Econazole is an

antifungal medication 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 cryp ...

of the

imidazole 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 ...

class. It was patented in 1968, and approved for medical use in 1974.

Medical uses

Econazole is used as a

cream Cream is a dairy product composed of the higher-fat layer skimmed from the top of milk before homogenization. In un-homogenized milk, the fat, which is less dense, eventually rises to the top. In the industrial production of cream, this process ...

to treat

skin infection A skin infection is an infection of the skin in humans and other animals, that can also affect the associated soft tissues such as loose connective tissue and mucous membranes. They comprise a category of infections termed skin and skin structur ...

s such as

athlete's foot 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 ...

tinea 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 ar ...

pityriasis versicolor Pityriasis commonly refers to flaking (or scaling) of the skin. The word comes from the Greek πίτυρον "bran". Classification Types include: * Pityriasis alba * Pityriasis lichenoides chronica * Pityriasis lichenoides et varioliformis ac ...

ringworm 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 ar ...

, and

jock itch Jock may refer to: Common meanings * Jock (stereotype), a North American term for a stereotypical male athlete * Jock, a derogatory term for Scottish people mostly used by the English * Short for jockstrap, an item of male protective undergarm ...

. It is also sold in Canada under the brand name Ecostatin as vaginal ovules to treat

vagina In mammals, the vagina is the elastic, muscular part of the female genital tract. In humans, it extends from the vestibule to the cervix. The outer vaginal opening is normally partly covered by a thin layer of mucosal tissue called the hymen ...

thrush ''The Man from U.N.C.L.E.'' is an American spy fiction television series produced by Metro-Goldwyn-Mayer Television and first broadcast on NBC. The series follows secret agents, played by Robert Vaughn and David McCallum, who work for a secret ...

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

Adverse effects

About 3% of patients treated with econazole nitrate cream reported side effects. The most common symptoms were burning, itching, redness (

erythema Erythema (from the Greek , meaning red) is redness of the skin or mucous membranes, caused by hyperemia (increased blood flow) in superficial capillaries. It occurs with any skin injury, infection, or inflammation. Examples of erythema not asso ...

), and one outbreak of a pruritic rash.

Synthesis

Imidazoles devoid of the

nitro group In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nitr ...

no longer have any

antiprotozoal Antiprotozoal agents ( ATC code: ATC P01) is a class of pharmaceuticals used in treatment of protozoan infection. A paraphyletic group, protozoans have little in common with each other. For example, ''Entamoeba histolytica'', a unikont eukar ...

activity, however, such drugs are effective antifungal agents. Econazole synthesis

Alkylation of

(2) with bromoketone (1) prepared from ''o,p''-dichloro

acetophenone Acetophenone is the organic compound with the chemical formula, formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances. Production Acetophenone is formed as a byprodu ...

affords the displacement product (3). Reduction of the ketone with

sodium borohydride Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula Na BH4. This white solid, usually encountered as an aqueous basic solution, is a reducing agent that finds applica ...

gives the corresponding alcohol (4). Alkylation of the

alkoxide In chemistry, an alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They are written as , where R is the organic substituent. Alkoxides are strong bases and, whe ...

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 The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., ...

) and Ecostatin (

Canada Canada is a country in North America. Its ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, covering over , making it the world's second-largest country by to ...

), among others. It is a component of Pevisone, Ecoderm-TAProduct descriptions
at REPHCO Pharmaceuticals Limited, Bangladesh. Retrieved June 2012 and ECOSONE (

econazole/triamcinolone Econazole/triamcinolone is a combination drug, consisting of econazole (an imidazole antifungal) and triamcinolone (a group III topical steroid). It is used as a topical cream against fungal skin infections, including ''Trichophyton mentagrophyt ...

References

External links

* 21-Hydroxylase inhibitors Aromatase inhibitors Chloroarenes CYP3A4 inhibitors CYP17A1 inhibitors Phenylethanolamine ethers Imidazole antifungals Lanosterol 14α-demethylase inhibitors General cytochrome P450 inhibitors {{antiinfective-drug-stub