Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H20Cl2O3 |
Molecular Weight | 391.288 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)OCC2=CC=CC(OC3=CC=CC=C3)=C2
InChI
InChIKey=RLLPVAHGXHCWKJ-HKUYNNGSSA-N
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/t17-,19-/m0/s1
Molecular Formula | C21H20Cl2O3 |
Molecular Weight | 391.288 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
(+)-cis-Permethrin is the active isomer of the insecticide permethrin. Topical formulations of permethrin (a mixture of isomers) are used for the treatment of lice infestations and scabeis. (+)-cis-Permethrin prolongs the activation of sodium channels in parasites and disrupts the function of neurons, leading to paralysis and death of the insects.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2362985 |
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Target ID: CHEMBL2362984 |
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Target ID: CHEMBL2362985 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25390654 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | ELIMITE Approved UseELIMITE (permethrin) 5% Cream is indicated for the treatment of infestation with Sarcoptesscabiei (scabies). Launch Date6.2000641E11 |
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Curative | NIX Approved UseTo treat head lice. Launch Date6.3391682E11 |
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Curative | NIX Approved UseA synthetic pyrethrin derivative; like natural pyrethrins, acts as a neurotoxin by depolarizing the nerve cell membrane. Disrupts the sodium channel current by which membrane repolarization is regulated resulting in fatal paralysis of the nerves in the exoskeletal respiratory muscles of susceptible arthropods, including lice and mites. Launch Date5.12611189E11 |
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Curative | NIX Approved UseA synthetic pyrethrin derivative; like natural pyrethrins, acts as a neurotoxin by depolarizing the nerve cell membrane. Disrupts the sodium channel current by which membrane repolarization is regulated resulting in fatal paralysis of the nerves in the exoskeletal respiratory muscles of susceptible arthropods, including lice and mites. Launch Date5.12611189E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
49.46 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768 |
460 mg/kg single, oral dose: 460 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029 |
10 mg/kg bw single, oral dose: 10 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN serum | Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
253 ng/mL |
143 g single, oral dose: 143 g route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
615 ng/mL |
143 g single, oral dose: 143 g route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
868 ng/mL |
143 g single, oral dose: 143 g route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
159 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768 |
46 mg/kg single, intravenous dose: 46 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PERMETHRIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
965 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768 |
460 mg/kg single, oral dose: 460 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.95 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029 |
10 mg/kg bw single, oral dose: 10 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN serum | Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
16.45 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029 |
10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
PERMETHRIN serum | Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.73 μg × h/mL |
143 g single, oral dose: 143 g route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
6.26 μg × h/mL |
143 g single, oral dose: 143 g route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768 |
46 mg/kg single, intravenous dose: 46 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PERMETHRIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
12.37 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768 |
460 mg/kg single, oral dose: 460 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.54 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029 |
10 mg/kg bw single, oral dose: 10 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN serum | Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.73 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029 |
10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
PERMETHRIN serum | Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.08 h |
143 g single, oral dose: 143 g route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.82 h |
143 g single, oral dose: 143 g route of administration: Oral experiment type: SINGLE co-administered: |
PERMETHRIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31248885 |
PERMETHRIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1 % 1 times / day multiple, topical Recommended Dose: 1 %, 1 times / day Route: topical Route: multiple Dose: 1 %, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: pediculosis Age Group: adult Sex: unknown Sources: |
Other AEs: Skin and subcutaneous conditions NEC... |
5 % 1 times / day multiple, topical Recommended Dose: 5 %, 1 times / day Route: topical Route: multiple Dose: 5 %, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: scabies Age Group: adult Sex: unknown Sources: |
Other AEs: Dystonia... |
200 ug/kg 1 times / day multiple, oral Recommended Dose: 200 ug/kg, 1 times / day Route: oral Route: multiple Dose: 200 ug/kg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: crusted scabies Age Group: adult Sex: unknown Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Skin and subcutaneous conditions NEC | 1 % 1 times / day multiple, topical Recommended Dose: 1 %, 1 times / day Route: topical Route: multiple Dose: 1 %, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: pediculosis Age Group: adult Sex: unknown Sources: |
|
Dystonia | 5 % 1 times / day multiple, topical Recommended Dose: 5 %, 1 times / day Route: topical Route: multiple Dose: 5 %, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: scabies Age Group: adult Sex: unknown Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
likely | ||||
likely | ||||
likely | ||||
likely | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes [Km 2.8 uM] | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
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Purification and preliminary characterization of permethrinase from a pyrethroid-transforming strain of Bacillus cereus. | 1993 Jul |
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Transfer efficiencies of pesticides from household flooring surfaces to foods. | 2003 Nov |
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Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection. | 2003 Nov-Dec |
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Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl. | 2004 |
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[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals]. | 2004 Apr |
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Determination of enantiomers of synthetic pyrethroids in water by solid phase microextraction - enantioselective gas chromatography. | 2004 Feb 25 |
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Neurological deficits induced by malathion, DEET, and permethrin, alone or in combination in adult rats. | 2004 Feb 27 |
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Microbial transformation of pyrethroid insecticides in aqueous and sediment phases. | 2004 Jan |
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Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes. | 2004 Jul 9 |
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Effectiveness of residual spraying of peridomestic ecotopes with deltamethrin and permethrin on Triatoma infestans in rural western Argentina: a district-wide randomized trial. | 2004 Mar |
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Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides. | 2005 |
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Diffusion of the synthetic pyrethroid permethrin into bed-sediments. | 2005 Jan 15 |
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HER-2/neu and CD117 (c-kit) overexpression in patients with pesticide exposure and extensive stage small cell lung carcinoma (ESSCLC). | 2005 Jun 9 |
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Rapid analysis of pyrethroids in whole urine by high-performance liquid chromatography using a monolithic column and off-line preconcentration in a restricted access material cartridge. | 2005 May |
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Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies. | 2005 Oct |
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Purification and characterization of a novel pyrethroid hydrolase from Aspergillus niger ZD11. | 2005 Sep 21 |
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Hydrolytic metabolism of pyrethroids by human and other mammalian carboxylesterases. | 2006 Feb 28 |
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Molecular cloning, purification, and biochemical characterization of a novel pyrethroid-hydrolyzing esterase from Klebsiella sp. strain ZD112. | 2006 Feb 8 |
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Laboratory and scaled up evaluation of cis-permethrin applied as a new ultra low volume formulation against Aedes aegypti (Diptera: Culicidae). | 2006 Jan |
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Enantioselective degradation and chiral stability of pyrethroids in soil and sediment. | 2006 Jul 12 |
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An intervention to reduce residential insecticide exposure during pregnancy among an inner-city cohort. | 2006 Nov |
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Enantiomeric differences in permethrin degradation pathways in soil and sediment. | 2006 Nov 29 |
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Method of analysis of a selected group of pyrethroids in soil samples using off-line flow-through extraction and on-column direct large-volume injection in reversed phase high performance liquid chromatography. | 2006 Sep |
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Permethrin may disrupt testosterone biosynthesis via mitochondrial membrane damage of Leydig cells in adult male mouse. | 2007 Aug |
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Pesticides and their metabolites in the homes and urine of farmworker children living in the Salinas Valley, CA. | 2007 Jul |
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An observational study of 127 preschool children at their homes and daycare centers in Ohio: environmental pathways to cis- and trans-permethrin exposure. | 2007 Jun |
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The in vitro metabolism of a pyrethroid insecticide, permethrin, and its hydrolysis products in rats. | 2007 Jun 25 |
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Synergism between cis-permethrin and benzoyl phenyl urea insect growth regulators against Aedes aegypti larvae. | 2007 Mar |
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Hydrolysis of pyrethroids by human and rat tissues: examination of intestinal, liver and serum carboxylesterases. | 2007 May 15 |
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Efficacy of permethrin cream and oral ivermectin in treatment of scabies. | 2007 Oct |
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Changes in pest infestation levels, self-reported pesticide use, and permethrin exposure during pregnancy after the 2000-2001 U.S. Environmental Protection Agency restriction of organophosphates. | 2008 Dec |
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Molecular cloning and characterization of a novel pyrethroid-hydrolyzing esterase originating from the Metagenome. | 2008 Dec 30 |
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Multimedia measurements and activity patterns in an observational pilot study of nine young children. | 2008 Jan |
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Permethrin may induce adult male mouse reproductive toxicity due to cis isomer not trans isomer. | 2008 Jun 27 |
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Mitigation assessment of vegetated drainage ditches for collecting irrigation runoff in California. | 2008 Mar-Apr |
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Neurobehavioral toxicology of pyrethroid insecticides in adult animals: a critical review. | 2008 Mar-Apr |
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Design of a compressed air modulator to be used in comprehensive multidimensional gas chromatography and its application in the determination of pesticide residues in grapes. | 2009 Apr 10 |
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Ability of four emergent macrophytes to remediate permethrin in mesocosm experiments. | 2009 Aug |
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In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. | 2009 Jan |
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Measuring pyrethroids in sediment pore water using matrix-solid phase microextraction. | 2009 Jan |
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American Healthy Homes Survey: a national study of residential pesticides measured from floor wipes. | 2009 Jun 15 |
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Evidence for dose-additive effects of pyrethroids on motor activity in rats. | 2009 Oct |
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Parallel metatranscriptome analyses of host and symbiont gene expression in the gut of the termite Reticulitermes flavipes. | 2009 Oct 15 |
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Effects of several pyrethroids on hepatic cytochrome P450 activities in rats. | 2010 Apr |
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Time-dependent integrity during storage of natural surface water samples for the trace analysis of pharmaceutical products, feminizing hormones and pesticides. | 2010 Apr 19 |
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In vitro dermal absorption of pyrethroid pesticides in human and rat skin. | 2010 Jul |
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Distribution and determinants of pesticide mixtures in cord serum using principal component analysis. | 2010 Jul 15 |
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Isotope dilution gas chromatography/mass spectrometry method for determination of pyrethroids in apple juice. | 2010 Mar |
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Current and historically used pesticides in residential soil from 11 homes in Atlanta, Georgia, USA. | 2010 May |
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Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids. | 2011 Sep 14 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/monograph/permethrin.html
Apply topically to hair and scalp as 1% lotion (cream rinse) or apply topically to skin as 5% cream.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25390654
To study effect of permethrin on sodium channel currents antennal lobe neurons of honeybees were used. Membrane currents were measured in the whole-cell configuration using a patch-clamp amplifier. Patch-clamp pipettes were pulled from borosilicate glass capillaries on a vertical pipette puller and then sylgard-coated to minimize pipette capacitance. The resistance of the recording electrode filled with intracellular solution ranged between 3 and 5 MΩ in standard extracellular solution. The liquid junction potential (<3 mV) was not corrected. Microelectrode offset potential was nulled before seal formation. After gigaseal formation and before membrane patch rupture, the resting holding potential was established at −80 mV and the residual microelectrode capacitance was nulled with a fast analog compensation circuit available on the amplifier. In the whole cell configuration, capacitance and series resistance were maximally compensated for. Passive leak currents and residual linear capacitative currents were subtracted using a P/4 protocol. Current-voltage relationships were generated by step depolarizations to test potentials from −80 to +70 mV (10 mV increment) from −80 mV. To assess pyrethroid effects, a single stimulation protocol consisted of a 3 ms depolarization from a holding potential of −80 mV to −10 mV. Trains of repetitive depolarizations at 13 Hz were also used and consisted of ten short stimulations (3 ms to −10 mV) with an interpulse duration (time lapse between the initiation of two successive pulses) of 78 ms. Permethrin was applied at a concentration of 10 uM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 14:10:23 UTC 2023
by
admin
on
Thu Jul 06 14:10:23 UTC 2023
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Record UNII |
GC30YV53C8
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Record Status |
Validated (UNII)
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Record Version |
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-
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EPA PESTICIDE CODE |
209500
Created by
admin on Thu Jul 06 14:10:23 UTC 2023 , Edited by admin on Thu Jul 06 14:10:23 UTC 2023
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GC30YV53C8
Created by
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61949-76-6
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DTXSID0038338
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52341-33-0
Created by
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263-346-3
Created by
admin on Thu Jul 06 14:10:23 UTC 2023 , Edited by admin on Thu Jul 06 14:10:23 UTC 2023
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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