Econazole

Last updated

Econazole
Econazole.svg
Clinical data
Trade names Spectazole, Ecostatin, others
AHFS/Drugs.com Monograph
MedlinePlus a684049
License data
Pregnancy
category
Routes of
administration
Topical
ATC code
Legal status
Legal status
Identifiers
  • (RS)-1-{2-[(4-Chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.043.932 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H15Cl3N2O
Molar mass 381.68 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • Clc1ccc(c(Cl)c1)C(OCc2ccc(Cl)cc2)Cn3ccnc3
  • InChI=1S/C18H15Cl3N2O/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21/h1-9,12,18H,10-11H2 Yes check.svgY
  • Key:LEZWWPYKPKIXLL-UHFFFAOYSA-N Yes check.svgY
   (verify)

Econazole is an antifungal medication of the imidazole class. [3]

Contents

It was patented in 1968, and approved for medical use in 1974. [4]

Medical uses

Econazole is used as a cream to treat skin infections such as athlete's foot, tinea, pityriasis versicolor, ringworm, and jock itch. It is also sold in Canada under the brand name Ecostatin as vaginal ovules to treat vaginal thrush.[ citation needed ]

Econazole nitrate exhibits strong anti-feeding properties against the keratin-digesting common clothes moth Tineola bisselliella . [5]

Adverse effects

About 3% of patients treated with econazole nitrate cream reported side effects. The most common symptoms were burning, itching, redness (erythema), and one outbreak of a pruritic rash. [6]

Synthesis

Imidazoles devoid of the nitro group no longer have any antiprotozoal activity, however, such drugs are effective antifungal agents.[ citation needed ]

Econazole synthesis:
.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}
DE 1940388 U.S. patent 3,717,655 (1970, 1973 both to Janssen). Econazole synthesis.svg
Econazole synthesis: DE 1940388   U.S. patent 3,717,655 (1970, 1973 both to Janssen).

Alkylation of imidazole (2) with bromoketone (1) prepared from o,p-dichloroacetophenone affords the displacement product (3). Reduction of the ketone with sodium borohydride gives the corresponding alcohol (4). Alkylation of the alkoxide from that alcohol with p-chlorobenzyl chloride leads to econazole (5); alkylation with o,p-dichlorobenzyl chloride gives miconazole.

Society and culture

Brand names

It is sold under the brand names Spectrazole (United States) and Ecostatin (Canada), among others. It is a component of Pevisone, Ecoderm-TA [8] and ECOSONE (econazole/triamcinolone).

Related Research Articles

Vaginitis, also known as vulvovaginitis, is inflammation of the vagina and vulva. Symptoms may include itching, burning, pain, discharge, and a bad smell. Certain types of vaginitis may result in complications during pregnancy.

<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">Nystatin</span> Antifungal medication

Nystatin, sold under the brand name Mycostatin among others, is an antifungal medication. It is used to treat Candida infections of the skin including diaper rash, thrush, esophageal candidiasis, and vaginal yeast infections. It may also be used to prevent candidiasis in those who are at high risk. Nystatin may be used by mouth, in the vagina, or applied to the skin.

<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">Miconazole</span> Chemical compound

Miconazole, sold under the brand name Monistat among others, is an antifungal medication used to treat ring worm, pityriasis versicolor, and yeast infections of the skin or vagina. It is used for ring worm of the body, groin, and feet. It is applied to the skin or vagina as a cream or ointment.

<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">Imidazole</span> Chemical compound

Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution.

<span class="mw-page-title-main">Baclofen</span> Medication for muscle movement disorders

Baclofen, sold under the brand name Lioresal among others, is a medication used to treat muscle spasticity such as from a spinal cord injury or multiple sclerosis. It may also be used for hiccups and muscle spasms near the end of life, and off-label to treat alcohol use disorder or opioid withdrawal symptoms. It is taken orally or by intrathecal pump. It is also sometimes used transdermally in combination with gabapentin and clonidine prepared at a compounding pharmacy.

<span class="mw-page-title-main">Tinea capitis</span> Cutaneous fungal infection of the scalp

Tinea capitis is a cutaneous fungal infection (dermatophytosis) of the scalp. The disease is primarily caused by dermatophytes in the genera Trichophyton and Microsporum that invade the hair shaft. The clinical presentation is typically single or multiple patches of hair loss, sometimes with a 'black dot' pattern, that may be accompanied by inflammation, scaling, pustules, and itching. Uncommon in adults, tinea capitis is predominantly seen in pre-pubertal children, more often boys than girls.

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

Terconazole is an antifungal drug used to treat vaginal yeast infection. It comes as a lotion or a suppository and disrupts the biosynthesis of fats in a yeast cell. It has a relatively broad spectrum compared to azole compounds but not triazole compounds. Testing shows that it is a suitable compound for prophylaxis for those that suffer from chronic vulvovaginal candidiasis.

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

Tioconazole is an antifungal medication of the imidazole class used to treat infections caused by a fungus or yeast. It is marketed under the brand names Trosyd and Gyno-Trosyd. Tioconazole ointments serve to treat women's vaginal yeast infections. They are available in one day doses, as opposed to the 7-day treatments commonly used in the past.

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

Sertaconazole, sold under the brand name Ertaczo among others, is an antifungal medication of the Benzothiophene class. It is available as a cream to treat skin infections such as athlete's foot.

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

Sulconazole is an antifungal medication of the imidazole class. It is available as a cream or solution to treat skin infections such as athlete's foot, ringworm, jock itch, and tinea versicolor. Although not used commercially for insect control, sulconazole nitrate exhibits a strong anti-feeding effect on the keratin-digesting Australian carpet beetle larvae Anthrenocerus australis.

<span class="mw-page-title-main">Sulfacetamide</span> Sulfonamide antibiotic

Sulfacetamide is a sulfonamide antibiotic commonly used in the treatment of bacterial infections, particularly those affecting the eyes and skin. It functions by inhibiting the synthesis of folic acid in bacteria, which is essential for their growth and reproduction, thereby exerting a bacteriostatic effect. Available in various forms, including eye drops, topical solutions, and creams, sulfacetamide is often prescribed for conditions such as conjunctivitis, seborrheic dermatitis, and acne vulgaris. Its efficacy, coupled with a relatively low risk of side effects, makes it a widely utilized agent in both ophthalmic and dermatologic care.

<i>Tineola bisselliella</i> Species of moth

Tineola bisselliella, known as the common clothes moth, webbing clothes moth, or simply clothing moth, is a species of fungus moth. It is the type species of its genus Tineola and was first described by the Swedish entomologist Arvid David Hummel in 1823. It and a number of closely-related species are together known as the clothes moths due to their function as pests in human households. The specific name is commonly misspelled biselliella – for example by G. A. W. Herrich-Schäffer, when he established Tineola in 1853.

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

Fenticonazole is an imidazole antifungal drug, used locally as the nitrate in the treatment of vulvovaginal candidiasis. It is active against a range of organisms including dermatophyte pathogens, Malassezia furfur, and Candida albicans. Fenticonazole has also been shown to exhibit antibacterial action, with a spectrum of activity that includes bacteria commonly associated with superinfected fungal skin and vaginal infections, and antiparasitic action against the protozoan Trichomonas vaginalis.

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

Bifonazole is an imidazole antifungal drug used in form of ointments.

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

Butoconazole is an imidazole antifungal used in gynecology. It is administered as a vaginal cream.

<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.

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. "Econazole topical Use During Pregnancy". Drugs.com. 3 September 2018. Retrieved 31 January 2020.
  2. "Spectazole (econazole nitrate 1%) Cream". DailyMed. U.S. National Library of Medicine. 30 September 2013. Retrieved 31 July 2021.
  3. Thienpont D, Van Cutsem J, Van Nueten JM, Niemegeers CJ, Marsboom R (February 1975). "Bilogical and toxicological properties of econazole, a broad-spectrum antimycotic". Arzneimittel-Forschung. 25 (2): 224–230. PMID   1173036.
  4. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 502. ISBN   9783527607495.
  5. Sunderland MR, Cruickshank RH, Leighs SJ (2014). "The efficacy of antifungal azole and antiprotozoal compounds in protection of wool from keratin-digesting insect larvae". Textile Research Journal. 84 (9): 924–931. doi:10.1177/0040517513515312. S2CID   135799368.
  6. "Econazole nitrate cream". Daily Med. U.S. National Library of Medicine.
  7. Godefroi EF, Heeres J, Van Cutsem J, Janssen PA (September 1969). "The preparation and antimycotic properties of derivatives of 1-phenethylimidazole". Journal of Medicinal Chemistry. 12 (5): 784–791. doi:10.1021/jm00305a014. PMID   4897900.
  8. "Product descriptions: Ecoderm Cream". Bangladesh: REPHCO Pharmaceuticals Limited. Archived from the original on 31 August 2011. Retrieved 1 June 2012.