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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/)

References
1. Ishida H, Noshiro M, Okuda K, Coon MJ. (1992)
Purification and characterization of 7 alpha-hydroxy-4-cholesten-3-one 12 alpha-hydroxylase.
J Biol Chem, 267 (30): 21319-23. [PMID:1400444]
2. Liu J, Carlson HA, Scott EE. (2022)
The structure and characterization of human cytochrome P450 8B1 supports future drug design for nonalcoholic fatty liver disease and diabetes.
J Biol Chem, 298 (9): 102344. [PMID:35944583]
3. Togashi K, Inada H, Tominaga M. (2008)
Inhibition of the transient receptor potential cation channel TRPM2 by 2-aminoethoxydiphenyl borate (2-APB).
Br J Pharmacol, 153 (6): 1324-30. [PMID:18204483]