Structure via PubChem · Public domain (PubChem)
itraconazole
Sign in to saveAlso known as R-51211, ITCZ
Itraconazole, sometimes abbreviated ITZ, is an antifungal medication used to treat a number of fungal infections. This includes aspergillosis, blastomycosis, coccidioidomycosis, histoplasmosis, and paracoccidioidomycosis. It may be given by mouth or intravenously.
In the Vinony graph
Within Vinony's link graph, itraconazole is referenced by 499 other articles, and connects out to heart failure, antifungal and 1-phenylpiperazine.
It sits within the topics 1,2,4-Triazol-3-ones, Belgian inventions and Chloroarenes.
Its subject is documented across 36 Wikipedia language editions.
Chemical data
- Formula
- C35H38Cl2N8O4
- Molecular weight
- 705.6 g/mol
- IUPAC name
- 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
- SMILES
- 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
- InChIKey
- VHVPQPYKVGDNFY-ZPGVKDDISA-N
- XLogP
- 5.7
- Polar surface area
- 101 Ų
- H-bond donors
- 0
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Research
13,270 papers- SUBA-itraconazole in the treatment of systemic fungal infections.Future microbiology · 2024
- Itraconazole.Expert opinion on pharmacotherapy · 2000
- Repurposed itraconazole for use in the treatment of malignancies as a promising therapeutic strategy.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2022
- Pharmacology of itraconazole.Drugs · 2001
- Itraconazole: pharmacokinetics and indications.Archives of medical research · 1993
via PubMed
Wikidata facts
- Mass
- 704.239307
Show 5 more facts
- chemical formula
- C₃₅H₃₈Cl₂N₈O₄
- World Health Organisation international non-proprietary name
- itraconazole
- Commons category
- Itraconazole
- canonical SMILES
- 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
- isomeric SMILES
- 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
via Wikidata · CC0
~8 min read
Encyclopedic overview
11 sectionsContents
- Medical uses
- Available forms
- Side effects
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- References
- External links
Itraconazole, sometimes abbreviated ITZ, is an antifungal medication used to treat a number of fungal infections. This includes aspergillosis, blastomycosis, coccidioidomycosis, histoplasmosis, and paracoccidioidomycosis. It may be given by mouth or intravenously.
Common side effects include nausea, diarrhea, abdominal pain, rash, and headache. Severe side effects may include liver problems, heart failure, Stevens–Johnson syndrome and allergic reactions including anaphylaxis. It is unclear if use during pregnancy or breastfeeding is safe. It is in the triazole family of medications. It stops fungal growth by affecting the cell membrane or affecting their metabolism.
Excerpted from Wikipedia’s “itraconazole” article, available under the CC BY-SA 4.0 licence.