Voriconazole

HCID 71616

Grundinformationen

CAS
137234-62-9
Standard-SMILES
C[C@@H](c1ncncc1F)[C@](O)(Cn1cncn1)c1ccc(F)cc1F
InChIKey
BCEHBSKCWLPMDN-MGPLVRAMSA-N
Summenformel
C16H14F3N5O
Durchschnittliche Molmasse
349,31 g/mol
Monoisotopische Masse
349,11504457

Überblick

Voriconazole is a triazole-based antifungal agent used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp. It is an inhibitor of cytochrome P450 2C9 (CYP2C9) and CYP3A4. It has a role as a P450 inhibitor. It is a tertiary alcohol, a difluorobenzene, a member of pyrimidines, a conazole antifungal drug and a triazole antifungal drug.

Namen und Bezeichner

Bevorzugter Name
Voriconazole
IUPAC
(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol
Englischer Name
Voriconazole-d3
Summenformel
C16H14F3N5O
Molmasse
349.31

Namen und Synonyme

Voriconazole137234-62-9Vfend(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-olUK-109496Voriconazol(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-olVoriconazolumUK-109,496UK 109496JFU09I87TRNSC-759888
Weitere Namen anzeigen
3R)-2-(2VORICONAZOLE-D3(±)-VoriconazoleVoriconazole PI-6(2R,3R)-VoriconazoleFluconazole Intermediate 2Voriconazole Intermediate IIIntermediate 2 of voriconazole4-triazol-1-yl)-2-butanol (RaceMic Voriconazole)4-Difluorophenyl)-3-(5-fluoro-4-pyriMidinyl)-1-(1H-1
DTXSID5046485(R-(R*,S*))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanolCHEBI:10023(alphaR,betaS)-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanolDTXCID3026485UK109496RefChem:56222UK109,496

Datenbank-Bezeichner

CAS
137234-62-9、188416-29-7
PubChem CID
71616
DTXSID
DTXSID201019420
ChEMBL
CHEMBL638
ChEBI
CHEBI:10023
UNII
JFU09I87TR、USG4B1CD29
EC Number
629-701-5、941-833-8
Nikkaji
J709.476K

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,5
Polarare Oberfläche (TPSA)
76,7 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
5
Schwere Atome
25

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use

PesticidesFungicides
LogP · 2 Einträge

1

1.7

Solubility · 2 Einträge

Low

9.78e-02 g/L

Human Drugs · 6 Einträge

Breast Feeding; Lactation; Milk, Human; Antifungal Agents

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Melting Point127 - 130 °C

Physikochemische Eigenschaften

Siedepunkt
508.6 · 508.6±60.0 °C(Predicted)
Dichte
1.42 · 1.42±0.1 g/cm3(Predicted)
storage temp.
2 · Storage temp. 2-8°C
pka
11.54 · 11.54±0.29(Predicted)
Aggregatzustand
Solid
Farbe
White to off-white

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (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.

Gefahrenhinweise

Regulatory InformationHazard Traits - Carcinogenicity
Hazard Classes and CategoriesAcute Tox. 3 (99.2%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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 · 5 Einträge

Voriconazole

Group 1: Carcinogenic to humans

Volume 137: (2026) Hydrochlorothiazide, Voriconazole, and Tacrolimus

2026 online

2024

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Voriconazole

vMost-DILI-concern

8

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 4 Einträge

J02AC03

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

J02AC03

Protein BindingVoriconazole is 58% bound to plasma proteins.
PharmacodynamicsVoriconazole is a fungistatic triazole antifungal used to treat infections by inhibiting fungal growth. It is known to cause hepatotoxic and photosensitivity reactions in some patients.
Mechanism of Action · 1 Eintrag

Voriconazole is used to treat fungal infections caused by a variety of organisms but including _Aspergillus spp._ and _Candida spp_. Voriconazole is a triazole antifungal exhibiting fungistatic activity against fungal pathogens. Like other triazoles, voriconazole binds to 14-alpha sterol demethylase, also known as CYP51, and inhibits the demethylation of lanosterol as part of the ergosterol synthesis pathway in yeast and other fungi. The lack of sufficient ergosterol disrupts fungal cell membrane function and limits fungal cell growth. With fungal growth limited, the host's immune system is able to clear the invading organism.

Biological Half-LifeVoriconazole follows non-linear kinetics and has a terminal half-life of elimination which is dose-dependent.
Metabolism/Metabolites · 2 Einträge

Voriconazole undergoes extensive hepatic metabolism through cytochrome enzymes CYP2C9, CYP2C19, and CYP3A4. CYP2C19 mediates N-oxidation with an apparent Km of 14 μM and an apparent Vmax of 0.22 nmol/min/nmol CYP2C19. Voriconazole N-oxide is the major circulating metabolite, accounting for 72% of radiolabeled metabolites found. CYP3A4 contributes to N-oxidation with a Km of 16 μM and Vmax of 0.05 nmol/min/nmol CYP3A4 as well as 4-hydroxylation with a Km of 11 μM and a Vmax of 0.10 nmol/min/nmol CYP3A4. CYP3A5 and CYP3A7 provide minor contributions to N-oxidation and 4-hydroxylation. The N-oxide and 4-hydroxylated metabolites undergo glucuronidation and are excreted through the urine with other minor glucuronidated metabolites.

Voriconazole has known human metabolites that include Voriconazole N-Oxide and Hydroxymethyl Voriconazole.

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >100
Use ClassificationFungicides
Anwendungen · 2 Einträge

BeschreibungVoriconazole-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.

VerwendenVoriconazole 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.

Anbieter67 Anbieter

郑州阿尔法化工有限公司+86-18530059196 · [email protected]
湖北威德利化学试剂有限公司181-6332-1995 18062128043 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]

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