Art. -Nr.: HY-B0874

Alpha-Cypermethrin

Name: Alpha-Cypermethrin
Brand: MedChemExpress
SKU: HY-B0874
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(Synonyms: FMC 45497; Fendona; WL 85871)

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Alpha-Cypermethrin (FMC 45497; Fendona; WL 85871) is a type II pyrethroid insecticide. Alpha-Cypermethrin acts by delaying the inactivation of voltage-gated sodium channels, prolonging sodium tail currents, and triggering repetitive neural discharges. Alpha-Cypermethrin exhibits knockdown and lethal activity against target insects such as Musca domestica and Anopheles culicifacies. Alpha-Cypermethrin induces neurotoxicity in mammals, alters placental and fetal neurodevelopment, and causes acute mortality in fish. Alpha-Cypermethrin can be used in studies related to neurotoxicity, vector-borne diseases, and malaria.

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Reinheit: 99.66%
CAS. Nr.: 67375-30-8
Formel: C₂₂H₁₉Cl₂NO₃
Molecular Weight:416.30

Speicherung:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

Alpha-Cypermethrin Chemical Structure

CAS. Nr.: 67375-30-8

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Biologische Aktivität
- Beschreibung
- In Vitro
- In Vivo
- Clinical Trial
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
Help & FAQs
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Bioz

Biologische Aktivität

Beschreibung

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In Vitro

Alpha-Cypermethrin is mainly metabolized to cyclopropanecarboxylic acid via ester hydrolysis by liver microsomal preparations from rats, rabbits, and humans^[2].
Alpha-Cypermethrin shows no mutagenicity in in vitro tests against Salmonella typhimurium, Escherichia coli, and Saccharomyces cerevisiae^[2].
Alpha-Cypermethrin (48-96 h) exhibits low growth inhibitory activity against the freshwater alga Selenastrum capricornutum, with an EC₅₀ value greater than 100 µg/litre^[2].
Alpha-Cypermethrin (3 mg/litre) does not inhibit the growth of sewage bacteria in a closed in vitro system^[2].
Polyamide nylon bed nets treated by immersion with Alpha-Cypermethrin (25 mg/m²) exhibit knockdown and killing activity against Anopheles culicifacies, making them suitable for vector control applications^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Alpha-Cypermethrin (14.5 mg/kg; p.o.; daily; 4 weeks) induces cerebellar neurotoxicity in rats, reduces GABA levels and the activities of AChE, CAT, SOD and GPx respectively, and increases MDA levels^[1].
Alpha-Cypermethrin (35-798 mg/kg) exhibits moderate to high acute oral toxicity in CD mice, and induces typical poisoning symptoms of cyano-containing pyrethroids, including ataxia, choreoathetosis, salivation, and clonic convulsions^[2].

Alpha-cypermethrin (40-368 mg/kg; p.o.; single dose) exhibits moderate to high acute oral toxicity, low acute dermal toxicity, and moderate acute intraperitoneal toxicity when administered to Wistar rats with corn oil as the solvent, with its toxic symptoms consistent with those of cypermethrin-containing insecticides^[2].
Alpha-cypermethrin (0.4 g/m³; inhalation; single 4 h exposure) shows low acute inhalation toxicity in Fischer-344 rats^[2].
At low doses, Alpha-cypermethrin (25-800 mg/kg in feed; oral administration; daily; for 5 weeks) causes no obvious adverse effects in Wistar rats, but at high doses, it induces intoxication, growth retardation, alterations in blood biochemical parameters, and increased organ weights^[2].
At low doses of alpha-cypermethrin (20-540 mg/kg in feed; p.o.; daily; for 13 weeks), no adverse effects are observed in Wistar rats; only slight growth effects occur at medium doses; while toxic symptoms, growth retardation and mild neurodegeneration appear at high doses^[2].
For alpha-cypermethrin (dietary dose: 30-270 mg/kg; oral administration; daily; for 13 consecutive weeks), the no-observed-effect level (NOEL) is 90 mg/kg diet. At the high dose, dogs exhibit typical pyrethroid intoxication symptoms, but no detectable changes occur in physiological or pathological parameters^[2].
Alpha-cypermethrin (semi-occlusive percutaneous application; single dose; 24 h) causes only mild irritation to rabbit skin^[2].
Alpha-Cypermethrin (0.05% (v/v) in corn oil; 50% (m/m) in vaseline; guinea pig percutaneous GPMT with intradermal induction + topical application/topical challenge; single procedure; 7 d induction with 48 h application, 24 h after 14 d challenge) shows no skin sensitization in guinea pigs^[2].
Exposure to Alpha-Cypermethrin (0.3-10 mg/kg/day; oral administration; daily dosing; for 11 consecutive days (gestational days 6-16)) causes dose-dependent fetal growth restriction, alterations in placental morphology and gene expression, as well as changes in microglia and transcriptome of the fetal dorsal forebrain in pregnant CD1 mice^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

albino rats (adult male, 180-200 g)^[1]
Dosage:

14.5 mg/kg
Administration:

p.o.; daily; 4 weeks
Result:

Decreased GABA level to 0.6 mg/mL/g tissue.
Decreased acetylcholinesterase (AChE) activity to 48.2 mU/mg protein.
Decreased catalase (CAT) activity to 21 U/mg protein.
Decreased superoxide dismutase (SOD) activity to 33.7 U/mg protein.
Decreased glutathione peroxidase (GPx) activity to 33.4 mU/mg protein.
Increased malondialdehyde (MDA) level to 31.8 nmol/g tissue.
Disrupted cerebellar cortex structure, causing reduced numbers of Purkinje cells and granule cells, vacuolation in the granular layer, degeneration of Purkinje cell dendrites, and a loose molecular layer.

Animal Model:

CD^[2]
Dosage:

35 mg/kg (5% in corn oil); 762 mg/kg (40% in DMSO); 798 mg/kg (50% aqueous suspension)
Administration:

p.o.; single dose
Result:

Induced clinical signs of intoxication including ataxia, abasia, gait abnormalities, choreoathetosis, "tip-toe" walk, increased salivation, lacrimation, piloerection, tremor, and clonic convulsions.
Caused most mortalities within the first 3 hours; surviving animals recovered within 7 days.
Exhibited LD₅₀ values of 35 mg/kg for 5% in corn oil, 762 mg/kg for 40% in DMSO, and 798 mg/kg for 50% aqueous suspension.

Animal Model:

Wistar^[2]
Dosage:

79 mg/kg (5% in corn oil); >4000 mg/kg (40% in DMSO); >5000 mg/kg (50% aqueous suspension); 40-80 mg/kg (10% in corn oil); 368 mg/kg (20% in corn oil); 500 mg/kg (25% in DMSO); 339 mg/kg (10% in corn oil)
Administration:

p.o.; single dose; dermal; single 24-h exposure; i.p.; single dose
Result:

Induced clinical signs including clonic convulsions, piloerection, salivation, and splayed hind-leg gait via oral administration in corn oil, with LD₅₀ values of 79 mg/kg for 5% in corn oil, 40-80 mg/kg for 10% in corn oil, and 368 mg/kg for 20% in corn oil.
Exhibited far lower acute oral toxicity with LD₅₀ values >4000 mg/kg for 40% in DMSO and >5000 mg/kg for 50% aqueous suspension.
Caused no mortality or intoxication signs via single 24-h dermal exposure to 500 mg/kg.
Induced characteristic pyrethroid intoxication signs including ataxia, abasia, choreoathetosis, gait abnormalities, "tip-toe" walk, salivation via intraperitoneal administration at 339 mg/kg, with an LD₅₀ of 339 mg/kg.

Animal Model:

Fischer-344^[2]
Dosage:

0.4 g/m³
Administration:

inhalation; single 4-h exposure
Result:

Showed no signs of intoxication during a 14-day post-exposure observation period.
Revealed no effects via macroscopic lung examination.
Exhibited an acute LC₅₀ >0.4 g active ingredient/m³.

Animal Model:

Wistar^[2]
Dosage:

25 mg/kg diet; 100 mg/kg diet; 200 mg/kg diet; 400 mg/kg diet; 800 mg/kg diet
Administration:

p.o.; daily; 5 weeks
Result:

Caused no effects at 200 mg/kg diet or lower.
Induced decreased food intake, decreased body weight, and increased blood urea levels in males, plus increased liver (males only) and kidney weights in both sexes at 400 mg/kg diet.
Caused intoxication signs including abnormal gait, hypersensitivity, decreased food intake, decreased body weight, decreased blood protein levels, increased blood urea levels, and increased liver and kidney weights in both sexes, plus sparse axonal degeneration in the sciatic nerve in one severely intoxicated male at 800 mg/kg diet.

Animal Model:

Wistar^[2]
Dosage:

20 mg/kg diet; 60 mg/kg diet; 180 mg/kg diet; 540 mg/kg diet
Administration:

p.o.; daily; 13 weeks
Result:

Caused no effects at 60 mg/kg diet or lower.
Induced marginal decreased growth in males during week 1 and from week 10 onwards at 180 mg/kg diet.
Caused intoxication signs including abnormal gait with splayed hind limbs in 3 out of 20 males, decreased growth and food intake in both sexes, and sparse axonal degeneration in the sciatic nerve in two males at 540 mg/kg diet; no dose-related changes to haematology, clinical chemistry, or organ weights were observed.

Animal Model:

Beagle^[2]
Dosage:

30 mg/kg diet; 90 mg/kg diet; 270 mg/kg diet
Administration:

p.o.; daily; 13 weeks
Result:

Caused no effects at 90 mg/kg diet or lower.
Induced intoxication signs including whole body tremors, head nodding, "lip-licking", subduedness, ataxia, agitation, and high-stepping gait in all animals, with increasing intensity over the study at 270 mg/kg diet; no dose-related changes to food consumption, body weight gain, organ weights, ophthalmoscopy, haematology, clinical chemistry, urinalysis, gross pathology, or histopathology were observed.

Animal Model:

Guinea-pig^[2]
Dosage:

0.05% (v/v) in corn oil; 50% (m/m) in vaseline
Administration:

intradermal injection; single dose; topical application; single dose; topical challenge; single dose
Result:

Showed no skin sensitization reactions in test animals.

Animal Model:

CD1-IGS (female, 7 to 9 weeks old, mated with GAD67-GFP+/− knock-in males on CD1 background, pregnant developmental toxicity model)^[4]
Dosage:

0.3 mg/kg/day; 3 mg/kg/day; 10 mg/kg/day
Administration:

p.o.; daily; 11 days (gestational days 6-16)
Result:

Reduced fetal body weight by 4.9%, 6.1%, and 10.0% relative to control for the 0.3, 3, and 10 mg/kg doses, respectively; the 10 mg/kg dose reduction was statistically significant.
Reduced fetal dorsal forebrain volume in a dose-dependent manner, with significant effects at 3 mg/kg and 10 mg/kg.
Significantly reduced placental labyrinth zone relative area, and significantly increased junctional zone relative area at 3 mg/kg and 10 mg/kg.
Reduced labyrinth zone thickness by 5.6%, 10.8%, and 15.7% relative to control for the 0.3, 3, and 10 mg/kg doses, respectively; the 10 mg/kg reduction was statistically significant.
Significantly increased junctional zone thickness at 10 mg/kg.
Reduced placental sinusoidal area by 7.7%, 11.0%, and 10.2% relative to control for the 0.3, 3, and 10 mg/kg doses, respectively; reductions at 3 mg/kg and 10 mg/kg were statistically significant.
Increased placental junctional zone glycogen cell number by 50.4%, 41.7%, and 74.1% relative to control for the 0.3, 3, and 10 mg/kg doses, respectively; the 10 mg/kg increase was statistically significant.
Reduced placental Lox gene expression by 56.2%, 67.8%, and 68.8% relative to control for the 0.3, 3, and 10 mg/kg doses, respectively, with all reductions statistically significant.
Increased placental Depp1 gene expression in a dose-dependent manner, with a statistically significant increase at 10 mg/kg.
Significantly increased placental junctional zone collagen content at 10 mg/kg.
Induced a dose-dependent shift of fetal dorsal forebrain microglia from ramified to ameboid morphology, with significant increases in ameboid microglia at all doses.
Significantly increased multivacuolated microglia at 3 mg/kg and 10 mg/kg.
Identified 1,018 differentially expressed genes in dorsal forebrain (3 mg/kg dose), with significant downregulation of cAMP-mediated signaling and synaptogenesis signaling pathway.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase A549
NCT01329991	Plexxikon\|		2011-05	PHASE1

Chemical Information

CAS. Nr. 67375-30-8
Appearance Solid
Molecular Weight 416.30
Formel C₂₂H₁₉Cl₂NO₃
Color White to off-white
SMILES

O=C([C@@H]1C(C)(C)[C@@H]1/C=C(Cl)\Cl)O[C@@H](C#N)C2=CC=CC(OC3=CC=CC=C3)=C2
Synonyms

FMC 45497; Fendona; WL 85871
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

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COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Elsawy H, et al. Protective effect of α-lipoic acid against α-cypermethrin-induced changes in rat cerebellum. Journal of chemical neuroanatomy. 2017 Dec;86:52-58.

[2]. World Health Organization. Alpha-cypermethrin[M]. World Health Organization, 1992.

[3]. Abbas N, et al. Alpha-Cypermethrin Resistance in Musca domestica: Resistance Instability, Realized Heritability, Risk Assessment, and Insecticide Cross-Resistance. Insects. 2023 Feb 26;14(3):233. [Content Brief]

[4]. Elser BA, et al. Maternal α-cypermethrin and permethrin exert differential effects on fetal growth, placental morphology, and fetal neurodevelopment in mice. Toxicological sciences : an official journal of the Society of Toxicology. 2025 Sep 01;207(1):91-108.

[5]. Shires SW. Toxicity of a new pyrethroid insecticide, WL85871, to rainbow trout. Bull Environ Contam Toxicol. 1985 Jan;34(1):134-7.

[6]. Ansari MA, et al. Bio-efficacy and operational feasibility of alphacypermethrin (Fendona) impregnated mosquito nets to control rural malaria in northern India. Journal of vector borne diseases. 2003;40(1-2):33-42.

Calculators

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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Alpha-Cypermethrin

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