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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
Structure of DERQUANTEL

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

HIDE SMILES / InChI
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Nicotinic acetylcholine receptors of parasitic nematodes
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
STARTECT

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Field efficacy and safety of an oral formulation of the novel combination anthelmintic, derquantel-abamectin, in sheep in New Zealand.
2010 Jun
Differences in efficacy of monepantel, derquantel and abamectin against multi-resistant nematodes of sheep.
2011 Jul
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
Resistance of Haemonchus sp. to monepantel and reduced efficacy of a derquantel / abamectin combination confirmed in sheep in NSW, Australia.
2016 Sep 15
Patents

Patents

Sample Use Guides

veterinary (in sheep): Oral (drench): 2 mg/kg
Route of Administration: Oral
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.
Name Type Language
DERQUANTEL
INN   USAN  
USAN   INN  
Official Name English
(1S,6R,7R,9S,11R)-6-HYDROXY-4',4',6,10,10,13-HEXAMETHYL-9',10'-DIHYDRO-4'H-SPIRO(3,13-DIAZATETRACYCLO(5.5.2.0(SUP 1,9).0(SUP 3,7))TETRADECANE-11,8'-(1,4)DIOXEPINO(2,3-G)INDOL)-14-ONE
Systematic Name English
PF-00520904
Code English
DERQUANTEL [USAN]
Common Name English
(1'R,5'AS,7'R,8'AS,9'AR)-1'-HYDROXY-1',4,4,8',8',11'-HEXAMETHYL-2',3',8'A,9,9',10-HEXAHYDROSPIRO(4H,8H-(1,4)DIOXEPINO(2,3-G)INDOLE-8,7'(8'H)-(5H,6H-5A,9A)(IMINOMETHANO)(1H)CYCLOPENTA(F)INDOLIZIN)-10'-ONE
Common Name English
SPIRO(4H,8H-(1,4)DIOXEPINO(2,3-G)INDOLE-8,7'(8'H)-(5H,6H-5A,9A)(IMINOMETHANO)(1H)CYCLOPENT(F)INDOLIZIN)-10'-ONE, 2',3',8'A,9,9',10-HEXAHYDRO-1'-HYDROXY-1',4,4,8',8',11'-HEXAMETHYL-, (1'R,5'AS,7'R,8'AS,9'AR)-
Common Name English
derquantel [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Fri Dec 15 16:04:56 GMT 2023 , Edited by admin on Fri Dec 15 16:04:56 GMT 2023
Code System Code Type Description
PUBCHEM
25154194
Created by admin on Fri Dec 15 16:04:56 GMT 2023 , Edited by admin on Fri Dec 15 16:04:56 GMT 2023
PRIMARY
NCI_THESAURUS
C75969
Created by admin on Fri Dec 15 16:04:56 GMT 2023 , Edited by admin on Fri Dec 15 16:04:56 GMT 2023
PRIMARY
SMS_ID
300000028992
Created by admin on Fri Dec 15 16:04:56 GMT 2023 , Edited by admin on Fri Dec 15 16:04:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103805
Created by admin on Fri Dec 15 16:04:55 GMT 2023 , Edited by admin on Fri Dec 15 16:04:55 GMT 2023
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FDA UNII
0L0UGK6OOX
Created by admin on Fri Dec 15 16:04:56 GMT 2023 , Edited by admin on Fri Dec 15 16:04:56 GMT 2023
PRIMARY
CAS
187865-22-1
Created by admin on Fri Dec 15 16:04:55 GMT 2023 , Edited by admin on Fri Dec 15 16:04:55 GMT 2023
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USAN
TT-57
Created by admin on Fri Dec 15 16:04:56 GMT 2023 , Edited by admin on Fri Dec 15 16:04:56 GMT 2023
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EPA CompTox
DTXSID50940260
Created by admin on Fri Dec 15 16:04:55 GMT 2023 , Edited by admin on Fri Dec 15 16:04:55 GMT 2023
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INN
9031
Created by admin on Fri Dec 15 16:04:56 GMT 2023 , Edited by admin on Fri Dec 15 16:04:56 GMT 2023
PRIMARY