Details of the Drug

General Information of Drug (ID: DMZ0Q1G)

Drug Name
Permethrin
Synonyms
Ambush; PerFoam; Transpermethrin; Acticin Cream; Elimite Cream; Nix Cream Rinse; Transpermethrin [ISO];FMC 35171; NRDC 146; NRDC 148; PS758_SUPELCO; Permethrin (isomers); Permethrin (isomers) solution; Permethrine,c&t; Trans-(+-)-Permethrin; [3-(phenyloxy)phenyl]methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; (+)-CIS-PERMETHRIN; (+)-trans-Permethrin; (+-)-cis-Fmc 33297; (+-)-cis-Permethrin; (+-)-trans-Permethrin; (3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate; 1RS,cis-Permethrin; 1RS-trans-Permethrin; 3-Phenoxybenzyle (1RS)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate; 3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Indication
Disease Entry ICD 11 Status REF
Pediculus capitis infestation 1G00.0 Approved [1]
Pediculus humanus corporis infestation N.A. Approved [1]
Pthirus pubis infestation N.A. Approved [1]
Sarcoptes scabiei infection 1G04 Approved [2]
Therapeutic Class
Insecticides
Affected Organisms
Scabies (Sarcoptes scabei) and other insects
ATC Code
P03AC04: Permethrin
P03AC: Pyrethrines, incl. synthetic compounds
P03A: ECTOPARASITICIDES, INCL. SCABICIDES
P03: ECTOPARASITICIDES, INCL. SCABICIDES, INSECTICIDES AND REPELLENTS
P: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 391.3
Logarithm of the Partition Coefficient (xlogp) 6.5
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption
The drug is poorly absorbed from the skin []
Bioavailability
60% of drug becomes completely available to its intended biological destination(s) [3]
Metabolism
The drug is metabolized via the ester hydrolysis to inactive metabolites []
Chemical Identifiers
Formula
C21H20Cl2O3
IUPAC Name
(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Canonical SMILES
CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
InChI
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
Cross-matching ID
PubChem CID
40326
ChEBI ID
CHEMBL34911
CAS Number
52645-53-1
UNII
509F88P9SZ
DrugBank ID
DB04930
TTD ID
D0K8MP
INTEDE ID
DR1262
ACDINA ID
D01337
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Sodium channel unspecific (NaC) TTRK8B9 NOUNIPROTAC Blocker [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [5]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase eta-1 (PLCH1) OT6Z1L2E PLCH1_HUMAN Gene/Protein Processing [6]
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1 (PFKFB1) OTTHX4NB F261_HUMAN Gene/Protein Processing [6]
Actin-like protein 7B (ACTL7B) OTCG3IGE ACL7B_HUMAN Gene/Protein Processing [6]
Acyl-CoA-binding domain-containing protein 5 (ACBD5) OT7L16DY ACBD5_HUMAN Gene/Protein Processing [6]
Adenylate kinase isoenzyme 1 (AK1) OT614AR3 KAD1_HUMAN Gene/Protein Processing [7]
Adherens junction-associated protein 1 (AJAP1) OTAAW121 AJAP1_HUMAN Gene/Protein Processing [6]
Afadin- and alpha-actinin-binding protein (SSX2IP) OTEIZ7N1 ADIP_HUMAN Gene/Protein Processing [6]
ALK and LTK ligand 2 (ALKAL2) OTTLHL64 ALKL2_HUMAN Gene/Protein Processing [6]
Alpha-2-macroglobulin-like protein 1 (A2ML1) OTWNUXIS A2ML1_HUMAN Gene/Protein Processing [6]
Angiopoietin-related protein 1 (ANGPTL1) OTXIN6V5 ANGL1_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Butylated hydroxytoluene E00336 31404 Antioxidant
Cetyl alcohol E00061 2682 Coating agent; Emollient; Emulsifying agent; Stiffening agent
Glyceryl monostearate E00310 24699 Emollient; Emulsifying agent; Emulsion stabilizing agent; Solubilizing agent; Surfactant; Viscosity-controlling agent
Isopropyl alcohol E00070 3776 Antimicrobial preservative; Solvent
Kyselina citronova E00014 311 Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
methylparaben E00149 7456 Antimicrobial preservative
Propylparaben sodium E00567 23679044 Antimicrobial preservative
Sunset yellow FCF E00255 17730 Colorant
Lauric acid E00071 3893 Antifoaming agent; Emulsifying agent; Lubricant; Penetration agent; Surfactant
Stearalkonium chloride E00328 31204 Antimicrobial preservative; Surfactant
Glycerin E00026 753 Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Sodium hydroxide E00234 14798 Alkalizing agent
Water E00035 962 Solvent
Formaldehyde E00024 712 Antimicrobial preservative
Isopropyl myristate E00161 8042 Emollient; Oleaginous vehicle; Penetration agent; Solvent
Polyoxyl 20 cetyl ether E00452 2724259 Emulsifying agent; Ointment base; Solubilizing agent; Surfactant
Hydroxyethyl cellulose E00700 Not Available Coating agent; Suspending agent; Binding agent; Viscosity-controlling agent
Polyoxyethylene 10 cetyl ether E00712 10305360 Dispersing agent; Emulsifying agent; Gelling agent; Surfactant; Penetrationagent; solubilizing agent; Viscosity-controlling agent
⏷ Show the Full List of 19 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Permethrin 1% lotion 1% Lotion Topical
Permethrin 5% cream 5% Cream Topical
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Permethrin FDA Label
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4 In vitro assays for repellents and deterrents for ticks: differing effects of products when tested with attractant or arrestment stimuli. Med Vet Entomol. 2003 Dec;17(4):370-8.
5 Human metabolic interactions of environmental chemicals. J Biochem Mol Toxicol. 2007;21(4):182-6.
6 Exposure to Insecticides Modifies Gene Expression and DNA Methylation in Hematopoietic Tissues In Vitro. Int J Mol Sci. 2023 Mar 26;24(7):6259. doi: 10.3390/ijms24076259.
7 Pyrethroids: cytotoxicity and induction of CYP isoforms in human hepatocytes. Drug Metabol Drug Interact. 2008;23(3-4):211-36.