DrugBank: Permethrin (DB04930)

targets (1) enzymes (2)

Identification

Name

Permethrin

Accession Number

DB04930

Type

small molecule

Groups

approved

Description

A pyrethroid insecticide commonly used in the treatment of lice infestations and scabies. It is a yellow to light orange-brown, low melt-ing solid or viscous liquid.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Salts

Not Available

Brand names

Name	Company
Acticin Cream
Elimite
Elimite Cream
Nix Cream Rinse
PerFoam

Brand mixtures

Not Available

Categories

Enzyme Inhibitors
Insecticides

CAS number

52645-53-1

Weight

Average: 391.288
Monoisotopic: 390.07894992

Chemical Formula

C₂₁H₂₀Cl₂O₃

InChI Key

InChIKey=RLLPVAHGXHCWKJ-UHFFFAOYSA-N

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

Plain Text

IUPAC Name

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

SMILES

CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC(OC2=CC=CC=C2)=CC=C1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Benzene and Derivatives
Benzyl Esters
Benzylacetates

Substructures

Carboxylic Acids and Derivatives
Benzyl Alcohols and Derivatives
Acetates
Phenols and Derivatives
Cyclopropane and Derivatives
Ethers
Halogen Derivatives
Benzene and Derivatives
Benzyl Esters
Benzylacetates
Aromatic compounds
Anisoles
Ketenes and Derivatives
Phenyl Esters

Pharmacology

Indication

For the treatment of infestation with Sarcoptes scabiei (scabies).

Pharmacodynamics

Permethrin, a pyrethroid, is active against a broad range of pests including lice, ticks, fleas, mites, and other arthropods.

Mechanism of action

Permethrin acts on the nerve cell membrane to disrupt the sodium channel current by which the polarization of the membrane is regulated. Delayed repolarization and paralysis of the pests are the consequences of this disturbance.

Absorption

Poorly absorbed through the skin.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.

Route of elimination

Permethrin is rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.

Half life

Not Available

Clearance

Not Available

Toxicity

Oral, rat LD₅₀: 430 - 4000 mg/kg; skin, rabbit LD₅₀: 2000 mg/kg.

Affected organisms

Scabies (Sarcoptes scabei) and other insects

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Allergan inc
Actavis mid atlantic llc
Perrigo new york inc
Glaxosmithkline
Insight pharmaceuticals corp

Packagers

Dosage forms

Form	Route	Strength
Cream	Topical
Liquid	Topical
Lotion	Topical

Prices

Unit description	Cost	Unit
Elimite 5% Cream 60 gm Tube	83.61 USD	tube
Permethrin 5% Cream 60 gm Tube	30.42 USD	tube
Acticin 5% Cream 60 gm Tube	30.31 USD	tube
Permethrin 1% Lotion 59ml Bottle	16.99 USD	bottle
Elimite 5% cream	1.33 USD	g
Permethrin technical liquid	1.32 USD	g
Acticin 5% cream	0.49 USD	g
Permethrin 5% cream	0.49 USD	g
Sm lice treatment permethrin	0.18 USD	ml
Nix 1% creme rinse liquid	0.15 USD	ml
Sm lice bedding spray	0.04 USD	g
CVS Pharmacy lice bedding spray	0.03 USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	34 °C	PhysProp
boiling point	220 °C at 5.00E-02 mm Hg	PhysProp
water solubility	0.006 mg/L (at 20 °C)	USDA PESTICIDE PROP DATABASE
logP	6.50	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
water solubility	6.91e-05 g/l	ALOGPS
logP	6.24	ALOGPS
logP	5.7	ChemAxon
logS	-6.8	ALOGPS
pKa (strongest basic)	-7.1	ChemAxon
physiological charge	0	ChemAxon
hydrogen acceptor count	1	ChemAxon
hydrogen donor count	0	ChemAxon
polar surface area	35.53	ChemAxon
rotatable bond count	7	ChemAxon
refractivity	114.28	ChemAxon
polarizability	39.43	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Abedin S, Narang M, Gandhi V, Narang S: Efficacy of permethrin cream and oral ivermectin in treatment of scabies. Indian J Pediatr. 2007 Oct;74(10):915-6. Pubmed

External Links

Resource	Link
KEGG Drug	D05443
KEGG Compound	C14388
PubChem Compound	40326
PubChem Substance	46505374
ChemSpider	36845
ChEBI	34911
ChEMBL	34911
Therapeutic Targets Database	DAP001235
PharmGKB	PA164743137
Drug Product Database	771368
RxList	http://www.rxlist.com/cgi/generic/elimite.htm
Drugs.com	http://www.drugs.com/cdi/permethrin-cream.html
Wikipedia	http://en.wikipedia.org/wiki/Permethrin

ATC Codes

P03AC04

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

show (171 KB)

MSDS

show (60.4 KB)

Interactions

Drug Interactions

Searched, but no interactions found.

Food Interactions

Not Available

Targets
1. Sodium channel protein type 1 subunit alpha Pharmacological action: yes Actions: inhibitor Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient Organism class: human UniProt ID: P35498 Gene: SCN1A Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Cao Z, Shafer TJ, Murray TF: Mechanisms of pyrethroid insecticide-induced stimulation of calcium influx in neocortical neurons. J Pharmacol Exp Ther. 2011 Jan;336(1):197-205. Epub 2010 Sep 29. Pubmed Liu N, Xu Q, Li T, He L, Zhang L: Permethrin resistance and target site insensitivity in the mosquito Culex quinquefasciatus in Alabama. J Med Entomol. 2009 Nov;46(6):1424-9. Pubmed Breckenridge CB, Holden L, Sturgess N, Weiner M, Sheets L, Sargent D, Soderlund DM, Choi JS, Symington S, Clark JM, Burr S, Ray D: Evidence for a separate mechanism of toxicity for the Type I and the Type II pyrethroid insecticides. Neurotoxicology. 2009 Nov;30 Suppl 1:S17-31. Epub 2009 Sep 18. Pubmed Chang C, Shen WK, Wang TT, Lin YH, Hsu EL, Dai SM: A novel amino acid substitution in a voltage-gated sodium channel is associated with knockdown resistance to permethrin in Aedes aegypti. Insect Biochem Mol Biol. 2009 Apr;39(4):272-8. Epub 2009 Jan 10. Pubmed McMahon C, Krober T, Guerin PM: 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. Pubmed

Targets

1. Sodium channel protein type 1 subunit alpha

Pharmacological action: yes
Actions: inhibitor

Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient

Organism class: human
UniProt ID: P35498 Link_out

Gene: SCN1A Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Cao Z, Shafer TJ, Murray TF: Mechanisms of pyrethroid insecticide-induced stimulation of calcium influx in neocortical neurons. J Pharmacol Exp Ther. 2011 Jan;336(1):197-205. Epub 2010 Sep 29. Pubmed
Liu N, Xu Q, Li T, He L, Zhang L: Permethrin resistance and target site insensitivity in the mosquito Culex quinquefasciatus in Alabama. J Med Entomol. 2009 Nov;46(6):1424-9. Pubmed
Breckenridge CB, Holden L, Sturgess N, Weiner M, Sheets L, Sargent D, Soderlund DM, Choi JS, Symington S, Clark JM, Burr S, Ray D: Evidence for a separate mechanism of toxicity for the Type I and the Type II pyrethroid insecticides. Neurotoxicology. 2009 Nov;30 Suppl 1:S17-31. Epub 2009 Sep 18. Pubmed
Chang C, Shen WK, Wang TT, Lin YH, Hsu EL, Dai SM: A novel amino acid substitution in a voltage-gated sodium channel is associated with knockdown resistance to permethrin in Aedes aegypti. Insect Biochem Mol Biol. 2009 Apr;39(4):272-8. Epub 2009 Jan 10. Pubmed
McMahon C, Krober T, Guerin PM: 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. Pubmed

Enzymes
1. Cytochrome P450 2B6 Actions: substrate, inducer Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics UniProt ID: P20813 Gene: CYP2B6 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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 2. Cytochrome P450 3A4 Actions: substrate Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide UniProt ID: P08684 Gene: CYP3A4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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

Enzymes

1. Cytochrome P450 2B6

Actions: substrate, inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P20813 Link_out

Gene: CYP2B6 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

2. Cytochrome P450 3A4

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out

Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Comments

Drug created on October 21, 2007 16:23 / Updated on February 08, 2013 16:23