A broad-spectrum antifungal agent administered orally to treat a variety of fungal infections.
[itra- (shortening and alteration of triazolo-, containing three azole groups : TRI- + AZOLE) + (MI)CONAZOLE.]
itraconazole
Dictionary:
it·ra·con·a·zole (ĭt'rə-kŏn'ĭ-zōl)  |
n.
A broad-spectrum antifungal agent administered orally to treat a variety of fungal infections.
A broad-spectrum antifungal agent administered orally to treat a variety of fungal infections.
| 5min Related Video: itraconazole |
| Dental Dictionary: itraconazole |
n
trade name: Sporanox; drug class: antifungal, systemic; action: inhibits cytochrome P-450 enzyme’s blocking synthesis of essential membrane sterols in fungal organism; uses: blastomycosis, histoplasmosis.
| Drug Info: Itraconazole |
Brand names: Sporanox®
Chemical formula:
- Drug Forms:
- Itraconazole capsules (below)
- Itraconazole Oral capsule
- Itraconazole Oral solution
- Itraconazole Solution for injection
- Español:
- Cápsulas de itraconazol
- Itraconazol, Cápsula oral
- Itraconazol, Solución oral
- Itraconazol, Solución para inyección
Itraconazole capsules
What are itraconazole capsules?
ITRACONAZOLE (Sporanox®) is an antifungal type of antibiotic. It treats serious fungal infections; especially those associated with the lungs. Generic itraconazole capsules 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:
• heart disease, including angina or heart failure
• liver disease
• lung disease, including COPD
• kidney disease or on dialysis
• an unusual or allergic reaction to itraconazole, or other azole medicines, foods, dyes or preservatives
• pregnant or trying to get pregnant
• breast-feeding
How should I take this medicine?
Take this medicine by mouth. Follow the directions on the prescription label. This medicine work best if you take it with food or a cola beverage. If you drink grapefruit juice, limit the amount you drink or avoid it while taking this medicine. Take your doses at regular intervals. Do not take your medicine more often than directed. Finish the full course prescribed 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 itraconazole capsules?
Do not take itraconazole with the following medications or foods:
• astemizole (Hismanal®)
• bosentan (Tracleer™)
• cerivastatin (Baycol®)
• cimetidine (Tagamet®)
• cisapride (Propulsid®)
• dofetilide (Tikosyn™)
• esomeprazole (Nexium®)
• famotidine (Pepcid®)
• lansoprazole (Prevacid®)
• lovastatin (Advicor®, Altocor™, Mevacor®)
• nizatidine (Axid®)
• omeprazole (Prilosec®)
• pantoprazole (Protonix®)
• pimozide (Orap®)
• quinidine (Cardioquin®, Quinidex®, Quinaglute®)
• rabeprazole (AcipHex™)
• ranitidine (Zantac®)
• simvastatin (Zocor®)
• terfenadine (Seldane®)
• triazolam (Halcion®)
• went yeast (Cholestin™)
Other drugs that may interact with itraconazole include:
• antacids
• atorvastatin
• cilostazol
• clarithromycin
• cyclosporine
• digoxin
• dihydroergotamine, ergotamine, or methysergide
• doxercalciferol
• erythromycin
• medicines for anxiety or sleep (e.g., alprazolam, estazolam)
• medicines for diabetes that are taken by mouth
• medicines for HIV infection or AIDS
• medicines for tuberculosis (e.g., isoniazid, INH, rifabutin, rifampin, rifapentine)
• methadone
• other medicines for fungal or yeast infections
• paricalcitol
• phenytoin
• pravastatin
• rosuvastatin
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 itraconazole capsules?
If you experience unusual fatigue, loss of appetite (anorexia), nausea and/or vomiting, yellowing of skin, dark urine, or pale stools, stop taking itraconazole immediately and contact your healthcare provider.
Tell your prescriber or health care professional if your symptoms do not begin to improve in 1 to 2 weeks. Some fungal infections need 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.
Do not take ranitidine (Zantac®), cimetidine (Tagamet®), famotidine (Pepcid®), or other agents [e.g., omeprazole (Prilosec®), lansoprazole (Prevacid®), pantoprazole (Protonix®)] that may decrease the acid in your stomach. Itraconazole needs acid in the stomach so that it can be absorbed. If you use antacids, do not take them at the same time as itraconazole. Take itraconazole 1 hour before or 4 hours after antacids.
What side effects may I notice from taking itraconazole capsules?
Side effects that you should report to your prescriber or health care professional as soon as possible:
Rare or uncommon:
• difficulty breathing or shortness of breath
• dark yellow or brown urine
• loss of appetite
• pale stools
• redness, blistering, peeling or loosening of the skin, including inside the mouth
• skin rash, itching
• stomach pain
• skin rash, itching, hives
• swelling, fluid retention
• unusual fatigue
• vomiting
• 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):
• diarrhea
• dizziness
• headache
• nausea
Where can I keep my medicine?
Keep out of the reach of children in a container that small children cannot open.
Store at or below 25 degrees C (77 degrees F). Do not freeze. 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: itraconazole |
A triazole antifungal agent, used parenterally in the treatment of cryptococcosis in cats.
| Wikipedia: Itraconazole |
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Itraconazole
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| Systematic (IUPAC) name | |
| (RS)-1-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2- (1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan- 4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one |
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| Identifiers | |
| CAS number | 84625-61-6 |
| ATC code | J02AC02 |
| PubChem | 55283 |
| DrugBank | APRD00040 |
| ChemSpider | 49927 |
| Chemical data | |
| Formula | C35H38Cl2N8O4 |
| Mol. mass | 705.64 |
| SMILES | eMolecules & PubChem |
| Pharmacokinetic data | |
| Bioavailability | 55%, maximal if taken with full meal |
| Protein binding | 99.8% |
| Metabolism | hepatic (CYP3A4) |
| Half life | 21 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
C (safety unknown) |
| Legal status | |
| Routes | Oral and i.v. (US), Oral only (UK) |
 (what is this?) (verify) |
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Itraconazole (marketed as Sporanox by Janssen Pharmaceutica), invented in 1984, is a triazole antifungal agent that is prescribed to patients with fungal infections. The drug may be given orally or intravenously.
Contents |
Pharmacology
The mechanism of action of itraconazole is the same as the other azole antifungals: it inhibits the fungal cytochrome P450 oxidase-mediated synthesis of ergosterol. Because of its ability to inhibit cytochrome P450 3A4, caution should be used when considering interactions with other medications.
Indication
Itraconazole has a broader spectrum of activity than fluconazole (but not as broad as voriconazole or posaconazole). In particular, it is active against aspergillus, which fluconazole is not. It is also licenced for use in blastomycosis, histoplasmosis and onychomycosis. Itraconazole is over 99% protein bound and has virtually no penetration into cerebrospinal fluid. Therefore, it should never be used to treat meningitis or other central nervous system infections.[1] According to the Johns Hopkins Abx Guide, it has "negligible CSF penetration, however treatment has been successful for cryptococcal and coccidioidal meningitis".[2] It is also prescribed for systemic infections such as aspergillosis, candidiasis and cryptococcosis where other antifungal drugs are inappropriate or ineffective.
Dosing
Itraconazole is available as capsules or as an oral solution. The dose is 200 mg once a day, to 400 mg in severe infection. There is an intravenous preparation available in the US, but not in the UK. In the UK, if an intravenous preparation is required, then an alternative antifungal drug should be used.
Itraconazole has relatively low bioavailability after oral administration, especially when given in capsule form on empty stomach. The oral solution is better absorbed. The cyclodextrin contained in the oral solution can cause an osmotic diarrhea, and if this is a problem, then half the dose can be given as oral solution and half as capsule in order to reduce the amount of cyclodextrin given. Itraconazole capsules should always be taken with food, as this improves absorption. Itraconazole oral solution should be taken an hour before food, or two hours after food (and likewise if a combination of capsules and oral solution are used). Itraconazole may be taken with orange juice or cola, as absorption is also improved by acid. Absorption of itraconazole is impaired when taken with an antacid, H2-blocker or proton pump inhibitor.
Some doctors give an oral loading dose of 200 mg three times a day for three days, before dropping down to the usual dose. Because itraconazole absorption is unreliable, blood levels should be monitored at least once a week in those patients who are being treated for life-threatening (or potentially life-threatening) fungal infections.
In intravenous dosing, four doses of itraconazole 200 mg are given 12 hours apart, before changing the dose to once daily. There is no safety data for giving the intravenous preparation for more than 14 days continuously.
Adverse effects
Itraconazole is a relatively well-tolerated drug (although not as well tolerated as fluconazole or voriconazole) and the range of adverse effects it produces is similar to the other azole antifungals.[3]
- Elevated alanine aminotransferase levels is found in 4% of people taking itraconazole
- "Small but real risk of developing" Congestive Heart Failure[3]
The cyclodextrin that is used to make the syrup preparation can cause diarrhea. Side-effects that may indicate a greater problem include:
- nausea
- vomiting
- abdominal pain
- fatigue
- loss of appetite
- yellow skin (jaundice)
- yellow eyes
- itching
- dark urine
- pale stool
Production and marketing
Itraconazole can be consumed orally in blue ⅞ in (22 mm) capsules with tiny 1.5 mm blue pellets inside. Each capsule contains 100 mg and is usually taken multiple times a day such as every twelve hours. Sporanox, the brand name of Itraconazole, has been developed and marketed by Janssen Pharmaceutica Products, L.P. a subsidiary of Johnson and Johnson. Apparently, the three layer structure of these blue capsules are quite complex because Itraconazole is insoluble and is sensitive to pH. The complicated procedure not only requires a specialized machine to create it, but the method used has manufacturing problems. Also, the pill is quite large, making it difficult for many patients to swallow. Parts of the processes of creating Sporanox were discovered by the Korean Patent Laid. The contents of the capsule, the tiny blue pellets, are manufactured in Beerse, Belgium.[4][5]
Consumption
Roughly 180 generic capsules costs $360. If a patient is prescribed three capsules twice daily for the minimum of three months, the patient would spend more than $1080 and consume over 540 capsules. The possible loss of motivation to spend thousands of dollars for continued use therefore constitutes a threat and a risk for the fungus to regrow in the body.[5]
Footnotes
- ^ Gilbert DN, Moellering, RC, Eliopoulos GM, Sande MA. The Sanford Guide to antimicrobial therapy 2006. ISBN 1-930808-30-5.
- ^ Pham, P; Bartlett, JG (2007-07-24). "Itraconazole". Johns Hopkins. http://www.hopkins-abxguide.org/terminals/antibiotics_more.cfm?id=81&fc=p.
- ^ a b "The Safety Of Sporanox Capsules And Lamisil Tablets For The Treatment Of Onychomycosis". FDA Public Health Advisory. May 9 2001. http://www.fda.gov/CDER/drug/advisory/sporanox-lamisil/advisory.htm. Retrieved 2006-08-10.
- ^ “Composition comprising Itraconazole for oral administration.” 2004. Fresh Patents.com. 26 October 2006. <http://www.freshpatents.com/Composition-comprising-itraconazole-for-oral-administration-dt20051013ptan20050226924.php?type=description>.
- ^ a b “Sporanox (Itraconazole Capsules).’’ June 2006. Janssen. 26 October 2006 http://www.sporanox.com/active/janus/en_US/assets/common/company/pi/sporanox.pdf.
See also
External links
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 | Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved. Read more |
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| Dental Dictionary. Mosby's Dental Dictionary. Copyright © 2004 by Elsevier, Inc. All rights reserved. Read more |
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| Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved. Read more |
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Mentioned in
- Itraconazole capsules
- Histoplasmosis: Treatment
- Antifungal Drugs, Systemic
- Antiulcer Drugs: Interactions
- Antianxiety Drugs: Interactions
- Antipsychotic Drugs, Atypical: Interactions
- Aspergillosis: Treatment
- Onychomycosis: Prognosis
- Hospital-Acquired Infections: Treatment
- Antifungal Drugs, Systemic: Recommended dosage
