Itraconazole |
Last updated: 06/03/2024 |
(Also known as: oriconazole; itrizole; ITZ) |
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An orally administeredl veterinary triazole fungicide | |
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Current | |
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1984, invented | |
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Used to treat a range of fungal infections including those that affect the skin, claws, brain, respiratory tract, bone and other tissues, for example cryptococcosis (cats) and dermatophyte infections (dogs and cats). | |
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Dogs; Cats; Birds |
Approval status |
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Approved | |
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Approved |
Chemical structure |
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C₃₅H₃₈Cl₂N₈O₄ | |
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CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5COC(O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl | |
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CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OC[C@H]5CO[C@](O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl | |
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VHVPQPYKVGDNFY-ZPGVKDDISA-N | |
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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 | |
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Yes |
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Common Name | Relationship | Link |
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itraconazole | - |
General status |
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Antifungl, Fungicide | |
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Triazole fungicide | |
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Synthetic | |
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Broad spectrum, systemic, inhibits ergosterol synthesis of the fungal cell membrane by binding to cytochrome P450 3A4 CC-3. | |
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[Ergosterol, Binder] | |
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84625-61-6 | |
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55283 | |
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Antiinfectants for systemic use: Antimycotics for systemic use | |
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QJ02AC02 | |
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No | |
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705.64 | |
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2-butan-2-yl-4-[4-[4-[4-[[(2R,4S)-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 | |
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rel-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]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one | |
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Brown to yellow coloured powder |
Formulations |
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Catzol Oral Solution | Vetpharma Animal Health S.L. | GB National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | ||||||
Fugasol Oral Solution | CP Pharma Handelsgesellschadft mbH | GB National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | |||||||
Fungitraxx Oral Solution for Birds | Avimedical B.V. | GB National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | |||||||
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Usually formulated as an oral solution |
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0.0005 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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162 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
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4.57 X 1005 | Calculated | - | |||||||
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5.66 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
High | ||||||||
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Likely to be soluble | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Based on chemical group | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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3.7 | L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source |
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Degradation |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Soil adsorption and mobility |
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Fate indices |
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Known soil and groundwater metabolites |
None
Other known metabolites |
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hydroxy-itraconazole Note: Major liver metabolite |
OH-ITZ | Human (Liver) | - | ||||
keto-itraconazole | Keto-ITZ | - | - | ||||
N-desalkyl-itraconazole | ND-ITZ | - | - |
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Terrestrial ecotoxicology |
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> 320 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
Moderate | ||||||||
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Aquatic ecotoxicology |
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General |
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High (class III) | - | - | ||||||||
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> 320 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
Moderate | ||||||||
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Intravenous LD₅₀ = 40 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Extensively metabolised by the liver to a large number of metabolites, excreted mainly in the faeces | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
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Health issues |
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Possible blood, liver and adrenal gland toxicant May cause dermatitis, nausea, upset stomach, abdominal cramps, vomiting and diarrhoea |
Handling issues |
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No information available | |||
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Not listed (Not listed) | |||
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itraconazole | ||
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itraconazol | ||
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Record last updated: | 06/03/2024 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |