Voriconazole
3R)-2-(2 · VORICONAZOLE-D3 · (±)-Voriconazole · Voriconazole PI-6 · (2R,3R)-Voriconazole · Fluconazole Intermediate 2 · Voriconazole Intermediate II · Intermediate 2 of voriconazole
Identifikatoren & physikalische Daten
| CAS No. | 137234-62-9 |
|---|---|
| Summenformel | C16H14F3N5O |
| Durchschnittliche Molmasse | 349,31 g/mol |
| Monoisotopische Masse | 349,11504457 g/mol |
| SMILES | C[C@@H](c1ncncc1F)[C@](O)(Cn1cncn1)c1ccc(F)cc1F |
| InChIKey | BCEHBSKCWLPMDN-MGPLVRAMSA-N |
| PubChem CID | 71616 |
| ChEMBL | CHEMBL638 |
| ChEBI | CHEBI:10023 |
| EC No. | 629-701-5 |
| DTXSID | DTXSID201019420 |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 76,7 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 25 |
| Formalladung | 0 |
| Komplexität | 448 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use |
| Pestizide | Fungicides |
| LogP (Verteilungskoeffizient) | 11.7 |
| Löslichkeit | Low9.78e-02 g/L |
| Human Drugs | Breast FeedingLactationMilk, HumanAntifungal AgentsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Schmelzpunkt | 127 - 130 °C |
| Physical Description | Solid |
| Siedepunkt | 508.6±60.0 °C(Predicted) |
| Dichte | 1.42±0.1 g/cm3(Predicted) |
| Lagerbedingungen | Storage temp. 2-8°C |
| pKa (Säurekonstante) | 11.54±0.29(Predicted) |
| Aggregatzustand | Solid |
| Farbe | White to off-white |
| InChI | InChI=1/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/s3 |
| InChIKey | BCEHBSKCWLPMDN-NLBNCHMPNA-N |
| SMILES | C[C@@H]([C@@](CN1C=NC=N1)(C1C(F)=CC(F)=CC=1)O)C1C(F)=CN=CN=1 |&1:1,2,r| |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (99.2%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P260, P264, P270, P273, P280, P301+P316, P318, P319, P321, P330, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 118 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Hazard Traits - Carcinogenicity |
| Hazard Classes and Categories | Acute Tox. 3 (99.2%) |
| Hepatotoxicity | Transient elevations in serum aminotransferase levels occur in 11% to 19% of patients on voriconazole. These elevations are usually asymptomatic and self-limited, but approximately 1% of patients require discontinuation of voriconazole because of ALT elevations. Clinically apparent hepatotoxicity is uncommon, but may be more frequent than with fluconazole and itraconazole. The injury arises within the first month of therapy and the pattern of serum enzyme elevations has been variable from cholestatic to hepatocellular. Several cases of acute liver failure attributed to voriconazole have been reported. Immunoallergic features and autoantibodies are uncommon. Recovery upon stopping therapy generally takes 6 to 10 weeks but, in some cases, the time to complete resolution may be prolonged. |
| Carcinogen Classification | VoriconazoleGroup 1: Carcinogenic to humansVolume 137: (2026) Hydrochlorothiazide, Voriconazole, and Tacrolimus2026 online2024 |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)VoriconazolevMost-DILI-concern8Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Alarmwort | Warnung |
| Gefahrenhinweise | Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302 |
Anwendungen & Verwendung
Beschreibung
Voriconazole-d3 is an Ergosterol biosynthesis inhibitor and a labeled form of Voriconazole. This mono triazole antifungal agent inhibits the growth of Candida, Cryptococcus, and Aspergillus species. Studies suggest that Voriconazole-d3 can be synthesized by modifying the structure of fluconazole. This antifungal agent functions by inhibiting cytochrome P450 dependent 14-α-sterol demethylase, which is responsible for the biosynthesis of Ergosterol. Furthermore, Voriconazole-d3 inhibits fungal growth, cell wall thinning, and cell membrane degradation.
Verwenden
Voriconazole is a triazole antifungal agent used primarily in the treatment or prevention of aspergillosis and candidal infections. However, its therapy may cause transient, asymptomatic serum aminotransferase elevations, and it is also a well-known cause of acute drug-induced liver injury.