Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01337)
Name
Permethrin
Synonyms    Click to Show/Hide the Synonyms of This API
Permethrin; 52645-53-1; Ambush; Transpermethrin; Pounce; Elimite; Imperator; UNII-509F88P9SZ; NRDC-143; (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate; (+)-trans-Permethrin; Permethrine; Permetrina; Acticin; Ambushfog; Corsair; Dragnet; Ectiban; Kaleait; Kestrel; Outflank; Perigen; Permasect; Perthrine; Stomoxin; Stomozan; Coopex; Eksmin; Picket; Expar; Kafil; Kavil; Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester; Anomethrin N; Ridect pour-on; CHEBI:34911; 509F88P9SZ; 1RS cis-Permethrin; 52341-32-9; 1RS,cis-Permethrin; NCGC00159390-02; 1RS-trans-Permethrin; Kudos; Transpermethrin [ISO]; (+-)-cis-Permethrin; DSSTox_CID_2292; 3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; trans-(+-)-Permethrin; DSSTox_RID_76537; DSSTox_GSID_22292; 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl ester; Permethrinum; S-3151; Chinetrin; Ecsumin; Efmethrin; Indothrin; Lyclear; NRDC 146; NRDC 148; Quamlin; Stomoxi; Cosair; Exmin; Exsmin; Ipitox; SBP-1513; (+-)-trans-Permethrin; trans-Permethrin D6 (dimethyl D6); Permethrine,c&t; (+-)-cis-Fmc 33297; Diffusil H; Insorbcid MP; Stomoxin P; Outflank-stockade; Perigen W; Dragnet FT; Picket G; Permethrin,racemic; [3-(phenyloxy)phenyl]methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; Mitin BC; Permanone 80; Permasect-25EC; FMC 35171; SMR000778043; Kestrel (pesticide); LE 79-519; Antiborer 3768; CAS-52645-53-1; Bematin 987; NRDC 143; Permethrinum [Latin]; Permetrin (Hungarian); Permitrene (Hungarian); Permetrina [Portuguese]; Caswell No. 652BB; FMC 33297; NIA 33297; PP 557; Permethrine [ISO-French]; BRN 4153590; Permethrn; Permethrin (isomers) solution; SBP-1513TEC; Permethrin [USAN:INN:BAN]; AI3-29296; CCRIS 2001; ICI-PP 557; MP79; SBP 15131TEC; 3-Phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate; HSDB 6790; m-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate; BW-21-Z; S 3151; 82523-59-9; Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, (1R-trans)-; OMS 1821; EINECS 258-067-9; Elimite (TN); FMC 41655; EPA Pesticide Chemical Code 109701; JF 7065; BRN 2063148; WL 43479; AI3-29158; Permethrin (USAN/INN); Hemoglobin atlanta-coventry; CHEMBL1525; SCHEMBL26543; 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-(+-)-; MLS001332525; MLS001332526; Permethrin [ANSI:BSI:ISO]; Permethrin cis/trans ~ 1:1; Permethrin, analytical standard; DTXSID8022292; SCHEMBL15218274; HMS2232L22; HMS3264N07; HMS3369D10; Pharmakon1600-01504932; 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-phenoxyphenyl)methyl ester, (1R-cis)-; HY-B0887; Tox21_111627; Tox21_201586; Tox21_300691; BBL005484; MFCD00041809; NSC760105; s6461; STL135986; AKOS005746953; CCG-213703; DB04930; KS-5079; MCULE-1256227237; NSC-760105; (+-)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate; (3-Phenoxyphenyl)methyl 3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropanecarboxylate; 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester; 3-Phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate; 3-Phenoxybenzyl (1RS,3RS;1RS,3SR)-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; Permethrin 10 microg/mL in Cyclohexane; 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; (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; Permethrin (isomers), analytical standard; DB-052153; Total Permethrin 100 microg/mL in Acetone; 541-EP2274983A1; 541-EP2275422A1; 541-EP2280009A1; 541-EP2292608A1; 541-EP2298076A1; 541-EP2298077A1; 541-EP2301353A1; 541-EP2305031A1; 541-EP2305034A1; 541-EP2305035A1; 541-EP2305658A1; 541-EP2305662A1; 541-EP2308857A1; 541-EP2308858A1; 541-EP2311816A1; 541-EP2311817A1; 541-EP2314583A1; FT-0630656; ST50975270; Permethrin, PESTANAL(R), analytical standard; C14388; D05443; AB00918441_05; 645P531; 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-dichlorovinyl)-2,2-dimethyl-cyclopropanecarboxylate; (3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxyl ate; 3-phenoxybenzyl (1RS)-cis,trans-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-Phenoxyphenyl)methyl (+/-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; 93389-07-2; Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, 3-phenoxybenzyl ester, (+-)-, (cis,trans)-; Permethrin (isomers) solution, 100 mug/mL in acetonitrile, PESTANAL(R), analytical standard; Permethrin (isomers) solution, cis/trans isomers, 1000 mug/mL in methanol, analytical standard
Clinical Status
Approved
PubChem CID
40326
Formula
C21H20Cl2O3
Canonical SMILES
CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
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3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 391.3 Topological Polar Surface Area 35.5
XlogP 6.5 Complexity 521
Heavy Atom Count 26 Rotatable Bond Count 7
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Permethrin 1% lotion Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Balsam Canada; Cetyl Alcohol; Citric Acid; Fd&C Yellow No 6; Fragrance; Hydrolyzed Animal Protein; Hydroxyethylcellulose; Polyoxyethylene 10 Cetyl Ether; Propylene Glycol; Stearalkonium Chloride; Water; Isopropyl Alcohol; Methylparaben; Propylparaben
                   Dosage Form Lotion
                   Company Insight Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [1]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [3]
Stearalkonium chloride DIG Info Dynamin-1 (IC50 = 19610 nM) [4]
Propylparaben sodium DIG Info Estrogen receptor alpha (EC50 = 38200 nM) [5]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [6]
Cetyl alcohol DIG Info Breast cancer FM3A cells (EC50 = 1600 nM) [7]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [8]
          Permethrin 5% cream Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated Hydroxytoluene; Carbomer Homopolymer Type B; Fractionated Coconut Oil; Glycerin; Glyceryl Monostearate; Isopropyl Myristate; Lanolin Alcohols; Mineral Oil; Polyoxyethylene Cetyl Ethers; Purified Water; Sodium Hydroxide; Formaldehyde
                   Dosage Form Cream
                   Company Rpk Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [9]
Lauric acid DIG Info Free fatty acid receptor 1 (EC50 = 758.58 nM) [10]
Glyceryl monostearate DIG Info Prostate cancer LNCaP cells (IC50 > 100000 nM) [11]
Polyoxyl 20 cetyl ether DIG Info Cholesterol 25-hydroxylase (EC50 = 211.5 uM) [12]
References
1 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 PubChem BioAssay data set.
4 Long chain amines and long chain ammonium salts as novel inhibitors of dynamin GTPase activity. Bioorg Med Chem Lett. 2004 Jun 21; 14(12):3275-8.
5 Discovery of natural estrogen receptor modulators with structure-based virtual screening. Bioorg Med Chem Lett. 2013 Jun 1; 23(11):3329-33.
6 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.
7 Synthesis and notable antimalarial activity of acyclic peroxides, L-(alkyldioxy)-L-(methyldioxy)cyclododecanes. J Med Chem. 2002 Mar 14; 45(6):1374-8.
8 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
9 Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem. 2009 Apr 15; 17(8):3207-11.
10 Development and Characterization of a Potent Free Fatty Acid Receptor 1 (FFA1) Fluorescent Tracer. J Med Chem. 2016 May 26; 59(10):4849-58.
11 Lignanamides and nonalkaloidal components of Hyoscyamus niger seeds. J Nat Prod. 2002 Feb; 65(2):206-9.
12 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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