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

• ChemBase ID: 4400
• Molecular Formular: C21H20Cl2O3
• Molecular Mass: 391.2877
• Monoisotopic Mass: 390.07894986
• SMILES: ClC(=CC1C(C1C(=O)OCc1cc(Oc2ccccc2)ccc1)(C)C)Cl
• Canonical SMILES: ClC(=CC1C(C1(C)C)C(=O)OCc1cccc(c1)Oc1ccccc1)Cl
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• IUPAC Traditional name: permethrin
• Brand Name: PerFoam; Acticin Cream; Elimite; Elimite Cream; Nix; Nix Cream Rinse
• Synonyms: Permethrin; permethrin; Permethrin; Permethrin (isomers) solution; Permethrin (isomers); 3-Phenoxybenzyle (1RS)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate; Ambush; Pounce; PERMETHRIN MIXTURES OF ISOMERS; 氯菊脂; 氯菊脂（异构体） 溶液; 氯菊脂; 氯菊脂（异构体）

Database IDs

• CAS Number: 52645-53-1
• EC Number: 258-067-9
• MDL Number: MFCD00041809
• Beilstein Number: 5765325
• PubChem SID: 46505374; 24871630; 24868001; 24869115; 24899290; 24869349; 160967832
• PubChem CID: 40326
• CHEBI ID: 34911
• ATC CODE: QP53AC04; P03AC04
• CHEMBL: 1525
• Chemspider ID: 36845
• DrugBank ID: DB04930
• KEGG ID: C14388
• Unique Ingredient Identifier: 509F88P9SZ
• Wikipedia Title: Permethrin

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.6960993
• LogD (pH = 7.4): 5.6960993
• Log P: 5.6960993
• Molar Refractivity: 114.2824 cm^3
• Polarizability: 40.698902 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.24
• LOG S: -6.75
• Solubility (Water): 6.91e-05 g/l

PROPERTIES

Physical Property

• Solubility: 6e-06 mg/mL at 20 oC [USDA PESTICIDE PROP DATABASE]; Insoluble (5.5 x 10^-3 ppm) in water
• Apperance: colourless crystals
• Melting Point: 34°C; 34-35 °C (pure)
• Boiling Point: 200°C; Very high (approximately 200 °C at 0.008 mmHg) (17); probably decomposes on heating.
• Flash Point: 10 °C; 2 °C; 35.6 °F; 50 °F
• Density: 1.19 g/cm3, solid; 1.19-1.27 at 20 °C (water = 1)
• Vapor Pressure: Very low (3.4 x 10-7 mm Hg at 25 °C), 0.045 mPa at 25 °C
• Hydrophobicity(logP): 6.50 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: 0°C, Protect from light
• RTECS: GZ1255000
• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T); Harmful (Xn)
• UN Number: 1230; 1648; 3077
• German water hazard class: 1; 2; 3
• Hazard Class: 3; 9
• Packing Group: 2; 3
• Risk Statements: 11-20/21/22-36-51/53; 11-23/24/25-39/23/24/25-50/53; 20/22-43-50/53; R:22
• Safety Statements: 13-24-36/37/39-60-61; 16-26-36/37-61; 16-36/37-45-61
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08; GHS09
• GHS Signal Word: Danger; Warning
• Main Hazard: Irritating to skin and eyes,; damaging to lungs
• GHS Hazard statements: H225-H301-H311-H331-H370-H410; H225-H302-H312-H319-H332-H411; H302-H317-H332-H410
• GHS Precautionary statements: P210-P260-P273-P280-P301 + P310-P311; P210-P273-P280-P305 + P351 + P338; P273-P280-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US); Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1230 3/PG 2; UN 1648 3/PG 2; UN 3077 9/PG 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Concentration: 100 ng/μL in acetonitrile; 1000 μg/mL in methanol
• Grade: analytical standard; PESTANAL®, analytical standard
• Packaging: ampule of 1 mL; ampule of 100 mg; ampule of 250 mg
• Description: mixture of cis and trans isomers
• Empirical Formula (Hill Notation): C21H20Cl2O3

DETAILS

MP Biomedicals - 02158977

Mixture of isomers
A weakly active Type I pyrethrin for use as a "negative" control for the inhibition of calcineurin (protein phosphatase 2B) by Type II pyrethrins.

DrugBank - DB04930

• Drug 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.
• Indication: For the treatment of infestation with Sarcoptes scabiei (scabies).
• Pharmacology: Permethrin, a pyrethroid, is active against a broad range of pests including lice, ticks, fleas, mites, and other arthropods.
• Toxicity: Oral, rat LD₅₀: 430 - 4000 mg/kg; skin, rabbit LD₅₀: 2000 mg/kg.
• Affected Organisms: Scabies (Sarcoptes scabei) and other insects
• Biotransformation: Rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.
• Absorption: Poorly absorbed through the skin.
• Elimination: Permethrin is rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.
• 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]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - 45893

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 45614

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

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