NAV

(S)-methoprene

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
(S)-methoprene
DrugBank Accession Number
DB11495
Background

Not Available

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 310.478
Monoisotopic: 310.250794955
Chemical Formula
C19H34O3
Synonyms
  • (7S)-Methoprene
  • isopropyl (2E,4E,7S)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
  • S-Methoprene
External IDs
  • ZR-2458
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Sesquiterpenoids
Direct Parent
Sesquiterpenoids
Alternative Parents
Fatty acid esters / Enoate esters / Monocarboxylic acids and derivatives / Dialkyl ethers / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl ether / Enoate ester / Ether / Farsesane sesquiterpenoid / Fatty acid ester
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
methoprene (CHEBI:39255)
Affected organisms
Not Available

Chemical Identifiers

UNII
4YIQ0A94UR
CAS number
65733-16-6
InChI Key
NFGXHKASABOEEW-GYMWBFJFSA-N
InChI
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+/t16-/m1/s1
IUPAC Name
propan-2-yl (2E,4E,7S)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
SMILES
[H]\C(C[C@@]([H])(C)CCCC(C)(C)OC)=C(\[H])/C(/C)=C(\[H])C(=O)OC(C)C

References

General References
  1. Henrick CA, Ko J, Nguyen J, Burleson J, Lindahl G, Van Gundy D, Edge JM: Investigation of the relationship between s-methoprene and deformities in anurans. J Am Mosq Control Assoc. 2002 Sep;18(3):214-21. [Article]
  2. Ritchie SA, Long S: Does S-methoprene affect oviposition by Aedes aegypti in an ovitrap? J Am Mosq Control Assoc. 2003 Jun;19(2):170-1. [Article]
  3. Gelbic I, Papacek M, Pokuta J: The effects of methoprene S on the aquatic bug Ilyocoris cimicoides (Heteroptera, Naucoridae). Ecotoxicology. 1994 Jun;3(2):89-93. doi: 10.1007/BF00143407. [Article]
  4. Ritchie SA, Asnicar M, Kay BH: Acute and sublethal effects of (S)-methoprene on some Australian mosquitoes. J Am Mosq Control Assoc. 1997 Jun;13(2):153-5. [Article]
  5. Horak IG, Fourie JJ, Stanneck D: Efficacy of slow-release collar formulations of imidacloprid/flumethrin and deltamethrin and of spot-on formulations of fipronil/(s)-- methoprene, dinotefuran/pyriproxyfen/permethrin and (s) -methoprene/amitraz/fipronil against Rhipicephalus sanguineus and Ctenocephalides felis felis on dogs. Parasit Vectors. 2012 Apr 22;5:79. doi: 10.1186/1756-3305-5-79. [Article]
  6. Chu KH, Wong CK, Chiu KC: Effects of the insect growth regulator (S)-methoprene on survival and reproduction of the freshwater cladoceran Moina macrocopa. Environ Pollut. 1997;96(2):173-8. [Article]
  7. Aubuchon MD, Mullen GR, Eubanks MD: Efficacy of broadcast and perimeter applications of S-methoprene bait on the red imported fire ant in grazed pastures. J Econ Entomol. 2006 Jun;99(3):621-5. [Article]
  8. Dhopeshwarkar AS, Jain S, Liao C, Ghose SK, Bisset KM, Nicholson RA: The actions of benzophenanthridine alkaloids, piperonyl butoxide and (S)-methoprene at the G-protein coupled cannabinoid CB(1) receptor in vitro. Eur J Pharmacol. 2011 Mar 1;654(1):26-32. doi: 10.1016/j.ejphar.2010.11.033. Epub 2010 Dec 21. [Article]
  9. Pfister K: Fipronil, amitraz and (S)-methoprene-a novel ectoparasiticide combination for dogs. Vet Parasitol. 2011 Jul 15;179(4):293. doi: 10.1016/j.vetpar.2011.03.039. [Article]
ChemSpider
1361490
ChEBI
39255
ChEMBL
CHEMBL1875086
ZINC
ZINC000002005163

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00307 mg/mLALOGPS
logP5.87ALOGPS
logP5.26Chemaxon
logS-5ALOGPS
pKa (Strongest Basic)-4.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area35.53 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity94.79 m3·mol-1Chemaxon
Polarizability38.25 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004u-0490000000-7480d36711a6676a28da
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1059000000-28bbd6e5f4d76956dc91
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0532-3191000000-977dc798654207a4e9db
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-009j-4950000000-b0fda47d7d4ac7f7db17
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-5290000000-7b4ce733cf0038dd6e2d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001r-9500000000-e551f983874283e08c15
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-204.7627832
predicted
DarkChem Lite v0.1.0
[M-H]-204.1066832
predicted
DarkChem Lite v0.1.0
[M-H]-195.01543
predicted
DeepCCS 1.0 (2019)
[M+H]+205.7813832
predicted
DarkChem Lite v0.1.0
[M+H]+205.4645832
predicted
DarkChem Lite v0.1.0
[M+H]+197.411
predicted
DeepCCS 1.0 (2019)
[M+Na]+205.3638832
predicted
DarkChem Lite v0.1.0
[M+Na]+204.2602832
predicted
DarkChem Lite v0.1.0
[M+Na]+203.3738
predicted
DeepCCS 1.0 (2019)

Drug created at February 26, 2016 17:22 / Updated at June 12, 2020 16:53