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Econazole Nitrate

Class: Azoles
ATC Class: D01AC03
VA Class: DE102
Chemical Name: (±)-1-[2-[(4-Chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole mononitrate
Molecular Formula: C18H15Cl3N2OβHNO3
CAS Number: 68797-31-9

Introduction

Antifungal; azole (imidazole derivative).2 3

Uses for Econazole Nitrate

Dermatophytoses

Treatment of tinea corporis (body ringworm) and tinea cruris (jock itch) caused by Epidermophyton floccosum, Microsporum audouinii, M. canis, M. gypseum, Trichophyton mentagrophytes, T. rubrum, or T. tonsurans.60 61

Treatment of tinea pedis (athlete’s foot) caused by E. floccosum, M. audouinii, M. canis, M. gypseum, T. mentagrophytes, T. rubrum, or T. tonsurans.60 61

Topical antifungals usually effective for treatment of uncomplicated tinea corporis or tinea cruris.46 47 50 51 52 62 An oral antifungal may be 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.46 47 50 51 52 62

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Topical antifungals usually effective for treatment of uncomplicated tinea pedis.46 47 50 51 52 62 An oral antifungal may be necessary for treatment of hyperkeratotic areas on the palms and soles,47 52 for chronic moccasin-type (dry-type) tinea pedis,46 47 51 and for tinea unguium (fingernail or toenail dermatophyte infections, onychomycosis).46 47 50 51 52 62

Pityriasis (Tinea) Versicolor

Treatment of pityriasis (tinea) versicolor caused by Malassezia furfur (Pityrosporum orbiculare or P. ovale).60 61 62

Topical antifungals usually effective; an oral antifungal (with or without a topical antifungal) may be necessary in patients who have extensive or severe infections or have failed to respond to or have frequent relapses with topical therapy.48 49 51 62

Cutaneous Candidiasis

Treatment of cutaneous candidiasis caused by Candida albicans.60 61

Econazole Nitrate Dosage and Administration

Administration

Topical Administration

Apply topically to the skin as a 1% cream.60 61

Do not apply to the eye60 61 or administer intravaginally.39

Apply a sufficient amount of cream to cover affected areas.60 61

Dosage

Pediatric Patients

Dermatophytoses
Tinea Corporis or Tinea Cruris
Topical

Apply once daily for 2 weeks.60 61 62

If clinical improvement does not occur after treatment, reevaluate diagnosis.60 61 Occasionally, a treatment duration of ≥6 weeks may be necessary.15 17 18 19 62

Tinea Pedis
Topical

Apply once daily for 1 month.60 61 62

If clinical improvement does not occur after treatment, reevaluate diagnosis.60 61 Occasionally, a treatment duration of ≥6 weeks may be necessary.15 17 18 19

Pityriasis (Tinea) Versicolor
Topical

Apply once daily for 2 weeks.60 61 62

If clinical improvement does not occur after treatment, reevaluate diagnosis.60 61

Cutaneous Candidiasis
Topical

Apply twice daily (morning and evening) for 2 weeks.60 61 62

If clinical improvement does not occur after treatment, reevaluate diagnosis.60 61 Occasionally, a treatment duration of ≥6 weeks may be necessary.15 17 18 19

Adults

Dermatophytoses
Tinea Corporis or Tinea Cruris
Topical

Apply once daily for 2 weeks.60 61

If clinical improvement does not occur after treatment, reevaluate diagnosis.60 61 Occasionally, a treatment duration of ≥6 weeks may be necessary.15 17 18 19

Tinea Pedis
Topical

Apply once daily for 1 month.60 61

If clinical improvement does not occur after treatment, reevaluate diagnosis.60 61 Occasionally, a treatment duration of ≥6 weeks may be necessary.15 17 18 19

Pityriasis (Tinea) Versicolor
Topical

Apply once daily for 2 weeks.60 61

If clinical improvement does not occur after treatment, reevaluate diagnosis.60 61

Cutaneous Candidiasis
Topical

Apply twice daily (morning and evening) for 2 weeks.60 61

If clinical improvement does not occur after treatment, reevaluate diagnosis.60 61 Occasionally, a treatment duration of ≥6 weeks may be necessary.15 17 18 19

Special Populations

No special population dosage recommendations at this time.60 61

Cautions for Econazole Nitrate

Contraindications

Known hypersensitivity to econazole or any ingredient in the formulation.60 61

Warnings/Precautions

Warnings

Administration Precautions

For external use only.60 61 Use only for topical application to the skin; not for ophthalmic60 61 or intravaginal use.39

Fetal/Neonatal Morbidity and Mortality

Fetotoxicity and embryotoxicity demonstrated in animals receiving oral econazole.60 61 (See Pregnancy under Cautions.)

Sensitivity Reactions

Hypersensitivity Reactions

Contact dermatitis reported following topical application of econazole or other imidazole-derivative azole antifungals.55 56 57 58 59

If irritation or sensitivity occurs, discontinue the drug.60 61

Possible cross-sensitization among the imidazoles.44 45 55 56 57 58 59

Specific Populations

Pregnancy

Category C.60 61

Use during first trimester of pregnancy only when considered essential to the welfare of the patient; use during second and third trimesters only if clearly needed.60 61 (See Fetal/Neonatal Morbidity and Mortality under Cautions.)

Lactation

Distributed into milk following oral administration in rats; not known whether distributed into human milk.60 61 Use caution.60 61

Pediatric Use

No unusual adverse effects reported when used in children ≥3 months of age.16 24

Common Adverse Effects

Burning,14 60 61 stinging,15 17 60 61 pruritus,19 60 61 erythema.14 60 61

Interactions for Econazole Nitrate

Specific Drugs

Drug

Interaction

Corticosteroids (hydrocortisone, triamcinolone acetonide)

Corticosteroids inhibit antifungal activity of econazole against Saccharomyces cerevisiae and Candida albicans36

Econazole does not alter activity of corticosteroid36

No effect on antibacterial activity of econazole against Staphylococcus36

Econazole Nitrate Pharmacokinetics

Absorption

Bioavailability

Minimal systemic absorption occurs following topical application to skin.13 60 61

Distribution

Extent

About 7.6–9.6% of a topical dose found in stratum corneum;13 also found in epidermis and middle region of dermis.13 60 61

Distributed into milk following oral administration in rats; not known whether distributed into human milk.60 61

Elimination

Elimination Route

Systemically absorbed drug excreted in urine and feces (<1% of topical dose).2 11 13 60 61

Stability

Storage

Topical

Cream

20–25°C60 or <30°C.61

Actions and Spectrum

  • Imidazole-derivative azole antifungal.2 3

  • Usually fungistatic; may be fungicidal at high concentrations or against very susceptible organisms.2 3 4 6 40

  • Presumably exerts its antifungal activity by altering cellular membranes,2 4 6 40 41 resulting in increased membrane permeability,4 6 41 secondary metabolic effects,2 and growth inhibition.2 Fungistatic activity may result from interference with ergosterol synthesis.4 5

  • Spectrum of antifungal activity includes many fungi, including yeasts and dermatophytes.2 3 8 9 10 11 42 60 61 Also has in vitro activity against some gram-positive bacteria3 8 and Trichomonas vaginalis.11

  • Dermatophytes: Active in vitro against Epidermophyton floccosum,3 60 61 Microsporum audouinii,3 60 61 M. canis,3 60 61 M. gypseum,3 60 61 Trichophyton mentagrophytes,3 9 60 61 T. rubrum,3 9 60 61 T. tonsurans,3 60 61 T. verrucosum,3 60 61 and T. violaceum.3

  • Other fungi: Active in vitro against Malassezia furfur (Pityrosporum orbiculare)60 61 and Candida albicans,7 8 10 60 61 C. guillermondii,60 61 C. parapsilosis,60 61 and C. tropicalis.60 61 Also active in vitro against Aspergillus,3 8 9 Cladosporium,3 and Sporothrix.3

  • Bacteria: Active in vitro against Corynebacterium diphtheriae,8 Staphylococcus aureus,3 8 11 S. epidermidis,8 and Streptococcus pyogenes.3 8

  • Cross-resistance can occur among the azole antifungals.12

Advice to Patients

  • Importance of completing full course of treatment, even if symptoms improve.1 37 60 61

  • Importance of contacting clinician if skin condition worsens during treatment or if improvement does not occur after completing full course of therapy.1 37 60 61

  • Importance of discontinuing use and contacting clinician if signs or symptoms of irritation or sensitization occur.60 61

  • Importance of applying to affected areas as directed and avoiding contact with eyes60 61 and not applying intravaginally.39

  • Importance of informing clinicians of existing or contemplated concomitant therapy, including prescription and OTC drugs.60 61

  • Importance of women informing clinicians if they are or plan to become pregnant or plan to breast-feed.60 61

  • Importance of informing patients of other important precautionary information.60 61 (See Cautions.)

Preparations

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

* available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name

Econazole Nitrate

Routes

Dosage Forms

Strengths

Brand Names

Manufacturer

Topical

Cream

1%*

Econazole Nitrate Cream (with benzoic acid)

Perrigo, Taro

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.

Econazole Nitrate 1% Cream (PERRIGO PHARMACEUTICALS): 85/$49.99 or 255/$133.98

Econazole Nitrate 1% Cream (PRASCO LABORATORIES): 30/$25.99 or 90/$65.97

Econazole Nitrate 1% Cream (TARO): 15/$17.99 or 45/$49.97

AHFS DI Essentials. © Copyright, 2004-2014, Selected Revisions July 1, 2007. American Society of Health-System Pharmacists, Inc., 7272 Wisconsin Avenue, Bethesda, Maryland 20814.

References

1. Ortho. Spectazole (econazole nitrate 1%) cream prescribing information. Raritan, NJ; 1990 Jun.

2. Heel RC, Brogden RN, Speight TM et al. Econazole: a review of its antifungal activity and therapeutic efficacy. Drugs. 1978; 16:177-201. [IDIS 93386] [PubMed 98315]

3. Thienpont D, Van Cutsem J, Van Nueten JM et al. Biological and toxicological properties of econazole, a broad-spectrum antimycotic. (German) Arzneim-Forsch. 1975; 25:224-30.

4. Borgers M. Mechanism of action of antifungal drugs, with special reference to the imidazole derivatives. Rev Infect Dis. 1980; 2:520-34. [IDIS 124096] [PubMed 7003674]

5. Marriot MS. Inhibition of sterol biosynthesis in Candida albicans by imidazole-containing antifungals. J Gen Microbiol. 1980; 117:253-5. [PubMed 6993625]

6. Preusser HJ. Effects of in vitro treatment with econazole on the ultrastructure of Candida albicans. Mykosen. 1976; 19:304-16.

7. Haller I, Plempel M. Experimental in vitro and in vivo comparison of modern antimycotics. Curr Med Res Opin. 1978; 5:315-27.

8. Schar G, Kayser FH, Dupont MC. Antimicrobial activity of econazole and miconazole in vitro and in experimental candidiasis and aspergillosis. Chemotherapy. 1976; 22:211-20. [IDIS 69602] [PubMed 817875]

9. Odds FC. Laboratory evaluation of antifungal agents: a comparative study of five imidazole derivatives of clinical importance. J Antimicrob Chemother. 1980; 6:749-61. [PubMed 7440468]

10. Bergan T, Vangdal M. In vitro activity of antifungal agents against yeast species. Chemotherapy. 1983; 29:104-10. [IDIS 169053] [PubMed 6301773]

11. Raab W. Clinical pharmacology of modern topical broad-spectrum antimicrobials. Curr Ther Res. 1977; 22:65-82.

12. Holt RJ, Azmi A. Miconazole-resistant Candida. Lancet. 1978; 1:50-1. Letter.

13. Schaefer H, Stuttgen G. Absolute concentrations of an antimycotic agent, econazole, in the human skin after local application. (German) Arzneim-Forsch. 1976; 26:432-5.

14. Gisslen H, Hersle K, Mobacken H et al. Topical treatment of dermatomycoses and tinea versicolor with econazole cream 1% (Pevaryl). Curr Ther Res. 1977; 21:681-4.

15. Verma BS. Econazole cream in fungal infections of the skin. Curr Ther Res. 1978; 24:745-52.

16. Mackie RM. Topical econazole in cutaneous fungal infections. Practitioner. 1980; 224:1311, 1313. [IDIS 128475] [PubMed 7220455]

17. Wishart JM, Gould PW. Econazole treatment of fungal infections. N Z Med J. 1981; 94:226-7. [IDIS 141713] [PubMed 7029364]

18. Fredriksson T. Treatment of dermatomycoses with topical econazole and clotrimazole. Curr Ther Res. 1979; 25:590-4.

19. Grigoriu D, Grigoriu A. Double-blind comparison of the efficacy, toleration and safety of tioconazole base 1% and econazole nitrate 1% creams in the treatment of patients with fungal infections of the skin or erythrasma. Dermatologica. 1983; 166(Suppl. 1):8-13. [PubMed 6350072]

20. O’Neill East M, Henderson JT, Jevons S. Tioconazole in the treatment of fungal infections of the skin. An international clinical research program. Dermatologica. 1983; 166(Suppl. 1):20-33. [PubMed 6884560]

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

22. Anon. Drugs for athlete’s foot and tinea cruris. Med Lett Drugs Ther. 1976; 18:101-2. [PubMed 1036605]

23. Fredriksson T. Treatment of dermatomycoses with topical econazole combined with a steroid as compared with a conventional oxichinoline-steroid combination. Curr Ther Res. 1979; 26:958-61.

24. Herz G. Experiences with triamcinolone acetonide 0.1% plus econazole nitrate 1% in paediatric dermatology. J Int Med Res. 1983; 11:320-3. [PubMed 6642071]

25. Rubin A, Russell JM, Mauff A. Efficacy of econazole in the treatment of candidiasis and other vaginal discharges. S Afr Med J. 1980; 57:407-8. [IDIS 112787] [PubMed 7403993]

26. Brown D Jr, Binder GL, Gardner HL et al. Comparison of econazole and clotrimazole in the treatment of vulvovaginal candidiasis. Obstet Gynecol. 1980; 56:121-3. [IDIS 119238] [PubMed 7383476]

27. Balmer JA. Three-day therapy of vulvovaginal candidiasis with econazole: a multicentric study comprising 996 cases. Am J Obstet Gynecol. 1976; 126:436-41. [IDIS 79224] [PubMed 984105]

28. Bloch B, Kretzel A. Econazole nitrate in the treatment of candidal vaginitis. S Afr Med J. 1980; 58:314-6. [IDIS 123262] [PubMed 6157203]

29. Popkin DR. Econazole in the treatment of vaginal candidiasis. Curr Ther Res. 1982; 32:948-51.

30. Larsson B, Kjaeldgaard A. Combined vaginal and vulval treatment of vaginal candidiasis with econazole. Curr Ther Res. 1980; 27:664-9.

31. Verma BS. Econazole in vaginal candidosis. Curr Ther Res. 1979; 26:634-9.

32. Fredricsson B, Frisk A, Hagstrom B et al. Vaginal mycoses: aspects on diagnosis and their treatment with econazole nitrate. Curr Ther Res. 1980; 27:309-22.

33. Stettendorf S, Benijts G, Vignali M et al. Three-day therapy of vaginal candidiasis with clotrimazole vaginal tablets and econazole ovules: a multicenter comparative study. Chemotherapy. 1982; 28(Suppl. 1):87-91. [IDIS 168389] [PubMed 6761088]

34. Udwadia RB, Dlo MS, Rathod V et al. Econazole: a study of its role in otomycosis. Curr Ther Res. 1982; 31:954-9.

35. Momii A, Funai K, Shingu H et al. Toxicological studies on econazole nitrate. IX. Mutagenicity tests with several bacterial strains. Iyakuhin Kenkyu. 1979; 10:351-7.

36. Raab W, Gmeiner B. Interactions between econazole, a broad-spectrum antimicrobic substance, and topically active glucocorticoids. Dermatologica. 1976; 153:14-22. [PubMed 791715]

37. Scrafani JT. Superficial fungal infections and their treatment. US Pharm. 1978; 3:26-40.

38. Thorne EG (Ortho Pharmaceutical Corporation, Raritan, NJ): Personal communication; 1984 Mar 21.

39. Reviewers’ comments (personal observations); 1984 Mar 20.

40. Kern R, Zimmermann FK. Physiological effects of econazole nitrate on yeast cells. Mykosen. 1978; Suppl. 1:339-45.

41. Preusser HJ, Rostek H. Econazole effects on Trichophyton rubrum and Candida albicans—electron microscopic and cytochemical studies. Mykosen. 1978; Suppl. 1:314-21.

42. Hantschke D. In vitro sensitivity tests with antimycotic imidazole derivatives and evaluation of results. Mykosen. 1978; Suppl. 1:222-9.

43. Ryley JF, Wilson RG, Barrett-Bee KJ. Azole resistance in Candida albicans. Sabouraudia. 1984; 22:53-63.

44. Raulin C, Frosch PJ. Contact allergy to imidazole antimycotics. Contact Dermatitis. 1988; 18:76-80. [PubMed 2966706]

45. Raulin C, Frosch PJ. Contact allergy to oxiconazole. Contact Dermatitis. 1987; 16:39-40. [PubMed 3816206]

46. 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]

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

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

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

50. Lesher JL. Recent developments in antifungal therapy. Dermatol Clin. 1996; 14:163-9. [PubMed 8821170]

51. 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.

52. 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]

53. 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]

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

55. Bigardi AS, Pigatto PD, Altomare G. Allergic contact dermatitis due to sulconazole. Contact Dermatitis. 1992; 26:281-2. [PubMed 1395584]

56. Machet L, Vaillant L, Muller C et al. Contact dermatitis and cross-sensitivity from sulconazole nitrate. Contact Dermatitis. 1992; 26:352-3. [PubMed 1395603]

57. Jones SK, Kennedy CTC. Contact dermatitis from tioconazole. Contact Dermatitis. 1990; 22:122-3. [PubMed 2138969]

58. Baes H. Contact sensitivity to miconazole with ortho-chloro cross-sensitivity to other imidazoles. Contact Dermatitis. 1991; 24:89-93. [PubMed 1828223]

59. Marren P, Powell S. Contact sensitivity to tioconazole and other imidazoles. Contact Dermatitis. 1992; 27:129-30. [PubMed 1395626]

60. Perrigo. Econazole nitrate cream, 1% prescribing information. Allegan, MI; Undated.

61. Taro Pharmaceuticals. Econazole nitrate cream 1% prescribing information. Brampton, Ontario, Canada. 2001 Sept.

62. American Academy of Pediatrics. 2006 Red Book: Report of the Committee on Infectious Diseases. 27th ed. Elk Grove Village, IL: American Academy of Pediatrics; 2006.

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