Ciclopirox

Last updated

Ciclopirox
Ciclopirox.svg
Clinical data
Trade names Many [1]
Other namesLoprox, CPX
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a604021
Pregnancy
category
  • B
Routes of
administration
Topical
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability <5% with prolonged use
Protein binding 94 to 97%
Elimination half-life 1.7 hours
Identifiers
  • 6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.045.056 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C12H17NO2
Molar mass 207.273 g·mol−1
3D model (JSmol)
  • O=C1/C=C(\C=C(/N1O)C2CCCCC2)C
  • 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 Yes check.svgY
  • Key:SCKYRAXSEDYPSA-UHFFFAOYSA-N Yes check.svgY
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Ciclopirox is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against tinea versicolor. It is often used clinically as ciclopirox olamine, the olamine salt of ciclopirox.

Contents

In 2021, it was the 271st most commonly prescribed medication in the United States, with more than 900,000 prescriptions. [2] [3]

Medical uses

Ciclopirox is indicated for the treatment of tinea pedis and tinea corporis due to Trichophyton rubrum , Trichophyton mentagrophytes and Epidermophyton floccosum , as well as seborrheic dermatitis. It is not to be used in the eyes or vagina, and nursing women should consult their doctors before use, since it is not known whether ciclopirox passes into human milk. A burning sensation may be felt when first applying ciclopirox on the skin.[ citation needed ]

Nail infections

In addition to other formulations, ciclopirox is used in lacquers for topical treatment of onychomycosis (fungal infections of the nails). A meta-analysis of the six trials of nail infections available in 2009 concluded that they provided evidence that topical ciclopirox had poor cure rates, and that amorolfine might be substantially more effective, but more research was required. "Combining data from 2 trials of ciclopiroxolamine versus placebo found treatments failure rates of 61% and 64% for ciclopiroxolamine. These outcomes followed long treatment times (48 weeks) and this makes ciclopiroxolamine a poor choice for nail infections. Better results were observed with the use of amorolfine lacquer; 6% treatment failure rates were found after 1 month of treatment but these data were collected on a very small sample of people and these high rates of success might be unreliable." [4]

Efinaconazole, an azole antifungal, led to cure rates two or three times better than the next-best topical treatment, ciclopirox. [5]

Pharmacology

Pharmacodynamics

In contrast to the azoles and other antimycotic drugs, the mechanism of action of ciclopirox is poorly understood. [6] 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 elucidate ciclopirox's mechanism, several Saccharomyces cerevisiae mutants were screened and tested. Results from interpretation of the effects of both the drug treatment and mutation suggested that ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport. [7]

Chemistry

Ciclopirox is a N-hydroxypyridone. Structurally, ciclopirox is the N-oxide of a 2-hydroxypyridine derivative and therefore can be termed a hydroxypyridine antifungal agent. Additionally, the structure as drawn above is the lactam tautomer and indicates the molecule being an N-hydroxy-2-pyridone. Hence the classification of ciclopirox as a 2-pyridone antifungal agent.[ citation needed ]

Society and culture

Brand names

It is sold under many brand names worldwide. [1]

Research

In 2007 it was investigated as an alternative treatment to ketoconazole for seborrhoeic dermatitis as it suppresses growth of the yeast Malassezia furfur . Initial results showed similar efficacy to ketoconazole with a relative increase in subjective symptom relief due to its inherent anti-inflammatory properties. [8]

Related Research Articles

<span class="mw-page-title-main">Dandruff</span> Skin condition of the scalp

Dandruff is a skin condition that mainly affects the scalp. Symptoms include flaking and sometimes mild itchiness. It can result in social or self-esteem problems. A more severe form of the condition, which includes inflammation of the skin, is known as seborrhoeic dermatitis.

<span class="mw-page-title-main">Tinea cruris</span> Medical condition

Tinea cruris, also known as jock itch, is a common type of contagious, superficial fungal infection of the groin and buttocks region, which occurs predominantly but not exclusively in men and in hot-humid climates.

<span class="mw-page-title-main">Tinea versicolor</span> Skin disease

Tinea versicolor is a condition characterized by a skin eruption on the trunk and proximal extremities. The majority of tinea versicolor is caused by the fungus Malassezia globosa, although Malassezia furfur is responsible for a small number of cases. These yeasts are normally found on the human skin and become troublesome only under certain circumstances, such as a warm and humid environment, although the exact conditions that cause initiation of the disease process are poorly understood.

<span class="mw-page-title-main">Nail disease</span> Medical condition

A nail disease or onychosis is a disease or deformity of the nail. Although the nail is a structure produced by the skin and is a skin appendage, nail diseases have a distinct classification as they have their own signs and symptoms which may relate to other medical conditions. Some nail conditions that show signs of infection or inflammation may require medical assistance.

<span class="mw-page-title-main">Seborrhoeic dermatitis</span> Skin disease

Seborrhoeic dermatitis is a long-term skin disorder. Symptoms include flaky, scaly, greasy, and occasionally itchy and inflamed skin. Areas of the skin rich in oil-producing glands are often affected including the scalp, face, and chest. It can result in social or self-esteem problems. In babies, when the scalp is primarily involved, it is called cradle cap. Seborrhoeic dermatitis of the scalp may be described in lay terms as dandruff due to the dry, flaky character of the skin. However, as dandruff may refer to any dryness or scaling of the scalp, not all dandruff is seborrhoeic dermatitis. Seborrhoeic dermatitis is sometimes inaccurately referred to as seborrhoea.

<span class="mw-page-title-main">Antifungal</span> Pharmaceutical fungicide or fungistatic used to treat and prevent mycosis

An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryptococcal meningitis, and others. Such drugs are usually obtained by a doctor's prescription, but a few are available over the counter (OTC). The evolution of antifungal resistance is a growing threat to health globally.

<span class="mw-page-title-main">Ketoconazole</span> Antifungal chemical compound

Ketoconazole, sold under the brand name Nizoral among others, is an antiandrogen, antifungal, and antiglucocorticoid medication used to treat a number of fungal infections. Applied to the skin it is used for fungal skin infections such as tinea, cutaneous candidiasis, pityriasis versicolor, dandruff, and seborrheic dermatitis. Taken by mouth it is a less preferred option and only recommended for severe infections when other agents cannot be used. Other uses include treatment of excessive male-patterned hair growth in women and Cushing's syndrome.

<span class="mw-page-title-main">Athlete's foot</span> Skin infection caused by fungus

Athlete's foot, known medically as tinea pedis, is a common skin infection of the feet caused by a fungus. Signs and symptoms often include itching, scaling, cracking and redness. In rare cases the skin may blister. Athlete's foot fungus may infect any part of the foot, but most often grows between the toes. The next most common area is the bottom of the foot. The same fungus may also affect the nails or the hands. It is a member of the group of diseases known as tinea.

<span class="mw-page-title-main">Terbinafine</span> Antifungal medication

Terbinafine, sold under the brand name Lamisil among others, is an antifungal medication used to treat pityriasis versicolor, fungal nail infections, and ringworm including jock itch and athlete's foot. It is either taken by mouth or applied to the skin as a cream or ointment. The cream and ointment are not effective for nail infections.

Dermatophyte is a common label for a group of fungus of Arthrodermataceae that commonly causes skin disease in animals and humans. Traditionally, these anamorphic mold genera are: Microsporum, Epidermophyton and Trichophyton. There are about 40 species in these three genera. Species capable of reproducing sexually belong in the teleomorphic genus Arthroderma, of the Ascomycota. As of 2019 a total of nine genera are identified and new phylogenetic taxonomy has been proposed.

<span class="mw-page-title-main">Dermatophytosis</span> Fungal infection of the skin

Dermatophytosis, also known as ringworm, is a fungal infection of the skin. Typically it results in a red, itchy, scaly, circular rash. Hair loss may occur in the area affected. Symptoms begin four to fourteen days after exposure. Multiple areas can be affected at a given time.

<span class="mw-page-title-main">Onychomycosis</span> Medical condition

Onychomycosis, also known as tinea unguium, is a fungal infection of the nail. Symptoms may include white or yellow nail discoloration, thickening of the nail, and separation of the nail from the nail bed. Fingernails may be affected, but it is more common for toenails. Complications may include cellulitis of the lower leg. A number of different types of fungus can cause onychomycosis, including dermatophytes and Fusarium. Risk factors include athlete's foot, other nail diseases, exposure to someone with the condition, peripheral vascular disease, and poor immune function. The diagnosis is generally suspected based on the appearance and confirmed by laboratory testing.

<i>Trichophyton rubrum</i> Species of fungus

Trichophyton rubrum is a dermatophytic fungus in the phylum Ascomycota. It is an exclusively clonal, anthropophilic saprotroph that colonizes the upper layers of dead skin, and is the most common cause of athlete's foot, fungal infection of nail, jock itch, and ringworm worldwide. Trichophyton rubrum was first described by Malmsten in 1845 and is currently considered to be a complex of species that comprises multiple, geographically patterned morphotypes, several of which have been formally described as distinct taxa, including T. raubitschekii, T. gourvilii, T. megninii and T. soudanense.

<span class="mw-page-title-main">Amorolfine</span> Chemical compound

Amorolfine, is a morpholine antifungal drug that inhibits Δ14-sterol reductase and cholestenol Δ-isomerase, which depletes ergosterol and causes ignosterol to accumulate in the fungal cytoplasmic cell membranes. Marketed as Curanail, Loceryl, Locetar, and Odenil, amorolfine is commonly available in the form of a nail lacquer, containing 5% amorolfine hydrochloride as the active ingredient. It is used to treat onychomycosis. Amorolfine 5% nail lacquer in once-weekly or twice-weekly applications was shown in two decades-old studies to be between 60% and 71% effective in treating toenail onychomycosis; complete cure rates three months after stopping treatment were 38% and 46%. However, full experimental details of these trials were not available, and since they were first reported in 1992 there have been no subsequent trials.

<span class="mw-page-title-main">Clotrimazole</span> Chemical compound

Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication. It is used to treat vaginal yeast infections, oral thrush, diaper rash, tinea versicolor, and types of ringworm including athlete's foot and jock itch. It can be taken by mouth or applied as a cream to the skin or in the vagina.

<span class="mw-page-title-main">Fungal folliculitis</span> Inflammation of hair follicles due to fungal infection

Majocchi's granuloma is a skin condition characterized by deep, pustular plaques, and is a form of tinea corporis. It is a localized form of fungal folliculitis. Lesions often have a pink and scaly central component with pustules or folliculocentric papules at the periphery. The name comes from Domenico Majocchi, who discovered the disorder in 1883. Majocchi was a professor of dermatology at the University of Parma and later the University of Bologna. The most common dermatophyte is called Trichophyton rubrum.

<span class="mw-page-title-main">Efinaconazole</span> Chemical compound

Efinaconazole, sold under the brand name Jublia among others, is a triazole antifungal medication. It is approved for use in the United States, Canada, and Japan as a 10% topical solution for the treatment of onychomycosis. Efinaconazole acts as a 14α-demethylase inhibitor.

<i>Epidermophyton floccosum</i> Species of fungus

Epidermophyton floccosum is a filamentous fungus that causes skin and nail infections in humans. This anthropophilic dermatophyte can lead to diseases such as tinea pedis, tinea cruris, tinea corporis and onychomycosis. Diagnostic approaches of the fungal infection include physical examination, culture testing, and molecular detection. Topical antifungal treatment, such as the use of terbinafine, itraconazole, voriconazole, and ketoconazole, is often effective.

Topical antifungaldrugs are used to treat fungal infections on the skin, scalp, nails, vagina or inside the mouth. These medications come as creams, gels, lotions, ointments, powders, shampoos, tinctures and sprays. Most antifungal drugs induce fungal cell death by destroying the cell wall of the fungus. These drugs inhibit the production of ergosterol, which is a fundamental component of the fungal cell membrane and wall.

References

  1. 1 2 Drugs.com International brand names for ciclopirox Page accessed January 201, 2016
  2. "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  3. "Ciclopirox - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  4. Crawford F (2007). "Topical treatments for fungal infections of the skin and nails of the foot". The Cochrane Database of Systematic Reviews. 2007 (3): CD001434. doi:10.1002/14651858.CD001434.pub2. PMC   7073424 . PMID   17636672.
  5. "A Closer Look At A New Topical Option For Onychomycosis" . Retrieved 21 May 2015.
  6. Niewerth M, Kunze D, Seibold M, Schaller M, Korting HC, Hube B (June 2003). "Ciclopirox Olamine Treatment Affects the Expression Pattern of Candida albicans Genes Encoding Virulence Factors, Iron Metabolism Proteins, and Drug Resistance Factors". Antimicrobial Agents and Chemotherapy. 47 (6): 1805–1817. doi:10.1128/AAC.47.6.1805-1817.2003. PMC   155814 . PMID   12760852.
  7. Leem SH, Park JE, Kim IS, Chae JY, Sugino A, Sunwoo Y (2003). "The possible mechanism of action of ciclopirox olamine in the yeast Saccharomyces cerevisiae". Mol. Cells. 15 (1): 55–61. doi:10.1016/S1016-8478(23)13707-1. PMID   12661761. Archived from the original on 20 June 2009. Retrieved 15 August 2008.
  8. Ratnavel RC, Squire RA, Boorman GC (2007). "Clinical efficacies of shampoos containing ciclopirox olamine (1.5%) and ketoconazole (2.0%) in the treatment of seborrhoeic dermatitis". J Dermatolog Treat. 18 (2): 88–96. doi:10.1080/16537150601092944. PMID   17520465. S2CID   34852507.