Permethrin
Identification
- Name
- Permethrin
- Accession Number
- DB04930
- 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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Permethrin (DB04930)
- Weight
- Average: 391.288
Monoisotopic: 390.07894992 - Chemical Formula
- C21H20Cl2O3
- 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
Pharmacology
- Indication
For the treatment of infestation with Sarcoptes scabiei (scabies).
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism ASodium channel protein type 1 subunit alpha inhibitorHumans UEstrogen receptor alpha Not Available Humans UNuclear receptor subfamily 1 group I member 2 Not Available Humans - 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
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- 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
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbametapir The serum concentration of Permethrin can be increased when it is combined with Abametapir. Cenobamate The serum concentration of Permethrin can be decreased when it is combined with Cenobamate. Lemborexant The serum concentration of Permethrin can be decreased when it is combined with Lemborexant. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- International/Other Brands
- Acticin / Lyclear (Johnson & Johnson)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataElimite Cream 50 mg/100g Topical Prestium Pharma, Inc. 2016-01-27 Not applicable US 
Elimite Cream 50 mg/1g Cutaneous Allergan 1989-12-01 2009-12-31 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataElimite Cream 50 mg/100g Topical Prestium Pharma, Inc. 2012-10-24 2016-06-25 US Permethrin Cream 50 mg/1g Topical A-S Medication Solutions 2004-11-30 2018-05-31 US Permethrin Cream 50 mg/1g Topical H.J. Harkins Company 2006-08-11 Not applicable US Permethrin Cream 50 mg/1g Topical Central Texas Community Health Centers 2004-11-30 Not applicable US Permethrin Cream 50 mg/1g Topical Northstar RxLLC 2019-04-08 Not applicable US Permethrin Cream 50 mg/1g Topical Nucare Pharmaceuticals,inc. 2019-04-08 Not applicable US Permethrin Cream 50 mg/1g Topical Perrigo New York Inc 2006-08-11 Not applicable US Permethrin Cream 50 mg/1g Topical A-S Medication Solutions 2006-08-11 Not applicable US Permethrin Cream 50 mg/1g Topical Nucare Pharmaceuticals,inc. 2006-08-11 2020-01-08 US Permethrin Cream 50 mg/1g Topical Physicians Total Care, Inc. 2007-10-30 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataEqualine Lice Treatment Lotion 1 mg/100mL Topical SUPERVALU INC 2011-01-28 2015-02-26 US Good Neighbor Pharmacy Lice Treatment Lotion 1 mg/100mL Topical Amerisource Bergen 2012-03-07 Not applicable US Good Sense Lice Killing Creme Rinse Lotion 1 mg/100mL Topical L. Perrigo Company 2019-07-24 Not applicable US Good Sense Lice Treatment Lotion 1 mg/100mL Topical L. Perrigo Company 2011-11-23 2016-04-22 US Health Mart Lice Treatment Lotion 1 mg/100mL Topical Strategic Sourcing Services LLC 2015-08-03 Not applicable US Kwellada-P CRème Rinse Liquid Topical Medtech Laboratories, Inc. 1998-11-16 Not applicable Canada 
Kwellada-P Lotion Lotion Topical Medtech Laboratories, Inc. 1997-10-16 Not applicable Canada Leader Lice Treatment Lotion 1 g/100mL Topical Cardinal Health 2020-03-19 Not applicable US Leader Lice Treatment Lotion 1 mg/100mL Topical Cardinal Health 2011-06-15 Not applicable US Lice Treatment Lotion 1 mg/100mL Topical Rite Aid 2011-01-26 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Nix Complete Lice Treatment Permethrin (280 mg/100mL) + Permethrin (25 mg/1mL) Topical Insight Pharmaceuticals LLC 2013-11-15 Not applicable US Nix Complete Lice Treatment Permethrin (280 mg/100mL) + Permethrin (25 mg/1mL) Topical Insight Pharmaceuticals LLC 2013-11-15 Not applicable US
Categories
- ATC Codes
- P03AC54 — Permethrin, combinations
- P03AC — Pyrethrines, incl. synthetic compounds
- P03A — ECTOPARASITICIDES, INCL. SCABICIDES
- P03 — ECTOPARASITICIDES, INCL. SCABICIDES, INSECTICIDES AND REPELLENTS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- Drug Categories
- Agrochemicals
- Antiparasitic Products, Insecticides and Repellents
- Compounds used in a research, industrial, or household setting
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (strength unknown)
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Ectoparasiticides, Incl. Scabicides
- Ectoparasiticides, Incl. Scabicides, Insecticides and Repellents
- Enzyme Inhibitors
- Insecticides
- Monoterpenes
- Pesticides
- Pyrethrines, Incl. Synthetic Compounds
- Pyrethrins
- Scabicides and Pediculicides
- Terpenes
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- 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
- Aromatic homomonocyclic compound / Benzenoid / Benzyloxycarbonyl / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Chloroalkene / Cyclopropanecarboxylic acid or derivatives / Diaryl ether / Diphenylether show 16 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- cyclopropanes, cyclopropanecarboxylate ester (CHEBI:34911) / a monoterpenoid (CPD-13115)
Chemical Identifiers
- UNII
- 509F88P9SZ
- CAS number
- 52645-53-1
- 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
References
- General References
- 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
- 33199
- ChEBI
- 34911
- ChEMBL
- CHEMBL1525
- Therapeutic Targets Database
- DAP001235
- PharmGKB
- PA164743137
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Permethrin
- AHFS Codes
- 84:04.12 — Scabicides and Pediculicides
- FDA label
- Download (171 KB)
- MSDS
- Download (60.4 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Prevention Parasitic Diseases / Plasmodium Infections 1 4 Completed Treatment Impetigo / Scabies / Yaws 1 4 Unknown Status Treatment Inflammation of the Eyelids 1 3 Completed Treatment Head Lice Infestation / Scabies 1 3 Completed Treatment Lice Infestations 4 3 Completed Treatment Pediculus Capitis Infestation 1 3 Completed Treatment Scabies 4 3 Terminated Treatment Head Louse Infestation / Pediculosis Capitis 1 3 Unknown Status Treatment Scabies 1 2 Completed Treatment Head Lice Infestation 1
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
Form Route Strength Liquid Topical 5 g/100mL Emulsion Topical 1 g/100mL Liquid Topical 1 g/100mL Lotion Cream 5 % Lotion 5 % Cream Cutaneous 50 mg/1g Cream Topical 50 mg/100g Cream Topical 5 g Emulsion Topical 1 g Lotion Topical 5 g Cream 1 g/100g Shampoo 1 % Cream 120 ml Cream 60 ml Liquid Topical Lotion Topical Lotion Topical 1 g/100mL Lotion Topical 1 mg/100mL Cream Topical 50 mg/g Shampoo 100 ml Shampoo 150 ml Rinse Topical 1 g/100mL Shampoo Topical 1 g/100mL Kit Topical 1 g/100mL Cream Topical Cream Topical 1 g Cream 5 g/100g Cream Topical 50 mg/1g Solution Topical Cream Cream Topical 5 % - Prices
Unit description Cost Unit Elimite 5% Cream 60 gm Tube 83.61USD tube Permethrin 5% Cream 60 gm Tube 30.42USD tube Acticin 5% Cream 60 gm Tube 30.31USD tube Permethrin 1% Lotion 59ml Bottle 16.99USD bottle Elimite 5% cream 1.33USD g Permethrin technical liquid 1.32USD g Acticin 5% cream 0.49USD g Permethrin 5% cream 0.49USD g Sm lice treatment permethrin 0.18USD ml Nix 1% creme rinse liquid 0.15USD ml Sm lice bedding spray 0.04USD g CVS Pharmacy lice bedding spray 0.03USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 34 °C PhysProp boiling point (°C) 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 mg/mL ALOGPS logP 6.24 ALOGPS logP 5.7 ChemAxon logS -6.8 ALOGPS pKa (Strongest Basic) -3.7 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 35.53 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 114.28 m3·mol-1 ChemAxon Polarizability 39.43 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.8736 Caco-2 permeable + 0.7366 P-glycoprotein substrate Non-substrate 0.5532 P-glycoprotein inhibitor I Inhibitor 0.5224 P-glycoprotein inhibitor II Non-inhibitor 0.8671 Renal organic cation transporter Non-inhibitor 0.8116 CYP450 2C9 substrate Non-substrate 0.7366 CYP450 2D6 substrate Non-substrate 0.9023 CYP450 3A4 substrate Substrate 0.672 CYP450 1A2 substrate Inhibitor 0.7309 CYP450 2C9 inhibitor Non-inhibitor 0.5985 CYP450 2D6 inhibitor Non-inhibitor 0.8796 CYP450 2C19 inhibitor Inhibitor 0.7386 CYP450 3A4 inhibitor Non-inhibitor 0.8296 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8687 Ames test AMES toxic 0.9107 Carcinogenicity Non-carcinogens 0.6594 Biodegradation Not ready biodegradable 0.9918 Rat acute toxicity 2.9777 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9758 hERG inhibition (predictor II) Non-inhibitor 0.9091
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- Kind
- Protein
- Organism
- Humans
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- Humans
- 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
- 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
- Humans
- 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
- 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
- Humans
- 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 un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- 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]
- Hedges L, Brown S, MacLeod AK, Vardy A, Doyle E, Song G, Moreau M, Yoon M, Osimitz TG, Lake BG: Metabolism of deltamethrin and cis- and trans-permethrin by human expressed cytochrome P450 and carboxylesterase enzymes. Xenobiotica. 2019 May;49(5):521-527. doi: 10.1080/00498254.2018.1474283. Epub 2018 Jun 4. [PubMed:29779438]
- Gong Y, Li T, Zhang L, Gao X, Liu N: Permethrin induction of multiple cytochrome P450 genes in insecticide resistant mosquitoes, Culex quinquefasciatus. Int J Biol Sci. 2013 Sep 5;9(9):863-71. doi: 10.7150/ijbs.6744. eCollection 2013. [PubMed:24155662]
Drug created on October 21, 2007 16:23 / Updated on October 21, 2020 01:55
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