253300
Deltamethrin
Synthetic type II pyrethroid. Potent inhibitor of calcineurin. Causes an increase in neurotransmitter release at synapses, and increases intrasynaptosomal Ca2+ levels.
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Synonym(s):
Deltamethrin, (S)-α-Cyano-3-phenoxybenzyl(1R)- cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate, (S)-α-Cyano-3-phenoxybenzyl(1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate
Empirical Formula (Hill Notation):
C22H19Br2NO3
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Quality Level
Assay
≥98% (TLC)
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
color
white
solubility
ethanol: 1 mg/mL
DMSO: 15 mg/mL
shipped in
ambient
storage temp.
2-8°C
InChI
1S/C22H19Br2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18+,20-/m0/s1
InChI key
OWZREIFADZCYQD-NSHGMRRFSA-N
General description
Synthetic type II pyrethroid insecticide. Potent inhibitor of calcineurin (protein phosphatase 2B, IC50 = 100 pM). May also have varied effects on ion channels. Causes an increase in neurotransmitter release at synapses and also increases intrasynaptosomal Ca2+ levels.
Synthetic type II pyrethroid. Potent inhibitor of calcineurin (protein phosphatase 2B; IC50 = 100 pM). May also have varied effects on ion channels. Causes an increase in neurotransmitter release at synapses, and increases intrasynaptosomal Ca2+ levels.
Biochem/physiol Actions
Cell permeable: no
Primary Target
protein phosphatase 2B
protein phosphatase 2B
Product does not compete with ATP.
Reversible: no
Target IC50: 100 pM against calcineurin (protein phosphatase 2B)
Warning
Toxicity: Highly Toxic (H)
Reconstitution
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C. Avoid acid or alkali conditions.
Other Notes
Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
Richter, A., et al. 1995. Biochem. Pharmacol.49, 367.
Enan, E., and Matsumura, F. 1993. Biochem. Pharmacol. 45, 703.
Enan, E., and Matsumura, F. 1992. Biochem. Pharmacol.43, 1777.
Narahasi, T. 1992. Trends Pharmacol. Sci.13, 236.
Enan, E., and Matsumura, F. 1993. Biochem. Pharmacol. 45, 703.
Enan, E., and Matsumura, F. 1992. Biochem. Pharmacol.43, 1777.
Narahasi, T. 1992. Trends Pharmacol. Sci.13, 236.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1
WGK
WGK 3
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Regulatory Information
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E Enan et al.
Biochemical pharmacology, 45(3), 703-710 (1993-02-09)
We have investigated the effects of a type II pyrethroid insecticide, deltamethrin, on changes in the protein phosphorylation pattern associated with neurotransmitter release in rat brain synaptosomal preparations. Deltamethrin was found to stimulate directly the activity of the protein kinase
T Narahashi
Trends in pharmacological sciences, 13(6), 236-241 (1992-06-01)
The mechanisms of action of neuroactive insecticides on the nervous system has been studied for many years. It is now well established that severe neurological symptoms of poisoning with pyrethroids and DDT in mammals and insects are the result of
A Richter et al.
Biochemical pharmacology, 49(3), 367-373 (1995-01-31)
The ability of the immunosuppressive agent FK506 to affect growth of the epidermal growth factor-receptor (EGF-R) overexpressing cell line, A431, was compared with that of the structurally unrelated immunosuppressive compound, cyclosporin A (CyA). Both were shown to inhibit growth, although
E Enan et al.
Biochemical pharmacology, 43(8), 1777-1784 (1992-04-15)
The inhibitory action of synthetic pyrethroids and some chlorinated hydrocarbon insecticides on the neural calcium-calmodulin-dependent protein phosphatase, calcineurin, was studied using one radiotracer and two colorimetric methods. It was found that all insecticidal Type II pyrethroids (cypermethrin, deltamethrin and fenvalerate)
Guey-Ying Liao et al.
SLAS discovery : advancing life sciences R & D, 28(3), 88-94 (2023-02-27)
Deficiencies in brain-derived neurotrophic factor (BDNF) have been linked to several brain disorders, making compounds that can boost neuronal BDNF synthesis attractive as potential therapeutics. However, a sensitive and quantitative BDNF assay for high-throughput screening (HTS) is still missing. Here
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