Identification

Name
Permethrin
Accession Number
DB04930
Type
Small Molecule
Groups
Approved, 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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ElimiteCream50 mg/1gCutaneousAllergan1989-12-012009-12-31Us
ElimiteCream50 mg/100gTopicalPrestium Pharma, Inc.2016-01-27Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ElimiteCream50 mg/100gTopicalPrestium Pharma, Inc.2012-10-242016-06-25Us
PermethrinCream50 mg/1gTopicalNucare Pharmaceuticals,inc.2006-08-112017-07-25Us
PermethrinCream50 mg/1gTopicalRebel Distributors2003-04-21Not applicableUs
PermethrinCream50 mg/1gTopicalA-S Medication Solutions2004-11-30Not applicableUs
PermethrinCream50 mg/1gTopicalCentral Texas Community Health Centers2004-11-30Not applicableUs
PermethrinCream50 mg/1gTopicalRemedy Repack2013-04-172015-03-04Us
PermethrinCream50 mg/1gTopicalH.J. Harkins Company2006-08-11Not applicableUs
PermethrinCream50 mg/1gTopicalRpk Pharmaceuticals, Inc.2006-08-11Not applicableUs
PermethrinCream50 mg/1gTopicalA-S Medication Solutions2013-06-272017-10-31Us
PermethrinCream50 mg/1gTopicalCentral Texas Community Health Centers2006-08-11Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Equaline Lice TreatmentLotion1 mg/100mLTopicalSupervalu2011-01-28Not applicableUs
Good Neighbor Pharmacy Lice TreatmentLotion1 mg/100mLTopicalAmerisource Bergen2012-03-07Not applicableUs
Good Sense Lice TreatmentLotion1 mg/100mLTopicalL. Perrigo Company2011-11-232016-04-22Us
Health Mart Lice TreatmentLotion1 mg/100mLTopicalMc Kesson2015-08-03Not applicableUs
Kwellada-P CRème RinseLiquid1.0 %TopicalMedtech Laboratories, Inc.1998-11-16Not applicableCanada
Kwellada-P LotionLotion5 %TopicalMedtech Laboratories, Inc.1997-10-16Not applicableCanada
Leader Lice TreatmentLotion1 mg/100mLTopicalCardinal Health2011-06-15Not applicableUs
Lice TreatmentLotion1 mg/100mLTopicalRebel Distributors2010-03-28Not applicableUs
Lice TreatmentLotion1 mg/100mLTopicalKinray2010-03-282016-05-31Us
Lice TreatmentLotion1 mg/100mLTopicalActavis Pharma Company2000-06-112017-04-30Us
International/Other Brands
Acticin / Lyclear (Johnson & Johnson)
Categories
UNII
509F88P9SZ
CAS number
52645-53-1
Weight
Average: 391.288
Monoisotopic: 390.07894992
Chemical Formula
C21H20Cl2O3
InChI Key
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

Pharmacology

Indication

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

Associated Conditions
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.

TargetActionsOrganism
ASodium channel protein type 1 subunit alpha
inhibitor
Human
UEstrogen receptor alphaNot AvailableHuman
UNuclear receptor subfamily 1 group I member 2Not AvailableHuman
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
No interactions found.
Food Interactions
Not Available

References

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
Human Metabolome Database
HMDB0015604
KEGG Drug
D05443
KEGG Compound
C14388
PubChem Compound
40326
PubChem Substance
46505374
ChemSpider
36845
ChEBI
34911
ChEMBL
CHEMBL1525
Therapeutic Targets Database
DAP001235
PharmGKB
PA164743137
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Permethrin
ATC Codes
P03AC54 — Permethrin, combinationsP03AC04 — Permethrin
AHFS Codes
  • 84:04.12 — Scabicides and Pediculicides
FDA label
Download (171 KB)
MSDS
Download (60.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentLice of the head1
3Active Not RecruitingTreatmentScabies1
3CompletedTreatmentLice Infestations3
3CompletedTreatmentPediculus Capitis Infestation1
3CompletedTreatmentScabies2
3CompletedTreatmentLice of the head / Scabies1
3RecruitingTreatmentScabies1
3TerminatedTreatmentHead Louse Infestation / Pediculosis Capitis1
4CompletedTreatmentImpetigo / Scabies / Yaws1
4Enrolling by InvitationTreatmentInflammation of the Eyelids1
4RecruitingPreventionParasitic Diseases / Plasmodium Infections1
Not AvailableCompletedTreatmentScabies1
Not AvailableTerminatedTreatmentBody's Louses1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Actavis Group
  • Allergan Inc.
  • A-S Medication Solutions LLC
  • CVS Pharmacy
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DSM Corp.
  • H.J. Harkins Co. Inc.
  • Mylan
  • Perrigo Co.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Professional Co.
  • Rebel Distributors Corp.
  • Sunmark
Dosage forms
FormRouteStrength
CreamCutaneous50 mg/1g
CreamTopical50 mg/100g
LotionTopical1 mg/100mL
LiquidTopical1.0 %
LotionTopical5 %
ShampooTopical1 g/100mL
Kit1 g/100mL
CreamTopical1 %
CreamTopical5 %
CreamTopical50 mg/1g
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)34 °CPhysProp
boiling point (°C)220 °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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-1900000000-956860faa94e3dea2ee2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-1900000000-ce2901f0a3049806d95f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-1900000000-b5846ca870454df7f44f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-474995c2ccb155f0975c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-1900000000-261c3708f1e50c4a8418
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-006t-2900000000-4915b2e2cee108c117a2

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acid esters
Direct Parent
Pyrethroids
Alternative Parents
Diphenylethers / Diarylethers / Benzyloxycarbonyls / Phenoxy compounds / Phenol ethers / Cyclopropanecarboxylic acids and derivatives / Ketene acetals / Carboxylic acid esters / Vinyl chlorides / Monocarboxylic acids and derivatives
show 5 more
Substituents
Pyrethroid skeleton / Diphenylether / Diaryl ether / Benzyloxycarbonyl / Phenoxy compound / Phenol ether / Monocyclic benzene moiety / Cyclopropanecarboxylic acid or derivatives / Benzenoid / Carboxylic acid ester
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
cyclopropanes, cyclopropanecarboxylate ester (CHEBI:34911) / a monoterpenoid (CPD-13115)

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...
Gene Name
SCN1A
Uniprot ID
P35498
Uniprot Name
Sodium channel protein type 1 subunit alpha
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. McCarthy AR, Thomson BM, Shaw IC, Abell AD: Estrogenicity of pyrethroid insecticide metabolites. J Environ Monit. 2006 Jan;8(1):197-202. Epub 2005 Dec 14. [PubMed:16395479]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Kojima H, Sata F, Takeuchi S, Sueyoshi T, Nagai T: Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. Toxicology. 2011 Feb 27;280(3):77-87. doi: 10.1016/j.tox.2010.11.008. Epub 2010 Nov 27. [PubMed:21115097]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
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 un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
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]
  2. Das PC, Streit TM, Cao Y, Rose RL, Cherrington N, Ross MK, Wallace AD, Hodgson E: Pyrethroids: cytotoxicity and induction of CYP isoforms in human hepatocytes. Drug Metabol Drug Interact. 2008;23(3-4):211-36. [PubMed:19326768]
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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]

Drug created on October 21, 2007 16:23 / Updated on December 14, 2018 17:10