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Sertaconazole Nitrate

Class: Azoles
VA Class: DE102
Chemical Name: (±)-1-[2,4-Dichloro-β-[(7-chlorobenzo[b]thien-3-yl)methoxy]phenylethyl]-imidazole mononitrate
Molecular Formula: C20H15Cl3N2OSH NO3
CAS Number: 99592-32-2
Brands: Ertaczo

Introduction

Antifungal; azole (imidazole derivative).1

Uses for Sertaconazole Nitrate

Dermatophytoses

Treatment of interdigital tinea pedis (athlete’s foot) caused by Epidermophyton floccosum, Trichophyton mentagrophytes, or T. rubrum in immunocompetent adults and children ≥12 years of age.1 2 16

Topical antifungals usually effective for treatment of uncomplicated tinea pedis;13 25 an oral antifungal usually necessary for treatment of hyperkeratotic areas on the palms and soles, for chronic moccasin-type (dry-type) tinea pedis, and for treatment of tinea unguium (onychomycosis).13 23 25

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Treatment of tinea corporis (ringworm of the body),16 tinea cruris (jock itch),16 or tinea manuum (hand ringworm)16 caused by E. floccosum, Microsporum (including M. canis), or Trichophyton (including T. mentagrophytes, T. rubrum, and T. schonleinii).16 19

Topical antifungals usually effective for uncomplicated tinea corporis, tinea cruris, and tinea manuum; an oral antifungal usually necessary 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 because of coexisting disease or concomitant therapy.13 20 23 25

Pityriasis (Tinea) Versicolor

Treatment of pityriasis (tinea) versicolor caused by Malassezia furfur (Pityrosporum orbiculare or P. ovale).17 19

Topical treatment usually effective; an oral antifungal (alone or in conjunction with a topical agent) may be necessary in patients who have extensive or severe infections or who fail to respond to or have frequent relapses with topical therapy.21 22 23

Cutaneous Candidiasis

Treatment of superficial cutaneous candidiasis caused by Candida albicans.18 19

Sertaconazole Nitrate Dosage and Administration

Administration

Topical Administration

Apply topically to the skin as a 2% cream.1

Do not apply to the eye or administer orally or intravaginally.1

Avoid contact with the nose, mouth, and other mucous membranes.1 19 20 21

Do not use with occlusive dressings or wrappings, unless otherwise directed by clinician.1

Apply a sufficient amount of cream twice daily; rub gently into affected area (e.g., between the toes) and immediately surrounding healthy skin.1

Dosage

Available as sertaconazole nitrate; dosage expressed in terms of sertaconazole nitrate.1

Pediatric Patients

Dermatophytoses
Tinea Pedis (Interdigital)
Topical

Children ≥12 years of age: Apply twice daily for 4 weeks.1

If clinical improvement does not occur after 2 weeks of treatment, reevaluate the diagnosis.1

Adults

Dermatophytoses
Tinea Pedis (Interdigital)
Topical

Apply twice daily for 4 weeks.1

If clinical improvement does not occur after 2 weeks of treatment, reevaluate the diagnosis.1

Tinea Corporis,Tinea Cruris, andTinea Manuum
Topical

Has been applied twice daily for 4 weeks.16 17

Pityriasis (Tinea) Versicolor
Topical

Has been applied twice daily for 4 weeks.17

Cutaneous Candidiasis
Topical

Has been applied twice daily for 4 weeks.18

Cautions for Sertaconazole Nitrate

Contraindications

  • Known hypersensitivity to sertaconazole, other imidazoles, or any ingredient in the formulation.1

Warnings/Precautions

Sensitivity Reactions

Hypersensitivity Reactions

Contact dermatitis reported rarely following topical application.1 5

If irritation or sensitivity occurs, discontinue the drug and initiate appropriate therapy.1 5

Possible cross-sensitization among the imidazoles.1 5

General Precautions

Selection and Use of Antifungals

Prior to initiation of therapy, confirm diagnosis by direct microscopic examination of scrapings from infected tissue mounted in potassium hydroxide (KOH) or by culture.1

Specific Populations

Pregnancy

Category C.1

Lactation

Not known whether distributed into milk following topical application of 2% cream.1 Use with caution.1

Pediatric Use

Safety and efficacy not established in children <12 years of age.1

Geriatric Use

Insufficient experience in patients ≥65 years of age to determine whether geriatric patients respond differently than younger adults.1

Common Adverse Effects

Contact dermatitis, dry skin, burning skin, application site reaction, skin tenderness.1

Sertaconazole Nitrate Pharmacokinetics

Absorption

Bioavailability

Does not appear to be appreciably absorbed systemically following topical application to skin.1

Not detected in plasma following repeated application of 2% cream to diseased skin.1

Distribution

Extent

Not known whether distributed into milk following topical application of 2% cream.1

Stability

Storage

Topical

Cream

25°C (may be exposed to 15–30°C).1

Actions and Spectrum

  • Imidazole-derivative azole antifungal.1 10 11

  • Usually fungistatic; may be fungicidal at high concentrations.6 12

  • Presumably exerts its antifungal activity by altering cellular membranes, resulting in increased membrane permeability, secondary metabolic effects, and growth inhibition.1 6 11

  • Fungistatic activity may result from interference with ergosterol synthesis.1 6 8 10 11 12 Fungicidal activity at high concentrations may result from a direct physiochemical effect on the fungal cell membrane.6 8 12

  • Spectrum of antifungal activity includes many fungi, including dermatophytes and yeasts.1 3 4 6 8 10 14 15 Also has in vitro activity against some gram-positive bacteria.4

  • Dermatophytes: Active in vitro against Epidermophyton floccosum,1 7 8 9 14 Microsporum audouini,7 8 9 14 M. canis,7 8 9 14 15 M. gypseum,7 8 9 14 15 M. racemosum,9 Trichophyton erinacei,9 T. interdigitale,7 9 14 T. mentagrophytes,1 7 8 9 14 15 T. rubrum,1 7 8 9 14 15 T. schoenleinii,7 9 T. soudanese,9 T. terreste,9 T. tonsurans,7 9 T. verrucosum,7 and T. violaceum.7 9

  • Also active in vitro against Malassezia furfur (Pityrosporum orbiculare or P. ovale).10 14

  • Candida: Active in vitro against C. albicans,4 6 8 14 15 C. beigelii,6 14 C. dubliniensis,4 C. famata,8 C. glabrata (formerly Torulopsis glabrata),4 6 7 8 14 C. guilliermondii,4 6 7 8 C. holmii,4 C. humicola,4 7 8 C. inconspicua,4 C. intermedia,4 8 C. krusei,4 6 8 14 15 C. lambica, 4 C. lipolytica,4 C. lusitaniae,4 6 C. parapsilosis,4 6 8 15 C. pulcherrima,4 C. pseudotropicalis,6 14 15 C. rugosa,4 and C. tropicalis.4 6 8 14 15

  • Although clinical importance unknown, T. mentagrophytes, T. rubrum, and M. canis clinical isolates with in vitro resistance to sertaconazole reported.9 Some of these also were resistant to other imidazoles (e.g., clotrimazole, fluconazole, ketoconazole, miconazole, tioconazole).9

  • C. albicans serotype B vaginal isolate with in vitro resistance to sertaconazole and other imidazoles (e.g., econazole, fluconazole, itraconazole, ketoconazole miconazole) reported.4

Advice to Patients

  • Importance of applying to affected areas as directed and avoiding contact with eyes, nose, mouth, or other mucous membranes.1 Importance of not using occlusive dressings, unless otherwise directed by clinician.1

  • Importance of washing hands after applying the cream.1

  • Advise patients to dry affected areas thoroughly before applying cream if it is used after bathing.1

  • Use only for condition prescribed.1

  • Importance of completing full course of therapy, even if symptoms improve; importance of contacting clinician if skin condition worsens during therapy or if improvement does not occur after completing full course of therapy.1

  • Importance of discontinuing drug and consulting clinician if treated area becomes irritated (e.g., redness, itching, burning, blistering, swelling, or oozing).1

  • Importance of informing clinicians of existing or contemplated concomitant therapy, including prescription and OTC drugs, and any concomitant illnesses.1

  • Importance of women informing clinicians if they are or plan to become pregnant or plan to breast-feed.1

  • Importance of informing patients of other important precautionary information.1 (See Cautions.)

Preparations

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

Sertaconazole Nitrate

Routes

Dosage Forms

Strengths

Brand Names

Manufacturer

Topical

Cream

2%

Ertaczo (with methylparaben)

OrthoNeutrogena

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.

Ertaczo 2% Cream (VALEANT): 30/$126.59 or 90/$342.87

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

† Use is not currently included in the labeling approved by the US Food and Drug Administration.

References

1. Orthoneutrogena. Ertaczo (sertaconazole nitrate) cream 2% prescribing information. Skillman, NJ. 2003 Dec.

2. Anon. Topical sertaconazole (ertaczo)--another azole for tinea pedis. Med Lett Drugs Ther. 2004; 46:50-1. [PubMed 15211288]

3. Center for Drug Evaluation and Research, Application Number: 21-385, Medical Review for Sertaconazole (Ertaczo). Food and Drug Administration website. Available from website. Accessed 2005 Jan 21.

4. Carrillo-Munoz AJ, Brio S, Quindos G et al. Sertaconazole: in-vitro antifungal activity against vaginal and other superficial yeast isolates. J Chemother. 2001;13:555-62.

5. Goday JJ, Yanguas I, Aguirre A et al. Allergic contact dermatitis from sertaconazole with cross-sensitivity to miconazole and econazole. Contact Dermatitis. 1995;32:370-1.

6. Palacin C, Tarrago C, Ortiz JA. Sertaconazole: pharmacology of a gynecological antifungal agent. Int J Gynaecol Obstet. 2000;71:S37-46.

7. Carrillo-Munoz AJ, Fernandez-Torres B, Guarro J. In vitro antifungal activity of sertaconazole against 309 dermatophyte clinical isolates. J Chemother. 2003;15:555-7.

8. Carillo-Munoz AJ, Tur-Tur C. Comparative study of antifungal activity of sertaconazole, terbinafine, and bifonazole against clinical isolates of Candida spp., Cryptococcus neoformans and dermatophytes. Chemotherapy. 1997;43:387-92.

9. Carrillo-Munoz AJ, Guglietta A, Palacin C, et al. In vitro antifungal activity of sertaconazole compared with nine other drugs against 250 clinical isolates of dermatophytes and Scopulariopsis brevicaulis. Chemotherapy. 2004;50:308-13.

10. Torres-Rodriguez JM. New topical antifungal drugs. Arch Med Res. 1993;24:371-5.

11. Agut J, Palacin C, Sacristan A, Ortiz JA. Inhibition of ergosterol synthesis by sertaconazole in Candida albicans. Arzneimittelforschung. 1992;42:718-20.

12. Agut J, Palacin C, Salgado Jet al. Direct membrane-damaging effect of sertaconazole on Candida albicans as a mechanism of its fungicidal activity. Arzneimittelforschung. 1992;42:721-4.

13. Piérard GE, Arrese JE, Piérard-Franchimont C. Treatment and prophylaxis of tinea infections. Drugs. 1996; 52:209-24. [PubMed 8841739]

14. Drouhet E, Dupont B. In vitro antifungal activity of sertaconazole. Arzneimittelforschung. 1992; 42:705-10. [PubMed 1627187]

15. Palacin C, Sacristan A, Ortiz JA. In vitro activity of sertaconazole. Arzneimittelforschung. 1992;42:699-705.

16. Alomar C, Bassas S, Casas M et al. Multi-centre double-blind trial on the efficacy and safety of sertaconazole 2% cream in comparison with miconazole 2% cream on patients suffering from cutaneous mycoses. Arzneimittelforschung. 1992 May;42:767-73.

17. Nasarre J, Umbert P, Herrero E et al. Therapeutic efficacy and safety of the new antimycotic sertaconazole in the treatment of Pityriasis versicolor. Arzneimittelforschung. 1992;42:764-7.

18. Umbert P, Nasarre J, Bello A et al. Phase II study of the therapeutic efficacy and safety of the new antimycotic sertaconazole in the treatment of superficial mycoses caused by Candida albicans. Arzneimittelforschung. 1992;42:757-60.

19. Torres J, Marquez M, Camps F. Sertaconazole in the treatment of mycoses: from dermatology to gynecology. Int J Gynaecol Obstet. 2000;71:S3-20.

20. Gupta AK, Einarson TR, Summerbell RC et al. An overview of topical antifungal therapy in dermatomycoses: a North American perspective. Drugs. 1998; 55:645-74. [PubMed 9585862]

21. Sunenshine PJ, Schwartz RA, Janniger CK. Tinea versicolor: an update. Cutis. 1998; 61:65-72. [PubMed 9515210]

22. Assaf RR, Weil ML. The superficial mycoses. Dermatol Clin. 1996; 14:57-67. [PubMed 8821158]

23. Hay RJ. Dermatophytosis and other superficial mycoses. In: Mandel GL, Douglas RG Jr, Bennett JE, eds. Principles and practices of infectious disease. 4th ed. New York: Churchill Livingston; 1995: 2375-86.

24. Drake LA, Dinehart SM, Farmer ER et al. Guidelines of care for superficial mycotic infections of the skin: pityriasis (tinea) versicolor. J Am Acad Dermatol. 1996; 34:287-9. [IDIS 363963] [PubMed 8642095]

25. Drake LA, Dincehart SM, Farmer ER et al. Guidelines of care for superficial mycotic infections of the skin: tinea corporis, tinea cruris, tinea faciei, tinea manuum, and tinea pedis. J Am Acad Dermatol. 1996; 34:282-6. [IDIS 363962] [PubMed 8642094]

26. Reviewers’ comments (personal observations) on Sulconazole 84:04.08.

27. Orthoneutrogena. Los Angeles, CA: Personal communication.

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