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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H25NO3
Molecular Weight 375.4602
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYPHENOTHRIN, (+)-TRANS-

SMILES

CC(C)=C[C@@H]1[C@@H](C(=O)O[C@H](C#N)C2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C

InChI

InChIKey=FJDPATXIBIBRIM-VSKRKVRLSA-N
InChI=1S/C24H25NO3/c1-16(2)13-20-22(24(20,3)4)23(26)28-21(15-25)17-9-8-12-19(14-17)27-18-10-6-5-7-11-18/h5-14,20-22H,1-4H3/t20-,21-,22+/m1/s1

HIDE SMILES / InChI

Molecular Formula C24H25NO3
Molecular Weight 375.4602
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://onlinelibrary.wiley.com/doi/10.1002/ps.2780110214/full | https://www.ncbi.nlm.nih.gov/pubmed/2449265

Cyphenothrin, (+)-trans- (d,d,trans-cyphenothrin) is the type II pyrethroid insecticide, acting by contact poisoning Cyphenothrin, (+)-trans- is used in public health against flies, mosquitoes, cockroaches, etc. Cyphenothrin is the ISO common name for a racemic mixture of 4 pairs of diastereoisomers, designated as (±)-α-cyano-3- phenoxybenzyl (±)-cis-trans- chrysanthemate. The name Cyphenothrin, (+)-trans- refers to an enantio-enriched mixture, comprised mainly of the single stereoisomer (S)-α-cyano-3- phenoxybenzyl (1R, 3R)-2,2-dimethyl-3-(2-methylprop-1-enyl) cyclopropanecarboxylate, with only small proportions of the other stereoisomers, as defined by the WHO specification. Cyphenothrin, (+)-trans- is almost insoluble in water but highly soluble in organic solvents, such as hexane, ethanol, acetone, toluene etc. Cyphenothrin, (+)-trans- stable under normal storage conditions but is readily hydrolyzed in water at higher pH and is sensitive to light. Cyphenothrin, (+)-trans- has a low potential for bioaccumulation due to hydrolysis, photolysis and metabolism in water, soil and in biota. The data for toxicology of Cyphenothrin, (+)-trans- partly rely on studies conducted with cyphenothrin. Cyphenothrin, (+)-trans- generally shows low mammalian toxicity and is not a sensitizer in the Buehler and is not irritating to the rabbit eye and skin. There was no evidence of carcinogenicity in the rat or mouse. There was no evidence of mutagenic responses in bacterial, micronucleus or sister chromatid exchange tests. In a 2-generation reproduction study in the rat, no reproductive effects were observed at any dose level. There was no evidence of teratogenicity or developmental effects in rats or rabbits, although there was a decrease in maternal weight gain and a consequential decrease in rat offspring viability at the high dose tested. Cyphenothrin, (+)-trans- is very toxic to Daphnia magna and fish but it has a low toxicity to bobwhite quails. On the basis of the one-year dog study, a NOEL of 16.8 to 19.6 mg/kg bw/d is established by the Swiss Office of Public Health. The Cyphenothrin, (+)-trans- TC was classified as moderately toxic (Class 3) in Switzerland and, although it has not been classified by the International Programme on Chemical Safety (IPCS), this organization has classified the closely related cyphenothrin (1R-isomers) as Class II, moderately hazardous.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ZAP AK

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Characteristics of the prolonged inhibition produced by a range of pyrethroids in the rat hippocampus.
1990 May
Patents

Patents

Sample Use Guides

Rat NOAEL = 300 ppm 16.8 mg/kg bw/day (male); 19.6 mg/kg bw/day (female) Mouse NOAEL = 500 mg/m³ (male, female).
Route of Administration: Oral
In Vitro Use Guide
Experiments were performed using the mouse neuroblastoma cell line NIE-115. Three main effects of the cyphenothrin (25 uM) was found: (1) the peak amplitude of the sodium current increased; (2) the declining phase of the sodium current during depolarization was greatly slowed down resuilting in a marked residual current towards the end of tlhe 15 ms pulse; and (3) after repolarization of the membrane to the holding potential a large, slowly decaying sodium tail current remained.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:03:42 GMT 2023
Edited
by admin
on Sat Dec 16 05:03:42 GMT 2023
Record UNII
K18840IATQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYPHENOTHRIN, (+)-TRANS-
Common Name English
GOKILAHT S
Brand Name English
D,D,TRANS-CYPHENOTHRIN
Common Name English
RU-29208
Code English
D?D-T-CYPHENOTHRIN [JAN]
Common Name English
D-D-T-CYPHENOTHRIN
Brand Name English
CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPEN-1-YL)-, (S)-CYANO(3-PHENOXYPHENYL)METHYL ESTER, (1R,3R)-
Common Name English
Code System Code Type Description
FDA UNII
K18840IATQ
Created by admin on Sat Dec 16 05:03:42 GMT 2023 , Edited by admin on Sat Dec 16 05:03:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID901111588
Created by admin on Sat Dec 16 05:03:42 GMT 2023 , Edited by admin on Sat Dec 16 05:03:42 GMT 2023
PRIMARY
CAS
64312-65-8
Created by admin on Sat Dec 16 05:03:42 GMT 2023 , Edited by admin on Sat Dec 16 05:03:42 GMT 2023
PRIMARY
PUBCHEM
12877168
Created by admin on Sat Dec 16 05:03:42 GMT 2023 , Edited by admin on Sat Dec 16 05:03:42 GMT 2023
PRIMARY