Basic information
- CAS
2049588-24-9- Standard SMILES
CCC(C)n1ncn(-c2ccc(N3CCN(c4ccc(OCC5COC(Cn6cncn6)(c6ccc(Cl)cc6Cl)O5)cc4)CC3)cc2)c1=O- InChIKey
VHVPQPYKVGDNFY-UHFFFAOYSA-N- Molecular formula
- C35H38Cl2N8O4
- Average molar mass
- 705.6 g/mol
- Monoisotopic mass
- 704.2393071
Overview
2-butan-2-yl-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-1,2,4-triazol-3-one is a member of piperazines.
Names & identifiers
- Preferred name
- Itrizole
- IUPAC
- 2-butan-2-yl-4-[4-[4-[4-[[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
Names & synonyms
Itrizole2-butan-2-yl-4-[4-[4-[4-[[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-one2-butan-2-yl-4-(4-(4-(4-((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-oneRefChem:10483192049588-24-91-(Butan-2-yl)-4-{4-[4-(4-{[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-oneItraconazolum [Latin]MLS000863291Oriconazole, R51211, SporanoxC35H38Cl2N8O4MFCD008701681217512-35-0
Show more names
SMR0000589594-(4-(4-(4-((2-((1H-1,2,4-triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-(sec-butyl)-1H-1,2,4-triazol-5(4H)-oneItraconazole D3ITRAZOLE2-butan-2-yl-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-1,2,4-triazol-3-one4-(4-(4-(4-((2-((1H-1,2,4-Triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-(sec-butyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneItraconazole (Sporanox)SR-01000003153
Properties
Computed structural properties
- XLogP
- 5.7
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 11
- Heavy atoms
- 49
- Formal charge
- 0
- Complexity
- 1,120
Experimental & physicochemical properties
DrugsPharmaceuticals
Human DrugsBreast Feeding; Lactation; Milk, Human; Antifungal Agents
Collision Cross Section
248.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
254.29 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Exposure RoutesThe absolute oral bioavailability of itraconazole is 55%, and is maximal when taken with a full meal.
Toxicity Summary
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.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataNo 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.
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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. 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
Uses & manufacturing
UsesFor the treatment of the following fungal infections in immunocompromised and non-immunocompromised patients: pulmonary and extrapulmonary blastomycosis, histoplasmosis, aspergillosis, and onychomycosis.
Related reactions
0 records
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Compound notes
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