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
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
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21786822 |
11.7 µM [IC50] | ||
Target ID: CHEMBL612348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21786822 |
6.9 µM [IC50] | ||
Target ID: CHEMBL360 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10552664 |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Pyrethrin I Approved UseThis medication is used to treat current and active lice infestations. |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16257148
Curator's Comment: also used topically http://reference.medscape.com/drug/rid-klout-shampoo-pyrethrins-piperonyl-butoxide-topical-343499
Humans: oral intake of 0.3mg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21786822
Pyrethrin I showed an IC50 of 6.9 uM against Trypanosoma brucei rhodesiense.
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EPA PESTICIDE CODE |
69008
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SUB15056MIG
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121-21-1
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C009119
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PYRETHRIN I
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100000078891
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m9345
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pyrethrin I
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METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
SUBSTANCE RECORD