DT-Web

DB01153 - Sertaconazole


Identification
Name Sertaconazole
Accession Number DB01153 (APRD00305)
Type small molecule
Description Sertaconazole nitrate is an antifungal medication of the imidazole class. It is available as a cream to treat skin infections such as athlete's foot. [Wikipedia]
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 437.77
Groups approved
Monoisotopic Weight 435.997066923
Pharmacology
Indication For the topical treatment of interdigital tinea pedis in immunocompetent patients 12 years of age and older, caused by Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton floccosum.
Mechanism of action Sertaconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Sertaconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
Absorption Bioavailability is negligible.
Protein binding >99% to plasma
Biotransformation Not Available
Route of elimination Not Available
Toxicity Not Available
Affected organisms
  • Yeast and other fungi
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Cytochrome P450 51
Name Cytochrome P450 51
Gene Name ERG11
Pharmacological action yes
Actions inhibitor
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
  • Agut J, Palacin C, Sacristan A, Ortiz JA: Inhibition of ergosterol synthesis by sertaconazole in Candida albicans. Arzneimittelforschung. 1992 May;42(5A):718-20. - Pubmed
  • Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. - Pubmed
  • Agut J, Palacin C, Salgado J, Casas E, Sacristan A, Ortiz JA: Direct membrane-damaging effect of sertaconazole on Candida albicans as a mechanism of its fungicidal activity. Arzneimittelforschung. 1992 May;42(5A):721-4. - Pubmed
  • Croxtall JD, Plosker GL: Sertaconazole: a review of its use in the management of superficial mycoses in dermatology and gynaecology. Drugs. 2009;69(3):339-59. - Pubmed
DTHybrid score 0.5424

Enzymes


Cytochrome P450 51A1
Name Cytochrome P450 51A1
Gene Name CYP51A1
Actions inhibitor
References
  • Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. - Pubmed
DTHybrid score 0.5129

Predictions


Id Partner name Gene Name Score
761 Cytochrome P450 51 ERG11 0.5424
3163 Cytochrome P450 51 cyp51 0.5424
6562 Putative cytochrome P450 130 cyp130 0.143
4512 Cytochrome P450 3A4 CYP3A4 0.0902
6016 Cytochrome P450 2C19 CYP2C19 0.0684
3811 Cytochrome P450 19A1 CYP19A1 0.0619
6013 Cytochrome P450 2E1 CYP2E1 0.0607
1588 Multidrug resistance protein 1 ABCB1 0.0438
4757 Cytochrome P450 2C9 CYP2C9 0.0402
6107 Cytochrome P450 3A7 CYP3A7 0.0369
6030 Cytochrome P450 2B6 CYP2B6 0.0356
805 Cytochrome P450 11B1, mitochondrial CYP11B1 0.034
4118 Cytochrome P450 3A5 CYP3A5 0.0319
4200 Cytochrome P450 1A2 CYP1A2 0.0296
4924 Cytochrome P450 2C8 CYP2C8 0.0289
6024 Cytochrome P450 1A1 CYP1A1 0.0216
4119 Cytochrome P450 2D6 CYP2D6 0.0215
6017 Cholesterol side-chain cleavage enzyme, mitochondrial CYP11A1 0.0178
5934 Cytochrome P450 26A1 CYP26A1 0.0177
5718 Cytochrome P450 2A6 CYP2A6 0.0157
6104 Dimethylaniline monooxygenase [N-oxide-forming] 1 FMO1 0.0129
1898 Cytochrome P450 1B1 CYP1B1 0.0113
462 Intermediate conductance calcium-activated potassium channel protein 4 KCNN4 0.0112
776 Bile salt export pump ABCB11 0.011
6101 Dimethylaniline monooxygenase [N-oxide-forming] 3 FMO3 0.0109
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0099
6931 Calcium-activated potassium channel subunit beta-1 KCNMB1 0.0069
6932 Calcium-activated potassium channel subunit beta-3 KCNMB3 0.0069
6933 Calcium-activated potassium channel subunit beta-4 KCNMB4 0.0069
6934 Small conductance calcium-activated potassium channel protein 1 KCNN1 0.0069
6935 Small conductance calcium-activated potassium channel protein 2 KCNN2 0.0069
6936 Small conductance calcium-activated potassium channel protein 3 KCNN3 0.0069
20 Prostaglandin G/H synthase 1 PTGS1 0.0068
5463 Calcium-activated potassium channel subunit beta 2 KCNMB2 0.0055
514 Potassium voltage-gated channel subfamily H member 6 KCNH6 0.0043
772 Potassium voltage-gated channel subfamily H member 7 KCNH7 0.0043
1709 Canalicular multispecific organic anion transporter 2 ABCC3 0.0042
610 Calcium-activated potassium channel subunit alpha 1 KCNMA1 0.0038
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0035
101 Potassium voltage-gated channel subfamily H member 2 KCNH2 0.0032
7 Nitric oxide synthase, inducible NOS2 0.0029
291 Nitric-oxide synthase, endothelial NOS3 0.0028
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