Prallethrin | CAS#23031-36-9 | pyrethroid insecticide

MedKoo Cat#: 461644 | Name: Prallethrin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Prallethrin is a pyrethroid insecticide. Prallethrin 1.6% w/w liquid vaporizer is a repellent insecticide which is generally used for the control of mosquitoes in the household. Prallethrin significantly increased MUC5AC expression in human airway NCI-H292 epithelial cells.

Chemical Structure

Prallethrin

CAS#23031-36-9

Theoretical Analysis

MedKoo Cat#: 461644

Name: Prallethrin

CAS#: 23031-36-9

Chemical Formula: C19H24O3

Exact Mass: 300.1725

Molecular Weight: 300.40

Elemental Analysis: C, 75.97; H, 8.05; O, 15.98

Price and Availability

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100mg	USD 550.00

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Synonym

Prallethrin; S 4068; S-4068; S4068;

IUPAC/Chemical Name

2-methyl-4-oxo-3-(prop-2-yn-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

InChi Key

SMKRKQBMYOFFMU-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H24O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h1,9,14,16-17H,8,10H2,2-6H3

SMILES Code

O=C(C1C(C)(C)C1/C=C(C)\C)OC2C(C)=C(CC#C)C(C2)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Prallethrin is a pyrethroid insecticide.

In vitro activity:

This study demonstrated effect of allethrin and prallethrin, and the mechanism involved, on the mucin expressions in human airway epithelial cells. In human airway NCI-H292 epithelial cells, the effects of allethrin and prallethrin and its signaling pathway for airway mucin, especially MUC5AC, were investigated by reverse transcriptase-polymerase chain reaction (RT-PCR), real-time PCR, and enzyme-linked immunosorbent assay (ELISA). The mechanism of allethrin and prallethrin-induced MUC5AC expression in airway epithelial cells was studied in terms of reactive oxygen species (ROS) by flow cytometry analysis. Allethrin and prallethrin significant increased MUC5AC expression in human airway NCI-H292 epithelial cells. Reference: Biochem Biophys Res Commun. 2018 Sep 3;503(1):316-322. https://pubmed.ncbi.nlm.nih.gov/29885834/

In vivo activity:

Prallethrin caused significant increase in LPO and decrease in superoxide dismutase, glutathione peroxidase and glutathione reduced. Consistent histological changes were found in the kidney of prallethrin treatment. Co-administration of essential oil attenuated the prallethrin induced renal toxicity and oxidative stress by decreasing LPO in kidney, creatinine, urea and uric acid levels in serum. In addition, superoxide dismutase, glutathione peroxidase activity and glutathione reduced level were increased in kidney in prallethrin-essential oil groups. Reference: Asian Pac J Trop Med. 2014 Sep;7S1:S506-13. https://pubmed.ncbi.nlm.nih.gov/25312175/

Preparing Stock Solutions

The following data is based on the product molecular weight 300.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Na HG, Kim YD, Choi YS, Bae CH, Song SY. Allethrin and prallethrin stimulates MUC5AC expression through oxidative stress in human airway epithelial cells. Biochem Biophys Res Commun. 2018 Sep 3;503(1):316-322. doi: 10.1016/j.bbrc.2018.06.022. Epub 2018 Jun 12. PMID: 29885834. 2. Mossa AT, Refaie AA, Ramadan A, Bouajila J. Antimutagenic effect of Origanum majorana L. essential oil against prallethrin-induced genotoxic damage in rat bone marrow cells. J Med Food. 2013 Dec;16(12):1101-7. doi: 10.1089/jmf.2013.0006. Epub 2013 Nov 6. PMID: 24195751. 3. Refaie AA, Ramadan A, Mossa AT. Oxidative damage and nephrotoxicity induced by prallethrin in rat and the protective effect of Origanum majorana essential oil. Asian Pac J Trop Med. 2014 Sep;7S1:S506-13. doi: 10.1016/S1995-7645(14)60282-0. PMID: 25312175. 4. Mossa AT, Refaie AA, Ramadan A, Bouajila J. Amelioration of prallethrin-induced oxidative stress and hepatotoxicity in rat by the administration of Origanum majorana essential oil. Biomed Res Int. 2013;2013:859085. doi: 10.1155/2013/859085. Epub 2013 Dec 5. PMID: 24381944; PMCID: PMC3870102.

In vitro protocol:

In vivo protocol:

1. Refaie AA, Ramadan A, Mossa AT. Oxidative damage and nephrotoxicity induced by prallethrin in rat and the protective effect of Origanum majorana essential oil. Asian Pac J Trop Med. 2014 Sep;7S1:S506-13. doi: 10.1016/S1995-7645(14)60282-0. PMID: 25312175. 2. Mossa AT, Refaie AA, Ramadan A, Bouajila J. Amelioration of prallethrin-induced oxidative stress and hepatotoxicity in rat by the administration of Origanum majorana essential oil. Biomed Res Int. 2013;2013:859085. doi: 10.1155/2013/859085. Epub 2013 Dec 5. PMID: 24381944; PMCID: PMC3870102.

1: Mossa AT, Refaie AA, Ramadan A, Bouajila J. Antimutagenic effect of Origanum majorana L. essential oil against prallethrin-induced genotoxic damage in rat bone marrow cells. J Med Food. 2013 Dec;16(12):1101-7. doi: 10.1089/jmf.2013.0006. Epub 2013 Nov 6. PubMed PMID: 24195751. 2: Refaie AA, Ramadan A, Mossa AT. Oxidative damage and nephrotoxicity induced by prallethrin in rat and the protective effect of Origanum majorana essential oil. Asian Pac J Trop Med. 2014 Sep;7S1:S506-13. doi: 10.1016/S1995-7645(14)60282-0. PubMed PMID: 25312175. 3: Mossa AT, Refaie AA, Ramadan A, Bouajila J. Amelioration of prallethrin-induced oxidative stress and hepatotoxicity in rat by the administration of Origanum majorana essential oil. Biomed Res Int. 2013;2013:859085. doi: 10.1155/2013/859085. Epub 2013 Dec 5. PubMed PMID: 24381944; PubMed Central PMCID: PMC3870102. 4: Senthilkumaran S, Menezes RG, Balamurugan N, Thirumalaikolundusubramanian P. Prallethrin poisoning that taxes the brain. J Anaesthesiol Clin Pharmacol. 2014 Jan;30(1):116-7. doi: 10.4103/0970-9185.125726. PubMed PMID: 24574614; PubMed Central PMCID: PMC3927277. 5: Chandra A, Dixit MB, Banavaliker JN. Prallethrin poisoning: A diagnostic dilemma. J Anaesthesiol Clin Pharmacol. 2013 Jan;29(1):121-2. doi: 10.4103/0970-9185.105820. PubMed PMID: 23494161; PubMed Central PMCID: PMC3590517. 6: Botnariu G, Birsan C, Podoleanu C, Moldovan C, Stolnicu S, Chiriac A. Skin necrosis caused by prallethrin-A worldwide used insecticide. Environ Toxicol Pharmacol. 2016 Apr;43:103-4. doi: 10.1016/j.etap.2016.03.002. Epub 2016 Mar 9. PubMed PMID: 26987111. 7: Bashini MM, Rajavel VP, Rahulan V. Complications and management of attempted suicide by intrapleural injection of prallethrin. Indian J Crit Care Med. 2016 Mar;20(3):182-4. doi: 10.4103/0972-5229.178184. PubMed PMID: 27076732; PubMed Central PMCID: PMC4810898. 8: Bhaskar EM, Moorthy S, Ganeshwala G, Abraham G. Cardiac conduction disturbance due to prallethrin (pyrethroid) poisoning. J Med Toxicol. 2010 Mar;6(1):27-30. doi: 10.1007/s13181-010-0032-7. PubMed PMID: 20195813; PubMed Central PMCID: PMC3550445. 9: Cooperband MF, Golden FV, Clark GG, Jany W, Allan SA. Prallethrin-induced excitation increases contact between sprayed ultralow volume droplets and flying mosquitoes (Diptera: Culicidae) in a wind tunnel. J Med Entomol. 2010 Nov;47(6):1099-106. PubMed PMID: 21175059. 10: Narendra M, Kavitha G, Helah Kiranmai A, Raghava Rao N, Varadacharyulu NC. Chronic exposure to pyrethroid-based allethrin and prallethrin mosquito repellents alters plasma biochemical profile. Chemosphere. 2008 Sep;73(3):360-4. doi: 10.1016/j.chemosphere.2008.05.070. Epub 2008 Jul 26. PubMed PMID: 18657844. 11: Sirak-Wizeman M, Faiman R, Al-Jawabreh A, Warburg A. Control of phlebotomine sandflies in confined spaces using diffusible repellents and insecticides. Med Vet Entomol. 2008 Dec;22(4):405-12. doi: 10.1111/j.1365-2915.2008.00762.x. PubMed PMID: 19120969. 12: Narendra M, Bhatracharyulu NC, Padmavathi P, Varadacharyulu NC. Prallethrin induced biochemical changes in erythrocyte membrane and red cell osmotic haemolysis in human volunteers. Chemosphere. 2007 Apr;67(6):1065-71. Epub 2007 Jan 22. PubMed PMID: 17240419. 13: Seki T, Ito S, Adachi H, Yoshioka K, Hosokawa S, Yoshitake A, Miyamoto J, Kurata Y. [One-year chronic dietary toxicity study of d.d-T80-prallethrin in rats]. J Toxicol Sci. 1987 Nov;12(4):397-428. Japanese. PubMed PMID: 3449642. 14: Hou FX, Yu T, Yang HF. [Teratogenic effect of R-d-trans-prallethrin on rats]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2008 Apr;26(4):241-2. Chinese. PubMed PMID: 18724904. 15: Ramesh A, Vijayalakshmi A. Monitoring of allethrin, deltamethrin, esbiothrin, prallethrin and transfluthrin in air during the use of household mosquito repellents. J Environ Monit. 2001 Feb;3(2):191-3. PubMed PMID: 11354726. 16: Al-Damegh MA. Toxicological impact of inhaled electric mosquito-repellent liquid on the rat: a hematological, cytokine indications, oxidative stress and tumor markers. Inhal Toxicol. 2013 Apr;25(5):292-7. doi: 10.3109/08958378.2013.781251. PubMed PMID: 23614730. 17: Clark GG, Golden FV, Allan SA, Cooperband MF, McNelly JR. Behavioral responses of two dengue virus vectors, Aedes aegypti and Aedes albopictus (Diptera: Culicidae), to DUET and its components. J Med Entomol. 2013 Sep;50(5):1059-70. PubMed PMID: 24180111. 18: Katsuda Y, Leemingsawat S, Thongrungkiat S, Prummonkol S, Samung Y, Kanzaki T, Watanabe T, Kahara T. Control of mosquito vectors of tropical infectious diseases: (2) pyrethroid susceptibility of Aedes aegypti ( l) collected from different sites in Thailand. Southeast Asian J Trop Med Public Health. 2008 Mar;39(2):229-34. PubMed PMID: 18564707. 19: Farajollahi A, Williams GM. An open-field efficacy trial using AquaDuet via an ultra-low volume cold aerosol sprayer against caged Aedes albopictus. J Am Mosq Control Assoc. 2013 Sep;29(3):304-8. PubMed PMID: 24199509. 20: Adedeji AA, Ahmed IA, Akinwunmi M, Aina SA, Tikare O, Adeboye AF, Badmos SO, Adedeji KA, Fehintola FA, Amoo AO. Use and effectiveness of commercial flit-spray insecticides in control of mosquito population in Sagamu, Southwest Nigeria. Afr J Med Med Sci. 2012 Jun;41(2):197-203. PubMed PMID: 23185919.