What Is Ciclopirox?

The chemical name of cyclopyridone is 6-cyclohexyl-1-hydroxy-4-methyl-2- (1H) -pyridone, which is a colorless or pale yellow, clear liquid with a strong pungent odor. Mainly used for fingernail (fungal nail) infection.

Chinese name: Ciclopirox
Foreign name: Ciclopirox

CAS number: 29342-05-0
Molecular formula: C12H17NO2

Ciclopirox Basic Information

Chinese name: Ciclopirox

Chinese alias: 6-cyclohexyl-1-hydroxy-4-methyl-2 (1H) -pyridone; 6-cyclohexyl-1-hydroxy-4-methyl-2 (IH) -pyridone; cyclopyridone ;

English name: Ciclopirox

English alias: CICLOPIROX; Ciclopirox; Ciclopiroxum; Loprox; Batrafen; Terit;

Hydroxy-4-methyl-6-cyclohexyl-2-pyridone; 6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one; Ciclopirox Olamine; 6-cyclohexyl-1-hydroxy-4-methyl-2 (1H)- pyridone; cyclopirox; 6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one; Penlac; Stieprox; 6-Cyclohexyl-1-hydroxy-4-methyl-2 (1H) -pyridone; Mycoster

CAS number: 29342-05-0

Molecular formula: C ₁₂ H ₁₇ NO ₂

_{Structural formula:}

Molecular weight: 207.26900

Exact mass: 207.12600

PSA: 42.23000

LogP: 2.44170

Ciclopirox Physicochemical Properties

Properties: White crystalline powder, odorless, bitter.

Melting point (ºC): 144

Solubility: easily soluble in methanol, ethanol or chloroform, slightly soluble in dimethylformamide or water, slightly soluble in ether ^[1]

Density: 1.193 g / cm ³

Boiling point: 350ºC at 760 mmHg

Flash point: 165.5ºC

Refractive index: 1.582

Vapor pressure: 2.71E-06mmHg at 25 ° C ^[2]

Ciclopirox Toxicology Data

Acutely toxic LD50 mice, rats (mg / kg): 2898, 3290 orally.

Ciclopirox molecular structure data

1. Molar refractive index: 57.96

2. Molar volume (cm3 / mol): 173.6

3. Isotonic specific volume (90.2K): 465.8

4. Surface tension (dyne / cm): 51.7

5. Polarizability (10-24cm3): 22.98

Ciclopirox calculated chemical data

1. Hydrophobic parameter calculation reference value (XlogP): 2

2.Number of hydrogen-bonded donors: 1

3.Number of hydrogen bond acceptors: 2

4.Number of rotatable chemical bonds: 1

5.Number of tautomers: 3

6. Topological molecular polar surface area 40.5

7.Number of heavy atoms: 15

8.Surface charge: 0

9.Complexity: 325

10.Number of isotope atoms: 0

11. Determine the number of atomic stereocenters: 0

12. Uncertain number of atomic stereocenters: 0

13. Determine the number of chemical bond stereocenters: 0

14. Uncertain number of chemical bond stereocenters: 0

15.Number of covalent bond units: 1

Ciclopirox synthesis method

4-methyl-3-penten-2-one was oxidized with sodium hypochlorite (yield 56%), and then methylated to give methyl 3-methyl-2-butenoate (I), cyclohexanecarboxylic acid and The reaction of thionyl chloride gives cyclohexaneformyl chloride. Under the action of aluminum trichloride, and methyl 3-methyl-2-butenoate (I) in a solvent of dichloromethane, the reaction was stirred for 4 h. After post-treatment, collected under vacuum at 140-145 ° C (0.4kPa) Fractions to give methyl 5-oxo-3-methyl-5-cyclohexyl-3-pentenoate (cyclopyridine, II) in a yield of 75%. Stir with hydroxylamine hydrochloride, sodium acetate, methanol and water at room temperature for 20 hours, add 50% sodium hydroxide and stir for 1 hour. After cooling, it was extracted with benzene and the aqueous phase was acidified to Ph = 6. The precipitated crystals are then recrystallized from ethanol to obtain ciclopirox.

Ciclopirox use

Pyridones are broad-spectrum antifungal drugs that inhibit a variety of skin fungi. It can prevent substances necessary for Candida albicans cells to survive, such as amino acids, potassium ions, and phosphates through the cell membrane to cause some important matrix or ion failure in the cells, and inhibit or kill fungal cells. Extensive antifungal effect, killing filamentous fungi and yeast fungi Bacteria have inhibitory effects. Commonly used in the treatment of dermatomycosis, tinea versicolor, vulvovaginal candidiasis, skin and finger (toe) candidiasis, etc., have significant effects, low toxicity and side effects. ^[1]

Ciclopirox Cyclopirox Related Drug Leaflet Information

Ciclopirox drug name:

[General name] Ciclopirox tincture

[Product Name] Baderfen

[English name] Ciclopirox Liniment

[Chinese Pinyin] Huan Bi Tong Cha Ji

Ciclopirox warning words:

To prevent the coating from drying out, the bottle cap should be tightened immediately after use, and the coating should not be splashed on the screw cap screw cap. Because this product is flammable, it should not be used near a heat source or an open flame.

Ciclopirox Ingredients:

The chemical name of cyclopyrone is: 6-cyclohexyl-1-hydroxy-4-methyl-2- (1H) -pyridone.

Molecular formula: C12H17NO2.

Molecular weight: 207.3.

Ciclopirox belongs to the category:

Chemicals & Biological Products >> Dermatological Drugs >> Skin Anti-Infectives >> Skin Antifungal Drugs

Chemicals & Biological Products >> Antimicrobials >> Antifungals >> Other Antifungals

Ciclopirox traits:

This product is a colorless or light yellow, clear liquid with a strong pungent odor.

Ciclopirox Pharmacology and Toxicology:

Ciclopirox is a broad-spectrum antifungal drug that has a killing effect on pathogenic fungi that can cause onychomycosis.

Human and animal pharmacokinetic studies have shown that ciclopirox is rapidly absorbed orally and is completely eliminated in stool and urine in a variety of forms (mostly prototypic or glucuronide conjugate). Healthy subjects took 10 mg of radiolabeled cyclopirone orally, and approximately 96% of the drug was excreted by the kidneys within 12 hours, of which 94% were glucuronide conjugates.

5 patients with onychomycosis were subjected to the cyclopyridone absorption test. 8% of the cyclopyrone was applied once a day to 20 skin affected by nails and adjacent 5 mm of skin, and the drugs were continuously administered for 6 months. Ciclopirox concentrations in serum and 24-hour urine were measured at 2 weeks and 1, 2, 4, and 6 months, and at 4 weeks after treatment. The concentration of ciclopirox in blood is 12-80 mg / mL. According to the analysis of urine data, the average absorption rate of ciclopirox is less than 5%. One month after stopping the drug, the concentration of ciclopirox in blood and urine has fallen below the detection limit. .

In two matrix-controlled trials, patients were treated with 8% ciclopirox liniments for all toenails and infected nails. Of the 66 patients randomly selected into the treatment group, 24 patients had cyclopyrone (10-24 mg / mL) detectable in the blood during the dosing interval, but it is worth noting that 11 of the 24 patients At the same time, ciclopiroxamine (Loprox ointment, 0.77%) was also used.

The in vitro permeability test results of 8% ciclopirox liniment show that ciclopirox can penetrate a depth of about 0.4 mm once applied to the nail, and the drug concentration in the nail decreases as the nail thickens. The clinical significance of this finding is unknown. The drug concentration in the nail bed was also not determined.

Ciclopirox Pharmacokinetics:

Human and animal pharmacokinetic studies have shown that ciclopirox is rapidly absorbed orally and is completely eliminated in stool and urine in a variety of forms (mostly prototypic or glucuronide conjugates). Healthy subjects took 10 mg of radiolabeled cyclopirone orally, and approximately 96% of the drug was excreted by the kidneys within 12 hours, of which 94% were glucuronide conjugates.

Ciclopirox indications:

Finger (toe) fungal infection (onychomycosis).

Ciclopirox usage and dosage:

Before using this medicine for the first time, the affected fingernails should be cut off as much as possible, and the nail polishes provided should be used to roughen the diseased nails. In the first month of treatment, apply a thin layer on the diseased nail every other day; within the second month, the amount can be reduced to at least twice a week; starting from the third month of treatment, every Apply medicine once a week. During the entire course of treatment, the entire film should be washed away with fingernail toenails once a week, and at the same time, the diseased nails should be removed again with a sand file if possible. If the coating film layer is damaged, it should be reapplied in time. Cover that part. The length of treatment depends on the severity of the infection, but should not exceed a 6-month period.

Ciclopirox adverse reactions:

Common adverse reactions include periarticular erythema, erythema near the folds of the nail, nail diseases (such as shape changes, irritation, ingrown toenail growth, discoloration, and toenail detachment, etc.), skin burning, and elevated creatine kinase. Very few people see allergic contact dermatitis, skin redness, and scaly formation.

Ciclopirox contraindications:

Not suitable for children.

Ciclopirox notes:

This product is for external use only. It is used only on the nails and the nail skin. Avoid contact with the skin, eyes, and mucous membranes that are not connected to the nails and toenails.
If you experience allergies or chemical irritation while using this product, you should stop using it immediately and report it to your doctor.
As no relevant clinical studies have been conducted on patients with insulin-dependent diabetes mellitus or patients with diabetic neuropathy,
The possible risks associated with bed sickness are recommended for patients with a history of insulin-dependent diabetes or a history of diabetic neuropathy.
The use of this medicine requires the removal of sick nails from the nail bed by medical personnel on a monthly basis.
This product should be evenly applied on the entire nail cover and on the skin within 5 mm. If possible, it should also be applied to the nail bed after nail peeling,
The surface of the hypodermis, the original nail cover. Contact with surrounding skin may cause slight transient irritation (redness).
The correct method of medication is to apply the medicine to the required area with a brush before going to bed or 8 hours before bathing. Wear socks after drying.
When using this product, the drug should not be washed off daily, but the entire layer of the drug film should be washed off every 7 days with finger (toe) nail cleaner.
Nail polish or other nail cosmetics should not be used on the treated nails.

Ciclopirox for pregnant and lactating women:

There is no corresponding research data on pregnant women's medication, but according to the results of animal tests, this product can only be used in pregnant women when necessary. It is unknown whether this product can be secreted by breast milk, and it should be used with caution by lactating women.

Ciclopirox Drug Interactions:

It is not clear that concurrent use of other topical skin preparations should be avoided.

Ciclopirox storage:

Shaded, sealed and stored at room temperature. Put the bottle into the carton after use. After the medicine bottle is opened, it can be kept stable for at least 6 months if it is stored as above. ^[3]