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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:34911
CAS Number: 52645-53-1
UNII: 509F88P9SZ
DrugBank ID: DB04930
TTD ID: D0K8MP
INTEDE ID: DR1262
ACDINA ID: D01337

Repurposed Drugs (RPD)

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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]

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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]

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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]
Aldehyde oxidase (AOX1)	OT2FZP6H	AOXA_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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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
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⏷ 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

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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.