Oxfendazole
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MedKoo CAT#: 462880

CAS#: 53716-50-0

Description: Oxfendazole is a benzimidazole anthelmintic. In vivo, oxfendazole is curative in pig models of H. rubidus or A. suum infection when administered at doses of 3 and 6 mg/kg, respectively. It is lethal to H. contortus and T. circumcincta when administered to infected cattle. Formulations containing oxfendazole have been used in the treatment and prevention of helminth infections in livestock.

Chemical Structure

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Oxfendazole
CAS# 53716-50-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 462880
Name: Oxfendazole
CAS#: 53716-50-0
Chemical Formula: C15H13N3O3S
Exact Mass: 315.07
Molecular Weight: 315.347
Elemental Analysis: C, 57.13; H, 4.16; N, 13.33; O, 15.22; S, 10.17

Price and Availability

Size Price Availability Quantity
100mg USD -2 2 Weeks
200mg USD -2 2 Weeks
500mg USD -2 2 Weeks
1g USD -2 2 Weeks
2g USD -2 2 Weeks
5mg USD 230 2 Weeks
10mg USD 380 2 Weeks
25mg USD 650 2 Weeks
50mg USD 1020 2 Weeks
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Synonym: Oxfenbendazole; Fenbendazole sulfoxide; HOE 8105; HOE8105; HOE-8105;

IUPAC/Chemical Name: methyl (6-(phenylsulfinyl)-1H-benzo[d]imidazol-2-yl)carbamate

InChi Key: BEZZFPOZAYTVHN-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H13N3O3S/c1-21-15(19)18-14-16-12-8-7-11(9-13(12)17-14)22(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19)

SMILES Code: O=S(C1=CC=CC=C1)C2=CC=C3N=C(NC3=C2)NC(OC)=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: >3 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: Oxfendazole is the sulfoxide form of fenbendazole which is a broad spectrum benzimidazole anthelmintic.
In vitro activity: Oxfendazole also suppressed the cell growth of non‑small cell lung cancer (NSCLC) cells, and overexpression of c‑Src decreased the cytotoxicity of oxfendazole against NSCLC cells. In addition, oxfendazole induced cell cycle arrest at the G0/G1 phase, and downregulated the protein levels of Cyclin‑dependent kinase (CDK)‑4, CDK6, retinoblastoma protein and E2 transcription factor 1, and upregulated the expression levels of p53 and p21 in NSCLC cells. Reference: Mol Med Rep. 2019 Apr;19(4):2921-2926. https://pubmed.ncbi.nlm.nih.gov/30720086/
In vivo activity: The numbers and areas of glutathione S-transferase placental form (GST-P)-positive foci were significantly increased in the livers of rats treated with OX (oxfendazole), with concomitantly increased cell proliferation, compared with those in the livers of the DEN alone group. Quantitative real-time RT-PCR analysis revealed that OX induced not only mRNA expression of phase I enzymes Cyp1a1, Cyp1a2, but also Nrf2-regulated phase II enzymes such as Gpx2, Nqo1, Yc2, Akr7a3 and Gstm1, presumably due to an adaptive response against OX-induced oxidative stress. Reactive oxygen species production increased in microsomes isolated from the livers of OX-treated rats. Reference: Arch Toxicol. 2009 May;83(5):503-11. https://pubmed.ncbi.nlm.nih.gov/18754104/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 14.1 44.66
DMSO:PBS (pH 7.2) (1:4) 0.2 0.63
Water 0.7 2.12

Preparing Stock Solutions

The following data is based on the product molecular weight 315.35 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.

Recalculate based on batch purity %
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. Xu D, Tian W, Jiang C, Huang Z, Zheng S. The anthelmintic agent oxfendazole inhibits cell growth in non‑small cell lung cancer by suppressing c‑Src activation. Mol Med Rep. 2019 Apr;19(4):2921-2926. doi: 10.3892/mmr.2019.9897. Epub 2019 Jan 28. PMID: 30720086. 2. Dewa Y, Nishimura J, Muguruma M, Jin M, Kawai M, Saegusa Y, Okamura T, Umemura T, Mitsumori K. Involvement of oxidative stress in hepatocellular tumor-promoting activity of oxfendazole in rats. Arch Toxicol. 2009 May;83(5):503-11. doi: 10.1007/s00204-008-0349-z. Epub 2008 Aug 27. PMID: 18754104. 3. Gleizes C, Eeckhoutte C, Pineau T, Alvinerie M, Galtier P. Inducing effect of oxfendazole on cytochrome P450IA2 in rabbit liver. Consequences on cytochrome P450 dependent monooxygenases. Biochem Pharmacol. 1991 Jun 15;41(12):1813-20. doi: 10.1016/0006-2952(91)90119-p. PMID: 2039538.
In vitro protocol: 1. Xu D, Tian W, Jiang C, Huang Z, Zheng S. The anthelmintic agent oxfendazole inhibits cell growth in non‑small cell lung cancer by suppressing c‑Src activation. Mol Med Rep. 2019 Apr;19(4):2921-2926. doi: 10.3892/mmr.2019.9897. Epub 2019 Jan 28. PMID: 30720086.
In vivo protocol: 1. Dewa Y, Nishimura J, Muguruma M, Jin M, Kawai M, Saegusa Y, Okamura T, Umemura T, Mitsumori K. Involvement of oxidative stress in hepatocellular tumor-promoting activity of oxfendazole in rats. Arch Toxicol. 2009 May;83(5):503-11. doi: 10.1007/s00204-008-0349-z. Epub 2008 Aug 27. PMID: 18754104. 2. Gleizes C, Eeckhoutte C, Pineau T, Alvinerie M, Galtier P. Inducing effect of oxfendazole on cytochrome P450IA2 in rabbit liver. Consequences on cytochrome P450 dependent monooxygenases. Biochem Pharmacol. 1991 Jun 15;41(12):1813-20. doi: 10.1016/0006-2952(91)90119-p. PMID: 2039538.

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1: Son DS, Lee ES, Adunyah SE. The Antitumor Potentials of Benzimidazole Anthelmintics as Repurposing Drugs. Immune Netw. 2020 Aug 4;20(4):e29. doi: 10.4110/in.2020.20.e29. PMID: 32895616; PMCID: PMC7458798.

2: Kabululu ML, Ngowi HA, Mlangwa JED, Mkupasi EM, Braae UC, Trevisan C, Colston A, Cordel C, Johansen MV. Endemicity of Taenia solium cysticercosis in pigs from Mbeya Rural and Mbozi districts, Tanzania. BMC Vet Res. 2020 Sep 3;16(1):325. doi: 10.1186/s12917-020-02543-9. PMID: 32883326; PMCID: PMC7470673.

3: Bach T, Galbiati S, Kennedy JK, Deye G, Nomicos EYH, Codd EE, Garcia HH, Horton J, Gilman RH, Gonzalez AE, Winokur P, An G. Pharmacokinetics, Safety, and Tolerability of Oxfendazole in Healthy Adults in an Open Label Phase 1 Multiple Ascending Dose and Food Effect Study. Antimicrob Agents Chemother. 2020 Aug 17:AAC.01018-20. doi: 10.1128/AAC.01018-20. Epub ahead of print. PMID: 32816721.

4: Megha GK, Aulakh RS, Singh BB. Effect of oxfendazole to control Taenia solium cysticercosis in pigs in Punjab state of India. J Parasit Dis. 2020 Sep;44(3):553-558. doi: 10.1007/s12639-020-01228-2. Epub 2020 May 4. PMID: 32801507; PMCID: PMC7410941.

5: Gabriël S, Mwape KE, Hobbs EC, Devleesschauwer B, Van Damme I, Zulu G, Mwelwa C, Mubanga C, Masuku M, Mambwe M, De Coster T, Phiri IK, Berkvens DL, Colston A, Bottieau E, Speybroeck N, Ketzis JK, Willingham AL, Trevisan C, Dorny P. Evidence for potential elimination of active Taenia solium transmission in Africa? N Engl J Med. 2020 Jul 23;383(4):396-397. doi: 10.1056/NEJMc1909955. PMID: 32699455; PMCID: PMC7289521.

6: Hübner MP, Martin C, Specht S, Koschel M, Dubben B, Frohberger SJ, Ehrens A, Fendler M, Struever D, Mitre E, Vallarino-Lhermitte N, Gokool S, Lustigman S, Schneider M, Townson S, Hoerauf A, Scandale I. Oxfendazole mediates macrofilaricidal efficacy against the filarial nematode Litomosoides sigmodontis in vivo and inhibits Onchocerca spec. motility in vitro. PLoS Negl Trop Dis. 2020 Jul 6;14(7):e0008427. doi: 10.1371/journal.pntd.0008427. PMID: 32628671; PMCID: PMC7365463.

7: Simanungkalit G, Hegarty RS, Cowley FC, McPhee MJ. Evaluation of remote monitoring units for estimating body weight and supplement intake of grazing cattle. Animal. 2020 Aug;14(S2):s332-s340. doi: 10.1017/S1751731120000282. Epub 2020 Mar 3. PMID: 32122426.

8: Turkan F, Harbi Calimli M, Akgun A, Gulbagca F, Sen F. Toxicological effects of some antiparasitic drugs on equine liver glutathione S-Transferase enzyme activity. J Pharm Biomed Anal. 2020 Feb 20;180:113048. doi: 10.1016/j.jpba.2019.113048. Epub 2019 Dec 17. PMID: 31887670.

9: Stasiuk SJ, MacNevin G, Workentine ML, Gray D, Redman E, Bartley D, Morrison A, Sharma N, Colwell D, Ro DK, Gilleard JS. Similarities and differences in the biotransformation and transcriptomic responses of Caenorhabditis elegans and Haemonchus contortus to five different benzimidazole drugs. Int J Parasitol Drugs Drug Resist. 2019 Dec;11:13-29. doi: 10.1016/j.ijpddr.2019.09.001. Epub 2019 Sep 9. PMID: 31542693; PMCID: PMC6796749.

10: Cho-Ngwa F, Mbah GE, Ayiseh RB, Ndi EM, Monya E, Tumanjong IM, Mainsah EN, Sakanari J, Lustigman S. Development and validation of an Onchocerca ochengi adult male worm gerbil model for macrofilaricidal drug screening. PLoS Negl Trop Dis. 2019 Jul 1;13(7):e0007556. doi: 10.1371/journal.pntd.0007556. PMID: 31260456; PMCID: PMC6625737.

11: Viviani P, Lifschitz AL, Luque SE, Lloberas MM, Maté ML, Cardozo PA, Lanusse CE, Virkel GL. Pharmacologic interaction between oxfendazole and triclabendazole: In vitro biotransformation and systemic exposure in sheep. Exp Parasitol. 2019 Sep;204:107718. doi: 10.1016/j.exppara.2019.107718. Epub 2019 Jun 12. PMID: 31201779.

12: Ngowi HA, Winkler AS, Braae UC, Mdegela RH, Mkupasi EM, Kabululu ML, Lekule FP, Johansen MV. Taenia solium taeniosis and cysticercosis literature in Tanzania provides research evidence justification for control: A systematic scoping review. PLoS One. 2019 Jun 5;14(6):e0217420. doi: 10.1371/journal.pone.0217420. PMID: 31166983; PMCID: PMC6550401.

13: Türkan F. Investigation of the toxicological and inhibitory effects of some benzimidazole agents on acetylcholinesterase and butyrylcholinesterase enzymes. Arch Physiol Biochem. 2019 May 28:1-5. doi: 10.1080/13813455.2019.1618341. Epub ahead of print. PMID: 31135232.

14: Kabululu ML, Ngowi HA, Kimera SI, Lekule FP, Kimbi EC, Johansen MV. Effectiveness of an integrated intervention in the control of endo- and ectoparasites of pigs kept by smallholder farmers in Mbeya rural and Mbozi districts, Tanzania. Vet Parasitol Reg Stud Reports. 2018 Aug;13:64-73. doi: 10.1016/j.vprsr.2018.03.009. Epub 2018 Apr 3. PMID: 31014892.

15: Bach T, Bae S, D'Cunha R, Winokur P, An G. Development and validation of a simple, fast, and sensitive LC/MS/MS method for the quantification of oxfendazole in human plasma and its application to clinical pharmacokinetic study. J Pharm Biomed Anal. 2019 Jul 15;171:111-117. doi: 10.1016/j.jpba.2019.03.048. Epub 2019 Mar 26. PMID: 30981954; PMCID: PMC6545882.

16: Morris LH, Colgan S, Leathwick DM, Nielsen MK. Anthelmintic efficacy of single active and combination products against commonly occurring parasites in foals. Vet Parasitol. 2019 Apr;268:46-52. doi: 10.1016/j.vetpar.2019.02.006. Epub 2019 Mar 1. PMID: 30981305.

17: Ceballos L, Canton C, Cadenazzi G, Virkel G, Dominguez P, Moreno L, Lanusse C, Alvarez L. Oxfendazole kinetics in pigs: In vivo assessment of its pattern of accumulation in Ascaris suum. Exp Parasitol. 2019 Apr;199:52-58. doi: 10.1016/j.exppara.2019.02.017. Epub 2019 Mar 1. PMID: 30831078.

18: Poudel I, Sah K, Subedi S, Kumar Singh D, Kushwaha P, Colston A, Gauci CG, Donadeu M, Lightowlers MW. Implementation of a practical and effective pilot intervention against transmission of Taenia solium by pigs in the Banke district of Nepal. PLoS Negl Trop Dis. 2019 Feb 25;13(2):e0006838. doi: 10.1371/journal.pntd.0006838. PMID: 30802248; PMCID: PMC6405169.

19: An G, Murry DJ, Gajurel K, Bach T, Deye G, Stebounova LV, Codd EE, Horton J, Gonzalez AE, Garcia HH, Ince D, Hodgson-Zingman D, Nomicos EYH, Conrad T, Kennedy J, Jones W, Gilman RH, Winokur P. Pharmacokinetics, Safety, and Tolerability of Oxfendazole in Healthy Volunteers: a Randomized, Placebo- Controlled First-in-Human Single-Dose Escalation Study. Antimicrob Agents Chemother. 2019 Mar 27;63(4):e02255-18. doi: 10.1128/AAC.02255-18. PMID: 30745383; PMCID: PMC6437481.

20: Xu D, Tian W, Jiang C, Huang Z, Zheng S. The anthelmintic agent oxfendazole inhibits cell growth in non‑small cell lung cancer by suppressing c‑Src activation. Mol Med Rep. 2019 Apr;19(4):2921-2926. doi: 10.3892/mmr.2019.9897. Epub 2019 Jan 28. PMID: 30720086.