Grundinformationen
- Standard-SMILES
c1ccc(-c2ccc(C(c3ccccc3)n3ccnc3)cc2)cc1- InChIKey
OCAPBUJLXMYKEJ-UHFFFAOYSA-N- Summenformel
- C22H18N2
- Durchschnittliche Molmasse
- 310,4 g/mol
- Monoisotopische Masse
- 310,14699858
Namen und Bezeichner
- Bevorzugter Name
- Bifonazole
- IUPAC
- 1-[phenyl-(4-phenylphenyl)methyl]imidazole
- Lokaler Name
- Bifonazol
- Englischer Name
- Bifonazole
- Summenformel
- C22H18N2
- Molmasse
- 310.39
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
60628-96-8- PubChem CID
- 2378
- DTXSID
DTXSID9045631- ChEMBL
CHEMBL277535- ChEBI
CHEBI:78692- UNII
- QYJ305Z91O
- EC Number
- 262-336-6
- Nikkaji
- J17.988D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,8
- Polarare Oberfläche (TPSA)
- 17,8 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 362
Experimentelle und physikochemische Eigenschaften
LogP
4.77
4.77
Solubility
2.45e-03 g/L
0.7 [ug/mL] (The mean of the results at pH 7.4)
Collision Cross Section
184.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
171.48 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];177.23 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 142 ℃ · 142℃
- Siedepunkt
- 440.55 °C · 440.55°C (rough estimate)
- Dichte
- 1.115 · 1.1150 (rough estimate)
- Brechungsindex
- 1.762 · 1.7620 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- Soluble in DMSO
- Aggregatzustand
- powder
- pka
- 6.55 · 6.55±0.22(Predicted)
- Farbe
- white to off-white
- Merck
- 14 · 14,1213
- Kosmetik-Inhaltsstoffe Funktionen
- ANTI-SEBORRHEICANTIMICROBIAL
- InChI
- InChI=1S/C22H18N2/c1-3-7-18(8-4-1)19-11-13-21(14-12-19)22(24-16-15-23-17-24)20-9-5-2-6-10-20/h1-17,22H
- InChIKey
- OCAPBUJLXMYKEJ-UHFFFAOYSA-N
- SMILES
- C(C1C=CC=CC=1)(N1C=NC=C1)C1C=CC(C2C=CC=CC=2)=CC=1
- LogP
- 4.77 · 4.770
- CAS Datenbank
- 60628 · 60628-96-8(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 72 reports by companies from 4 notifications to the ECHA C&L Inventory.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Sicherheitsdaten
- wgk
- 1
- hs_code
- 29332900
- RTECS-Nr.
- NI3517000
- risk_code
- 22
- Toxizität
- LD50 in male mice, rats (mg/kg): 2629, 2854 orally (Schlüter)
- hazard_code
- Xn
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Pharmakologische Informationen
ATC Code
D01AC10
D - Dermatologicals;D01 - Antifungals for dermatological use;D01A - Antifungals for topical use;D01AC - Imidazole and triazole derivatives;D01AC10 - Bifonazole
QD - Dermatologicals;QD01 - Antifungals for dermatological use;QD01A - Antifungals for topical use;QD01AC - Imidazole and triazole derivatives;QD01AC10 - Bifonazole
Mechanism of Action
Bifonazole works by inhibiting the production of a substance called ergosterol, which is an essential component of fungal cell membranes.It acts to destabilize the fungal cyctochrome p450 51 enzyme (also known as Lanosterol 14-alpha demethylase). This is vital in the cell membrance structure of the fungus. Its inhibition leads to cell lysis. The disruption in production of ergosterol disrupts the cell membrane and causes holes to appear. The cell membranes of fungi are vital for their survival. They keep unwanted substances from entering the cells and stop the contents of the cells from leaking out. As bifonazole causes holes to appear in the cell membranes, essential constituents of the fungal cells can leak out. This kills the fungi.
Verwendung und Herstellung
Anwendungen
BeschreibungBifonazole represents the first topical broad spectrum antimycotic approved for once daily administration. Its in vitro activity appears equivalent to its structural relative clotrimazole, being effective against dermatophytes, other filamentous fungi, dimorphic fungi and yeasts.
VerwendenBifonazole is an imidazole antifungal agent and calmodulin antagonist. It causes a reduction in glycolysis and ATP levels in B16 melanoma cells. Bifonazole is an inhibitor of C14orf1. Bifonazole is an imidazole-based anti-fungal agent with broad spectrum activity against many fungi, molds, yeast and some gram-positive bacteria. Bifonazole inhibits ergosterol biosynthetic protein 28 and Cytochrome P450 2B4.
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