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Ciclopirox Olamine

Class: Hydroxypyridones
Chemical Name: 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone compound with 2-aminoethanol (1:1)
Molecular Formula: C12H17NO2βC2H7NO
CAS Number: 41621-49-2
Brands: Loprox, Penlac Nail Lacquer

Introduction

Antifungal;1 2 3 chemically unrelated to imidazoles or other antifungal agents currently available in US.4

Uses for Ciclopirox Olamine

Dermatophytoses and Cutaneous Candidiasis

Treatment of tinea pedis, tinea cruris, and tinea corporis caused by Trichophyton mentagrophytes, T. rubrum, Epidermophyton floccosum, or Microsporum canis.1 25 27 31 66

Efficacy in the treatment of plantar and vesicular types of tinea pedis not established.28 Oral antifungal agent usually necessary for the treatment of hyperkeratotic areas on palms and soles or chronic moccasin-type tinea pedis.31 32 36

Oral antifungal agents preferred when tinea corporis or tinea cruris is extensive, dermatophyte folliculitis is present, infection is chronic or does not respond to topical therapy, or patient is immunocompromised or has coexisting disease.31 32 35 36 37

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Treatment of cutaneous candidiasis caused by Candida albicans.1 66

Pityriasis (Tinea) Versicolor

Treatment of pityriasis (tinea) versicolor caused by Malassezia furfur (Pityrosporum orbiculare or P. ovale).1 25 66

Oral antifungal agents preferred in patients who have extensive or severe infections or who fail to respond to or have frequent relapses with topical therapy.33 34 36

Seborrheic Dermatitis

Treatment of seborrheic dermatitis of the scalp.28 65

Has not been studied in immunocompromised patients (e.g., HIV or transplant patients),28 65 patients with a history of immunosuppression (e.g., extensive, persistent, or unusual distribution of dermatomycoses; recent or recurring herpes zoster; persistent herpes simplex), 65 or those with diabetic neuropathy.65

Onychomycosis

Treatment of mild to moderate onychomycosis of fingernails and toenails, without lunula involvement, caused by T. rubrum in immunocompetent patients.40 43 45 49 56 57 58 59 60

Oral antifungal therapy usually preferred for extensive (e.g., >30%) nail involvement.46

Has not been studied in immunocompromised individuals (e.g., those with insulin-dependent diabetes, diabetic neuropathy, severe plantar/moccasin-type tinea pedis, HIV infection, or solid organ transplantation).40

Ciclopirox Olamine Dosage and Administration

Administration

Topical Administration

Apply topically to the skin as a cream,1 gel,28 lotion,66 or shampoo65 and to nails as a solution (nail lacquer).40

Do not apply to the eye1 25 28 40 65 66 or administer orally or intravaginally.23 24 40 65 Avoid contact with mucous membranes.28 40 65

Cream, Gel, or Lotion

Apply a sufficient amount of cream, gel, or lotion in the morning and evening; rub gently into cleansed, affected area and surrounding skin.1 23 25 31 66

Do not use with occlusive dressings or wrappings.1 28 66

Shampoo

If contact with eye(s) occurs, rinse thoroughly with water.65

Solution (Nail Lacquer)

Use in conjunction with frequent (e.g., monthly) appointments with a qualified clinician in nail disorders and weekly self-trimming of infected nail(s).40

Remove any loose nail or nail material (using nail clippers or nail files) before initiating therapy.40

Apply solution evenly over entire nail bed, undersurface of nail plate (if free of nail bed), and 5 mm of surrounding skin using applicator brush provided by the manufacturer.40

Avoid contact with skin other than that immediately surrounding the treated nail(s) (because of risk of adverse dermatologic reactions).40

After applying solution, wait ≥8 hours before bathing.40

Allow nail(s) to dry (about 30 seconds) before wearing socks or stockings.40

Do not apply nail polish or other cosmetic nail products on treated nail(s).40

Dosage

Available as ciclopirox and ciclopirox olamine; dosage expressed in terms of ciclopirox.1 28 40 65 66

Pediatric Patients

Dermatophytoses and Cutaneous Candidiasis
Topical

Children ≥10 years of age: Apply 0.77% cream or lotion twice daily.1 23 25 31 66

If clinical improvement does not occur after 4 weeks of treatment, reevaluate the diagnosis.1 25 66

Pityriasis (Tinea) Versicolor
Topical

Children ≥10 years of age: Apply 0.77% cream or lotion twice daily.1 23 25 31 66

Clinical improvement usually occurs after 2 weeks of treatment.1 25 66

Adults

Dermatophytoses and Cutaneous Candidiasis
Topical

Apply 0.77% cream or lotion twice daily.1 23 25 31 66 Alternatively, in the treatment of interdigital tinea pedis or tinea corporis, apply 0.77% gel twice daily.28

If clinical improvement does not occur after 4 weeks of treatment, reevaluate the diagnosis.1 25 66

Pityriasis (Tinea) Versicolor
Topical

Apply 0.77% cream or lotion twice daily.1 23 25 31 66

Clinical improvement usually occurs after 2 weeks of treatment.1 25 66

Seborrheic Dermatitis
Topical

Apply 0.77% gel to affected areas twice daily.28

Alternatively, apply approximately 5 mL (10 mL for long hair) of 1% shampoo to wet hair and scalp and lather.65 Allow drug to remain on the scalp for 3 minutes and then rinse.65 Repeat treatment twice weekly for 4 weeks, with a minimum of 3 days between applications.65

If clinical improvement does not occur after 4 weeks of treatment, reevaluate the diagnosis.65

Onychomycosis
Topical

Apply 8% topical solution (nail lacquer) once daily (preferably at bedtime).40 Remove accumulated applications of the drug with alcohol every 7 days; daily removal of solution is not recommended.40

Initial improvement of symptoms may require 6 months of therapy and up to 48 weeks of continuous comprehensive therapy to achieve clear or almost clear nail(s).40

Cautions for Ciclopirox Olamine

Contraindications

  • Known hypersensitivity to ciclopirox, ciclopirox olamine, or any ingredient in the formulation.1 25 28 40 65 66

Warnings/Precautions

Sensitivity Reactions

If irritation or sensitivation occurs, discontinue the drug and initiate appropriate therapy.1 25 40 66

General Precautions

Local Effects

Possible pruritus, transient burning sensation, and/or pain at the site of application.1 28 40 66

Specific Populations

Pregnancy

Category B.1 28 65 66

Lactation

Not known whether ciclopirox is distributed into milk.1 28 40 65 66 Use with caution in nursing women.1 25 28 40 65 66

Pediatric Use

Safety and efficacy of topical ciclopirox solution (nail lacquer) not established in children.40

Safety and efficacy of topical ciclopirox olamine preparations (i.e., cream, lotion) and topical ciclopirox gel not established in children ≤10 and 16 years of age, respectively.1 28 66

Insufficient experience with ciclopirox shampoo in children ≤16 years of age to determine whether pediatric patients respond differently than adults.65

Geriatric Use

No substantial differences in safety and efficacy of ciclopirox topical solution (nail lacquer) relative to younger adults.40

No substantial differences in safety of ciclopirox shampoo relative to younger adults.65 Insufficient experience in patients ≥65 years of age to determine whether efficacy in geriatric patients is different from that in younger adults.65

Race

Insufficient experience in black patients to determine whether they respond differently to ciclopirox shampoo than other races.65

Common Adverse Effects

Local burning sensation or pain; mild, transient erythema.1 28 40 66

Interactions for Ciclopirox Olamine

Systemic Antifungal Agents

No studies conducted in patients with onychomycosis to determine whether topical ciclopirox solution might reduce efficacy of systemic antifungals; combined use of the topical solution with a systemic antifungal agent is not recommended.40

Ciclopirox Olamine Pharmacokinetics

Absorption

Percutaneous absorption appears to be rapid but minimal following topical application to intact skin.11 40

Penetration of drug following topical application of 0.77% lotion is equivalent to that of 0.77% cream.25 27

Systemic absorption of 0.77% gel is higher than that of 0.77% cream.28

Distribution

Extent

Penetrates into hair and nail40 and is absorbed through the epidermis and hair follicles into sebaceous glands and dermis, while a portion remains in the stratum corneum.1 11 25 66

Crosses the placenta in very small amounts in animals.11

Plasma Protein Binding

Approximately 94–98%.11

Elimination

Metabolism

Almost completely conjugated with glucuronic acid;11 about 1–2% of the drug appears to be metabolized to N-desoxyciclopirox and another unidentified metabolite.11

Elimination Route

Excreted rapidly and almost completely in urine;11 25 negligible fecal excretion.1 11 25 66

Half-life

Biologic half-life of approximately 1.7 hours following application of 0.77% cream or lotion.1 11 25 66

Renal elimination half-life of approximately 5.5 hours following application of 0.77% gel.28

Stability

Storage

Topical

Cream, Gel, or Shampoo

15–30°C.1 28 65

Lotion

5–25°C.66

Solution

15–30°C.40 Keep away from heat and flame.40

Actions and Spectrum

  • Chelates polyvalent cations (e.g., aluminum, iron), which can result in inhibition of metal-dependent enzymes that are responsible for degradation of peroxides within the fungal cell.28 40 65

  • Active in vitro against Trichophyton equinum,10 T. mentagrophytes,1 8 9 10 25 27 28 40 66 T. rubrum,1 8 9 10 25 28 40 66 T. schoenleinii,8 10 T. tonsurans,8 10 T. verrucosum,8 T. violaceum,8 10 E. floccosum,1 8 9 10 25 28 66 Microsporum audouinii,1 8 10 M. canis,8 10 25 66 C. albicans,1 8 9 10 25 27 66 and M. furfur (P. orbiculare).1 65 66

Advice to Patients

  • Importance of consulting clinician if treated area becomes irritated (e.g., erythema, pruritus, burning, blistering, swelling, oozing).1 25 28 40 66

  • Importance of completing full course of therapy and of contacting clinician if symptoms of skin condition do not improve after 4 weeks of treatment.1 25 28 66 Six months of therapy may be required for initial improvement of infected nail(s).40

  • Importance of adhering to prescribed directions for use, including using the drug only for prescribed indications.28 40 (See Administration under Dosage and Administration.)

  • If topical solution (nail lacquer) is to be used, provide patient a copy of manufacturer’s patient information.40

  • Importance of women informing their clinician if they are or plan to become pregnant or plan to breast-feed.1 28 40 65 66

  • Importance of informing clinicians of existing or contemplated concomitant therapy, including prescription and OTC drugs, as well as concomitant illnesses.1 28 40 65 66

  • Importance of informing patients of other important precautionary information.1 28 40 65 66 (See Cautions.)

Preparations

Excipients in commercially available drug preparations may have clinically important effects in some individuals; consult specific product labeling for details.

Ciclopirox

Routes

Dosage Forms

Strengths

Brand Names

Manufacturer

Topical

Gel

0.77%

Loprox (with isopropyl alcohol)

Medicis

Shampoo

1%

Loprox

Medicis

Solution

8%

Penlac Nail Lacquer (with isopropyl alcohol)

Dermik

Ciclopirox Olamine

Routes

Dosage Forms

Strengths

Brand Names

Manufacturer

Topical

Cream

0.77% (of ciclopirox)

Loprox (with benzyl alcohol 1%)

Medicis

Lotion

0.77% (of ciclopirox)

Loprox (with benzyl alcohol 1%)

Medicis

Comparative Pricing

This pricing information is subject to change at the sole discretion of DS Pharmacy. This pricing information was updated 02/2014. Actual costs to patients will vary depending on the use of specific retail or mail-order locations and health insurance copays.

Ciclopirox 0.77% Gel (FOUGERA): 45/$120.99 or 135/$329.96

Ciclopirox 0.77% Gel (FOUGERA): 100/$175.97 or 300/$499.95

Ciclopirox 0.77% Gel (PADDOCK): 30/$75.99 or 90/$199.97

Ciclopirox 8% Solution (G & W LABS): 7/$19.99 or 20/$49.97

Ciclopirox Olamine 0.77% Cream (PERRIGO PHARMACEUTICALS): 15/$25.99 or 45/$71.97

Ciclopirox Olamine 0.77% Cream (PERRIGO PHARMACEUTICALS): 30/$44.99 or 90/$124.97

Ciclopirox Olamine 0.77% Suspension (FOUGERA): 30/$44.99 or 90/$122.98

Ciclopirox Olamine 0.77% Suspension (FOUGERA): 60/$95.99 or 180/$259.98

CNL8 Nail 8 & 2% Kit (JSJ PHARMACEUTICALS): 1/$243.20 or 3/$694.82

Loprox 0.77% Gel (MEDICIS): 30/$183.96 or 90/$530.24

Loprox 0.77% Gel (MEDICIS): 45/$280.80 or 135/$804.19

Loprox 0.77% Gel (MEDICIS): 100/$482.98 or 300/$1,320.88

AHFS DI Essentials. © Copyright, 2004-2014, Selected Revisions July 1, 2005. American Society of Health-System Pharmacists, Inc., 7272 Wisconsin Avenue, Bethesda, Maryland 20814.

References

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2. Hoechst-Roussel Pharmaceuticals, Inc. Pharmacy and therapeutics committee report: Loprox (ciclopirox olamine) cream 1%. Somerville, NJ; 1983 Mar.

3. Dittmar W, Druckey E, Urbach H. Quantitative structure-activity analysis in a series of antimycotically active N-hydroxypyridones. J Med Chem. 1974; 17:753-6. [PubMed 4836409]

4. Anon. New topical antifungal drugs. Med Lett Drugs Ther. 1983; 25:98-100. [PubMed 6621505]

5. Reynolds JEF, ed. Martindale: the extra pharmacopeia. 28th ed. London: The Pharmaceutical Press; 1982:720.

6. Sakurai K, Sakaguchi T, Yamaguchi H et al. Mode of action of 6-cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone ethanolamine salt (Hoe 296). Chemotherapy. 1978; 24:68-76. [IDIS 93074] [PubMed 340169]

7. Iwata VK, Yamaguchi H. Studies on the mechanism of antifungal action of ciclopiroxolamine: inhibition of transmembrane transport of amino acid, K+ and phosphate in Candida albicans cells. (German) Arzneim-Forsch. 1981; 31:1323-7.

8. Dittmar W, Lohaus G. HOE 296, a new antimycotic compound with a broad antimicrobial spectrum. (German) Arzneim-Forsch. 1973; 23:670-4.

9. Dittmar W, Grau W, Raether W et al. Microbiological laboratory studies with ciclopiroxolamine. (German) Arzneim-Forsch. 1981; 31:1317-22.

10. Sakurai K, Sakaguchi T, Yamaguchi H et al. Antimicrobial activity of Hoe 296, a new synthetic antifungal agent. I. In vitro antimicrobial activity and curative effect against experimental Trichophyton mentagrophytes infection. (Japanese) Jpn J Med Mycol. 1975; 16:35-40.

11. Kellner, HM, Arnold C, Christ OE et al. Studies on pharmacokinetics and biotransformation of the antimycotic drug ciclopiroxolamine in animals and man after topic and systemic application. (German) Arzneim-Forsch. 1981; 31:1337-53.

12. Dittmar W. Penetration and antifungal activity of ciclopiroxolamine in hornified tissue. (German) Arzneim-Forsch. 1981; 31:1353-9.

13. Adam, VW, Peil HG, Savopoulos C et al. Clinical results with the antimycotic agent ciclopiroxolamine. (German) Arzneim-Forsch. 1981; 31:1360-8.

14. Fredriksson T, Savopoulos C. Comparative double-blind study on ciclopiroxolamine cream and placebo cream in dermatophytoses. (German) Arzneim-Forsch. 1981; 31:1376-8.

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65. Medicis Pharmaceutical Corp. Loprox (ciclopirox) shampoo 1% prescribing information. Scottsdale, AZ; 2003 Feb.

66. Medicis Pharmaceutical Corp. Loprox (ciclopirox olamine) lotion 0.77% prescribing information. Scottsdale, AZ; 2002 Feb.

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