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Ketoconazole is an antifungal medication which is used primarily to treat fungal infections. Ketoconazole is sold commercially as a tablet for oral administration (although this use has been discontinued in a number of countries), and in a variety of formulations for topical administration, such as creams (used to treat tinea ; cutaneous candidiasis, including candidal paronychia ; and pityriasis versicolor ) and shampoos (used primarily to treat dandruff – seborrhoeic dermatitis of the scalp).
In terms of chemical structure, ketoconazole is an imidazole. The less toxic and generally more effective triazole antifungal agents fluconazole and itraconazole are usually preferred for systemic use. In 2013 the European Medicines Agency ‘s Committee on Medicinal Products for Human Use (CHMP) recommended that a ban be imposed on the use of oral ketoconazole for systemic use in humans throughout the European Union, after concluding that the risk of serious liver injury from systemic ketoconazole outweighs its benefits.
Contents
1 Medical uses
1.1 Antifungal
1.1.1 Topical antifungal
1.1.2 Systemic antifungal
1.2 Hormonal
1.3 Off-label uses
1.3.1 Hair loss
2 Side effects
3 Pharmacology
3.1 Pharmacodynamics
3.1.1 Antifungal activity
3.1.2 Antihormonal activity
3.1.3 Other activities
3.2 Pharmacokinetics
4 Chemistry
5 History
6 Society and culture
6.1 Generic names
6.2 Brand names
6.3 Availability
7 Veterinary use
8 References
9 External links
Medical uses
A bottle of ketoconazole shampoo.
Antifungal
Topical antifungal
Topically administered ketoconazole is usually prescribed for fungal infections of the skin and mucous membranes, such as athlete’s foot, ringworm, candidiasis (yeast infection or thrush), jock itch, and tinea versicolor.
Systemic antifungal
Ketoconazole has activity against many kinds of fungi that may cause human disease, such as Candida, Histoplasma, Coccidioides, and Blastomyces (although it is not active against Aspergillus ).
Ketoconazole is used orally in dosages of 200 to 400 mg per day in the treatment of superficial and deep fungal infections.
Hormonal
See also: Steroidogenesis inhibitor and CYP17A1 inhibitor
The side effects of ketoconazole are sometimes harnessed in the treatment of non-fungal conditions. While ketoconazole blocks the synthesis of the sterol ergosterol in fungi, in humans, at high dosages (>800 mg/day), it potently inhibits the activity of several enzymes necessary for the conversion of cholesterol to steroid hormones such as testosterone and cortisol.
Ketoconazole has been used to prevent the testosterone flare at the initiation of GnRH agonist therapy in men with prostate cancer.
Off-label uses
Hair loss
Nizoral (ketoconazole) 2% shampoo.
Ketoconazole shampoo in conjunction with an oral 5α-reductase inhibitor such as finasteride or dutasteride has been used off label to treat androgenic alopecia. The antifungal properties of ketoconazole reduce scalp microflora and consequently may reduce follicular inflammation that contributes to alopecia.
Limited clinical studies suggest ketoconazole shampoo used either alone may be useful in reducing hair loss.
At least one study has been performed showing that ketoconazole may be useful in temporarily reducing erectile function in postoperative penile surgery patients.
Side effects
This section needs expansion. You can help by adding to it. (May 2013)
Ketoconazole is a pregnancy category C drug because animal testing has shown it to cause teratogenesis when administered in high doses. Recently, the administration of systemic ketoconazole to two pregnant women for treatment of Cushing’s syndrome was reported to have no adverse effects,
On July 2013, the U.S. Food and Drug Administration (FDA) issued a warning that taking ketoconazole orally can cause severe liver injuries and adrenal gland problems. It recommends Nizoral oral tablets should not be a first-line treatment for any fungal infection. Nizoral should be used for the treatment of certain fungal infections, known as endemic mycoses, only when alternative antifungal therapies are not available or tolerated.
The topical formulations of Nizoral have not been associated with liver damage, adrenal problems, or drug interactions. These formulations include creams, shampoos, foams, and gels applied to the skin, unlike the Nizoral tablets, which are taken by mouth.
Pharmacology
Pharmacodynamics
Antifungal activity
This section needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (May 2013) ( Learn how and when to remove this template message )
As an antifungal, ketoconazole is structurally similar to imidazole, and interferes with the fungal synthesis of ergosterol, a constituent of fungal cell membranes, as well as certain enzymes. As with all azole antifungal agents, ketoconazole works principally by inhibiting the enzyme cytochrome P450 14α-demethylase (CYP51A1). This enzyme participates in the sterol biosynthesis pathway that leads from lanosterol to ergosterol. Lower doses of fluconazole and itraconazole are required to kill fungi compared to ketoconazole, as they have been found to have a greater affinity for fungal cell membranes.
Resistance to ketoconazole has been observed in a number of clinical fungal isolates, including Candida albicans. Experimentally, resistance usually arises as a result of mutations in the sterol biosynthesis pathway. Defects in the sterol 5-6 desaturase enzyme reduce the toxic effects of azole inhibition of the 14-alpha demethylation step. Multidrug-resistance (MDR) genes can also play a role in reducing cellular levels of the drug. As azole antifungals all act at the same point in the sterol pathway, resistant isolates are normally cross-resistant to all members of the azole family.
Antihormonal activity
As an antiandrogen, ketoconazole operates through at least two mechanisms of action. First, and most notably, high oral doses of ketoconazole (e.g. 400 mg three times per day) block both testicular and adrenal androgen biosynthesis, leading to a reduction in circulating testosterone levels.
Ketoconazole, along with miconazole, has been found to act as an antagonist of the glucocorticoid receptor.
Ketoconazole is a racemic mixture consisting of cis -(2 S,4 R )-(−) and cis -(2 R,4 S )-(+) enantiomers.
Other activities
Ketoconazole has been found to inhibit the activity of the cation channel TRPM5.
Pharmacokinetics
When administered orally, ketoconazole is best absorbed at highly acidic levels, so antacids or other causes of decreased stomach acid levels will lower the drug’s absorption. Absorption can be increased by taking it with an acidic beverage, such as cola. Ketoconazole is very lipophilic and tends to accumulate in fatty tissues.
Chemistry
Ketoconazole is a synthetic imidazole. Levoketoconazole is under development for potential clinical use as a steroidogenesis inhibitor with better tolerability and less toxicity than ketoconazole. Other steroidogenesis inhibitors besides ketoconazole and levoketoconazole include the nonsteroidal compound aminoglutethimide and the steroidal compound abiraterone acetate.
History
Ketoconazole was discovered in 1976 at Janssen Pharmaceutica.
Society and culture
Generic names
Ketoconazole is the generic name of the drug and its INN, USAN, BAN, and JAN.
Brand names
Ketoconazole has been marketed under a large number of brand names.
Availability
Ketoconazole is available widely throughout the world.
Veterinary use
Ketoconazole is sometimes prescribed as an antifungal by veterinarians for use in pets, often as unflavored tablets that may need to be cut to smaller size for correct dosage.

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