-2]. White crystalline powder, odorless, bitter taste. Soluble in methanol, ethanol or chloroform, slightly soluble in dimethylformamide or water, slightly soluble in ether. Melting point 124-128 ℃. Acute toxicity LD50 in mice, rats (mg/kg): 2898,3290 orally.
| [Uses]
Pyridine ketones broad-spectrum antifungal agents, have inhibiting effects on a variety of skin fungi . They can prevent the substances necessary for Candida albicans cells survival such as amino acids, potassium ions, phosphate,going through the cell membrane ,which can cause by certain important matrix or intracellular ions failure,and then inhibit or kill fungal cells. There are a wide range of anti-fungal effects, they can have a killing effect on the skin filamentous bacteria, yeast fungi , they have inhibition effects on a variety of Gram positive and negative bacteria, chlamydia, trichomoniasis, Proteus, E. coli, Pseudomonas and Staphylococcus bacteria. They are used to treat fungal skin disease, tinea versicolor, vulvovaginal Candida disease, skin and fingers (toe) candidiasis ,they have significant effects , and lower side effects.
| [production method]
4-methyl-3-penten-2-one by oxidation of sodium hypochlorite (56% yield), is esterified to produce methyl-2-butenoate (the I), 67% yield, b.p. 135~139 ℃.
Cyclohexane carboxylic acid and thionyl chloride react to obtain cyclohexane carboxylic acid chloride. In the role of aluminum chloride,it reacts with methyl-2-butenoate (I) in a methylene chloride solvent, and the reaction is stirred for 4h, after post-treatment, vacuum collect 140-145 ℃ (0.4kPa) the distillate, 3-methyl-5-oxo-5-cyclohexyl-3-pentenoate (ciclopirox, II) is generated in 75% yield. And then it is stirred at room temperature for 20h together with hydroxylamine hydrochloride, sodium acetate, methanol and water , then it is added 50% sodium hydroxide , then it is stirred for 1h. After cooling with benzene extraction, the aqueous phase is acidified to Ph = 6. The precipitated crystals are recrystallized from ethanol, to give ciclopirox, m.p. 140~142 ℃, yield 48.3%. Finally,it is salified with the hydroxyl amine in methylene chloride to give almost quantitative ciclopirox, melting point 97~99 ℃.
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