Monepantel
featured

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

Hodoodo CAT#: H319893

CAS#: 887148-69-8

Description: Monepantel, also known as AAD 1566, is a new anthelmintic agent approved for the treatment of nematode infections in farm animals. As a nematicide, it acts through a nematode-specific nicotinic receptor subtype which explains its exceptional safety in rodents and mammals. Monepantel is also a promising anticancer agent, which suppressed cellular thymidine incorporation thus impairing DNA synthesis and inducing cleavage of poly (ADP-ribose) polymerase (PARP-1).

Chemical Structure

img
Monepantel
CAS# 887148-69-8
Instruction

Theoretical Analysis

Hodoodo Cat#: H319893
Name: Monepantel
CAS#: 887148-69-8
Chemical Formula: C20H13F6N3O2S
Exact Mass: 473.06
Molecular Weight: 473.393
Elemental Analysis: C, 50.74; H, 2.77; F, 24.08; N, 8.88; O, 6.76; S, 6.77

Price and Availability

Size Price Availability Quantity
5mg USD 650 2 Weeks
10mg USD 1250 2 Weeks
Bulk inquiry

Synonym: AAD 1566; AAD1566; AAD-1566; MPL, Monepantel

IUPAC/Chemical Name: (S)-N-(2-cyano-1-(5-cyano-2-(trifluoromethyl)phenoxy)propan-2-yl)-4-((trifluoromethyl)thio)benzamide

InChi Key: WTERNLDOAPYGJD-SFHVURJKSA-N

InChi Code: InChI=1S/C20H13F6N3O2S/c1-18(10-28,11-31-16-8-12(9-27)2-7-15(16)19(21,22)23)29-17(30)13-3-5-14(6-4-13)32-20(24,25)26/h2-8H,11H2,1H3,(H,29,30)/t18-/m0/s1

SMILES Code: O=C(N[C@@](C)(C#N)COC1=CC(C#N)=CC=C1C(F)(F)F)C2=CC=C(SC(F)(F)F)C=C2

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, not in water

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 473.39 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:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Cintra MC, Teixeira VN, Nascimento LV, Sotomaior CS. Lack of efficacy of monepantel against Trichostrongylus colubriformis in sheep in Brazil. Vet Parasitol. 2016 Jan 30;216:4-6. doi: 10.1016/j.vetpar.2015.11.013. Epub 2015 Nov 28. PubMed PMID: 26801587.

2: Bartley DJ, Devin L, Nath M, Morrison AA. Selection and characterisation of monepantel resistance in Teladorsagia circumcincta isolates. Int J Parasitol Drugs Drug Resist. 2015 May 15;5(2):69-76. doi: 10.1016/j.ijpddr.2015.05.001. eCollection 2015 Aug. PubMed PMID: 26042197; PubMed Central PMCID: PMC4443404.

3: Van den Brom R, Moll L, Kappert C, Vellema P. Haemonchus contortus resistance to monepantel in sheep. Vet Parasitol. 2015 Apr 30;209(3-4):278-80. doi: 10.1016/j.vetpar.2015.02.026. Epub 2015 Mar 5. PubMed PMID: 25770852.

4: Stuchlíková L, Matoušková P, Bártíková H, Vokřál I, Lamka J, Štolcová T, Pětníková H, Szotáková B, Kubíček V, Skálová L. Monepantel induces hepatic cytochromes p450 in sheep in vitro and in vivo. Chem Biol Interact. 2015 Feb 5;227:63-8. doi: 10.1016/j.cbi.2014.12.025. Epub 2014 Dec 31. PubMed PMID: 25555458.

5: Mederos AE, Ramos Z, Banchero GE. First report of monepantel Haemonchus contortus resistance on sheep farms in Uruguay. Parasit Vectors. 2014 Dec 17;7:598. doi: 10.1186/s13071-014-0598-z. PubMed PMID: 25515711; PubMed Central PMCID: PMC4305228.

6: Monepantel resistance reported on Dutch sheep farms. Vet Rec. 2014 Nov 1;175(17):418. doi: 10.1136/vr.g6475. PubMed PMID: 25359740.

7: Baur R, Beech R, Sigel E, Rufener L. Monepantel irreversibly binds to and opens Haemonchus contortus MPTL-1 and Caenorhabditis elegans ACR-20 receptors. Mol Pharmacol. 2015 Jan;87(1):96-102. doi: 10.1124/mol.114.095653. Epub 2014 Oct 28. PubMed PMID: 25352042.

8: Bahrami F, Pourgholami MH, Mekkawy AH, Rufener L, Morris DL. Monepantel induces autophagy in human ovarian cancer cells through disruption of the mTOR/p70S6K signalling pathway. Am J Cancer Res. 2014 Sep 6;4(5):558-71. eCollection 2014. PubMed PMID: 25232497; PubMed Central PMCID: PMC4163620.

9: Bahrami F, Morris DL, Rufener L, Pourgholami MH. Anticancer properties of novel aminoacetonitrile derivative monepantel (ADD 1566) in pre-clinical models of human ovarian cancer. Am J Cancer Res. 2014 Sep 6;4(5):545-57. eCollection 2014. PubMed PMID: 25232496; PubMed Central PMCID: PMC4163619.

10: Lecová L, Stuchlíková L, Prchal L, Skálová L. Monepantel: the most studied new anthelmintic drug of recent years. Parasitology. 2014 Nov;141(13):1686-98. doi: 10.1017/S0031182014001401. Epub 2014 Sep 9. PubMed PMID: 25200288.

11: Fru MF, Puoti A. Acquired resistance to monepantel in C. elegans: What about parasitic nematodes? Worm. 2014 Oct 31;3(3):e959416. doi: 10.4161/21624046.2014.959416. eCollection 2014 Jul-Sep. PubMed PMID: 26430545; PubMed Central PMCID: PMC4588160.

12: Lifschitz A, Ballent M, Virkel G, Sallovitz J, Viviani P, Lanusse C. Accumulation of monepantel and its sulphone derivative in tissues of nematode location in sheep: pharmacokinetic support to its excellent nematodicidal activity. Vet Parasitol. 2014 Jun 16;203(1-2):120-6. doi: 10.1016/j.vetpar.2014.02.049. Epub 2014 Mar 2. PubMed PMID: 24647279.

13: Stuchlíková L, Jirásko R, Vokřál I, Valát M, Lamka J, Szotáková B, Holčapek M, Skálová L. Metabolic pathways of anthelmintic drug monepantel in sheep and in its parasite (Haemonchus contortus). Drug Test Anal. 2014 Oct;6(10):1055-62. doi: 10.1002/dta.1630. Epub 2014 Mar 10. PubMed PMID: 24616229.

14: Scott I, Pomroy WE, Kenyon PR, Smith G, Adlington B, Moss A. Lack of efficacy of monepantel against Teladorsagia circumcincta and Trichostrongylus colubriformis. Vet Parasitol. 2013 Nov 15;198(1-2):166-71. doi: 10.1016/j.vetpar.2013.07.037. Epub 2013 Aug 1. PubMed PMID: 23953148.

15: Rufener L, Bedoni N, Baur R, Rey S, Glauser DA, Bouvier J, Beech R, Sigel E, Puoti A. acr-23 Encodes a monepantel-sensitive channel in Caenorhabditis elegans. PLoS Pathog. 2013;9(8):e1003524. doi: 10.1371/journal.ppat.1003524. Epub 2013 Aug 8. PubMed PMID: 23950710; PubMed Central PMCID: PMC3738477.

16: Dadak AM, Asanger H, Tichy A, Franz S. Establishing an efficacious dose rate of monepantel for treating gastrointestinal nematodes in llamas under field conditions. Vet Rec. 2013 Feb 9;172(6):155. doi: 10.1136/vr.101109. Epub 2013 Jan 3. PubMed PMID: 23292846.

17: Stuchlíková L, Jirásko R, Vokřál I, Lamka J, Spulák M, Holčapek M, Szotáková B, Bártíková H, Pour M, Skálová L. Investigation of the metabolism of monepantel in ovine hepatocytes by UHPLC/MS/MS. Anal Bioanal Chem. 2013 Feb;405(5):1705-12. doi: 10.1007/s00216-012-6584-4. Epub 2012 Nov 25. PubMed PMID: 23183590.

18: Sager H, Bapst B, Strehlau GA, Kaminsky R. Efficacy of monepantel, derquantel and abamectin against adult stages of a multi-resistant Haemonchus contortus isolate. Parasitol Res. 2012 Nov;111(5):2205-7. doi: 10.1007/s00436-012-2949-z. Epub 2012 May 11. PubMed PMID: 22576857.

19: George SD, George AJ, Stein PA, Rolfe PF, Hosking BC, Seewald W. The comparative efficacy of abamectin, monepantel and an abamectin/derquantel combination against fourth-stage larvae of a macrocyclic lactone-resistant Teladorsagia spp. isolate infecting sheep. Vet Parasitol. 2012 Aug 13;188(1-2):190-3. doi: 10.1016/j.vetpar.2012.03.001. Epub 2012 Mar 9. PubMed PMID: 22459111.

20: Tritten L, Silbereisen A, Keiser J. In vitro and in vivo efficacy of Monepantel (AAD 1566) against laboratory models of human intestinal nematode infections. PLoS Negl Trop Dis. 2011 Dec;5(12):e1457. doi: 10.1371/journal.pntd.0001457. Epub 2011 Dec 27. PubMed PMID: 22216366; PubMed Central PMCID: PMC3246443.