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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28O5
Molecular Weight 372.4547
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of PYRETHRIN II

SMILES

COC(=O)C(\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=VJFUPGQZSXIULQ-XIGJTORUSA-N
InChI=1S/C22H28O5/c1-7-8-9-10-15-14(3)18(12-17(15)23)27-21(25)19-16(22(19,4)5)11-13(2)20(24)26-6/h7-9,11,16,18-19H,1,10,12H2,2-6H3/b9-8-,13-11+/t16-,18+,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H28O5
Molecular Weight 372.4547
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 2
Optical Activity UNSPECIFIED

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. 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. Pyrethrin II has strong activity against Plasmodium falciparum.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Pyrethrins/piperonyl butoxide

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Apply to completelly wet infested areas, leave on 10 min & wash with large amount of warm water Use fine toothed comb to remove lice and egg from hair Do not exceed 2 consecutive applications within 24 hr Retreat in 7-10 days
Route of Administration: Topical
In Vitro Use Guide
Pyrethrin II showed an IC50 of 4.0 uM against Plasmodium falciparum
Substance Class Chemical
Record UNII
5N9245585U
Record Status Validated (UNII)
Record Version