Rafoxanide | CAS#22662-39-1 | anthelmintic

MedKoo Cat#: 526081 | Name: Rafoxanide

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Description:

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

Rafoxanide is a salicylanilide used as an anthelmintic. It is used to treat fluke, hookworm and other infestations. Rafoxanide can potentially negatively modulate STAT3/NF-kappaB and inflammation-associated CRC.

Chemical Structure

Rafoxanide

CAS#22662-39-1

Theoretical Analysis

MedKoo Cat#: 526081

Name: Rafoxanide

CAS#: 22662-39-1

Chemical Formula: C19H11Cl2I2NO3

Exact Mass: 624.8205

Molecular Weight: 626.01

Elemental Analysis: C, 36.45; H, 1.77; Cl, 11.33; I, 40.54; N, 2.24; O, 7.67

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 150.00
200mg	USD 250.00
500mg	USD 450.00
1g	USD 650.00
2g	USD 950.00
5g	USD 1,650.00

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Synonym

Rafoxanide; BRN 2228187; Disalan; Duofas; EINECS 245-148-9 ; Flukanide ; NSC 355278; Rafoxanida.

IUPAC/Chemical Name

N-(3-chloro-4-(4-chlorophenoxy)phenyl)-2-hydroxy-3,5-diiodobenzamide

InChi Key

NEMNPWINWMHUMR-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H11Cl2I2NO3/c20-10-1-4-13(5-2-10)27-17-6-3-12(9-15(17)21)24-19(26)14-7-11(22)8-16(23)18(14)25/h1-9,25H,(H,24,26)

SMILES Code

OC1=C(I)C=C(I)C=C1C(NC2=CC=C(OC3=CC=C(Cl)C=C3)C(Cl)=C2)=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, DMF, and ethanol

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO, DMF, and ethanol

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:

In vitro kinase assays using Rafoxanide showed it to be a low micromolar inhibitor of OSR1 T185E in vitro, IC50 = 8.18 μM. Rafoxanide is also a low micromolar inhibitor of SPAK T233E in vitro with IC50 value of 13.03 μM.

In vitro activity:

Rafoxanide acts as a selective TRAIL sensitizer in vitro and in a syngeneic experimental model of CRC by decreasing the levels of c-FLIP and survivin. These data suggest that rafoxanide could be deployed as an anti-cancer drug in combinatorial approaches aimed at overcoming CRC cell resistance to TRAIL-based therapies. Reference: Biomed Pharmacother. 2022 Nov;155:113794. https://pubmed.ncbi.nlm.nih.gov/36271571/

In vivo activity:

There was a marked increase of tumor-free survival among immunocompetent mice immunized with rafoxanide-treated dying tumor cells as compared with placebo. These data indicate rafoxanide as a immunogenic cell death inducer. Reference: Cancers (Basel). 2020 May 21;12(5):1314. https://pubmed.ncbi.nlm.nih.gov/32455811/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	47.92
	DMSO	30.0	47.92
	Ethanol	2.0	3.19

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 626.01 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. Laudisi F, Pacifico T, Maresca C, Luiz-Ferreira A, Antonelli S, Ortenzi A, Colantoni A, Di Grazia A, Franzè E, Colella M, Di Fusco D, Sica GS, Monteleone I, Monteleone G, Stolfi C. Rafoxanide sensitizes colorectal cancer cells to TRAIL-mediated apoptosis. Biomed Pharmacother. 2022 Nov;155:113794. doi: 10.1016/j.biopha.2022.113794. Epub 2022 Oct 4. PMID: 36271571. 2. Ramírez-Hernández M, Norambuena J, Hu H, Thomas B, Tang C, Boyd JM, Asefa T. Repurposing Anthelmintics: Rafoxanide- and Copper-Functionalized SBA-15 Carriers against Methicillin-Resistant Staphylococcus aureus. ACS Appl Mater Interfaces. 2023 Apr 12;15(14):17459-17469. doi: 10.1021/acsami.2c19899. Epub 2023 Mar 28. PMID: 36975176; PMCID: PMC10257252. 3. Di Grazia A, Laudisi F, Di Fusco D, Franzè E, Ortenzi A, Monteleone I, Monteleone G, Stolfi C. Rafoxanide Induces Immunogenic Death of Colorectal Cancer Cells. Cancers (Basel). 2020 May 21;12(5):1314. doi: 10.3390/cancers12051314. PMID: 32455811; PMCID: PMC7281008. 4. He W, Xu Z, Song D, Zhang H, Li B, Gao L, Zhang Y, Feng Q, Yu D, Hu L, Chen G, Tao Y, Wu X, Shi J, Zhu W. Antitumor effects of rafoxanide in diffuse large B cell lymphoma via the PTEN/PI3K/Akt and JNK/c-Jun pathways. Life Sci. 2020 Feb 15;243:117249. doi: 10.1016/j.lfs.2019.117249. Epub 2020 Jan 8. PMID: 31926247.

In vitro protocol:

In vivo protocol:

1. Di Grazia A, Laudisi F, Di Fusco D, Franzè E, Ortenzi A, Monteleone I, Monteleone G, Stolfi C. Rafoxanide Induces Immunogenic Death of Colorectal Cancer Cells. Cancers (Basel). 2020 May 21;12(5):1314. doi: 10.3390/cancers12051314. PMID: 32455811; PMCID: PMC7281008. 2. He W, Xu Z, Song D, Zhang H, Li B, Gao L, Zhang Y, Feng Q, Yu D, Hu L, Chen G, Tao Y, Wu X, Shi J, Zhu W. Antitumor effects of rafoxanide in diffuse large B cell lymphoma via the PTEN/PI3K/Akt and JNK/c-Jun pathways. Life Sci. 2020 Feb 15;243:117249. doi: 10.1016/j.lfs.2019.117249. Epub 2020 Jan 8. PMID: 31926247.

1: Saad AS, Hamdy AM, Salama FM, Abdelkawy M. Validated UPLC and TLC-Densitometry Stability Indicating Methods for the Determination of Rafoxanide in the Presence of Its Degradation Products. J Chromatogr Sci. 2016 Jul 1. pii: bmw112. [Epub ahead of print] PubMed PMID: 27368343. 2: Saad AS, Attia AK, Alaraki MS, Elzanfaly ES. Comparative study on the selectivity of various spectrophotometric techniques for the determination of binary mixture of fenbendazole and rafoxanide. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Nov 5;150:682-90. doi: 10.1016/j.saa.2015.05.098. Epub 2015 Jun 4. PubMed PMID: 26093118. 3: Power C, Danaher M, Sayers R, O'Brien B, Whelan M, Furey A, Jordan K. Investigation of the persistence of rafoxanide residues in bovine milk and fate during processing. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(6):1087-95. doi: 10.1080/19440049.2013.787655. Epub 2013 May 28. PubMed PMID: 23713694. 4: Matsubara K, Sanoh S, Ohta S, Kitamura S, Sugihara K, Fujimoto N. An improved thyroid hormone reporter assay to determine the thyroid hormone-like activity of amiodarone, bithionol, closantel and rafoxanide. Toxicol Lett. 2012 Jan 5;208(1):30-5. doi: 10.1016/j.toxlet.2011.10.004. Epub 2011 Oct 13. PubMed PMID: 22015988. 5: Lai SS, Yeung HS, Lee WO, Ho C, Wong YT. Determination of closantel and rafoxanide in animal tissues by online anionic mixed-mode solid-phase extraction followed by isotope dilution liquid chromatography tandem mass spectrometry. J Sep Sci. 2011 Jun;34(12):1366-74. doi: 10.1002/jssc.201000675. Epub 2011 May 10. PubMed PMID: 21560244. 6: Yeung HS, Ching WH, Lai SS, Lee WO, Wong YT. Quantitative analysis of closantel and rafoxanide in bovine and ovine muscles by high-performance liquid chromatography with fluorescence detection. J AOAC Int. 2010 Sep-Oct;93(5):1672-7. PubMed PMID: 21140680. 7: Yeung HS, Lee WO, Wong YT. Screening of closantel and rafoxanide in animal muscles by HPLC with fluorescence detection and confirmation using MS. J Sep Sci. 2010 Feb;33(2):206-11. doi: 10.1002/jssc.200900503. PubMed PMID: 19998374. 8: El-Banna HA, Goudah A, El-Zorba H, Abd-El-Rahman S. Comparative pharmacokinetics of ivermectin alone and a novel formulation of ivermectin and rafoxanide in calves and sheep. Parasitol Res. 2008 May;102(6):1337-42. doi: 10.1007/s00436-008-0915-6. Epub 2008 Feb 23. PubMed PMID: 18297309. 9: Swan GE, Oliver DW, Van Rensburg J, Steyn HS, Mülders MS. Stability and partitioning of closantel and rafoxanide in ruminal fluid of sheep. Onderstepoort J Vet Res. 2000 Jun;67(2):97-103. PubMed PMID: 11028745. 10: Swan GE, Koeleman HA, Steyn HS, Mülders MS. Intravascular plasma disposition and salivary secretion of closantel and rafoxanide in sheep. J S Afr Vet Assoc. 1999 Jun;70(2):75-9. PubMed PMID: 10855826. 11: Swan GE, Koeleman HA, Steyn HS, Mülders MS. Relative bioavailability of rafoxanide following intraruminal and intra-abomasal administration in sheep. J S Afr Vet Assoc. 1999 Jun;70(2):71-4. PubMed PMID: 10855825. 12: Waruiru RM. The efficacy of closantel and rafoxanide against fenbendazole- and levamisole-resistant Haemonchus contortus in small ruminants. Vet Res Commun. 1997 Oct;21(7):493-7. PubMed PMID: 9345716. 13: Maurer K, Decere M, Fried B. Effects of the anthelmintics clorsulon, rafoxanide, mebendazole and arprinocid on Echinostoma caproni in ICR mice. J Helminthol. 1996 Mar;70(1):95-6. PubMed PMID: 8960203. 14: Swan GE, Botha CJ, Taylor JH, Mülders MS, Minnaar PP, Kloeck A. Differences in the oral bioavailability of three rafoxanide formulations in sheep. J S Afr Vet Assoc. 1995 Dec;66(4):197-201. PubMed PMID: 8691406. 15: Maurer K, Decere M, Fried B. Effects of the anthelmintics clorsulon, rafoxanide, mebendazole and arprinocid on Echinostoma caproni in ICR mice [corrected and reapublished in J Helminthol 1996 Mar;70(1):95-6]. J Helminthol. 1995 Dec;69(4):373-4. Corrected and republished in: J Helminthol. 1996 Mar;70(1):95-6. PubMed PMID: 8583133. 16: Benchaoui HA, McKellar QA. Determination of rafoxanide and closantel in ovine plasma by high performance liquid chromatography. Biomed Chromatogr. 1993 Jul-Aug;7(4):181-3. PubMed PMID: 8219694. 17: Swan GE, Mülders MS. Pharmacokinetics of rafoxanide in suckling and weaned lambs following oral administration. J S Afr Vet Assoc. 1993 Jun;64(2):67-70. PubMed PMID: 8410945. 18: Benchaoui HA, McKellar QA. Effect of early treatment with rafoxanide on antipyrine clearance in sheep infected with Fasciola hepatica. Xenobiotica. 1993 Apr;23(4):439-48. PubMed PMID: 8101676. 19: Poul JM, Verlinde V, Abjean JP, Laurentie M. Oral toxicity in weanling and adult rats and in vitro genotoxicity of the veterinary anthelmintic rafoxanide. J Appl Toxicol. 1993 Mar-Apr;13(2):117-22. PubMed PMID: 8486909. 20: Srivastava RP, Sharma S. Synthesis of 2,5-disubstituted benzimidazoles, 1,3,4-thiadiazoles and 3,5-diiodosalicylanilides as structural congeners of rafoxanide and closantel. Pharmazie. 1990 Jan;45(1):34-7. PubMed PMID: 2333310.