Basic information
- CAS
128326-82-9- Standard SMILES
Clc1cc(Cl)c2c(c1)CCc1ccccc1C2n1ccnc1- InChIKey
MPTJIDOGFUQSQH-UHFFFAOYSA-N- Molecular formula
- C18H14Cl2N2
- Average molar mass
- 329.2 g/mol
- Monoisotopic mass
- 328.0534038
Overview
1-(2,4-dichloro-10,11-dihydrodibenzo[a,d][7]annulen-5-yl)imidazole is a member of the class of dibenzannulenes that is 10,11-dihydrodibenzo[a,d][7]annulene carrying two chloro substituents at positions 2 and 4 as well as an imidazol-1-yl substituent at position 5. It is a member of imidazoles, a dibenzannulene and an organochlorine compound. It derives from a hydride of a dibenzo[a,d][7]annulene.
Names & identifiers
- Preferred name
- Eberconazole
- IUPAC
- 1-(4,6-dichloro-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl)imidazole
- English name
- Eberconazole
- Molecular formula
- C18H14Cl2N2
- Molecular weight
- 329.22
Names & synonyms
Eberconazole128326-82-9EberconazolEberconazolumV7O1U41C9BDTXSID909261041-(2,4-dichloro-10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-yl)-1H-imidazoleRefChem:920795CHEBI:82862D01AC17DTXCID6013549231-(4,6-dichlorotricyclo(9.4.0.0^(3,8))pentadeca-1(15),3,5,7,11,13-hexaen-2-yl)-1H-imidazole
Show more names
1H-Imidazole, 1-(2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-(+/-)-1-(2,4-Dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)imidazole
Eberconazole [INN]1-(4,6-dichloro-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl)imidazole1-(2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl)-1H-imidazoleEberconazole (INN)Eberconazol [INN-Spanish]Eberconazolum [INN-Latin]UNII-V7O1U41C9BWAS-2160
Database identifiers
- CAS
128326-82-9- PubChem CID
- 72051
- DTXSID
DTXSID90926104
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 17.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 391
Physicochemical properties
- Boiling point
- 495 · 495.0±45.0 °C(Predicted)
- Density
- 1.35 · 1.35±0.1 g/cm3(Predicted)
- pka
- 5.84 · 5.84±0.10(Predicted)
- FDA UNII
- 7 O1U41C9B · V7O1U41C9B
- ATC code
- 1 AC17 · D01AC17
Chemistry & industry
Pharmacology
ATC Code
D - Dermatologicals
QD - Dermatologicals
PharmacodynamicsEberconazole is active against Gram-positive bacteria, dermatophytes, and yeasts.
Mechanism of ActionEberconazole shares a mechanism of action with other antimycotic azoles: It inhibits lanosterol 14a-demethylase, thereby blocking the synthesis of precursors of ergosterols.
Applications
DescriptionEberconazole is a new member of the azole class of antifungal agents, and it is indicated for the topical treatment of cutaneous fungal infections, including tinea corporis (ringworm of the body), tinea cruris (ringworm of the groin) and tinea pedis (athlete’s foot) infections. Its mode of action is similar to that of other azole antifungals, namely inhibition of fungal lanosterol 14α-demethylase. Eberconazole exhibits good in vitro activity against a wide range of Candida species, including Candida. tropicalis, dermatophytes and Malassezia spp. yeasts. It shows good activity against Candida. Parapsilosis (MIC90=0.125 mg/mL), which is a relevant species in skin and nail disorders. In addition, eberconazole is effective against some of the highly triazole-resistant yeasts such as Candida. glabrata and Candida. krusei, as well as fluconazole-resistant Candida. albicans. However, eberconazole is less active than clotrimazole and ketoconazole against Candida. neoformans and a number of clinically relevant molds. Eberconazole is supplied as a 1% or 2% cream, and the topical application does not result in detectable serum, urine, or fecal levels. In a phase II study of 60 patients with tinea corporis and tinea cruris, treatment with topical eberconazole (1% or 2% cream), applied once or twice daily for 6 weeks, resulted in cure rates ranging from 73.3–93.3% at the end of therapy, and 66.7–100% six weeks post-therapy.
UsesEberconazole can be used for a novel antifungal formulation.
Suppliers9 total
Related reactions
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Compound notes
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