itraconazole

American Heritage Dictionary:

it·ra·con·a·zole

(ĭt'rə-kŏn'ĭ-zōl) pronunciation

n.
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.]

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Itraconazole

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Brand names: Sporanox®

Chemical formula:

Drug Forms:

Espa�ol:

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.

Oxford A-Z of Medicinal Drugs:

itraconazole

Top

A triazole antifungal drug that is used to treat a wide variety of fungal infections, including tinea (ringworm) of the skin, scalp, and nails, and candidiasis (thrush), and to prevent fungal infections in people whose immune systems are functioning poorly, such as AIDS patients and the recipients of transplants. Itraconazole is taken by mouth, as capsules or a liquid, or given by intravenous infusion and is available on prescription only.

Side effects:
include nausea, abdominal pain, indigestion, constipation (people taking the liquid may have diarrhoea), itching, headache, dizziness, menstrual disorders, and allergic reactions.

Precautions:
itraconazole should not be taken by people with liver disease or porphyria or by women who are breastfeeding. It should be used with caution during pregnancy.

Interactions with other drugs:

Antacids reduce the absorption of itraconazole.
Antibiotics rifabutin and rifampicin reduce the plasma concentration of itraconazole, which should not be taken with rifabutin.
Anticoagulants the effects of warfarin and acenocoumarol are enhanced; rivaroxaban should not be taken with itraconazole.
Antipsychotics: pimozide and sertindole should not be taken with itraconazole because of the risk of irregular heart rhythms.
Antiviral drugs efavirenz reduces the plasma concentration of itraconazole; itraconazole increases the plasma concentration of indinavir, whose dosage may therefore need to be reduced; the plasma concentrations of both drugs may be increased if itraconazole is taken with ritonavir.
Ciclosporin: its plasma concentrations (and therefore side effects) are increased by itraconazole.
Cytotoxic drugs lapatinib and nilotinib should not be taken with itraconazole; the risk of nerve damage is increased if vincristine is given with itraconazole.
Digoxin its plasma concentrations (and therefore side effects) are increased by itraconazole.
Eletriptan its plasma concentration is increased and it should not be taken with itraconazole.
Eplerenone its plasma concentration is increased and it should not be taken with itraconazole.
Ergotamine: its adverse effects are increased and it should not be taken with itraconazole.
Ivabradine its plasma concentration is increased and it should not be taken with itraconazole.
Midazolam its plasma concentrations (and therefore side effects) are increased by itraconazole.
Mizolastine its plasma concentration is increased and it should not be taken with itraconazole.
Phenytoin reduces the plasma concentration of itraconazole.
Ranolazine its plasma concentration is increased and it should not be taken with itraconazole.
Reboxetine should not be taken with itraconazole.
Sirolimus its plasma concentration is increased and it should not be taken with itraconazole.
Statins there is an increased risk of myopathy (muscle disease) with atorvastatin and simvastatin and therefore these drugs should not be used with itraconazole.
Tacrolimus its plasma concentration is increased.
Ulcer-healing drugs: H₂-receptor antagonists and proton pump inhibitors reduce the absorption of itraconazole.
Vardenafil its plasma concentration is increased and it should not be taken with itraconazole.

Proprietary preparations:
Sporanox; Sporanox Capsules; Sporanox Pulse.

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Oxford Dictionary of Biochemistry:

itraconazole

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a complex derivative of triazole, useful as an antimycotic. It inhibits cytochrome P450-dependent enzymes, thereby impairing the synthesis of ergosterol.

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Next:	iupaciubin, ivermectin, j

Saunders Veterinary Dictionary:

itraconazole

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A triazole antifungal agent, used parenterally in the treatment of cryptococcosis in cats.

Mosby's Dental Dictionary:

itraconazole

Top

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.

Wikipedia on Answers.com:

Itraconazole

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Itraconazole

Systematic (IUPAC) name
(2R,4S)-rel-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
Clinical data
Trade names	Sporanox
AHFS/Drugs.com	monograph
MedlinePlus	a692049
Pregnancy cat.	C (safety unknown)
Legal status	POM (UK) ℞-only (US)
Routes	Oral and i.v. (US), Oral only (UK)
Pharmacokinetic data
Bioavailability	55%, maximal if taken with full meal
Protein binding	99.8%
Metabolism	hepatic (CYP3A4)
Half-life	21 hours
Identifiers
CAS number	84625-61-6^Y
ATC code	J02AC02
PubChem	CID 55283
DrugBank	APRD00040
ChemSpider	49927^Y
UNII	304NUG5GF4^Y
KEGG	D00350^Y
ChEBI	CHEBI:6076^Y
ChEMBL	CHEMBL22587^Y
Chemical data
Formula	C₃₅H₃₈Cl₂N₈O₄
Mol. mass	705.64
SMILES	eMolecules & PubChem
InChI InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1^Y Key:VHVPQPYKVGDNFY-ZPGVKDDISA-N^Y
N(what is this?) (verify)

Itraconazole , 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

1 Medical uses
2 Pharmacology
3 Formulation
4 Adverse effects
5 Production and marketing
6 See also
7 Footnotes
8 External links

Medical uses

Itraconazole has a broanst 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. Itraconazole is currently being explored as an anti-cancer agent for patients with basal cell carcinoma, non-small cell lung cancer, and prostate cancer.^[3]

Pharmacology

The mechanism of action of itraconazole is the same as the other azole antifungals: it inhibits the fungal -mediated synthesis of ergosterol. Because of its ability to inhibit cytochrome P450 3A4 CC-3, caution should be used when considering interactions with other medications.^{[citation needed]}

Itraconazole is pharmacologically distinct from other azole antifungal agents in that itraconazole is the only inhibitor in this class that has been shown to inhibit both the hedgehog signaling pathway^[4] and angiogenesis.^[5]^[6] These distinct activities are unrelated to inhibition of the cytochrome P450 Lanosterol 14 alpha-demethylase and the exact molecular targets responsible remain unidentified. Functionally, the antiangiogenic activity of itraconazole has been shown to be linked to inhibition of glycosylation, VEGFR2 phosphorylation,^[6] trafficking,^[7] and cholesterol biosynthesis pathways.^[5] Evidence suggests that structural determinants for inhibition of hedgehog signaling by itraconazole are recognizably different from those associated with anti-angiogenic activity.^[8]

Formulation

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.^{[citation needed]}

Itraconazole has relatively low bioavailability after oral administration, especially when given in capsule form on an empty stomach. The capsule form is a molecular dispersion of itraconazole in amorphous HPMC polymer. The fast dissolving polymer targets a supersaturated solution of itraconazole from which enhanced absorption can be expected. Recently, it was evidenced that itraconazole contributes to the formation of nanofibers in certain simulated intestinal fluids. These nanofibers have a uniform width of 12 nm and a length up to several micrometers.^[9] 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 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.^{[citation needed]}

The following drugs should not be taken together with itraconazole:^{[citation needed]}

cisapride (Propulsid);
dofetilide (Tikosyn);
nisoldipine (Sular);
pimozide (Orap);
quinidine (Quinaglute, Quinidex, Quin-Release);
lovastatin (Altocor, Altoprev, Mevacor) or simvastatin (Zocor);
midazolam (Versed) or triazolam (Halcion);
ergot medicines such as dihydroedrgotamine (D.H.E. 45, Migranal), ergonavine (Ergotrate), ergotamine (Ergomar, Cafergot, Ercaf, Migergot), or methylergonovine (Methergine).

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.^[10]

Elevated alanine aminotransferase levels is found in 4% of people taking itraconazole
"Small but real risk" of developing congestive heart failure^[10]
Liver failure, sometimes fatal

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 is produced as blue 22 mm (0.87 in) capsules with tiny 1.5 mm (0.059 in) blue pellets inside. Each capsule contains 100 mg and is usually taken twice a day i.e. every twelve hours. The Sporanox the brand name of itraconazole has been developed and marketed by Janssen Pharmaceutica, a subsidiary of Johnson & Johnson. The three layer structure of these blue capsules are complex because itraconazole is insoluble and is sensitive to pH. The complicated procedure not only requires a specialized machine to create it, but also 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.^[11]^[12]

Footnotes

This article uses bare URLs for citations. Please consider adding full citations so that the article remains verifiable. Several templates and the Reflinks tool are available to assist in formatting. (Reflinks documentation) (November 2011)

^ Gilbert DN, Moellering, RC, Eliopoulos GM, Sande MA (2006). The Sanford Guide to antimicrobial therapy. ISBN 1-930808-30-5. ^{[page needed]}
^ Pham, P; Bartlett, JG (2007-07-24). "Itraconazole". Johns Hopkins. http://www.hopkins-abxguide.org/terminals/antibiotics_more.cfm?id=81&fc=p.
^ clinicaltrials.gov
^ Kim, James; Tang, Jean Y.; Gong, Ruoyu; Kim, Jynho; Lee, John J.; Clemons, Karl V.; Chong, Curtis R.; Chang, Kris S. et al. (2010). "Itraconazole, a Commonly Used Antifungal that Inhibits Hedgehog Pathway Activity and Cancer Growth". Cancer Cell 17 (4): 388–99. doi:10.1016/j.ccr.2010.02.027. PMID 20385363.
^ ^a ^b Chong, Curtis R.; Xu, Jing; Lu, Jun; Bhat, Shridhar; Sullivan, David J.; Liu, Jun O. (2007). "Inhibition of Angiogenesis by the Antifungal Drug Itraconazole". ACS Chemical Biology 2 (4): 263–70. doi:10.1021/cb600362d. PMID 17432820.
^ ^a ^b Aftab, B. T.; Dobromilskaya, I.; Liu, J. O.; Rudin, C. M. (2011). "Itraconazole Inhibits Angiogenesis and Tumor Growth in Non-Small Cell Lung Cancer". Cancer Research 71 (21): 6764–72. doi:10.1158/0008-5472.CAN-11-0691. PMC 3206167. PMID 21896639. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3206167.
^ Xu, J.; Dang, Y.; Ren, Y. R.; Liu, J. O. (2010). "Cholesterol trafficking is required for mTOR activation in endothelial cells". Proceedings of the National Academy of Sciences 107 (10): 4764–9. doi:10.1073/pnas.0910872107. PMC 2842052. PMID 20176935. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2842052.
^ Shi, Wei; Nacev, Benjamin A.; Aftab, Blake T.; Head, Sarah; Rudin, Charles M.; Liu, Jun O. (2011). "Itraconazole Side Chain Analogues: Structure–Activity Relationship Studies for Inhibition of Endothelial Cell Proliferation, Vascular Endothelial Growth Factor Receptor 2 (VEGFR2) Glycosylation, and Hedgehog Signaling". Journal of Medicinal Chemistry 54 (20): 7363–74. doi:10.1021/jm200944b. PMID 21936514.
^ Mellaerts, Randy; Aerts, Alexander; Caremans, Tom P.; Vermant, Jan; Van Den Mooter, Guy; Martens, Johan A.; Augustijns, Patrick (2010). "Growth of Itraconazole Nanofibers in Supersaturated Simulated Intestinal Fluid". Molecular Pharmaceutics 7 (3): 905–13. doi:10.1021/mp900300j. PMID 20232903.
^ ^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. ^{[dead link]}
^ Composition comprising Itraconazole for oral administration. 2004. Fresh Patents.com. 26 October 2006.
^ Sporanox (Itraconazole Capsules). June 2006. Janssen. 26 October 2006

External links

Antifungals (D01 and J02)

Wall/
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Ergosterol
inhibitors

Azoles
(lanosterol 14
alpha-demethylase inhibitors)

Imidazoles	topical: Bifonazole, Clomidazole, Clotrimazole^#, Croconazole, Econazole, Fenticonazole, Ketoconazole, Isoconazole, Miconazole^#, Neticonazole, Oxiconazole, Sertaconazole, Sulconazole, Tioconazole

Triazoles	topical: (Fluconazole^#, Fosfluconazole) systemic: (Fluconazole, Hexaconazole, Itraconazole, Posaconazole, Voriconazole)

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topical: (Natamycin, Nystatin^#)
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itraconazole

it·ra·con·a·zole

Itraconazole

itraconazole

itraconazole

itraconazole

itraconazole

Itraconazole

Medical uses

Pharmacology

Formulation

Adverse effects

Production and marketing

See also

Footnotes

External links