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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O3
Molecular Weight 328.4452
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PYRETHRIN I

SMILES

CC(C)=C[C@@H]1[C@@H](C(=O)O[C@H]2CC(=O)C(C\C=C/C=C)=C2C)C1(C)C

InChI

InChIKey=ROVGZAWFACYCSP-VUMXUWRFSA-N
InChI=1S/C21H28O3/c1-7-8-9-10-15-14(4)18(12-17(15)22)24-20(23)19-16(11-13(2)3)21(19,5)6/h7-9,11,16,18-19H,1,10,12H2,2-6H3/b9-8-/t16-,18+,19+/m1/s1

HIDE SMILES / InChI

Description

Pyrethrins are natural insecticides derived from chrysanthemum flowers containing a mixture of six components: pyrethrin I, cinerin I, jasmolin I, pyrethrin II, cinerin II, and jasmolin II. Pyrethrin I is one of the two pyrethrins, natural organic compounds with potent insecticidal activity. It is an ester of ( )-trans-chrysanthemic acid with (S)-(Z)-pyrethrolone. Pyrethrins induce a toxic effect in insects when they penetrate the cuticle and reach the nervous system. Pyrethrins bind to sodium channels that occur along the length of nerve cells. Sodium channels are responsible for nerve signal transmission along the length of the nerve cell by permitting the flux of sodium ions. When pyrethrins bind to sodium channels, normal function of the channels is obstructed thereby resulting in hyperexcitation of the nerve cell and, consequently, a loss of function of the nerve cell. The shutdown of the insect nervous system and death are most often the consequences of insect exposure to pyrethrins.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
11.7 µM [IC50]
6.9 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Pyrethrin I

PubMed

Sample Use Guides

In Vivo Use Guide
Humans: oral intake of 0.3mg
Route of Administration: Oral
In Vitro Use Guide
Pyrethrin I showed an IC50 of 6.9 uM against Trypanosoma brucei rhodesiense.