Oxantel Pamoate | CAS#68813-55-8 | Anthelmintic

MedKoo Cat#: 525807 | Name: Oxantel Pamoate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxantel Pamoate is an anthelmintic used to treat Trichuris trichiura infection.

Chemical Structure

Oxantel Pamoate

CAS#68813-55-8 (pamoate)

Theoretical Analysis

MedKoo Cat#: 525807

Name: Oxantel Pamoate

CAS#: 68813-55-8 (pamoate)

Chemical Formula: C36H32N2O7

Exact Mass: 0.0000

Molecular Weight: 604.65

Elemental Analysis: C, 71.51; H, 5.33; N, 4.63; O, 18.52

Price and Availability

Size	Price	Availability
50mg	USD 150.00	Ready to ship
100mg	USD 250.00	Ready to ship
200mg	USD 450.00	Ready to ship
500mg	USD 950.00	Ready to ship

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Related CAS #

36531-26-7 (free base) 68813-55-8 (pamoate)

Synonym

Telopar; Oxantel Pamoate

IUPAC/Chemical Name

(E)-3-(2-(1-methyl-1,4,5,6-tetrahydropyrimidin-2-yl)vinyl)phenol 4,4'-methylenebis(3-hydroxy-2-naphthoate)

InChi Key

CCOAINFUFGBHBA-UETGHTDLSA-N

InChi Code

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+

SMILES Code

OC1=CC=CC(/C=C/C2=NCCCN2C)=C1.O=C(C3=C(O)C(CC4=C5C=CC=CC5=CC(C(O)=O)=C4O)=C6C=CC=CC6=C3)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# S21G11M11

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Oxantel Pamoate is the pamoate salt form of oxantel, a tetrahydropyrimidine anthelmintic used against intesitnal worms.

In vitro activity:

In vitro studies with Necator americanus (N. americanus) L3, when incubated with oxantel pamoate, revealed high survival rates (100%, SD ±0.05% at 0.1 µg/ml, 97.7%, SD ±0.04% at 1 µg/ml, 97.1%, SD ±0.003% at 10 µg/ml and 96.6%, SD ±0.0% at 100 µg/ml), compared to controls. In contrast, adult worms were markedly affected by the drug, resulting in an average motility of 100% (SD ±0.0%) at 0.1 µg/ml, 50% (SD ±25.0%) at 1 µg/ml, 62.5% (SD ±40.5%) at 10 µg/ml and only 12.5% (SD ±25.0%) at 100 µg/ml compared to controls (motility of 100% (SD ±0.0%)). An IC50 of 11.80 µg/ml (r = 0.89) was calculated for oxantel pamoate on N. americanus adult worms Reference: PLoS Negl Trop Dis. 2013;7(3):e2119. https://pubmed.ncbi.nlm.nih.gov/23556013/

In vivo activity:

Oxantel pamoate displayed a high activity against T. muris in vivo, with an ED50 of 4.71 mg/kg. In more detail, a WBR of 92.5% and WER of 88.4% were achieved after administration of 10 mg/kg. Administration of 5 mg/kg resulted in a WBR of 81.1% and a WER of 78.2%. A low activity was observed with oxantel pamoate at 2.5 mg/kg (WER = 24.3%, WBR = 13.5%) and no effect was observed when mice were treated with 1 mg/kg (WER = 1.5%, WBR = 0%). The worm burden in orally oxantel pamoate treated mice was significantly different from untreated mice (P = 0.041). An intraperitoneal treatment of 10 mg/kg lacked activity against T. muris (both WER and WBR = 0%). For comparison, 10 mg/kg ivermectin given intraperitoneally resulted in a worm burden reduction of 93.5%. Reference: PLoS Negl Trop Dis. 2013;7(3):e2119. https://pubmed.ncbi.nlm.nih.gov/23556013/

	Solvent	mg/mL	mM
Solubility
	DMSO	75.0	124.04

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 604.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Keiser J, Tritten L, Silbereisen A, Speich B, Adelfio R, Vargas M. Activity of oxantel pamoate monotherapy and combination chemotherapy against Trichuris muris and hookworms: revival of an old drug. PLoS Negl Trop Dis. 2013;7(3):e2119. doi: 10.1371/journal.pntd.0002119. Epub 2013 Mar 21. PMID: 23556013; PMCID: PMC3605275. 2. Wimmersberger D, Tritten L, Keiser J. Development of an in vitro drug sensitivity assay for Trichuris muris first-stage larvae. Parasit Vectors. 2013 Feb 22;6:42. doi: 10.1186/1756-3305-6-42. PMID: 23433224; PMCID: PMC3606346.

In vitro protocol:

In vivo protocol:

1: Schärer A, Biendl S, Keiser J. Trichuris muris egg-hatching assay for anthelminthic drug discovery and characterization. Int J Parasitol Drugs Drug Resist. 2023 Dec;23:63-70. doi: 10.1016/j.ijpddr.2023.10.001. Epub 2023 Oct 9. PMID: 37856948; PMCID: PMC10590722. 2: Easland E, Biendl S, Keiser J. Development of a hookworm egg hatching assay to determine the ovicidal effects of anthelminthics. Parasit Vectors. 2023 May 4;16(1):157. doi: 10.1186/s13071-023-05771-8. PMID: 37143169; PMCID: PMC10161531. 3: Pfarr KM, Krome AK, Al-Obaidi I, Batchelor H, Vaillant M, Hoerauf A, Opoku NO, Kuesel AC. The pipeline for drugs for control and elimination of neglected tropical diseases: 1. Anti-infective drugs for regulatory registration. Parasit Vectors. 2023 Mar 1;16(1):82. doi: 10.1186/s13071-022-05581-4. PMID: 36859332; PMCID: PMC9979492. 4: Olliaro PL, Vaillant MT, Diawara A, Speich B, Albonico M, Utzinger J, Keiser J. Egg excretion indicators for the measurement of soil-transmitted helminth response to treatment. PLoS Negl Trop Dis. 2022 Aug 2;16(8):e0010593. doi: 10.1371/journal.pntd.0010593. PMID: 35917364; PMCID: PMC9374261. 5: Li C, Ji Q, Fu X, Yu X, Ye Z, Zhang M, Sun C, Qiu Y. Low-Cost Detection of Methane Gas in Rice Cultivation by Gas Chromatography-Flame Ionization Detector Based on Manual Injection and Split Pattern. Molecules. 2022 Jun 21;27(13):3968. doi: 10.3390/molecules27133968. PMID: 35807216; PMCID: PMC9267938. 6: Hong S, Jung BK, Song H, Cho J, Sohn WM, Hong SJ, Ryu JY, Kim HS, Jeong MH, Htoon TT, Tin HH, Chai JY. Failure of Repeated MDA with Albendazole for Trichuriasis Control in Schoolchildren of the Yangon Region, Myanmar. Korean J Parasitol. 2021 Dec;59(6):607-613. doi: 10.3347/kjp.2021.59.6.607. Epub 2021 Dec 22. PMID: 34974667; PMCID: PMC8721305. 7: Palmeirim MS, Specht S, Scandale I, Gander-Meisterernst I, Chabicovsky M, Keiser J. Preclinical and Clinical Characteristics of the Trichuricidal Drug Oxantel Pamoate and Clinical Development Plans: A Review. Drugs. 2021 Jun;81(8):907-921. doi: 10.1007/s40265-021-01505-1. Epub 2021 Apr 30. PMID: 33929716; PMCID: PMC8144136. 8: Brussee JM, Neodo A, Schulz JD, Coulibaly JT, Pfister M, Keiser J. Pharmacometric Analysis of Tribendimidine Monotherapy and Combination Therapies To Achieve High Cure Rates in Patients with Hookworm Infections. Antimicrob Agents Chemother. 2021 Jan 20;65(2):e00714-20. doi: 10.1128/AAC.00714-20. PMID: 33139276; PMCID: PMC7849000. 9: Barda B, Schindler C, Wampfler R, Ame S, Ali SM, Keiser J. Comparison of real-time PCR and the Kato-Katz method for the diagnosis of soil-transmitted helminthiasis and assessment of cure in a randomized controlled trial. BMC Microbiol. 2020 Oct 2;20(1):298. doi: 10.1186/s12866-020-01963-9. PMID: 33008301; PMCID: PMC7531123. 10: Cortez-Maya S, Moreno-Herrera A, Palos I, Rivera G. Old Antiprotozoal Drugs: Are They Still Viable Options for Parasitic Infections or New Options for Other Diseases? Curr Med Chem. 2020;27(32):5403-5428. doi: 10.2174/0929867326666190628163633. PMID: 31264538. 11: Schulz JD, Neodo A, Coulibaly JT, Keiser J. Pharmacokinetics of Albendazole, Albendazole Sulfoxide, and Albendazole Sulfone Determined from Plasma, Blood, Dried-Blood Spots, and Mitra Samples of Hookworm-Infected Adolescents. Antimicrob Agents Chemother. 2019 Mar 27;63(4):e02489-18. doi: 10.1128/AAC.02489-18. PMID: 30745388; PMCID: PMC6437472. 12: Neodo A, Schulz JD, Huwyler J, Keiser J. In Vitro and In Vivo Drug-Drug Interaction Study of the Effects of Ivermectin and Oxantel Pamoate on Tribendimidine. Antimicrob Agents Chemother. 2018 Dec 21;63(1):e00762-18. doi: 10.1128/AAC.00762-18. PMID: 30323047; PMCID: PMC6325189. 13: Wagner-Hattler L, Schoelkopf J, Huwyler J, Puchkov M. Stability investigation of FCC-based tablets for oral suspension with caffeine and oxantel pamoate as model drugs. Drug Dev Ind Pharm. 2019 Feb;45(2):222-230. doi: 10.1080/03639045.2018.1529784. Epub 2018 Oct 17. PMID: 30260721. 14: Schneeberger PHH, Coulibaly JT, Gueuning M, Moser W, Coburn B, Frey JE, Keiser J. Off-target effects of tribendimidine, tribendimidine plus ivermectin, tribendimidine plus oxantel-pamoate, and albendazole plus oxantel-pamoate on the human gut microbiota. Int J Parasitol Drugs Drug Resist. 2018 Dec;8(3):372-378. doi: 10.1016/j.ijpddr.2018.07.001. Epub 2018 Jul 2. PMID: 30007544; PMCID: PMC6068340. 15: Maheu-Giroux M, Joseph SA. Moxidectin for deworming: from trials to implementation. Lancet Infect Dis. 2018 Aug;18(8):817-819. doi: 10.1016/S1473-3099(18)30270-6. Epub 2018 May 29. PMID: 29858152. 16: Barda B, Ame SM, Ali SM, Albonico M, Puchkov M, Huwyler J, Hattendorf J, Keiser J. Efficacy and tolerability of moxidectin alone and in co-administration with albendazole and tribendimidine versus albendazole plus oxantel pamoate against Trichuris trichiura infections: a randomised, non-inferiority, single- blind trial. Lancet Infect Dis. 2018 Aug;18(8):864-873. doi: 10.1016/S1473-3099(18)30233-0. Epub 2018 May 29. PMID: 29858149. 17: Clarke NE, Doi SAR, Wangdi K, Chen Y, Clements ACA, Nery SV. Efficacy of Anthelminthic Drugs and Drug Combinations Against Soil-transmitted Helminths: A Systematic Review and Network Meta-analysis. Clin Infect Dis. 2019 Jan 1;68(1):96-105. doi: 10.1093/cid/ciy423. PMID: 29788074. 18: Brooker SJ. Soil-transmitted helminth treatment: multiple-drug regimens. Lancet Infect Dis. 2018 Jul;18(7):698-699. doi: 10.1016/S1473-3099(18)30268-8. Epub 2018 Apr 16. PMID: 29673736. 19: Moser W, Sayasone S, Xayavong S, Bounheuang B, Puchkov M, Huwyler J, Hattendorf J, Keiser J. Efficacy and tolerability of triple drug therapy with albendazole, pyrantel pamoate, and oxantel pamoate compared with albendazole plus oxantel pamoate, pyrantel pamoate plus oxantel pamoate, and mebendazole plus pyrantel pamoate and oxantel pamoate against hookworm infections in school- aged children in Laos: a randomised, single-blind trial. Lancet Infect Dis. 2018 Jul;18(7):729-737. doi: 10.1016/S1473-3099(18)30220-2. Epub 2018 Apr 16. PMID: 29673735. 20: Moser W, Coulibaly JT, Ali SM, Ame SM, Amour AK, Yapi RB, Albonico M, Puchkov M, Huwyler J, Hattendorf J, Keiser J. Efficacy and safety of tribendimidine, tribendimidine plus ivermectin, tribendimidine plus oxantel pamoate, and albendazole plus oxantel pamoate against hookworm and concomitant soil-transmitted helminth infections in Tanzania and Côte d'Ivoire: a randomised, controlled, single-blinded, non-inferiority trial. Lancet Infect Dis. 2017 Nov;17(11):1162-1171. doi: 10.1016/S1473-3099(17)30487-5. Epub 2017 Aug 29. PMID: 28864027.