Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H37N3O4 |
Molecular Weight | 479.6111 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC34N(CC[C@@]3(C)O)C[C@@]1(C[C@@]5(CNC6=C5C=CC7=C6OC=CC(C)(C)O7)C2(C)C)N(C)C4=O
InChI
InChIKey=DYVLXWPZFQQUIU-WGNDVSEMSA-N
InChI=1S/C28H37N3O4/c1-23(2)10-12-34-21-18(35-23)8-7-17-20(21)29-15-26(17)14-27-16-31-11-9-25(5,33)28(31,22(32)30(27)6)13-19(27)24(26,3)4/h7-8,10,12,19,29,33H,9,11,13-16H2,1-6H3/t19-,25+,26-,27+,28-/m0/s1
Derquantel is a so-called spiroindole, is obtained from fermentation extracts of Penicillium simplicissimum, a particular species of soil fungi. This drug is used in veterinary under brand name Startect, in combination with abamectin against several gastrointestinal roundworms that affect sheep. At the recommended therapeutic dose derquantel is highly effective against Haemonchus spp, Cooperia spp, and Trichostrongylus spp, including those resistant to most classic anthelmintics (benzimidazoles, levamisole, macrocyclic lactones). However it has a lower and variable efficacy against Ostertagia spp (= Teladorsagia), and is basically ineffective against Oesophagostomum spp and Trichuris spp, other important gastrointestinal worms of sheep. It is also ineffective against lungworms and other roundworms that infect sheep outside the gastrointestinal system. Derquantel is a nicotinic cholinergic antagonist: it blocks cholinergic neuromuscular transmission. The effect on the worms is that they are paralyzed and die or are expelled.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Nicotinic acetylcholine receptors of parasitic nematodes Sources: https://www.ncbi.nlm.nih.gov/pubmed/24497826 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | STARTECT Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Field efficacy and safety of an oral formulation of the novel combination anthelmintic, derquantel-abamectin, in sheep in New Zealand. | 2010 Jun |
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Differences in efficacy of monepantel, derquantel and abamectin against multi-resistant nematodes of sheep. | 2011 Jul |
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Efficacy of a combined oral formulation of derquantel-abamectin against the adult and larval stages of nematodes in sheep, including anthelmintic-resistant strains. | 2011 Sep 27 |
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Resistance of Haemonchus sp. to monepantel and reduced efficacy of a derquantel / abamectin combination confirmed in sheep in NSW, Australia. | 2016 Sep 15 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23523993
A two-micropipette current-clamp technique was used to study electrophysiological effects of the anthelmintics on: (1) acetylcholine responses in somatic muscle and; (2) on l-glutamate responses in pharyngeal preparations. On somatic muscle, derquantel (0.1-30μM) produced a potent (IC50 0.22, CI 0.18-0.28μM) reversible antagonism of acetylcholine depolarizations. Abamectin (0.3μM) produced a slow onset inhibition of acetylcholine depolarizations. It was compared effects of abamectin and derquantel on muscle preparations pretreated for 30 min with these drugs. The effect of the combination was significantly greater than the predicted additive effect of both drugs at higher acetylcholine concentrations. On the pharynx, application of derquantel produced no significant effect by itself or on responses to abamectin and l-glutamate. Abamectin increased the input conductance of the pharynx (EC50 0.42, CI 0.13-1.36μM). It was demontrsated that abamectin and derquantel interact at nicotinic acetylcholine receptors on the somatic muscle and suggested synergism can occur.
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ACTIVE MOIETY