Permethrin

Details

• Internal ID: 4539061c-ae41-470c-aece-6bd8a8fced2f
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters > Pyrethroids
• IUPAC Name: (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• SMILES (Canonical): CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
• SMILES (Isomeric): CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
• 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
• InChI Key: RLLPVAHGXHCWKJ-UHFFFAOYSA-N
• Popularity: 6,519 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀Cl₂O₃
• Molecular Weight: 391.30 g/mol
• Exact Mass: 390.0789499 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 6.11
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 52645-53-1
• Ambush
• Transpermethrin
• Pounce
• Elimite
• 1RS,cis-Permethrin
• Permethrine
• Permethrinum
• Acticin
• Corsair
• Dragnet
• Ectiban
• Imperator
• Kestrel
• Lyclear
• Outflank
• Perigen
• Permasect
• Permetrina
• Perthrine
• Quamlin
• Stomoxi
• Stomoxin
• Coopex
• Cosair
• Dragon
• Eksmin
• Picket
• Exmin
• Expar
• Kafil
• Kavil
• Kudos
• 1RS-trans-Permethrin
• Transpermethrin [ISO]
• Ridect pour-on
• (+-)-cis-Permethrin
• Insorbcid MP
• Perigen W
• Permethrin,racemic
• trans-(+-)-Permethrin
• Mitin BC
• Permanone 80
• (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• Chinetrin
• Ecsumin
• Efmethrin
• Indothrin
• NRDC 146
• NRDC 148
• Exsmin
• Ipitox
• Caswell No. 652BB
• 52341-32-9
• (+-)-trans-Permethrin
• Permethrine,c&t
• (+-)-cis-Fmc 33297
• Diffusil H
• Stomoxin P
• Outflank-stockade
• Dragnet FT
• Picket G
• Activyl tick plus
• Permasect-25EC
• FMC 35171
• Permit
• Pramex
• Kestrel (pesticide)
• UNII-509F88P9SZ
• Antiborer 3768
• Bematin 987
• CCRIS 2001
• ICI-PP 557
• NRDC 143
• SBP 15131TEC
• Permethrinum [Latin]
• DTXSID8022292
• CHEBI:34911
• Permetrin (Hungarian)
• HSDB 6790
• Permitrene (Hungarian)
• Permetrina [Portuguese]
• trans-Permethrin D6 (dimethyl D6)
• EINECS 258-067-9
• FMC 33297
• FMC 41655
• NIA 33297
• PP 557
• Hemoglobin atlanta-coventry
• Permethrine [ISO-French]
• EPA Pesticide Chemical Code 109701
• NSC-760105
• JF 7065
• BRN 2063148
• BRN 4153590
• (+)-trans-Permethrin
• Ambushfog
• Kaleait
• Stomozan
• WL 43479
• SBP-1513TEC
• Permethrin [USAN:INN:BAN]
• AI3-29296
• Anomethrin N
• DTXCID102292
• MP79
• BW-21-Z
• S 3151
• 509F88P9SZ
• OMS 1821
• 1RS cis-Permethrin
• 3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
• C21H20Cl2O3
• 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl ester
• Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester
• NRDC-143
• Permethrinum (Latin)
• NSC 760105
• NCGC00159390-02
• AI3-29158
• (+-)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
• 3-Phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
• m-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
• 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester
• 3-Phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
• 82523-59-9
• Cooper
• Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, cis-(+-)-
• Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, trans-(+-)-
• Cyclopropanecarboxylicacid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester,(1R,3S)-rel-
• Permethrin (ANSI:BSI:ISO)
• Permethrin [ANSI:BSI:ISO]
• NRDC 147
• S-3151
• PerFoam
• SBP-1513
• Acticin Cream
• Elimite Cream
• Nix Cream Rinse
• (3-Phenoxyphenyl)methyl 3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropanecarboxylate
• [3-(phenyloxy)phenyl]methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
• 3-Phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
• 3-Phenoxybenzyl(+-)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate
• m-Phenoxybenzyl (+-)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
• m-Phenoxybenzyl (+1)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
• (3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
• 3-(Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
• 52341-33-0
• 93389-07-2
• Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-,(3-phenoxyphenyl)methyl ester, (1R,3R)-rel-
• Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-,(3-phenoxyphenyl)methyl ester, (1R,3S)-rel-
• Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, 3-phenoxybenzyl ester, (+-)-, (cis,trans)-
• SMR000778043
• LE 79-519
• CAS-52645-53-1
• C21-H20-Cl2-O3
• Permethrn
• 3-Phenoxybenzyl-cis,trans-(1RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
• Permethrin, (cis-(+-))-Isomer
• Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, (1R-trans)-
• Permethrin, (trans-(+-))-Isomer
• RU 22090
• Hb Atlanta-coventry
• Elimite (TN)
• AI3-29190
• Hb At-Co
• Permethrin (isomers)
• ( -)-cis-Permethrin
• OUTFLANK STOCKADE
• Permethrin (USAN/INN)
• PERMETHRIN (IARC)
• PS758_SUPELCO
• cispermethrin (cis isomer)
• D0K8MP
• PERMETHRIN (MART.)
• 3-Phenoxybenzyle (1RS)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate
• biopermethrin (trans isomer)
• CHEMBL1525
• SCHEMBL26543
• MLS001332525
• MLS001332526
• Permethrin [USAN:BAN:INN]
• Permethrin cis/trans ~ 1:1
• Permethrin, analytical standard
• NDRC 143
• 3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
• SCHEMBL15218274
• BW 21-Z
• P03AC04
• RLLPVAHGXHCWKJ-UHFFFAOYSA-N
• HMS2232L22
• HMS3264N07
• HMS3369D10
• Pharmakon1600-01504932
• (3-Phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
• (3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-dichloroethenyl)-2,2-bis(trideuteriomethyl)cyclopropane-1-carboxylate
• HY-B0887
• SBP 1513
• Tox21_111627
• Tox21_201586
• Tox21_300691
• MFCD00041809
• NSC760105
• s6461
• STL135986
• COMPONENT OF ACTIVYL TICK PLUS
• VECTRA 3D COMPONENT PERMETHRIN
• AKOS005746953
• CCG-213703
• CS-O-10185
• DB04930
• KS-5079
• Permethrin 1000 microg/mL in Acetone
• PERMETHRIN (EMA EPAR VETERINARY)
• Permethrin (including cis- and trans-)
• Permethrin 10 microg/mL in Cyclohexane
• USEPA/OPP Pesticide Code: 109701
• NCGC00159390-00
• NCGC00159390-04
• NCGC00159390-05
• NCGC00159390-06
• NCGC00159390-07
• NCGC00159390-08
• NCGC00159390-09
• NCGC00159390-10
• NCGC00159390-11
• NCGC00159390-12
• NCGC00159390-13
• NCGC00159390-14
• NCGC00254599-01
• NCGC00259135-01
• Permethrin 100 microg/mL in Cyclohexane
• PERMETHRIN COMPONENT OF VECTRA 3D
• LS-58636
• LS-58640
• Permethrin (isomers), analytical standard
• Total Permethrin 100 microg/mL in Acetone
• ACTIVYL TICK PLUS COMPONENT PERMETHRIN
• FT-0630656
• Permethrin, PESTANAL(R), analytical standard
• D05443
• AB00918441_05
• Permethrin is known as a pyrethroid insecticide.
• EN300-19628849
• MIXTURE OF CIS AND TRANS PERMETHRIN ISOMERS
• Q411635
• J-523915
• Permethrin (25:75), EuropePharmacopoeia (EP) Reference Standard
• (1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclo-propanecarboxylate
• 3-phenoxybenzyl 2-(2,2-dichlorovinyl)3,3-dimethylcyclopropanecarboxylate
• (+/-)-3-PHENOXYBENZYL 3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
• (3-Phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-carboxylate
• (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
• (3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropanecarboxylate
• (3-phenoxyphenyl)methyl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylate
• 3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
• M-PHENOXYBENZYL (+/-)-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
• m-phenoxybenzyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate
• Permethrin for system suitability, EuropePharmacopoeia (EP) Reference Standard
• (3-Phenoxyphenyl)methyl (+/-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
• 3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYLCYCLOPROPANE CARBOXYLIC ACID, (3-PHENOXY-PHENYL)METHYL ESTER
• 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid, (3-phenoxyphenyl)methyl ester
• Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, cis-(.+.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6137	61.37%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.9211	92.11%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.9309	93.09%
OATP1B3 inhibitior	+	0.9543	95.43%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9583	95.83%
P-glycoprotein inhibitior	-	0.7519	75.19%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	+	0.6338	63.38%
CYP2C9 substrate	+	0.5905	59.05%
CYP2D6 substrate	-	0.8659	86.59%
CYP3A4 inhibition	-	0.8296	82.96%
CYP2C9 inhibition	-	0.5985	59.85%
CYP2C19 inhibition	+	0.7386	73.86%
CYP2D6 inhibition	-	0.8796	87.96%
CYP1A2 inhibition	+	0.7309	73.09%
CYP2C8 inhibition	+	0.7245	72.45%
CYP inhibitory promiscuity	+	0.8687	86.87%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6289	62.89%
Carcinogenicity (trinary)	Non-required	0.5111	51.11%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.8046	80.46%
Skin irritation	-	0.8094	80.94%
Skin corrosion	-	0.9150	91.50%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7886	78.86%
Micronuclear	-	0.6284	62.84%
Hepatotoxicity	+	0.5533	55.33%
skin sensitisation	+	0.7158	71.58%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	-	0.6333	63.33%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	+	0.7839	78.39%
Acute Oral Toxicity (c)	II	0.7456	74.56%
Estrogen receptor binding	+	0.7398	73.98%
Androgen receptor binding	+	0.7376	73.76%
Thyroid receptor binding	+	0.6352	63.52%
Glucocorticoid receptor binding	+	0.8238	82.38%
Aromatase binding	-	0.6599	65.99%
PPAR gamma	-	0.7016	70.16%
Honey bee toxicity	+	0.9768	97.68%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.9200	92.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	14125.4 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	22387.2 nM	Potency	via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	39810.7 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	5623.4 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.37%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	96.77%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.81%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.67%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.76%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.01%	94.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.49%	94.45%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	89.75%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.50%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.01%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.60%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	85.81%	94.73%
CHEMBL240	Q12809	HERG	85.19%	89.76%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.05%	96.95%
CHEMBL226	P30542	Adenosine A1 receptor	83.54%	95.93%
CHEMBL2581	P07339	Cathepsin D	83.05%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	82.96%	91.19%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.10%	99.15%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	81.15%	92.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.21%	95.89%

Plants that contains it

• Myristica fragrans

Cross-Links

• PubChem: 40326
• NPASS: NPC320287
• ChEMBL: CHEMBL1525