Itraconazole
Identification
- Summary
Itraconazole is an antifungal agent used for the treatment of various fungal infections in immunocompromised and non-immunocompromised patients, such as pulmonary and extrapulmonary blastomycosis, histoplasmosis, and onychomycosis.
- Brand Names
- Sporanox, Tolsura
- Generic Name
- Itraconazole
- DrugBank Accession Number
- DB01167
- Background
One of the triazole antifungal agents that inhibits cytochrome P-450-dependent enzymes resulting in impairment of ergosterol synthesis. It has been used against histoplasmosis, blastomycosis, cryptococcal meningitis & aspergillosis.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Itraconazole (DB01167)
- Weight
- Average: 705.633
Monoisotopic: 704.239307158 - Chemical Formula
- C35H38Cl2N8O4
- Synonyms
- Itraconazol
- Itraconazole
- Itraconazolum
- Oriconazole
- External IDs
- R 51,211
- R-51211
- R51211
Pharmacology
- Indication
For the treatment of the following fungal infections in immunocompromised and non-immunocompromised patients: pulmonary and extrapulmonary blastomycosis, histoplasmosis, aspergillosis, and onychomycosis.
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Associated Conditions
- Aspergillosis
- Blastomycosis
- Chromomycosis
- Coccidioidal meningitis
- Dermatomycoses
- Esophageal Candidiasis
- Histoplasmosis
- Infections, Fungal
- Onychomycosis
- Oropharyngeal Candidiasis
- Paracoccidioidomycosis
- Penicillium marneffei infection
- Pulmonary coccidioides
- Sporotrichosis
- Vulvovaginal Candidiasis
- Disseminated Other specified protozoal diseases
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Itraconazole is an imidazole/triazole type antifungal agent. Itraconazole is a highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethylation via the inhibition of the enzyme cytochrome P450 14α-demethylase. This enzyme converts lanosterol to ergosterol, and is required in fungal cell wall synthesis. The subsequent loss of normal sterols correlates with the accumulation of 14 α-methyl sterols in fungi and may be partly responsible for the fungistatic activity of fluconazole. Mammalian cell demethylation is much less sensitive to fluconazole inhibition. Itraconazole exhibits in vitro activity against Cryptococcus neoformans and Candida spp. Fungistatic activity has also been demonstrated in normal and immunocompromised animal models for systemic and intracranial fungal infections due to Cryptococcus neoformans and for systemic infections due to Candida albicans.
- Mechanism of action
Itraconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Itraconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
Target Actions Organism ALanosterol 14-alpha demethylase inhibitorHumans ALanosterol 14-alpha demethylase inhibitor- Absorption
The absolute oral bioavailability of itraconazole is 55%, and is maximal when taken with a full meal.
- Volume of distribution
- 796 ± 185 L
- Protein binding
99.8%
- Metabolism
Itraconazole is extensively metabolized by the liver into a large number of metabolites, including hydroxyitraconazole, the major metabolite. The main metabolic pathways are oxidative scission of the dioxolane ring, aliphatic oxidation at the 1-methylpropyl substituent, N-dealkylation of this 1-methylpropyl substituent, oxidative degradation of the piperazine ring and triazolone scission.
Hover over products below to view reaction partners
- Route of elimination
Itraconazole is metabolized predominately by the cytochrome P450 3A4 isoenzyme system (CYP3A4) in the liver, resulting in the formation of several metabolites, including hydroxyitraconazole, the major metabolite. Fecal excretion of the parent drug varies between 3-18% of the dose. Renal excretion of the parent drug is less than 0.03% of the dose. About 40% of the dose is excreted as inactive metabolites in the urine. No single excreted metabolite represents more than 5% of a dose.
- Half-life
21 hours
- Clearance
- 381 +/- 95 mL/minute [IV administration]
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
No significant lethality was observed when itraconazole was administered orally to mice and rats at dosage levels of 320 mg/kg or to dogs at 200 mg/kg.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Itraconazole can be increased when it is combined with Abametapir. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Itraconazole. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Itraconazole. Aceclofenac The risk or severity of hyperkalemia can be increased when Itraconazole is combined with Aceclofenac. Acemetacin The risk or severity of hyperkalemia can be increased when Itraconazole is combined with Acemetacin. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Itraconazole. Acetaminophen Itraconazole may increase the hepatotoxic activities of Acetaminophen. Acetyldigitoxin The serum concentration of Acetyldigitoxin can be increased when it is combined with Itraconazole. Acetylsalicylic acid The risk or severity of hyperkalemia can be increased when Acetylsalicylic acid is combined with Itraconazole. Acrivastine The risk or severity of QTc prolongation can be increased when Itraconazole is combined with Acrivastine. 
Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- Avoid grapefruit products.
- Avoid multivalent ions. Calcium, iron, and aluminum containing products taken up to 2 hours before and 6 hours after administration can decrease drug concentrations.
- Take with food.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Images
- International/Other Brands
- Itrizole / Oriconazole / Sporal
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Itraconazole Capsule 100 mg/1 Oral Patriot Pharmaceuticals 2005-02-01 Not applicable US 
Itraconazole Solution 10 mg/1mL Oral Patriot Pharmaceuticals, LLC 1997-02-21 Not applicable US Itraconazole Capsule 100 mg/1 Oral Carilion Materials Management 2005-02-01 Not applicable US 
Onmel Tablet 200 mg/1 Oral Stiefel Laboratories, Inc. 2011-12-01 2013-01-25 US Onmel Tablet 200 mg/1 Oral Merz Pharmaceuticals, LLC 2012-11-01 2020-11-30 US Sporanox Capsule 100 mg/1 Oral bryant ranch prepack 1992-09-11 2017-12-31 US Sporanox Capsule 100 mg/1 Oral Physicians Total Care, Inc. 2004-07-19 2005-10-31 US Sporanox Capsule 100 mg/1 Oral Janssen Pharmaceuticals, Inc. 1992-09-11 Not applicable US Sporanox Capsule 100 mg Oral Janssen Pharmaceuticals 1993-12-31 Not applicable Canada 
Sporanox Capsule 100 mg/1 Oral Physicians Total Care, Inc. 1996-01-22 2011-06-30 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Itraconazole Capsule 100 mg/1 Oral Torrent Pharmaceuticals Limited 2018-08-24 Not applicable US Itraconazole Solution 10 mg/1mL Oral Amneal Pharmaceuticals LLC 2014-04-30 Not applicable US Itraconazole Capsule, coated pellets 100 mg/1 Oral REMEDYREPACK INC. 2020-09-09 Not applicable US Itraconazole Capsule, coated pellets 100 mg/1 Oral Ascend Laboratories, LLC 2017-06-12 Not applicable US Itraconazole Capsule 100 mg/1 Oral Mylan Pharmaceuticals Inc. 2012-07-26 Not applicable US Itraconazole Capsule 100 mg/1 Oral Amneal Pharmaceuticals LLC 2016-09-27 Not applicable US Itraconazole Capsule 100 mg/1 Oral Par Pharmaceutical, Inc. 2016-07-01 Not applicable US Itraconazole Capsule, coated pellets 100 mg/1 Oral bryant ranch prepack 2017-06-12 Not applicable US Itraconazole Capsule 100 mg/1 Oral Eon Labs, Inc. 2004-05-28 2017-04-30 US 
Itraconazole Capsule 100 mg/1 Oral Zydus Pharmaceuticals (USA) Inc. 2018-03-06 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ราเสท Capsule 100 mg Oral บริษัท ยูนีซัน จำกัด 2007-02-13 Not applicable Thailand 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ALBISEC® Itraconazole (154.66 mg) + Secnidazole (166.66 mg) Capsule, coated Oral 2006-11-10 2013-06-13 Colombia 
BIOPROX® TABLETA RECUBIERTA Itraconazole (133.33 mg) + Secnidazole (666.667 mg) Tablet, coated Oral BIOCHEM FARMACEUTICA DE COLOMBIAS.A. 2018-03-22 Not applicable Colombia ITRACONAZOL 33.3 MG + SECNIDAZOL 166.66 MG CÁPSULA Itraconazole (33.33 mg) + Secnidazole (166.66 mg) Capsule, coated Oral 2016-08-10 Not applicable Colombia Sporanox Itraconazole (10 mg/1mL) + Sodium chloride (900 mg/100mL) Kit Intravenous Ortho-McNeil-Janssen Pharmaceuticals, Inc. 1999-03-30 2008-12-31 US SPORASEC ® CAPSULAS Itraconazole (33.33 mg) + Secnidazole (166.66 mg) Capsule, coated Oral JANSSEN CILAG S.A. 2006-11-10 2021-07-01 Colombia - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ciclopirox 3% / Itraconazole 5% / Urea 20% Itraconazole (5 g/100g) + Ciclopirox olamine (3 g/100g) + Urea (20 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-20 Not applicable US Fluconazole 4% / Ibuprofen 2% / Itraconazole 1% / Terbinafine HCl 4% Itraconazole (1 g/100g) + Fluconazole (4 g/100g) + Ibuprofen (2 g/100g) + Terbinafine (4 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-01 Not applicable US
Categories
- ATC Codes
- J02AC02 — Itraconazole
- Drug Categories
- 14-alpha Demethylase Inhibitors
- Agents causing hyperkalemia
- Anti-Infective Agents
- Antifungal Agents
- Antiinfectives for Systemic Use
- Antimycotics for Systemic Use
- Azole Antifungals
- BCRP/ABCG2 Inhibitors
- Chemically-Induced Disorders
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strong)
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (weak)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strong)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strong)
- Cytochrome P-450 CYP3A7 Inhibitors
- Cytochrome P-450 CYP3A7 Inhibitors (strong)
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Enzyme Inhibitors
- Hormone Antagonists
- Hormones, Hormone Substitutes, and Hormone Antagonists
- P-glycoprotein inhibitors
- Photosensitizing Agents
- Piperazines
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Steroid Synthesis Inhibitors
- Triazole Derivatives
- Triazoles
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazinanes
- Sub Class
- Piperazines
- Direct Parent
- Phenylpiperazines
- Alternative Parents
- N-arylpiperazines / Phenyl-1,2,4-triazoles / Aminophenyl ethers / Phenoxy compounds / Aniline and substituted anilines / Dichlorobenzenes / Dialkylarylamines / Alkyl aryl ethers / Ketals / Aryl chlorides show 8 more
- Substituents
- 1,2,4-triazole / 1,3-dichlorobenzene / Acetal / Alkyl aryl ether / Amine / Aminophenyl ether / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide show 30 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- N-arylpiperazine, triazole antifungal drug, conazole antifungal drug, dioxolane, dichlorobenzene, triazoles, cyclic ketal (CHEBI:6076)
- Affected organisms
- Fungi, yeast and protozoans
Chemical Identifiers
- UNII
- 304NUG5GF4
- CAS number
- 84625-61-6
- InChI Key
- VHVPQPYKVGDNFY-ZPGVKDDISA-N
- 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
- IUPAC Name
- 1-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one
- SMILES
- CCC(C)N1N=CN(C1=O)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1
References
- Synthesis Reference
Jong-Soo Woo, Hong-Gi Yi, "Antifungal oral composition containing itraconazole and process for preparing same." U.S. Patent US6039981, issued May, 1998.
US6039981- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015298
- KEGG Drug
- D00350
- PubChem Compound
- 55283
- PubChem Substance
- 46505954
- ChemSpider
- 49927
- BindingDB
- 50127138
- 28031
- ChEBI
- 6076
- ChEMBL
- CHEMBL22587
- Therapeutic Targets Database
- DAP000631
- PharmGKB
- PA450132
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Itraconazole
- AHFS Codes
- 08:14.08 — Azoles
- FDA label
- Download (1.58 MB)
- MSDS
- Download (73.6 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Basic Science Pharmacodynamics / Pharmacokinetics 1 4 Completed Other Neutropenia 1 4 Completed Prevention Cystic Fibrosis (CF) 1 4 Completed Prevention Invasive Fungal Infections 1 4 Completed Prevention Mycoses / Neoplasms, Brain / Neuroblastomas / Retinoblastoma / Wilms' tumor 1 4 Completed Treatment Chronic Cavitary Pulmonary Aspergillosis 1 4 Completed Treatment Onychomycosis, Toe 1 4 Completed Treatment Pulmonary Fungal Infection 1 4 Recruiting Basic Science Infections, Fungal 1 4 Terminated Prevention Graft Versus Host Disease (GVHD) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Advanced Pharmaceutical Services Inc.
- AQ Pharmaceuticals Inc.
- Centocor Ortho Biotech Inc.
- Eon Labs
- Hospira Inc.
- Janssen-Ortho Inc.
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Patriot Pharmaceuticals
- Physicians Total Care Inc.
- Resource Optimization and Innovation LLC
- Dosage Forms
Form Route Strength Capsule, coated Oral Tablet, coated Oral Cream Topical Capsule, coated Oral 100 mg Solution Topical Solution Oral 1 g Capsule Oral 100 mg Capsule Oral Capsule, coated pellets Oral 100 mg/1 Solution Oral 10 mg/1mL Capsule Oral 50 MG Capsule, coated Oral 50 mg Capsule, coated pellets Oral Tablet Oral 100 mg Tablet Oral 200 mg/1 Capsule, coated Oral 200 mg Solution Oral 50 mg/5ml Capsule Oral 100 mg/1 Injection, solution, concentrate Parenteral Kit Intravenous Solution Oral Solution Oral 10 mg / mL Solution Intravenous 10 mg Capsule, coated pellets Oral 100 mg Capsule, gelatin coated Oral 65 mg/1 - Prices
Unit description Cost Unit Itraconazole 28 100 mg capsule Disp Pack 270.89USD disp Itraconazole powder 32.13USD g Sporanox 100 mg capsule 12.14USD capsule Itraconazole 100 mg capsule 9.46USD capsule Sporanox 10 mg/ml Solution 1.41USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5633015 No 1997-05-27 2014-05-27 US CA2142848 No 1999-11-16 2013-08-27 Canada CA1336498 No 1995-08-01 2012-08-01 Canada US6407079 No 2002-06-18 2019-06-18 US US6509038 No 2003-01-21 2017-05-12 US US7081255 No 2006-07-25 2017-05-12 US US8486456 No 2013-07-16 2028-10-03 US US8591948 No 2013-11-26 2017-05-12 US US9713642 No 2017-07-25 2033-06-21 US US8771739 No 2014-07-08 2023-07-25 US US8921374 No 2014-12-30 2033-06-21 US US9272046 No 2016-03-01 2033-06-21 US US10463740 No 2019-11-05 2033-06-21 US US10806792 No 2013-06-21 2033-06-21 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 166.2 °C Not Available water solubility Insoluble Not Available logP 5.66 HTTP://WWW.RXLIST.COM pKa 3.70 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00964 mg/mL ALOGPS logP 5.48 ALOGPS logP 7.31 ChemAxon logS -4.9 ALOGPS pKa (Strongest Basic) 3.91 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 100.79 Å2 ChemAxon Rotatable Bond Count 11 ChemAxon Refractivity 200.4 m3·mol-1 ChemAxon Polarizability 74.71 Å3 ChemAxon Number of Rings 7 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9973 Blood Brain Barrier - 0.6151 Caco-2 permeable + 0.5511 P-glycoprotein substrate Substrate 0.6397 P-glycoprotein inhibitor I Inhibitor 0.7973 P-glycoprotein inhibitor II Non-inhibitor 0.88 Renal organic cation transporter Non-inhibitor 0.7497 CYP450 2C9 substrate Non-substrate 0.8116 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.7408 CYP450 1A2 substrate Non-inhibitor 0.7666 CYP450 2C9 inhibitor Inhibitor 0.618 CYP450 2D6 inhibitor Non-inhibitor 0.8622 CYP450 2C19 inhibitor Inhibitor 0.5703 CYP450 3A4 inhibitor Inhibitor 0.5279 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8219 Ames test AMES toxic 0.5303 Carcinogenicity Non-carcinogens 0.7478 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 3.3118 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5782 hERG inhibition (predictor II) Inhibitor 0.6096
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0udi-0329000000-18fc35342fd0b509b439 MS/MS Spectrum - , positive LC-MS/MS splash10-0a4i-0112100900-c45b863fbc00a8c449b4
Targets
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with our fully connected ADMET & drug target dataset.
Accelerate your drug discovery research with our ADMET & drug target dataset
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Sterol 14-demethylase activity
- Specific Function
- Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
- Gene Name
- CYP51A1
- Uniprot ID
- Q16850
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 56805.26 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Cotrim PC, Garrity LK, Beverley SM: Isolation of genes mediating resistance to inhibitors of nucleoside and ergosterol metabolism in Leishmania by overexpression/selection. J Biol Chem. 1999 Dec 31;274(53):37723-30. [Article]
- Carrillo-Munoz AJ, Giusiano G, Ezkurra PA, Quindos G: Antifungal agents: mode of action in yeast cells. Rev Esp Quimioter. 2006 Jun;19(2):130-9. [Article]
- Kind
- Protein
- Organism
- Not Available
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Sterol 14-demethylase activity
- Specific Function
- Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol (By similarity).
- Gene Name
- ERG11
- Uniprot ID
- P50859
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 61304.95 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Gachotte D, Pierson CA, Lees ND, Barbuch R, Koegel C, Bard M: A yeast sterol auxotroph (erg25) is rescued by addition of azole antifungals and reduced levels of heme. Proc Natl Acad Sci U S A. 1997 Oct 14;94(21):11173-8. [Article]
- Henry KW, Nickels JT, Edlind TD: Upregulation of ERG genes in Candida species by azoles and other sterol biosynthesis inhibitors. Antimicrob Agents Chemother. 2000 Oct;44(10):2693-700. [Article]
- Morales IJ, Vohra PK, Puri V, Kottom TJ, Limper AH, Thomas CF Jr: Characterization of a lanosterol 14 alpha-demethylase from Pneumocystis carinii. Am J Respir Cell Mol Biol. 2003 Aug;29(2):232-8. Epub 2003 Feb 26. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [Article]
- Sakaeda T, Iwaki K, Kakumoto M, Nishikawa M, Niwa T, Jin JS, Nakamura T, Nishiguchi K, Okamura N, Okumura K: Effect of micafungin on cytochrome P450 3A4 and multidrug resistance protein 1 activities, and its comparison with azole antifungal drugs. J Pharm Pharmacol. 2005 Jun;57(6):759-64. [Article]
- Dresser GK, Spence JD, Bailey DG: Pharmacokinetic-pharmacodynamic consequences and clinical relevance of cytochrome P450 3A4 inhibition. Clin Pharmacokinet. 2000 Jan;38(1):41-57. [Article]
- Flockhart Table of Drug Interactions [Link]
- Link [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Korashy HM, Shayeganpour A, Brocks DR, El-Kadi AO: Induction of cytochrome P450 1A1 by ketoconazole and itraconazole but not fluconazole in murine and human hepatoma cell lines. Toxicol Sci. 2007 May;97(1):32-43. Epub 2007 Feb 5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Tassaneeyakul W, Birkett DJ, Miners JO: Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents. Xenobiotica. 1998 Mar;28(3):293-301. doi: 10.1080/004982598239579 . [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [Article]
- Wang EJ, Lew K, Casciano CN, Clement RP, Johnson WW: Interaction of common azole antifungals with P glycoprotein. Antimicrob Agents Chemother. 2002 Jan;46(1):160-5. [Article]
- Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [Article]
- Takara K, Tanigawara Y, Komada F, Nishiguchi K, Sakaeda T, Okumura K: Cellular pharmacokinetic aspects of reversal effect of itraconazole on P-glycoprotein-mediated resistance of anticancer drugs. Biol Pharm Bull. 1999 Dec;22(12):1355-9. [Article]
- Masuda S, Inui K: [Molecular mechanisms on drug transporters in the drug absorption and disposition]. Nihon Rinsho. 2002 Jan;60(1):65-73. [Article]
- Lilja JJ, Backman JT, Laitila J, Luurila H, Neuvonen PJ: Itraconazole increases but grapefruit juice greatly decreases plasma concentrations of celiprolol. Clin Pharmacol Ther. 2003 Mar;73(3):192-8. [Article]
- Sakaeda T, Iwaki K, Kakumoto M, Nishikawa M, Niwa T, Jin JS, Nakamura T, Nishiguchi K, Okamura N, Okumura K: Effect of micafungin on cytochrome P450 3A4 and multidrug resistance protein 1 activities, and its comparison with azole antifungal drugs. J Pharm Pharmacol. 2005 Jun;57(6):759-64. [Article]
- Saito M, Hirata-Koizumi M, Miyake S, Hasegawa R: Comparison of information on the pharmacokinetic interactions of Ca antagonists in the package inserts from three countries (Japan, USA and UK). Eur J Clin Pharmacol. 2005 Aug;61(7):531-6. Epub 2005 Jul 23. [Article]
- Shon JH, Yoon YR, Hong WS, Nguyen PM, Lee SS, Choi YG, Cha IJ, Shin JG: Effect of itraconazole on the pharmacokinetics and pharmacodynamics of fexofenadine in relation to the MDR1 genetic polymorphism. Clin Pharmacol Ther. 2005 Aug;78(2):191-201. [Article]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76709.98 Da
References
- Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]
Drug created on June 13, 2005 13:24 / Updated on June 17, 2021 15:27