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Identification
NamePermethrin
Accession NumberDB04930
TypeSmall Molecule
GroupsApproved, Investigational
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
Thumb
Synonyms
(3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl ester
Permethrin
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Elimitecream50 mg/100gtopicalPrestium Pharma, Inc.2016-01-272016-04-05Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Elimitecream50 mg/100gtopicalPrestium Pharma, Inc.2012-10-242016-04-05Us
Permethrincream50 mg/gtopicalCentral Texas Community Health Centers2006-08-112016-04-05Us
Permethrincream50 mg/gtopicalActavis Mid Atlantic LLC2004-11-302016-04-23Us
Permethrincream50 mg/gtopicalPhysicians Total Care, Inc.2007-10-302016-04-05Us
Permethrincream50 mg/gtopicalH.J. Harkins Company, Inc.2006-08-112016-04-05Us
Permethrincream50 mg/gtopicalREMEDYREPACK INC.2013-06-042016-04-05Us
Permethrincream50 mg/gtopicalPerrigo New York Inc2006-08-112016-04-05Us
Permethrincream50 mg/gtopicalRenaissance Pharma, Inc.2013-06-272016-04-05Us
Permethrincream50 mg/gtopicalRebel Distributors Corp2003-04-212016-04-05Us
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Equaline Lice Treatmentlotion1 mg/100mLtopicalSupervalu Inc2011-01-282016-04-05Us
Good Neighbor Pharmacy Lice Treatmentlotion1 mg/100mLtopicalAmerisource Bergen2012-03-072016-04-05Us
Good Sense Lice Treatmentlotion1 mg/100mLtopicalL Perrigo Company2011-11-232016-04-23Us
Health Mart Lice Treatmentlotion1 mg/100mLtopicalMc Kesson2015-08-032016-04-05Us
Kwellada-P CRème Rinseliquid1.0 %topicalMedtech Products Inc1998-11-16Not applicableCanada
Kwellada-P Lotionlotion5 %topicalMedtech Products Inc1997-10-16Not applicableCanada
Leader Lice Treatmentlotion1 mg/100mLtopicalCardinal Health2011-06-152016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalCVS Pharmacy2000-04-012016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalRebel Distributors Corp2010-03-282016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalMc Kesson2012-06-012016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalMeijer Distribution Inc2000-08-012016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalFred's Inc.2008-04-112016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalHEB2001-08-102016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalChain Drug Consortium, LLC2005-03-082016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalMc Kesson2000-03-282016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalKinray, Inc.2010-03-282016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalRite Aid Corporation2011-01-262016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalActavis Mid Atlantic LLC2010-03-282016-04-23Us
Lice Treatmentlotion1 mg/100mLtopicalHy Vee Inc2011-01-222016-04-05Us
Lice Treatmentlotion1 mg/100mLtopicalWalgreen Company2010-07-152016-04-23Us
Nixshampoo560 mg/59mLtopicalInsight Pharmaceuticals2009-06-052016-04-05Us
Nix Complete Maximum Strength Lice EliminationkitInsight Pharmaceuticals2013-11-152016-04-05Us
Nix Creme Rinsecream1 %topicalInsight Pharmaceuticals LLC1988-12-31Not applicableCanada
Nix Dermal Creamcream5 %topicalGlaxosmithkline Consumer Healthcare Inc.1999-07-01Not applicableCanada
Nix Dermal Cream 5%cream5 %topicalBurroughs Wellcome Inc., Consumer Prod Division1991-12-311999-08-24Canada
Smart Sense Lice Treatmentlotion1 mg/100mLtopicalKmart Corporation2011-03-012016-04-05Us
Sunmark Lice Treatmentlotion1 mg/100mLtopicalMcKesson2015-08-032016-04-05Us
Topcare Lice Treatmentlotion1 mg/100mLtopicalTopco Associates LLC2011-09-142016-04-05Us
International Brands
NameCompany
ActicinNot Available
LyclearJohnson & Johnson
Brand mixturesNot Available
SaltsNot Available
Categories
UNII509F88P9SZ
CAS number52645-53-1
WeightAverage: 391.288
Monoisotopic: 390.07894992
Chemical FormulaC21H20Cl2O3
InChI KeyInChIKey=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
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentPyrethroids
Alternative Parents
Substituents
  • Pyrethroid skeleton
  • Diphenylether
  • Diaryl ether
  • Benzyloxycarbonyl
  • Benzenoid
  • Cyclopropanecarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Ketene acetal or derivatives
  • Carboxylic acid ester
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of infestation with Sarcoptes scabiei (scabies).
PharmacodynamicsPermethrin, a pyrethroid, is active against a broad range of pests including lice, ticks, fleas, mites, and other arthropods.
Mechanism of actionPermethrin 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.
Related Articles
AbsorptionPoorly absorbed through the skin.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

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

Route of eliminationPermethrin is rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.
Half lifeNot Available
ClearanceNot Available
ToxicityOral, rat LD50: 430 - 4000 mg/kg; skin, rabbit LD50: 2000 mg/kg.
Affected organisms
  • Scabies (Sarcoptes scabei) and other insects
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8736
Caco-2 permeable+0.7366
P-glycoprotein substrateNon-substrate0.5532
P-glycoprotein inhibitor IInhibitor0.5224
P-glycoprotein inhibitor IINon-inhibitor0.8671
Renal organic cation transporterNon-inhibitor0.8116
CYP450 2C9 substrateNon-substrate0.7366
CYP450 2D6 substrateNon-substrate0.9023
CYP450 3A4 substrateSubstrate0.672
CYP450 1A2 substrateInhibitor0.7309
CYP450 2C9 inhibitorNon-inhibitor0.5985
CYP450 2D6 inhibitorNon-inhibitor0.8796
CYP450 2C19 inhibitorInhibitor0.7386
CYP450 3A4 inhibitorNon-inhibitor0.8296
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8687
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.6594
BiodegradationNot ready biodegradable0.9918
Rat acute toxicity2.9777 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9758
hERG inhibition (predictor II)Non-inhibitor0.9091
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Creamtopical50 mg/100g
Lotiontopical1 mg/100mL
Liquidtopical1.0 %
Lotiontopical5 %
Shampootopical560 mg/59mL
Kit
Creamtopical1 %
Creamtopical5 %
Creamtopical50 mg/g
Prices
Unit descriptionCostUnit
Elimite 5% Cream 60 gm Tube83.61USD tube
Permethrin 5% Cream 60 gm Tube30.42USD tube
Acticin 5% Cream 60 gm Tube30.31USD tube
Permethrin 1% Lotion 59ml Bottle16.99USD bottle
Elimite 5% cream1.33USD g
Permethrin technical liquid1.32USD g
Acticin 5% cream0.49USD g
Permethrin 5% cream0.49USD g
Sm lice treatment permethrin0.18USD ml
Nix 1% creme rinse liquid0.15USD ml
Sm lice bedding spray0.04USD g
CVS Pharmacy lice bedding spray0.03USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point34 °CPhysProp
boiling point220 °C at 5.00E-02 mm HgPhysProp
water solubility0.006 mg/L (at 20 °C)USDA PESTICIDE PROP DATABASE
logP6.50HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility6.91e-05 mg/mLALOGPS
logP6.24ALOGPS
logP5.7ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity114.28 m3·mol-1ChemAxon
Polarizability39.43 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  1. 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:17978449 ]
External Links
ATC CodesP03AC04P03AC54
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (171 KB)
MSDSDownload (60.4 KB)
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated sodium channel activity
Specific Function:
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.
Gene Name:
SCN1A
Uniprot ID:
P35498
Molecular Weight:
228969.49 Da
References
  1. 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. doi: 10.1124/jpet.110.171850. Epub 2010 Sep 29. [PubMed:20881019 ]
  2. 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:19960691 ]
  3. 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. doi: 10.1016/j.neuro.2009.09.002. Epub 2009 Sep 18. [PubMed:19766671 ]
  4. 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. doi: 10.1016/j.ibmb.2009.01.001. Epub 2009 Jan 10. [PubMed:19171193 ]
  5. 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:14651650 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinducer
General Function:
Steroid hydroxylase activity
Specific Function:
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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on October 21, 2007 16:23 / Updated on September 16, 2013 17:26