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HomeProduct name listCiclopirox

Ciclopirox

Synonym(s):6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone;6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone;Ciclopirox;HOE 296b

  • CAS NO.:29342-05-0
  • Empirical Formula: C12H17NO2
  • Molecular Weight: 207.27
  • MDL number: MFCD00599441
  • EINECS: 249-577-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 11:59:05
Ciclopirox Structural

What is Ciclopirox?

Absorption

Rapidly absorbed after oral administration. Mean absorption of ciclopirox after application to nails of all twenty digits and adjacent 5 millimeters of skin once daily for 6 months in patients with dermatophytic onychomycoses was less than 5% of the applied dose. Ciclopirox olamine also penetrates into hair and through the epidermis and hair follicles into sebaceous glands and dermis.

Toxicity

Oral LD50 in rat is >10 ml/kg. Symptoms of overexposure include drowsiness and headache.

Chemical properties

White or Light-Yellow Powder

Originator

Fungirox Esmalte, UCI-Farma

The Uses of 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

The Uses of Ciclopirox

Broad spectrum antimycotic agent with some antibacterial activity.

Indications

Used as a topical treatment in immunocompetent patients with mild to moderate onychomycosis of fingernails and toenails without lunula involvement, due to Trichophyton rubrum.

Background

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.

What are the applications of Application

Ciclopirox is a broad spectrum antimycotic agent

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.

Indications

Ciclopirox penetrates rapidly into and through the skin and nail keratin. After dermal application ofa1% cream formulation, about 1.3 % of the dose is absorbed. Serum levels range around 10 μg/L after application of a dose of 37 mg of ciclopirox. After vaginal administration, 15 – 20 % of the dose is absorbed. Ciclopirox penetrates well into the skin and nail matrix. Absorbed ciclopirox is mainly eliminated by the kidneys; 1.1 – 1.7 % of the topical dose is eliminated in the urine within four days. Only a fraction thereof is unaltered ciclopirox. Approximately 96% of the absorbed drug is bound to human serum proteins.

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

Antimicrobial activity

Ciclopirox has a broad in vitro antifungal activity spectrum, including dermatophytes, yeasts, and moulds. The most important fungi within the activity spectrum of ciclopirox. Ciclopirox is primarily fungistatic, but if the contact time is long enough and the concentration exceeds 20 μg/mL, it exerts a fungicidal effect on yeasts and dermatophytes. In vitro, the effect is limited to proliferating fungi and is greatly dependent on the nutrient medium.

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.

Mechanism of action

Ciclopirox is a substituted pyridione derivative. Experiments show that the mechanism of action involves a disruption of transport mechanisms into the cell plasma, especially the uptake of leucine. Further, the uptake of other amino acids such as phenylalanine and lysine, as well as the uptake of potassium and phosphate ions is impaired. This all probably involves a change in membrane permeability, as reported for some other antimycotics, although ciclopirox does not show lytic activity. Consecutively, the substance significantly reduces fungal growth rates.

Pharmacokinetics

Ciclopirox is a broad-spectrum antifungal medication that also has antibacterial and anti-inflammatory properties. Its main mode of action is thought to be its high affinity for trivalent cations, which inhibit essential co-factors in enzymes. Ciclopirox exhibits either fungistatic or fungicidal activity in vitro against a broad spectrum of fungal organisms, such as dermatophytes, yeasts, dimorphic fungi, eumycetes, and actinomycetes. In addition to its broad spectrum of action, ciclopirox also exerts antibacterial activity against many Gram-positive and Gram-negative bacteria. Furthermore, the anti-inflammatory effects of ciclopirox have been demonstrated in human polymorphonuclear cells, where ciclopirox has inhibited the synthesis of prostaglandin and leukotriene. Ciclopirox can also exhibit its anti-inflammatory effects by inhibiting the formation of 5-lipoxygenase and cyclooxygenase.

Clinical Use

Ciclopirox is a hydroxylated pyridinone that is employed for superficial dermatophytic infections, principally onychomycosis.

Side Effects

Topically applied, ciclopirox is well tolerated. The incidence of local irritations such as itching and burning sensations range between 1 and 4 % and are often due to the galenic formulation.

Metabolism

Glucuronidation is the main metabolic pathway of ciclopirox.

storage

Store at +4°C

Properties of Ciclopirox

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
CAS DataBase Reference 29342-05-0(CAS DataBase Reference)

Safety information for Ciclopirox

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H319:Serious eye damage/eye irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Ciclopirox

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