A broad-spectrum antifungal agent administered either orally or topically to treat a variety of fungal infections.
[KETO(NE) + (MI)CONAZOLE.]
ketoconazole
Dictionary:
ke·to·co·na·zole (kē'tō-kə-nā'zōl')  |
n.
A broad-spectrum antifungal agent administered either orally or topically to treat a variety of fungal infections.
A broad-spectrum antifungal agent administered either orally or topically to treat a variety of fungal infections.
| 5min Related Video: ketoconazole |
| Dental Dictionary: ketoconazole |
n
A broad-spectrum synthetic antifungal agent applied to the skin to inhibit the growth of dermatophytes and yeasts, effective in Candida infections and in the treatment of seborrheic dermatitis; trade name: Nizoral; drug class: imidazole antifungal; action: alters cell membranes and inhibits several fungal enzymes; uses: systemic candidiasis, chronic mucocutaneous candidiasis, candiduria, coccidioidomycosis, histoplasmosis, chromomycosis, paracoccidioidomycosis, tinea pedis.
| Drug Info: Ketoconazole |
Brand names: Extina®Kuric™Nizoral ShampooNizoral®Nizoral® A-DXolegel™
Chemical formula:
- Drug Forms:
- Ketoconazole tablets (below)
- Ketoconazole skin cream
- Ketoconazole Shampoo
- Ketoconazole Topical cream
- Ketoconazole Oral tablet
- Ketoconazole gel
- Ketoconazole foam
- Ketoconazole Topical foam
- Ketoconazole Topical gel
- Español:
- Tabletas de quetoconazol
- Crema de quetoconazol para la piel
- Quetoconazol, Champú
- Quetoconazol, Crema tópica
- Quetoconazol, Tableta oral
- Quetoconazol, Espuma tópica
- Quetoconazol, Gel tópico
Ketoconazole tablets
What are ketoconazole tablets?
KETOCONAZOLE (Nizoral®) is an antifungal type of antibiotic. It treats fungal infections such as ringworm of the body (tinea corporis), ringworm of the groin (tinea cruris or jock itch), sun fungus (tinea versicolor, pityriasis versicolor), dandruff, and other systemic (throughout the body) fungal infections. Generic ketoconazole oral tablets are available.
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
• an alcohol abuse problem
• low stomach acid production (achlorhydria or hypochlorhydria)
• liver disease
• other chronic illness
• an unusual or allergic reaction to ketoconazole, itraconazole, miconazole, other foods, dyes or preservatives
• pregnant or trying to get pregnant
• breast-feeding
How should I take this medicine?
Take ketoconazole tablets by mouth. Follow the directions on the prescription label. Take your doses at regular intervals. Ketoconazole works best if you take it with food. If you have a low production of stomach acid you may have to take your tablets dissolved in dilute hydrochloric acid. Drink this mixture through a straw to avoid contact with the teeth. Then drink a glass of water, swishing it round your teeth before you swallow. Do not take or use your medicine more often than directed. Finish the full course prescribed by your prescriber or health care professional even if you feel better. Do not stop taking except on your prescriber's advice.
Contact your pediatrician or health care professional regarding the use of this medicine in children. Special care may be needed.
What if I miss a dose?
If you miss a dose, take it as soon as you can. If it is almost time for your next dose, take only that dose. Do not take double or extra doses.What drug(s) may interact with ketoconazole?
• alcohol
• antacids
• astemizole
• bosentan
• cisapride
• cyclosporine
• didanosine (ddI)
• dofetilide
• doxercalciferol
• ergotamine, dihydroergotamine or methysergide
• hormones such as prednisone or cortisone
• isoniazid
• certain medicines for anxiety or difficulty sleeping
• medicines for lowering cholesterol (such as atorvastatin, lovastatin, simvastatin)
• medicines for movement abnormalities as in Parkinson's disease, or for gastrointestinal problems
• medicines for stomach ulcers and other stomach problems
• other medicines for fungal or yeast infections
• paricalcitol
• pimozide
• pioglitazone
• quinidine
• phenytoin
• rifampin
• terfenadine
• tolbutamide
• warfarin
Tell your prescriber or health care professional about all other medicines you are taking, including non-prescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.
What should I watch for while taking ketoconazole?
Tell your prescriber or health care professional if your symptoms do not begin to improve in 1 to 2 weeks. Some fungal infections can take many weeks or months of treatment to cure. Take your medicine regularly for as long as your prescriber or health care professional tells you to.
You may get dizzy; until you know how ketoconazole affects you, do not drive, use machinery, or do anything that needs mental alertness.
Alcohol may make you more dizzy, feel sick and increase possible damage to your liver. Avoid alcoholic drinks while you are taking ketoconazole and for two days afterwards. Other medicines you get on prescription, or buy at the pharmacy may contain small amounts of alcohol.
Do not take terfenadine (Seldane®) or astemizole (Hismanal®) with ketoconazole. This combination of medicines can produce serious effects on your heart.
Ketoconazole may make your eyes more sensitive to light. Wear dark glasses in bright sun, or under any bright lights.
What side effects may I notice from taking ketoconazole?
Side effects that you should report to your prescriber or health care professional as soon as possible:
• dark yellow or brown urine
• loss of appetite
• redness, blistering, peeling or loosening of the skin, including inside the mouth
• skin rash, itching
• stomach pain
• yellowing of the eyes or skin
Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
• breast swelling and tenderness, or sexual difficulties (impotence) in men
• drowsiness or dizziness
• eyes get more sensitive to light
• nausea, vomiting
Where can I keep my medicine?
Keep out of the reach of children in a container that small children cannot open.
Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Keep container tightly closed. Throw away any unused medicine after the expiration date.
Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
| Veterinary Dictionary: ketoconazole |
An imidazole antifungal agent, used orally and topically as the nitrate in the treatment of cutaneous and systemic fungal infections. It also inhibits steroidogenesis and has been used in the treatment of canine hyperadrenocorticism; infertility and teratogenicity may occur.
| Wikipedia: Ketoconazole |
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Ketoconazole
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| Systematic (IUPAC) name | |
| 1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)- 2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan- 4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one |
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| Identifiers | |
| CAS number | 65277-42-1 |
| ATC code | J02AB02 D01 G01 |
| PubChem | 47576 |
| DrugBank | APRD00401 |
| ChemSpider | 401695 |
| Chemical data | |
| Formula | C26H28Cl2N4O4 |
| Mol. mass | 531.43 g/mol |
| Pharmacokinetic data | |
| Bioavailability | Variable |
| Protein binding | 84 to 99% |
| Metabolism | Hepatic |
| Half life | Biphasic:
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| Excretion | Biliary and renal |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | Oral, topical |
 (what is this?) (verify) |
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Ketoconazole (pronounced /ˌkiːtəʊˈkoʊnəzol/) is a synthetic antifungal drug used to prevent and treat skin and fungal infections, especially in immunocompromised patients such as those with AIDS. Ketoconazole is sold commercially as an anti-dandruff shampoo, under brand names Perkhotal by Gepach International, and Nizoral, by Johnson & Johnson.
Ketoconazole is very lipophilic, which leads to accumulation in fatty tissues. The less toxic and more effective triazole compounds fluconazole and itraconazole have largely replaced ketoconazole for internal use. Ketoconazole is best absorbed at highly acidic levels, so antacids or other causes of decreased stomach acid levels will lower the drug's absorption when taken orally.
Contents |
History
Ketoconazole was discovered in 1976 and released in 1981[1]. It followed griseofulvin as one of the first available oral treatments for fungal infections.
Usage
Ketoconazole is usually prescribed for topical infections such as athlete's foot, ringworm, candidiasis (yeast infection or thrush), and jock itch. The over-the-counter shampoo version can also be used as a body wash for the treatment of tinea versicolor[2][3].
Ketoconazole is used to treat eumycetoma, the fungal form of mycetoma.
The side-effects of ketoconazole are sometimes used to treat non-fungal problems. The decrease in testosterone caused by the drug makes it useful for treating prostate cancer and for preventing post-operative erections[4] following penile surgery. Another use is the suppression of glucocorticoid synthesis, where it is used in the treatment of Cushing's disease.[5] These side effects have also been studied for use in reducing depressive symptoms[6] and drug addiction;[7] however, it has not succeeded in either of these roles.[8][9]
Ketoconazole can be prescribed as a 200-mg pill, a 2% cream, a 2% gel,a 2% foam,or 2% shampoo for the treatment of dandruff or seborrhoeic dermatitis, or as a 1% over-the-counter shampoo (Perkhotal)& (Nizoral). However, 2% shampoo is sold over-the-counter in many countries as well.
Ketoconazole is also available as a topical mousse, using patented Versafoam technology, marketed under the brand name Ketomousse. In clinical studies, the Versafoam proved to be a superior mechanism of delivery to the shampoo. Currently it is only available in Europe.
The anti-dandruff shampoo is designed for people who have a more serious case of dandruff where symptoms include, but are not limited to constant non-stop flaking, and severe itchiness.
It is a pregnancy category C drug because animal testing has shown it to cause teratogenesis in high dosages. Until recently, there were two human test cases on record (both during the treatment of Cushing's syndrome)[10][11] and no adverse effects were reported, but this is not a broad enough data sample to draw any meaningful conclusions. A subsequent trial in Europe failed to show a risk to infants of mothers receiving ketoconazole.[12]
This medication is also sometimes prescribed by veterinarians for use on pets, often as 200 mg unflavored tablets that may need to be cut to smaller size for correct dosage.[13]
Mechanism of action
Ketoconazole is structurally similar to imidazole, and interferes with the fungal synthesis of ergosterol, a constituent of cell membranes, as well as certain enzymes. It is specific for fungi, as the equivalent mammalian pathway, leading to the biosynthesis of cholesterol, is not sensitive to ketoconazole. However, other mammalian cytochrome P450 enzymes can be sensitive to ketoconazole, and inhibition of steroid hormone synthesis is a possible side effect of ketoconazole treatment.
As with all azole antifungal agents, ketoconazole works principally by inhibition of an enzyme, cytochrome P450 14-alpha-demethylase (P45014DM). This enzyme is in the sterol biosynthesis pathway that leads from lanosterol to ergosterol. Fluconazole and itraconazole have been found to have a greater affinity for fungal cell membrane than ketoconazole, and thus lower doses of these azoles are required to kill fungi.
Sensitive fungi
Ketoconazole inhibits growth of dermatophytes and yeast species such as Candida albicans. The rise in the number of HIV/AIDS immune compromised patients has led to an increase in the frequency and significance of opportunistic fungal infections. Resistance to ketoconazole has been observed in a number of clinical fungal isolates, including C. 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. MDR or multidrug resistance 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.
Hair loss benefits
A study in mice indicated that ketoconazole may have a stimulatory effect on hair growth.[14] Nizoral shampoo has shown to be beneficial in men suffering from androgenic alopecia. One 1998 study showed that Nizoral 2% worked just as well as minoxidil 2% (brand name Rogaine) in men with androgenic alopecia. Both medicines increased hair thickness and increased the number of anagen-phase hair follicles on the scalp. Researchers were guarded about the meaning of these results, saying that more rigorous studies on larger groups of men should be done to confirm the findings, both to evaluate the ideal dosage and formulation, and to assess the desirability of routine treatment in this condition. Nizoral Shampoo only has U.S. Food and Drug Administration (FDA) approval for the treatment of dandruff and seborrheic dermatitis of the scalp, so although Nizoral may be useful as a hair loss remedy, it cannot be endorsed or marketed as one to the general public.[15]
Results so far indicate that both the 1% and 2% dosages have positive hair loss benefits; however the more potent 2% formulation could have better results. Optimal usage is speculated at every third day, leaving the shampoo on the scalp for 3–5 minutes before rinsing. It has been stated that medications capable of maintaining the existing hair population should be regarded as effective treatments for androgenic alopecia. The present data suggest that ketoconazole should enter this group of drugs.[16]
References
- ^ http://www.medicinenet.com/ketoconazole/article.htm
- ^ MedlinePlus Medical Encyclopedia: Tinea versicolor
- ^ Tinea Versicolor
- ^ Evans, K. C.; A. C. Peterson, H. E. Ruiz and R. A. Costabile (August 2004). "Use of oral ketoconazole to prevent postoperative erections following penile surgery". International Journal of Impotence Research 16 (4): 346–349. doi:. PMID 14973533. http://www.nature.com/ijir/journal/v16/n4/full/3901160a.html.
- ^ Loli, Paola; Maria Elisa Berselli and Mariantonella Tagliaferri (1986). "Use of ketoconazole in the treatment of Cushing's syndrome". Journal of Clinical Endocrinology & Metabolism 63 (6): 1365–71. PMID 3023421.
- ^ Wolkowitz, Owen M.; Victor I. Reus (01 Sep 1999). "Treatment of Depression With Antiglucocorticoid Drugs". Psychosomatic Medicine 61 (5): 698–711. PMID 10511017. http://www.psychosomaticmedicine.org/cgi/content/full/61/5/698.
- ^ Goeders, Nick E.; Rachel L. Peltiera and Glenn F. Guerin (December 1998). "Ketoconazole reduces low dose cocaine self-administration in rats". Drug and Alcohol Dependence 53 (1): 67–77. doi:. PMID 10933341. http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&list_uids=10933341&dopt=ExternalLink.
- ^ Malison, Robert T.; Amit Anand, Gregory H. Pelton, Paul Kirwin, Linda Carpenter, Christopher J. McDougle, George R. Heninger and Lawrence H. Price (October 1999). "Limited Efficacy of Ketoconazole in Treatment-Refractory Major Depression". Journal of Clinical Psychopharmacology 19 (5): 466–470. doi:. PMID 10505589.
- ^ Ward, Amie S.; Eric D. Collins, Margaret Haney, Richard W. Foltin and Marian W Fischman (November 1998). "Ketoconazole attenuates the cortisol response but not the subjective effects of smoked cocaine in humans". Behavioural Pharmacology 9 (7): 577–86. doi:. PMID 9862083.
- ^ Amado, José Antonio; Carlos Pesquera, Eva M. Gonzalez, Macarena Otero, Julio Freijanes, and Angel Alvarez (March 1990). "Successful treatment with ketoconazole of Cushing's syndrome in pregnancy". Postgraduate Medical Journal 66 (773): 221–3. doi:. PMID 2362890.
- ^ Berwaerts, Joris; Johan Verhelst, Charles Mahler and Roger Abs (June 1999). "Cushing's syndrome in pregnancy treated by ketoconazole: case report and review of the literature". Gynecological Endocrinology 13 (3): 175–82. PMID 10451809. http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&list_uids=10451809&dopt=ExternalLink.
- ^ Kazy, Zoltán; Erzsébet Puhó and Andrew E. Czeizel (March 2005). "Population-based case–control study of oral ketoconazole treatment for birth outcomes". Congenital Anomalies 45 (1): 5–8. doi:. PMID 15737124. http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&list_uids=15737124&dopt=ExternalLink.
- ^ Ketoconazole for Your Pet at Petscriptions
- ^ Jiang J, Tsuboi R, Kojima Y, Ogawa H (April 2005). "Topical application of ketoconazole stimulates hair growth in C3H/HeN mice". J. Dermatol. 32 (4): 243–7. PMID 15863844. http://www.dermatol.or.jp/Journal/JD/2005/032040243.html.
- ^ Nizoral Shampoo as a Hair Loss Remedy? http://www.dermadoctor.com/pages/newsletter198.asp
- ^ http://www.hairlosstalk.com/download/nizoral.pdf
External links
- PubPK - Ketoconazole Pharmacokinetics
- Janssen Pharmaceutica fungal infections page
- Doctor Fungus ketoconazole page
- Nizoral (manufacturer's website)
- Ketoconazole (patient information)
- Ketoconazole (Up to date product information)
- Piérard-Franchimont C, Goffin V, Decroix J, Piérard GE (2002). "A multicenter randomized trial of ketoconazole 2% and zinc pyrithione 1% shampoos in severe dandruff and seborrheic dermatitis". Skin Pharmacol. Appl. Skin Physiol. 15 (6): 434–41. PMID 12476017. http://content.karger.com/produktedb/produkte.asp?typ=fulltext&file=sph15434. – ketoconazole (Nizoral) versus zinc pyrithione (Head & Shoulders)
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Mentioned in
- Nizoral (trademark)
- imidazoles
- clotrimazole
- azole antifungals
