Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1262)
Drug Name
Permethrin
Synonyms
Perigen; Permasect; Permethrin; Permethrine; Permetrina; Perthrine; Picket; Pounce; Pramex; Quamlin; Stomoxi; Stomoxin; Stomozan; Transpermethrin; Acticin; Ambush; Ambushfog; Chinetrin; Coopex; Corsair; Dragnet; Ecsumin; Ectiban; Efmethrin; Eksmin; Elimite; FMC 35171; Imperator; Indothrin; Kaleait; Kestrel; Lyclear; NRDC 146; NRDC 148; Outflank; Transpermethrin [ISO]; trans-(+-)-Permethrin; (+)-trans-Permethrin; (+-)-cis-Fmc 33297; (+-)-cis-Permethrin; (+-)-trans-Permethrin; 1RS,cis-Permethrin; 1RS-trans-Permethrin; 52645-53-1; BRN 4153590; Kudos
Indication Scabies [ICD11: 1G04] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 391.3 Topological Polar Surface Area 35.5
Heavy Atom Count 26 Rotatable Bond Count 7
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
40326
PubChem SID
5646900 ; 8176555 ; 10525033 ; 10525292 ; 10526594 ; 14854178 ; 17395388 ; 24868001 ; 24869115 ; 24869349 ; 24871630 ; 24899290 ; 26675675 ; 26754479 ; 26754481 ; 26754482 ; 26754483 ; 26754484 ; 29215320 ; 29215321 ; 34706112 ; 46505374 ; 47207113 ; 48415484 ; 48421679 ; 48425983 ; 49833360 ; 49959692 ; 49959696 ; 50109850 ; 56310674 ; 56312325 ; 56314259 ; 57260102 ; 57260103 ; 57288423 ; 57312421 ; 57650455 ; 57650562 ; 74717839 ; 85088539 ; 85189547 ; 91696064 ; 103559256 ; 104334065 ; 117452446 ; 118783839 ; 121362319 ; 124800250 ; 124892140
ChEBI ID
ChEBI:34911
CAS Number
52645-53-1
TTD Drug ID
D0K8MP
Formula
C21H20Cl2O3
Canonical SMILES
CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
InChI
1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3
InChIKey
RLLPVAHGXHCWKJ-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Phenoxybenzyl alcohol DM001219
22137599
Hydrolysis - Hydrolysis 1 [3] , [4]
2-Phenoxybenzaldehyde DM001220
88060
Oxidation - Dehydrogenation 2 [3]
2-Phenoxybenzoic acid DM001221
75237
Oxidation - Oxidation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002004 Permethrin Phenoxybenzyl alcohol Hydrolysis - Hydrolysis CYP2B6 ... [3], [4]
MR002002 Phenoxybenzyl alcohol 2-Phenoxybenzaldehyde Oxidation - Dehydrogenation ADH [3]
MR002003 2-Phenoxybenzaldehyde 2-Phenoxybenzoic acid Oxidation - Oxidation ALDH [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Alcohol dehydrogenase (ADH) DME1317 Lactobacillus reuteri
A4L2V0_LACRE
1.1.1.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Permethrin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Human metabolic interactions of environmental chemicals J Biochem Mol Toxicol. 2007;21(4):182-6. doi: 10.1002/jbt.20175.
3 Human metabolic interactions of environmental chemicals. J Biochem Mol Toxicol. 2007;21(4):182-6.
4 Pharmacokinetics, Metabolite Measurement, and Biomarker Identification of Dermal Exposure to Permethrin Using Accelerator Mass Spectrometry. Toxicol Sci. 2021 Aug 30;183(1):49-59. doi: 10.1093/toxsci/kfab082.

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