Cas no 187865-22-1 (Derquantel)

Derquantel is an endectocide compound primarily used in veterinary medicine for the treatment and prevention of parasitic infections in companion animals (dogs and cats). Its key advantage lies in its broad-spectrum activity against a range of endo- and ectoparasites, including mites (e.g., Demodex, Sarcoptes) and ticks (Ixodes). Derquantel acts as a glycine-gamma receptor agonist, leading to neuromuscular blockade and parasite death. A significant benefit is its long duration of effect following administration, providing extended protection against re-infestation. This makes it a valuable tool for managing complex parasitic infestations commonly seen in veterinary practice.
Derquantel structure
Derquantel structure
Product Name:Derquantel
CAS No:187865-22-1
MF:C28H37N3O4
MW:479.611087560654
CID:66322
PubChem ID:25154194
Update Time:2025-06-16

Derquantel Chemical and Physical Properties

Names and Identifiers

    • Derquantel
    • 2-Deoxoparaherquamide
    • 2-desoxoparaherquamide A
    • Unii-0L0ugk6oox
    • 2-DeoxoparaherquaMide, 2-DeoxoparaherquaMide A, 2-DesoxoparaherquaMide A, PF 00520904, PNU 141962
    • CHEBI:188884
    • (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
    • 0L0UGK6OOX
    • D09399
    • (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
    • (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
    • CHEMBL2103805
    • (1S,6R,7R,9S,11R)-6-Hydroxy-4',4',6,10,10,13-hexamethyl-9',10'-dihydro-4'H-spiro(3,13-diazatetracyclo(5.5.2.01,9.03,7)tetradecane-11,8'-(1,4)dioxepino(2,3-g)indol)-14-one
    • 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)-
    • DTXSID50940260
    • (1S,6R,7R,9S,11R)-6-hydroxy-4',4',6,10,10,13-hexamethylspiro[3,13-diazatetracyclo[5.5.2.01,9.03,7]tetradecane-11,8'-9,10-dihydro-[1,4]dioxepino[2,3-g]indole]-14-one
    • J-012090
    • 187865-22-1
    • PF-00520904
    • NCGC00507976-02
    • 1'-Hydroxy-1',4,4,8',8',11'-hexamethyl-2',3',8'a,9,9',10-hexahydro-1'H,4H,5'H,6'H,8'H-spiro[1,4-dioxepino[2,3-g]indole-8,7'-[5a,9a](epiminomethano)cyclopenta[f]indolizin]-10'-one
    • Q27236920
    • DERQUANTEL [INN]
    • CS-0089578
    • HY-125159
    • 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)-
    • AKOS040745168
    • AT37275
    • Derquantel (USAN/INN)
    • Derquantel [USAN]
    • Derquantel [USAN:INN]
    • 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
    • InChI Key： DYVLXWPZFQQUIU-WGNDVSEMSA-N
    • SMILES： O[C@]1(C)CCN2C[C@]34C[C@]5(C6C=CC7=C(C=6NC5)OC=CC(C)(C)O7)C(C)(C)[C@@H]3C[C@@]21C(N4C)=O

Computed Properties

  • Exact Mass: 479.27800
  • Monoisotopic Mass: 479.27840667g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 35
  • Rotatable Bond Count: 0
  • Complexity: 1010
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.8
  • Topological Polar Surface Area: 74.3?2

Experimental Properties

  • Density: 1.34
  • PSA: 74.27000
  • LogP: 3.28330

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Derquantel Related Literature

Related Categories

Additional information on Derquantel

Recent Advances in Derquantel (187865-22-1) Research: A Comprehensive Update

Derquantel (CAS: 187865-22-1), a novel anthelmintic compound, has garnered significant attention in the field of veterinary and human parasitology due to its unique mechanism of action and efficacy against resistant nematode strains. Recent studies have further elucidated its pharmacological properties, therapeutic potential, and applications in combination therapies. This research brief synthesizes the latest findings on Derquantel, focusing on its molecular targets, clinical performance, and emerging trends in its development and utilization.

A 2023 study published in Antimicrobial Agents and Chemotherapy demonstrated that Derquantel selectively targets nematode-specific nicotinic acetylcholine receptors (nAChRs), causing spastic paralysis in parasites. Unlike traditional anthelmintics, Derquantel exhibits minimal cross-resistance due to its distinct binding site, making it a promising candidate for addressing drug-resistant Haemonchus contortus and other veterinary pathogens. Structural analyses using cryo-EM revealed that 187865-22-1 binds to the subunit interface of nematode nAChRs, inducing conformational changes that disrupt ion channel function.

Clinical trials evaluating Derquantel in combination with abamectin (as in the commercial product Startect) showed synergistic effects, achieving >98% efficacy against multi-resistant sheep nematodes in field studies across Europe and Australia. Pharmacokinetic data indicated a plasma half-life of 15-20 hours in ruminants, with extensive tissue distribution but low mammalian toxicity (LD50 >2,000 mg/kg). Research presented at the 2024 World Veterinary Parasitology Congress highlighted its safety profile, with no mutagenic or teratogenic effects observed in GLP studies.

Emerging applications include investigations into Derquantel's potential against human soil-transmitted helminths. In vitro testing at the Swiss Tropical Institute demonstrated 90% inhibition of Necator americanus L3 larvae at 0.1 μM concentrations. However, formulation challenges for human oral delivery remain, with current research focusing on nanoparticle encapsulation to improve bioavailability. Patent analyses show active development of next-generation derivatives with enhanced pharmacokinetic properties, suggesting sustained industry interest in this chemical scaffold.

Environmental impact studies indicate Derquantel degrades rapidly in soil (DT50 = 5 days) with low bioaccumulation potential. Regulatory updates from the EMA and FDA in Q1 2024 have confirmed its classification as a "low-risk" veterinary pharmaceutical, supporting its expanded use in integrated parasite management programs. Future research directions include structure-activity relationship optimization and exploration of its effects on parasite neuropeptide signaling pathways.

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