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.
OverviewAI-generated
Itraconazole is a chemical compound with the formula C₃₅H₃₈Cl₂N₈O₄. Its molecular mass is listed as 704.239307, while its weight is recorded as 705.6. The substance has a charge of 0 and an xlogp value of 5.7.
In terms of molecular structure, itraconazole features 9 hydrogen bond acceptors and 0 hydrogen bond donors. The topological polar surface area is 101. The compound is referenced by 499 other encyclopedia articles.
Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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
- Subclass of
- azole
- Mass
- 704.239307
Show 8 more facts
- chemical formula
- C₃₅H₃₈Cl₂N₈O₄
- medical condition treated
- onychomycosis
- 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
- significant drug interaction
- tacrolimus
- legal status (medicine)
- boxed warning
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.