Ravuconazole
Grundinformationen
- CAS
182760-06-1- Standard-SMILES
C[C@@H](c1nc(-c2ccc(C#N)cc2)cs1)[C@](O)(Cn1cncn1)c1ccc(F)cc1F- InChIKey
OPAHEYNNJWPQPX-RCDICMHDSA-N- Summenformel
- C22H17F2N5OS
- Durchschnittliche Molmasse
- 437,5 g/mol
- Monoisotopische Masse
- 437,1121876
Überblick
Ravuconazole is a member of the class of triazoles that is 1-butyl-1H-1,2,4-triazole in which the butyl group is substituted at positions 2, 2, and 3 by hydroxy, 2,4-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively (the R,R stereoisomer). It exhibits antifungal activity by inhibition of 14alpha demethylase, an enzyme involved in sterol synthesis, resulting in lysis of the fungal cell wall and fungal cell death. (NCIO4). It has a role as an EC 1.14.14.154 (sterol 14alpha-demethylase) inhibitor, an antileishmanial agent, an ergosterol biosynthesis inhibitor and an antifungal drug. It is a nitrile, a tertiary alcohol, a member of fluorobenzenes, a member of triazoles and a member of 1,3-thiazoles.
Namen und Bezeichner
- Bevorzugter Name
- Ravuconazole
- IUPAC
- 4-[2-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile
- Englischer Name
- Ravuconazole
- Summenformel
- C22H17F2N5OS
- Molmasse
- 437.47
Namen und Synonyme
Ravuconazole182760-06-1ER-30346BMS-207147ER 30346BMS 20714795YH599JWVBenzonitrile, 4-[2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]-4-{2-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1h-1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl}benzonitrileCHEBI:143825DTXSID40171329p-(2-((alphaR,betaR)-2,4-Difluoro-beta-hydroxy-alpha-methyl-beta-(1H-1,2,4-triazol-1-ylmethyl)phenethyl)-4-thiazolyl)benzonitrile
Weitere Namen anzeigen
RczAids057176The healthBms-207,147Aids-057176RafconazoleLevaconazole
3-(4-(4-cyanophenyl)thiazol-2-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanolBenzonitrile, 4-(2-((1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl)-4-thiazolyl)-4-(2-((2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl)-1,3-thiazol-4-yl)benzonitrileRefChem:875184DTXCID7093820Ravuconazole [INN]ravuconazolravuconazolum
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,5
- Polarare Oberfläche (TPSA)
- 116 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 31
- Formalladung
- 0
- Komplexität
- 657
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
PesticidesFungicides
Physikochemische Eigenschaften
- Schmelzpunkt
- 64 · 64-66°C
- Siedepunkt
- 674.9 · 674.9±65.0 °C(Predicted)
- Dichte
- 1.38 · 1.38±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- Löslichkeit
- 25 mg/ml; · DMF: 25 mg/ml; DMF:PBS (pH 7.2) (1:4): 0.25 mg/ml; DMSO: 20 mg/ml; Ethanol: 5 mg/ml
- Aggregatzustand
- A crystalline solid
- pka
- 11.62 · 11.62±0.29(Predicted)
- Farbe
- Off-white to yellow
- InChI
- InChI=1S/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-7-6-17(23)8-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1
- InChIKey
- OPAHEYNNJWPQPX-RCDICMHDSA-N
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Sicherheitsdaten
- wgk
- WGK 3
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Verwendung und Herstellung
Use ClassificationFungicides
Anwendungen
BeschreibungRavuconazole is an orally available triazole fungicide that potently inhibits the growth of a wide range of fungi (MICs range from 25 to 780 ng/ml). Like other azoles, ravuconazole inhibits cytochrome P450 (CYP) isoforms that are involved in ergosterol biosynthesis, interfering with the generation of the fungal and protozoan cell membranes. Ravuconazole specifically inhibits sterol 14α-demethylase (CYP51). As this enzyme is also important in the development of trypanosomes, ravuconazole is effective against T. cruzi infections in animal models of Chagas disease.
VerwendenErgosterol biosynthesis inhibitor. Antifungal.
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