CAS 52645-53-1|Elimite|permethrin|permethrin|Acticin Cream|Nix|Permethrin|Elimite Cream|PerFoam|(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate|Nix Cream Rinse...

General Information

Structure

Molecular Formula

C₂₁H₂₀Cl₂O₃

Molecular Mass

391.2877

Exact Mass

390.07894986

Charge

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

Canonic Smiles

ClC(=CC1C(C1(C)C)C(=O)OCc1cccc(c1)Oc1ccccc1)Cl

Isomeric Smiles

ClC(=CC1C(C1C(=O)OCc1cc(Oc2ccccc2)ccc1)(C)C)Cl

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

5.6960993

LogD (pH = 7.4)

5.6960993

Log P

5.6960993

Molar Refractivity

114.2824

Polarizability

40.698902

Polar Surface Area

35.53

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

6.24

LOG S

-6.75

Solubility (Water)

6.91e-05 g/l

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Brand Name

ElimiteNixNix Cream RinsePerFoamActicin CreamElimite Cream

Synonyms

permethrinPermethrinAmbushPERMETHRIN MIXTURES OF ISOMERSPounce3-Phenoxybenzyle (1RS)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylatePermethrin氯菊脂Permethrin (isomers) solution氯菊脂（异构体）溶液Permethrin (isomers)氯菊脂氯菊脂（异构体）

IUPAC Traditional name

permethrin

IUPAC name

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

Names and Identifiers

Registration numbers

MDL Number

MFCD00041809

PubChem SID

248716304650537424899290248680011609678322486934924869115

Beilstein Number

CAS Number

EC Number

PubChem CID

Wikipedia Title

DrugBank ID

KEGG ID

Chemspider ID

ATC CODE

CHEBI ID

Unique Ingredient Identifier

509F88P9SZ

CHEMBL

1525

Registration numbers

Properties

Physical Property

6e-06 mg/mL at 20 oC [USDA PESTICIDE PROP DATABASE]

Insoluble (5.5 x 10^-3 ppm) in water

6.50 [HANSCH,C ET AL. (1995)]

1.19-1.27 at 20 °C (water = 1)

1.19 g/cm3, solid

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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.

Wikipedia

Permethrin

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

45614

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

45893

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Commercial Catalog

• Academic Data

Names and Identifiers

• Brand Name

• Synonyms

• IUPAC Traditional name

• IUPAC name

Registration numbers

• MDL Number

• PubChem SID

• Beilstein Number

• CAS Number

• EC Number

• PubChem CID

• Wikipedia Title

• DrugBank ID

• KEGG ID

• Chemspider ID

• ATC CODE

• CHEBI ID

• Unique Ingredient Identifier

• CHEMBL

Registration numbers

Properties

• Physical Property

• Product Information

• Safety Information

Related Proteins

Molecular Spectra

Molecule Details

• MP Biomedicals

• Wikipedia

• DrugBank

• Sigma Aldrich

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Brand Name

ElimiteNixNix Cream RinsePerFoamActicin CreamElimite Cream

Synonyms

IUPAC Traditional name

permethrin

IUPAC name

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

MDL Number

Beilstein Number

CAS Number

Wikipedia Title

Unique Ingredient Identifier

509F88P9SZ

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

45614

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

45893

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

From Data Sources

• 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

Physical Property

6e-06 mg/mL at 20 oC [USDA PESTICIDE PROP DATABASE]

Insoluble (5.5 x 10^-3 ppm) in water

6.50 [HANSCH,C ET AL. (1995)]

1.19-1.27 at 20 °C (water = 1)

1.19 g/cm3, solid

Melting Point

34-35 °C (pure)

34°C

Vapor Pressure

Very low (3.4 x 10-7 mm Hg at 25 °C), 0.045 mPa at 25 °C

Apperance

colourless crystals

Flash Point

2 °C

35.6 °F

50 °F

10 °C

Product Information

Safety Information

Nature polluting (N)

Flammable (F)

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Flammable gases, category 1

Flammable aerosols, categories 1,2

Flammable liquids, categories 1,2,3

Self-reactive substances and mixtures, Types B,C,D,E,F

Pyrophoric liquids, category 1

Pyrophoric solids, category 1

Self-heating substances and mixtures

Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3

Organic peroxides, Types B,C,D,E,F

Acute toxicity (oral, dermal, inhalation), categories 1,2,3

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

H225-H301-H311-H331-H370-H410

P210-P260-P273-P280-P301+P310-P311

16-36/37-45-61

Molecule

ID:4400