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itraconazole
4-(4-(4-(4-(2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-(1-methylpropyl)-2,4-dihydro-1,2,4-triazol-3-one

Supplier Sponsors

Name:2-butan-2-yl-4-[4-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one
CAS Number: 84625-61-6Picture of molecule3D/inchi
Other(deleted CASRN):84604-65-9
ECHA EINECS - REACH Pre-Reg:283-347-2
FDA UNII: 304NUG5GF4
Nikkaji Web:J930.335I
Beilstein Number:6042047
MDL:MFCD00870168
XlogP3-AA:5.70 (est)
Molecular Weight:705.64466000
Formula:C35 H38 Cl2 N8 O4
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:antimicrobial agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 0.0004719 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antimicrobial agents
 
Suppliers:
BOC Sciences
For experimental / research use only.
Itraconazole >98%
Odor: characteristic
Use: Itraconazole, a triazole antifungal agent, is a relatively potent inhibitor of CYP3A4.
Glentham Life Sciences
Itraconazole
Sigma-Aldrich
For experimental / research use only.
Itraconazole European Pharmacopoeia (EP) Reference Standard
TCI AMERICA
For experimental / research use only.
Itraconazole >98.0%(HPLC)(T)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
antimicrobial agents
Recommendation for itraconazole usage levels up to:
 not for fragrance use.
 
Recommendation for itraconazole flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6917738
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-butan-2-yl-4-[4-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one
Chemidplus:0084625616
RTECS:XZ5481000 for cas# 84625-61-6
 
References:
 2-butan-2-yl-4-[4-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):6917738
Pubchem (sid):135013328
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2941.90.5000
MedlinePlusSupp:View
ChemSpider:View
Wikipedia:View
Wikipedia2:View2
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
2-butan-2-yl-4-[4-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one
4-(4-(4-(4-(2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-(1-methylpropyl)-2,4-dihydro-1,2,4-triazol-3-one
 sporanox
 

Articles:

PubMed:Pharmacokinetic drug interactions of the selective androgen receptor modulator GTx-024(Enobosarm) with itraconazole, rifampin, probenecid, celecoxib and rosuvastatin.
PubMed:Antifungal Drugs for Onychomycosis: Efficacy, Safety, and Mechanisms of Action.
PubMed:Characterization of Solid Dispersion of Itraconazole Prepared by Solubilization in Concentrated Aqueous Solutions of Weak Organic Acids and Drying.
PubMed:Efinaconazole and Tavaborole: Emerging Antifungal Alternatives for the Topical Treatment of Onychomycosis.
PubMed:Simultaneous determination of benznidazole and itraconazole using spectrophotometry applied to the analysis of mixture: A tool for quality control in the development of formulations.
PubMed:Evaluation of Ketoconazole and Its Alternative Clinical CYP3A4/5 Inhibitors as Inhibitors of Drug Transporters: The In Vitro Effects of Ketoconazole, Ritonavir, Clarithromycin, and Itraconazole on 13 Clinically-Relevant Drug Transporters.
PubMed:Posaconazole: Use in the Prophylaxis and Treatment of Fungal Infections.
PubMed:Population pharmacokinetic modeling of itraconazole and hydroxyitraconazole for oral SUBA-itraconazole and sporanox capsule formulations in healthy subjects in fed and fasted states.
PubMed:Best practices for the use of itraconazole as a replacement for ketoconazole in drug-drug interaction studies.
PubMed:Development and validation of an RP-HPLC method for the quantitation of odanacatib in rat and human plasma and its application to a pharmacokinetic study.
PubMed:Candidiasis (vulvovaginal).
PubMed:Development and validation of a RP-HPLC method for the quantitation of tofacitinib in rat plasma and its application to a pharmacokinetic study.
PubMed:Comparative Pharmacoeconomic Analysis of the Application of Posaconazole, Fluconazole and Itraconazole With the Purpose of Primary Prevention of Invasive Fungal Infection In Patients With Neutropenia During Chemotherapy for Acute Myelogenous Leukemia Or Myelodysplastic Syndrome.
PubMed:Liver injury associated with ketoconazole: review of the published evidence.
PubMed:Interaction of gelatin with polyenes modulates antifungal activity and biocompatibility of electrospun fiber mats.
PubMed:Dielectric spectroscopy for the determination of the glass transition temperature of pharmaceutical solid dispersions.
PubMed:Itraconazole and clarithromycin as ketoconazole alternatives for clinical CYP3A inhibition studies.
PubMed:A rapid microplate method for the proliferation assay of fungi and the antifungal susceptibility testing using the colorimetric microbial viability assay.
PubMed:Fungal toenail infections.
PubMed:[Investigation of antimicrobial and antibiofilm effects of some preservatives used in drugs, cosmetics and food products].
PubMed:Open-label, exploratory phase II trial of oral itraconazole for the treatment of basal cell carcinoma.
PubMed:Use of different parameters and equations for calculation of IC₅₀ values in efflux assays: potential sources of variability in IC₅₀ determination.
PubMed:In vitro predictability of drug-drug interaction likelihood of P-glycoprotein-mediated efflux of dabigatran etexilate based on [I]2/IC50 threshold.
PubMed:Candidiasis (oropharyngeal).
PubMed:Targeting of the Hedgehog signal transduction pathway suppresses survival of malignant pleural mesothelioma cells in vitro.
PubMed:Validation of a population-based method to assess drug-induced alterations in the QT interval: a self-controlled crossover study.
PubMed:ONMEL (itraconazole) 200-mg tablet.
PubMed:Utility of a column-switching LC/MS/MS method in cytochrome P450 inhibition assays using human liver microsomes.
PubMed:Pharmacokinetic and pharmacodynamic interaction of nadolol with itraconazole, rifampicin and grapefruit juice in healthy volunteers.
PubMed:Nasal cutaneous infection in a healthy boy caused by Fusarium moniliforme.
PubMed:The diversity and antifungal susceptibility of the yeasts isolated from coconut water and reconstituted fruit juices in Brazil.
PubMed:Accurate mass screening of pharmaceuticals and fungicides in water by U-HPLC-Exactive Orbitrap MS.
PubMed:Candidiasis (oropharyngeal).
PubMed:Hedgehog signaling pathway and its targets for treatment in basal cell carcinoma.
PubMed:Periostitis secondary to prolonged voriconazole therapy in a lung transplant recipient.
PubMed:The difficulties of polytherapy: examples from antimicrobial chemotherapy.
PubMed:Fungal toenail infections.
PubMed:Potent dried drug nanosuspensions for oral bioavailability enhancement of poorly soluble drugs with pH-dependent solubility.
PubMed:Prophylaxis and treatment of invasive aspergillosis with voriconazole, posaconazole and caspofungin: review of the literature.
PubMed:Drug supersaturation in simulated and human intestinal fluids representing different nutritional states.
PubMed:Management of drug and food interactions with azole antifungal agents in transplant recipients.
PubMed:Pharmacokinetic/pharmacodynamic profile of posaconazole.
PubMed:Bioequivalence study of two formulations of 100 mg capsule of itraconazole. Quantification by tandem mass spectrometry.
PubMed:Increased oral bioavailability of itraconazole and its active metabolite, 7-hydroxyitraconazole, when coadministered with a vitamin C beverage in healthy participants.
PubMed:Arthrographis kalrae, a rare causal agent of onychomycosis, and its occurrence in natural and commercially available soils.
PubMed:Candidiasis (vulvovaginal).
PubMed:HIV: primary and secondary prophylaxis for opportunistic infections.
PubMed:Method for therapeutic drug monitoring of azole antifungal drugs in human serum using LC/MS/MS.
PubMed:[Influence of black vinegar on itraconazole absorption].
PubMed:Candidiasis (oropharyngeal).
PubMed:Population pharmacokinetic analysis of a novel muscarinic receptor antagonist, imidafenacin, in healthy volunteers and overactive bladder patients.
PubMed:In vitro evaluation of the dissolution behaviour of itraconazole in bio-relevant media.
PubMed:Posaconazole: an oral triazole with an extended spectrum of activity.
PubMed:Aspergillosis of a dog genital tract-Case report.
PubMed:[Mycotoxin research in humans].
PubMed:Reviews of anti-infective agents: posaconazole: a broad-spectrum triazole antifungal agent.
PubMed:Reduced food-effect and enhanced bioavailability of a self-microemulsifying formulation of itraconazole in healthy volunteers.
PubMed:Examining sex-related differences in enteric itraconazole metabolism in healthy adults using grapefruit juice.
PubMed:Fungal toenail infections.
PubMed:Posaconazole: an extended-spectrum triazole antifungal agent.
PubMed:The assessment and management of tinea capitis in children.
PubMed:[Pharmacology of azoles].
PubMed:Pharmacokinetics of itraconazole after intravenous and oral dosing of itraconazole-cyclodextrin formulations.
PubMed:Posaconazole: a next-generation triazole antifungal.
PubMed:Inhibition of angiogenesis by the antifungal drug itraconazole.
PubMed:Posaconazole (Noxafil): a new triazole antifungal agent.
PubMed:Surgical excision of mycotic (Cladosporium sp.) granulomas from the mantle of a cuttlefish (Sepia officinalis).
PubMed:Candidiasis (vulvovaginal).
PubMed:Comparative analysis of the effects of rice and bread meals on bioavailability of itraconazole using NONMEM in healthy volunteers.
PubMed:Comparison of lanosterol-14 alpha-demethylase (CYP51) of human and Candida albicans for inhibition by different antifungal azoles.
PubMed:Therapies for onychomycosis: a review.
PubMed:[In vitro activity of voriconazole against yeast and algae isolates according to new resistance pattern cut-off points].
PubMed:A new self-emulsifying formulation of itraconazole with improved dissolution and oral absorption.
PubMed:Pharmacokinetics of telithromycin: application to dosing in the treatment of community-acquired respiratory tract infections.
PubMed:Clinical pharmacokinetics of telithromycin, the first ketolide antibacterial.
PubMed:Comparison of information on the pharmacokinetic interactions of Ca antagonists in the package inserts from three countries (Japan, USA and UK).
PubMed:The systemic treatment of onychomycosis.
PubMed:Posaconazole: a potent, extended-spectrum triazole anti-fungal for the treatment of serious fungal infections.
PubMed:Influence of grapefruit juice on the systemic availability of itraconazole oral solution in healthy adult volunteers.
PubMed:Clinical pharmacokinetics of atorvastatin.
PubMed:Lopinavir/ritonavir: a review of its use in the management of HIV infection.
PubMed:Food-drug interactions.
PubMed:Fusarium infections of the skin.
PubMed:Caspofungin: pharmacology, safety and therapeutic potential in superficial and invasive fungal infections.
PubMed:Advisory for fungal drugs.
PubMed:The role of cytochrome P450-mediated drug-drug interactions in determining the safety of statins.
PubMed:Congestive heart failure associated with itraconazole.
PubMed:Oxymetholone.
PubMed:Enhanced cyclosporine-itraconazole interaction with cola in lung transplant recipients.
PubMed:Treating onychomycosis.
PubMed:Ciclopirox nail lacquer and podiatric practice.
PubMed:Occurrence of itraconazole-tolerant micromycetes in the soil and food products.
PubMed:Oral griseofulvin remains the treatment of choice for tinea capitis in children.
PubMed:Drug interactions with cisapride: clinical implications.
PubMed:Injectable antifungal approved.
PubMed:Successful treatment of invasive nasal cryptococcosis in a ferret.
PubMed:Pharmacokinetic and pharmacodynamic consequences of metabolism-based drug interactions with alprazolam, midazolam, and triazolam.
PubMed:Dermatophyte infections in free-ranging Florida panthers (Felis concolor coryi).
PubMed:Antiinfectives update: focus on treatment and prevention of viral and associated infections.
PubMed:Clinical pharmacokinetics and pharmacodynamics of buspirone, an anxiolytic drug.
PubMed:The evolving role of itraconazole, fluconazole and terbinafine in the treatment of tinea capitis.
PubMed:Optimisation of itraconazole therapy using target drug concentrations.
PubMed:Itraconazole oral solution for the treatment of onychomycosis.
PubMed:Rational assessment of the interaction profile of cerivastatin supports its low propensity for drug interactions.
PubMed:Food interaction and steady-state pharmacokinetics of itraconazole oral solution in healthy volunteers.
PubMed:[Influence of foods on the absorption of antimicrobial agents].
PubMed:Current issues in onychomycosis.
PubMed:A case of feline cryptococcosis treated with itraconazole.
PubMed:Effect of food intake on the bioavailability of itraconazole.
PubMed:Itraconazole plasma and tissue concentrations in the spiny lizard (Sceloporus sp.) following once-daily dosing.
PubMed:Update on the management of onychomycosis: highlights of the Third Annual International Summit on Cutaneous Antifungal Therapy.
PubMed:Diagnosis and treatment of tinea versicolor.
PubMed:Effect of food on the pharmacokinetics of a new hydroxypropyl-beta-cyclodextrin formulation of itraconazole.
PubMed:Post-antibiotic effect and post-expositional polyene antagonism of azole antifungal agents in Candida albicans: dependence on substance lipophilia.
PubMed:Plasma concentrations of triazolam are increased by concomitant ingestion of grapefruit juice.
PubMed:The systemic treatment of onychomycosis.
PubMed:Comparative pharmacokinetics of fluconazole and of itraconazole in Japanese and in German subjects.
PubMed:Costs of therapy for dermatophyte infections.
PubMed:The effects of itraconazole on the immune responses in ICR mice.
PubMed:Influence of concomitant food intake on the oral absorption of two triazole antifungal agents, itraconazole and fluconazole.
PubMed:Influence of concomitant food intake on the gastrointestinal absorption of fluconazole and itraconazole in Japanese subjects.
PubMed:Pharmacokinetic optimisation of oral antifungal therapy.
PubMed:A banner year for AIDS therapy.
PubMed:Food interaction and steady-state pharmacokinetics of itraconazole capsules in healthy male volunteers.
PubMed:Azoles and AIDS.
PubMed:Amphotericin-resistant aspergillus osteomyelitis controlled by itraconazole.
PubMed:The effects of food and dose on the oral systemic availability of itraconazole in healthy subjects.
PubMed:The influence of food on the pharmacokinetics of itraconazole in patients with superficial fungal infection.
PubMed:Studies in sporotrichosis: fungal morphogenesis and pathogenicity in differing environments.
 
Notes:
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