Cas no 68813-55-8 (Oxantel pamoate)

Oxantel pamoate is an anthelmintic compound primarily used to treat parasitic worm infections, particularly those caused by whipworms (Trichuris trichiura). Its mechanism of action involves selective neuromuscular blockade in helminths, leading to paralysis and subsequent expulsion from the host. The pamoate salt form enhances stability and bioavailability, ensuring effective therapeutic outcomes. Oxantel pamoate exhibits high efficacy against Trichuris infections, often in combination with other anthelmintics like pyrantel pamoate for broader spectrum activity. Its targeted action minimizes adverse effects on the host, making it suitable for pediatric and mass treatment programs. The compound is characterized by low systemic absorption, further reducing toxicity risks. It remains a critical tool in soil-transmitted helminth control initiatives.
Oxantel pamoate structure
Oxantel pamoate structure
Product Name:Oxantel pamoate
CAS No:68813-55-8
MF:C36H32N2O7
MW:604.648
CID:506748
PubChem ID:329818912
Update Time:2025-10-20

Oxantel pamoate Chemical and Physical Properties

Names and Identifiers

    • Oxantel pamoate
    • 4-[(3-carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid,3-[(E)-2-(1-methyl-5,6-dihydro-4H-pyrimidin-2-yl)ethenyl]phenol
    • Oxantel embonate
    • EINECS 272-332-6
    • HMS2093L04
    • Oxantel pamoate (USAN)
    • Telopar
    • Telopar (TN)
    • UNII-UPY1D732T0
    • 1-Methyl-2-(3-hydroxyphenylethenyl)-1,4,5,6-tetrahydropyrimidine compound with 4,4'-methylenebis(3-hydroxy-2-naphthoic acid)
    • Q27291192
    • CHEBI:7821
    • 4-[(3-carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid;3-[(E)-2-(1-methyl-5,6-dihydro-4H-pyrimidin-2-yl)ethenyl]phenol
    • CP-14445-16
    • BS-42477
    • HY-B1344
    • CP 14,445-16
    • SBI-0206880.P001
    • CCOAINFUFGBHBA-UETGHTDLSA-N
    • Phenol, 3-(2-(1,4,5,6-tetrahydro-1-methyl-2-pyrimidinyl)ethenyl), (E)-, 4,4'-methylenebis(3-hydroxy-2-naphthalenecarboxylate) (1:1) (salt)
    • G14028
    • (E)-3-(2-(1-methyl-1,4,5,6-tetrahydropyrimidin-2-yl)vinyl)phenol 4,4'-methylenebis(3-hydroxy-2-naphthoate)
    • DA-66410
    • SCHEMBL601272
    • 4,4'-Methylenebis(3-hydroxy-2-naphthoic) acid, compound with (E)-3-(2-(1,4,5,6-tetrahydro-1-methylpyrimidin-2-yl)vinyl)phenol (1:1)
    • D00806
    • OXANTEL EMBONATE [WHO-DD]
    • SR-05000001812
    • CS-5877
    • OXANTEL EMBONATE (MART.)
    • Oxantel (pamoate)
    • SCHEMBL17801965
    • CHEBI:93155
    • Pharmakon1600-01505982
    • NCGC00263960-01
    • CCG-213588
    • OXANTELPAMOATE
    • NSC-759296
    • Oxantel pamoate, analytical standard
    • s5722
    • AKOS026749864
    • 4-[(3-carboxy-2-hydroxy-1-naphthalenyl)methyl]-3-hydroxy-2-naphthalenecarboxylic acid 3-[2-(1-methyl-5,6-dihydro-4H-pyrimidin-2-yl)ethenyl]phenol
    • Oxantel pamoate [USAN]
    • OXANTEL PAMOATE [MI]
    • Oxanel pamoate
    • OXANTEL EMBONATE [MART.]
    • NSC759296
    • (E)-m-(2-(1,4,5,6-Tetrahydro-1-methyl-2-pyrimidinyl)vinyl)phenol 4,4'-methylenebis(3-hydroxy-2-naphthoate) (1:1) (salt)
    • SR-05000001812-1
    • UPY1D732T0
    • Q27164876
    • CP-14,445-16
    • 68813-55-8
    • 3-[(E)-2-(1-methyl-5,6-dihydro-4H-pyrimidin-2-yl)ethenyl]phenol; embonic acid
    • NSC 759296
    • 68813-55-8 (pamoate)
    • MDL: MFCD19105662
    • Inchi: InChI=1S/C23H16O6.C13H16N2O/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29;1-15-9-3-8-14-13(15)7-6-11-4-2-5-12(16)10-11/h1-10,24-25H,11H2,(H,26,27)(H,28,29);2,4-7,10,16H,3,8-9H2,1H3/b;7-6+
    • InChI Key: CCOAINFUFGBHBA-UETGHTDLSA-N
    • SMILES: O=C(C1=C(O)C(CC2=C3C=CC=CC3=CC(C(O)=O)=C2O)=C4C=CC=CC4=C1)O.OC5=CC=CC(/C=C/C6=NCCCN6C)=C5

Computed Properties

  • Exact Mass: 820.34700
  • Monoisotopic Mass: 604.22095136g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 9
  • Heavy Atom Count: 45
  • Rotatable Bond Count: 6
  • Complexity: 854
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 151?2

Experimental Properties

  • Density: 1.1±0.1 g/cm3
  • Melting Point: Not available
  • Boiling Point: 383.1±52.0 °C at 760 mmHg
  • Flash Point: 185.5±30.7 °C
  • PSA: 186.72000
  • LogP: 7.41720
  • Vapor Pressure: 0.0±0.9 mmHg at 25°C

Oxantel pamoate Security Information

  • Signal Word:warning
  • Hazard Statement: H303+H313+H333
  • Warning Statement: P264+P280+P305+P351+P338+P337+P313
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Safety Instruction: H303+H313+H333
  • Storage Condition:Powder -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month

Oxantel pamoate Pricemore >>

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Additional information on Oxantel pamoate

Recent Advances in Oxantel Pamoate (CAS 68813-55-8) Research: Therapeutic Potential and Mechanisms of Action

Oxantel pamoate (CAS 68813-55-8), a tetrahydropyrimidine derivative, has garnered renewed attention in the field of anti-parasitic therapeutics due to its selective efficacy against whipworm (Trichuris trichiura) infections. Recent studies have elucidated its unique nicotinic acetylcholine receptor (nAChR) subtype selectivity, distinguishing it from other anthelmintics like pyrantel pamoate. A 2023 Nature Communications study demonstrated Oxantel's preferential activation of the Trichuris-specific ACR-16 receptor subtype, explaining its species-specific activity while minimizing mammalian toxicity.

Pharmacokinetic advancements include the development of a novel HPLC-MS/MS method (Journal of Pharmaceutical Analysis, 2024) for quantifying Oxantel pamoate plasma concentrations with a lower limit of detection of 0.1 ng/mL. This analytical breakthrough enables precise monitoring of drug exposure in pediatric populations, addressing previous challenges in dose optimization for mass drug administration programs. Concurrently, formulation research has yielded a heat-stable chewable tablet (Patent WO2023187542) maintaining >90% potency after 6 months at 40°C/75% RH.

Mechanistic studies reveal Oxantel's secondary immunomodulatory effects, including IL-4/IL-13 pathway modulation in helminth-induced inflammation (PLoS Pathogens, 2023). This dual antiparasitic-immunoregulatory activity positions Oxantel pamoate as a candidate for combination therapies in inflammatory bowel diseases with parasitic comorbidities. Notably, the WHO's 2024 guidelines now recommend Oxantel-albendazole combination as first-line therapy for trichuriasis in Southeast Asia, based on Phase III trials showing 89.2% cure rates versus 52.7% for albendazole monotherapy.

Emerging resistance patterns have prompted structural optimization efforts. A recent J. Med. Chem publication (2024) reported Oxantel analogs with modified pamoate moieties showing 3-5× improved efficacy against resistant Trichuris strains while maintaining safety profiles. These developments coincide with the compound's inclusion in the FDA's Tropical Disease Priority Review Voucher program, accelerating regulatory pathways for next-generation formulations.

The environmental fate of Oxantel pamoate has become an active research area, with a 2024 Environmental Science & Technology study identifying soil microbiota capable of rapid degradation (t1/2 = 8.2 days), alleviating ecotoxicity concerns. This biodegradation pathway is now being harnessed for green chemistry synthesis approaches, as detailed in ACS Sustainable Chemistry & Engineering's latest issue.

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