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Details

Stereochemistry ACHIRAL
Molecular Formula C12H8Cl6O
Molecular Weight 380.909
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENDRIN

SMILES

[H][C@]12[C@@H]3C[C@@H]([C@H]4O[C@@H]34)[C@@]1([H])[C@@]5(Cl)C(Cl)=C(Cl)[C@]2(Cl)C5(Cl)Cl

InChI

InChIKey=DFBKLUNHFCTMDC-GKRDHZSOSA-N
InChI=1S/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2/t2-,3+,4-,5+,6-,7+,10-,11+

HIDE SMILES / InChI

Molecular Formula C12H8Cl6O
Molecular Weight 380.909
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Endrin is an organochlorine pesticide used as a non-systemic insecticide, acaricide, and rodenticide for protecting grain. As a central spasmodic agent, endrin is highly toxic to humans and skin resorption is possible. Endrin is rapidly metabolized by animals and does not accumulate in fat to the same extent as other compounds with similar structures. Endrin is also damaging to the liver, kidneys and central nervous system.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
The acute oral LD50 of Endrin is in the range of 3 mg/kg body weight in monkeys to 36 mg/kg in guinea pigs.
Route of Administration: Oral
In Vitro Use Guide
Endrin inhibits adipocyte differentiation by selectively altering expression pattern of CCAAT/enhancer binding protein-alpha in 3T3-L1 cells. Endrin's inhibitory effect was effective only when the pesticide was present in the medium during the first 48 h after exposure of 3T3-L1 cells to adipogenic inducers. Immunoblots analysis revealed that endrin caused a dose-dependent, selective inhibition of the intracellular levels of CCAAT enhancer binding protein (C/EBP)alpha without altering the expression patterns of C/EBPbeta or C/EBPdelta along the differentiation. Endrin inhibited the normal decrease in nuclear factor-kappaB-DNA binding observed as cells are acquiring the adipocyte phenotype at a late stage of differentiation. It was suggested that endrin inhibits adipocyte differentiation through the specific suppression of C/EBPalpha.
Substance Class Chemical
Record UNII
OB9NVE7YCL
Record Status Validated (UNII)
Record Version