Itraconazole: Difference between revisions
imported>David E. Volk m (testing chem_infobox large IUPAC name) |
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{{Chem infobox | {{Chem infobox | ||
|align=right | |||
|image={{Image|Itraconazole structure.jpg|center|350px|Itraconazole, a triazole-based antifungal agent.}} | |||
|width=350px | |||
|molname=itraconazole | |molname=itraconazole | ||
|synonyms= itraconazol, itraconazolum | |synonyms= itraconazol, itraconazolum | ||
|molformula= C<sub>35</sub>H<sub>38</sub>C<sub>l2</sub>N<sub>8</sub>O<sub>4</sub> | |molformula= C<sub>35</sub>H<sub>38</sub>C<sub>l2</sub>N<sub>8</sub>O<sub>4</sub> | ||
|molmass= 705.6334 | |molmass= 705.6334 | ||
|uses=antifungal drug | |uses=antifungal drug | ||
|properties=triazole compound | |properties=triazole compound | ||
|hazards=see drug interactions | |hazards=see drug interactions | ||
|iupac= 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 | |iupac= <nowiki>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</nowiki> | ||
|casnumber= | |casnumber=84625-61-6 | ||
}} | }} | ||
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== Mechanism of action == | == Mechanism of action == | ||
Like other azole-based antifungal agents, itraconazole interacts with 14-<math>\alpha</math>-demethylase, a cytochrome P-450 enzyme necessary to convert [[lanosterol]] to [[ergosterol]], an essential component of fungal cell membranes, by stopping [[sterol]] C-14 <math>\alpha</math>-demethylation. 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<ref> {{ | Like other azole-based antifungal agents, itraconazole interacts with 14-<math>\alpha</math>-demethylase, a cytochrome P-450 enzyme necessary to convert [[lanosterol]] to [[ergosterol]], an essential component of fungal cell membranes, by stopping [[sterol]] C-14 <math>\alpha</math>-demethylation. 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<ref> {{CZMed|Itraconzole|DB01167}}</ref>. | ||
== Drug interactions == | == Drug interactions == | ||
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<b> This section is under construction, see [[ketoconazole]] for a partial list of drug interactions.</b> | <b> This section is under construction, see [[ketoconazole]] for a partial list of drug interactions.</b> | ||
== | == Chemical information == | ||
The IUPAC name for itraconazole is 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, and its chemical formula, C<sub>35</sub>H<sub>38</sub>C<sub>l2</sub>N<sub>8</sub>O<sub>4</sub>, gives a molecular mass of 705.6334 g/mol. | The IUPAC name for itraconazole is 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, and its chemical formula, C<sub>35</sub>H<sub>38</sub>C<sub>l2</sub>N<sub>8</sub>O<sub>4</sub>, gives a molecular mass of 705.6334 g/mol. | ||
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== References and external links == | == References and external links == | ||
<references/> | <references/> | ||
Latest revision as of 08:21, 8 June 2009
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| itraconazole | |||||||
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| Uses: | antifungal drug | ||||||
| Properties: | triazole compound | ||||||
| Hazards: | see drug interactions | ||||||
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Itraconazole is an azole-based antifungal drug containing three azoles, like fluconazole. It inhibits cytochrom P450-dependent enzymes and impairs the biosynthesis of ergosterol. It can be used to treate apergillosis, blasoplasmosis, cryptococcal meningitis, histoplasmosis and onychomycosis.
Mechanism of action
Like other azole-based antifungal agents, itraconazole interacts with 14--demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol, an essential component of fungal cell membranes, by stopping sterol C-14 -demethylation. 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[1].
Drug interactions
The azole-based antifungal agents have many drug interactions and some can be sever. This section is under construction, see ketoconazole for a partial list of drug interactions.
Chemical information
The IUPAC name for itraconazole is 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, and its chemical formula, C35H38Cl2N8O4, gives a molecular mass of 705.6334 g/mol.
Synonyms
- ITC
- ITCZ
- ITR
- Itraconazol
- Itraconazolum
- ITZ
Brand names
- Itrizole®
- Oriconazole®
- Sporal®
- Sporanos®
- Sporanox®
- Sporonox®
- Triasporn®
References and external links
- ↑ The most up-to-date information about Itraconzole and other drugs can be found at the following sites.
- Itraconzole - FDA approved drug information (drug label) from DailyMed (U.S. National Library of Medicine).
- Itraconzole - Drug information for consumers from MedlinePlus (U.S. National Library of Medicine).
- Itraconzole - Detailed information from DrugBank.