Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C19H34O3 |
| Molecular Weight | 310.4715 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(C)(C)CCCC(C)C\C=C\C(C)=C\C(=O)OC(C)C
InChI
InChIKey=NFGXHKASABOEEW-LDRANXPESA-N
InChI=1S/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14+
| Molecular Formula | C19H34O3 |
| Molecular Weight | 310.4715 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 2 |
| Optical Activity | ( + / - ) |
Methoprene is a pesticide that acts as a juvenile hormone agonist. Although developed initially against insects, it has since been shown to have toxic effects on larval and adult crustaceans. Methoprene was one of the several pesticides applied to the Western Long Island Sound (WLIS) watershed area during the summer of 1999. Methoprene is a racemic mixture of two enantiomers (R and S in a ratio of 1:1). The activity of the compound as a juvenile hormone is restricted to the S enantiomer. Recent data have been describing the male sexual enhancement after methoprene treatment in Anastrepha fraterculus (Diptera: Tephritidae). It has been shown, that a sustained response doesn`t not fade away after sexual maturation, thus the potential benefits of using methoprene to increase the efficiency of the sterile insect technique, which is an environmentally safe method to control this fruit pest, have been proposed.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: juvenile hormone Sources: https://www.ncbi.nlm.nih.gov/pubmed/21676752 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Identification of plant compounds that disrupt the insect juvenile hormone receptor complex. | 2015-02-10 |
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| Retinoic acids induce neurosteroid biosynthesis in human glial GI-1 Cells via the induction of steroidogenic genes. | 2009-12 |
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| Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. | 2006-08 |
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| Regulation of JH epoxide hydrolase versus JH esterase activity in the cabbage looper, Trichoplusia ni, by juvenile hormone and xenobiotics. | 2005-05 |
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| Regulation of differentiating pig preadipocytes by retinoic acid. | 2005-01 |
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| Crystal structure of the heterodimeric complex of LXRalpha and RXRbeta ligand-binding domains in a fully agonistic conformation. | 2003-09-15 |
|
| Both retinoic-acid-receptor- and retinoid-X-receptor-dependent signalling pathways mediate the induction of the brown-adipose-tissue-uncoupling-protein-1 gene by retinoids. | 2000-01-01 |
Patents
| Substance Class |
Chemical
Created
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admin
on
Edited
Wed Apr 02 08:18:26 GMT 2025
by
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on
Wed Apr 02 08:18:26 GMT 2025
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| Record UNII |
8B830OJ2UX
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| Record Status |
Validated (UNII)
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WHO-VATC |
QP53AX28
Created by
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EPA PESTICIDE CODE |
105401
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WHO-VATC |
QP53AX78
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METHOPRENE
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758655
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m7325
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SUB08853MIG
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5366546
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8B830OJ2UX
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D008726
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6926
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254-993-2
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methoprene
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41205-06-5
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100000081434
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6382
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CHEMBL1875086
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40596-69-8
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34839
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C175133
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DTXSID8032627
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| Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
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ACTIVE MOIETY |