Oxantel | CAS#36531-26-7

MedKoo Cat#: 525870 | Name: Oxantel

Description:

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

Oxantel is a fumarate reductase inhibitor and has anthelmintic properties.

Chemical Structure

Oxantel

CAS#36531-26-7 (free base)

Theoretical Analysis

MedKoo Cat#: 525870

Name: Oxantel

CAS#: 36531-26-7 (free base)

Chemical Formula: C13H16N2O

Exact Mass: 216.1263

Molecular Weight: 216.28

Elemental Analysis: C, 72.19; H, 7.46; N, 12.95; O, 7.40

Price and Availability

Size	Price	Availability	Quantity

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

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

Synonym

Oxantel

IUPAC/Chemical Name

3-[(E)-2-(1-Methyl-5,6-dihydro-4H-pyrimidin-2-yl)ethenyl]phenol

InChi Key

VRYKTHBAWRESFI-VOTSOKGWSA-N

InChi Code

InChI=1S/C13H16N2O/c1-15-9-3-8-14-13(15)7-6-11-4-2-5-12(16)10-11/h2,4-7,10,16H,3,8-9H2,1H3/b7-6+

SMILES Code

OC1=CC=CC(/C=C/C2=NCCCN2C)=C1

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

Instruction

View handling instruction

Biological target:

Oxantel (CP-14445), a m-oxyphenol derivative of Pyrantel (HY-12641), is a N-subtype AChR agonist.

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/

Preparing Stock Solutions

The following data is based on the product molecular weight 216.28 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: 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: 2. Oral anti-infective drugs and drug combinations for off- label use. Parasit Vectors. 2023 Oct 31;16(1):394. doi: 10.1186/s13071-023-05909-8. PMID: 37907954; PMCID: PMC10619278. 2: 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. 3: 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. 4: 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. 5: 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. 6: 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. 7: 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. 8: Hansen TVA, Grencis RK, Issouf M, Neveu C, Charvet CL. Functional Characterization of the Oxantel-Sensitive Acetylcholine Receptor from Trichuris muris. Pharmaceuticals (Basel). 2021 Jul 20;14(7):698. doi: 10.3390/ph14070698. PMID: 34358124; PMCID: PMC8308736. 9: 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. 10: Okuda T, Nomura Y, Konishi A, Misawa H. Competitive inhibition of the high- affinity choline transporter by tetrahydropyrimidine anthelmintics. Eur J Pharmacol. 2021 May 5;898:173986. doi: 10.1016/j.ejphar.2021.173986. Epub 2021 Feb 26. PMID: 33640406. 11: Hansen TVA, Cirera S, Neveu C, Courtot E, Charvet CL, Calloe K, Klaerke DA, Martin RJ. The narrow-spectrum anthelmintic oxantel is a potent agonist of a novel acetylcholine receptor subtype in whipworms. PLoS Pathog. 2021 Feb 5;17(2):e1008982. doi: 10.1371/journal.ppat.1008982. PMID: 33544769; PMCID: PMC7891710. 12: Kaji MD, Geary TG, Beech RN. A Functional Comparison of Homopentameric Nicotinic Acetylcholine Receptors (ACR-16) Receptors From Necator americanus and Ancylostoma ceylanicum. Front Mol Neurosci. 2020 Nov 26;13:601102. doi: 10.3389/fnmol.2020.601102. PMID: 33324163; PMCID: PMC7725692. 13: 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. 14: 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. 15: Choudhary S, Tipton JG, Abongwa M, Brewer MT, Chelladurai JJ, Musselman N, Martin RJ, Robertson AP. Pharmacological characterization of a homomeric nicotinic acetylcholine receptor formed by Ancylostoma caninum ACR-16. Invert Neurosci. 2019 Sep 5;19(4):11. doi: 10.1007/s10158-019-0231-0. PMID: 31486912; PMCID: PMC7869652. 16: 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. 17: 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. 18: 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. 19: 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. 20: Jesudoss Chelladurai J, Kifleyohannes T, Scott J, Brewer MT. Praziquantel Resistance in the Zoonotic Cestode Dipylidium caninum. Am J Trop Med Hyg. 2018 Nov;99(5):1201-1205. doi: 10.4269/ajtmh.18-0533. PMID: 30226153; PMCID: PMC6221203.

View History

Azide-PEG4-Amine HCl

MedKoo CAT#: 571841

CAS#: 777081-35-3 (HCl)