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miconazole   Click here for help

GtoPdb Ligand ID: 2449

Synonyms: florid(nitrate) | Monistat® | R-14889
Approved drug
miconazole is an approved drug (FDA (1974))
Compound class: Synthetic organic
Comment: The approved drug miconazole is a racemic mixture of two enantiomers. The structure shown here does not specify stereochemistry and represents the mixture.
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View more information in the IUPHAR Pharmacology Education Project: miconazole

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 27.05
Molecular weight 413.99
XLogP 6.09
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES Clc1ccc(c(c1)Cl)COC(c1ccc(cc1Cl)Cl)Cn1cncc1
Isomeric SMILES Clc1ccc(c(c1)Cl)COC(c1ccc(cc1Cl)Cl)Cn1cncc1
InChI InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2
InChI Key BYBLEWFAAKGYCD-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Bioactivity Comments
Binds to and inhibits human CYP8B1 [2].
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPM2 Hs Channel blocker Antagonist - - 1x10-5 3
Conc range: 1x10-5 M [3]
Voltage: -60.0 mV
TRPV5 Hs Channel blocker - - - -
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CYP8B1 Hs Inhibitor Inhibition 7.0 pKd - 2
pKd 7.0 (Kd 9.8x10-8 M) [2]
CYP8B1 Hs Inhibitor Inhibition 6.3 pIC50 - 2
pIC50 6.3 (IC50 4.6x10-7 M) [2]
Description: Inhibition of catalytic activity
Targets where the ligand is described in the comment field
Target Comment
Ligand mentioned in the following text fields