Derquantel | CAS#187865-22-1 | spiroindole

MedKoo Cat#: 333086 | Name: Derquantel

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Description:

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

Derquantel is a so-called spiroindole, is obtained from fermentation extracts of Penicillium simplicissimum, a particular species of soil fungi. This drug is used in veterinary under brand name Startect, in combination with abamectin against several gastrointestinal roundworms that affect sheep. At the recommended therapeutic dose derquantel is highly effective against Haemonchus spp, Cooperia spp, and Trichostrongylus spp, including those resistant to most classic anthelmintics (benzimidazoles, levamisole, macrocyclic lactones).

Chemical Structure

Derquantel

CAS#187865-22-1

Theoretical Analysis

MedKoo Cat#: 333086

Name: Derquantel

CAS#: 187865-22-1

Chemical Formula: C28H37N3O4

Exact Mass: 479.2784

Molecular Weight: 479.62

Elemental Analysis: C, 70.12; H, 7.78; N, 8.76; O, 13.34

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 650.00	2 Weeks
25mg	USD 2,250.00	2 Weeks

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Related CAS #

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Synonym

Derquantel; PF-00520904; PF 00520904; PF00520904; PNU 141962; PNU-141962; PNU141962; 2-deoxy-Paraherquamide;

IUPAC/Chemical Name

(1'R,5a'S,8R,8a'S,9a'R)-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-2',3',8a',9,9',10-hexahydro-1'H,4H,5'H,6'H,8'H-spiro[[1,4]dioxepino[2,3-g]indole-8,7'-[5a,9a](epiminomethano)cyclopenta[f]indolizin]-10'-one

InChi Key

DYVLXWPZFQQUIU-WGNDVSEMSA-N

InChi Code

InChI=1S/C28H37N3O4/c1-23(2)10-12-34-21-18(35-23)8-7-17-20(21)29-15-26(17)14-27-16-31-11-9-25(5,33)28(31,22(32)30(27)6)13-19(27)24(26,3)4/h7-8,10,12,19,29,33H,9,11,13-16H2,1-6H3/t19-,25+,26-,27+,28-/m0/s1

SMILES Code

CC(C=CO1)(C)OC2=C1C(NC3)=C(C=C2)[C@]3(C4(C)C)C[C@]5(N(C)C6=O)[C@@]4([H])C[C@]6([C@](C)(O)CC7)N7C5

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 479.62 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

1: Ahuir-Baraja AE, Cibot F, Llobat L, Garijo MM. Anthelmintic resistance: is a solution possible? Exp Parasitol. 2021 Nov;230:108169. doi: 10.1016/j.exppara.2021.108169. Epub 2021 Oct 7. PMID: 34627787. 2: Abongwa M, Martin RJ, Robertson AP. A BRIEF REVIEW ON THE MODE OF ACTION OF ANTINEMATODAL DRUGS. Acta Vet (Beogr). 2017 Jun;67(2):137-152. doi: 10.1515/acve-2017-0013. Epub 2017 Jun 26. PMID: 29416226; PMCID: PMC5798647. 3: Lamb J, Elliott T, Chambers M, Chick B. Broad spectrum anthelmintic resistance of Haemonchus contortus in Northern NSW of Australia. Vet Parasitol. 2017 Jul 15;241:48-51. doi: 10.1016/j.vetpar.2017.05.008. Epub 2017 May 15. PMID: 28579030. 4: Hodgson B, Mulvaney CJ. Resistance to a triple-combination anthelmintic in Trichostrongylus spp. on a commercial sheep farm in New Zealand. N Z Vet J. 2017 Sep;65(5):277-281. doi: 10.1080/00480169.2017.1333468. Epub 2017 Jun 5. PMID: 28532295. 5: Verma S, Kashyap SS, Robertson AP, Martin RJ. Functional genomics in Brugia malayi reveal diverse muscle nAChRs and differences between cholinergic anthelmintics. Proc Natl Acad Sci U S A. 2017 May 23;114(21):5539-5544. doi: 10.1073/pnas.1619820114. Epub 2017 May 9. PMID: 28487481; PMCID: PMC5448196. 6: Sales N, Love S. Resistance of Haemonchus sp. to monepantel and reduced efficacy of a derquantel / abamectin combination confirmed in sheep in NSW, Australia. Vet Parasitol. 2016 Sep 15;228:193-196. doi: 10.1016/j.vetpar.2016.08.016. Epub 2016 Aug 23. PMID: 27692326. 7: Dzhafarov MKh, Vasilevich F, Dovgalev AS, Imamkuliev KD, Pautova EA. [ANTHELMINTIC SUBSTANCES: MAIN CLASSES, PROBLEMS, TRENDS IN DEVELOPMENT AND PROSPECTS]. Med Parazitol (Mosk). 2016 Apr-Jun;(2):47-53. Russian. PMID: 27405218. 8: Abongwa M, Buxton SK, Robertson AP, Martin RJ. Curiouser and Curiouser: The Macrocyclic Lactone, Abamectin, Is also a Potent Inhibitor of Pyrantel/Tribendimidine Nicotinic Acetylcholine Receptors of Gastro-Intestinal Worms. PLoS One. 2016 Jan 11;11(1):e0146854. doi: 10.1371/journal.pone.0146854. PMID: 26751958; PMCID: PMC4709073. 9: Lanusse C, Lifschitz A, Alvarez L. Basic and clinical pharmacology contribution to extend anthelmintic molecules lifespan. Vet Parasitol. 2015 Aug 15;212(1-2):35-46. doi: 10.1016/j.vetpar.2015.07.015. Epub 2015 Jul 21. PMID: 26220023. 10: Li BW, Rush AC, Weil GJ. Expression of five acetylcholine receptor subunit genes in Brugia malayi adult worms. Int J Parasitol Drugs Drug Resist. 2015 Jun 23;5(3):100-9. doi: 10.1016/j.ijpddr.2015.04.003. PMID: 26199859; PMCID: PMC4506985. 11: World Health Organization. Evaluation of certain veterinary drug residues in food. Seventy-eighth report of the Joint FAO/WHO Expert Committee on Food Additives. World Health Organ Tech Rep Ser. 2014;(988):1-123, back cover. PMID: 25591324. 12: Miller CM, Ganesh S, Garland CB, Leathwick DM. Production benefits from pre- and post-lambing anthelmintic treatment of ewes on commercial farms in the southern North Island of New Zealand. N Z Vet J. 2015 Jul;63(4):211-9. doi: 10.1080/00480169.2015.1007108. Epub 2015 May 15. PMID: 25589215. 13: Geurden T, Slootmans N, Glover M, Bartram DJ. Production benefit of treatment with a dual active oral formulation of derquantel-abamectin in slaughter lambs. Vet Parasitol. 2014 Sep 15;205(1-2):405-7. doi: 10.1016/j.vetpar.2014.06.012. Epub 2014 Jun 17. PMID: 24986436. 14: Martin RJ, Puttachary S, Buxton SK, Verma S, Robertson AP. The Conqueror Worm: recent advances with cholinergic anthelmintics and techniques excite research for better therapeutic drugs. J Helminthol. 2015 Jul;89(4):387-97. doi: 10.1017/S0022149X1400039X. Epub 2014 May 29. PMID: 24871674; PMCID: PMC4247809. 15: Buxton SK, Charvet CL, Neveu C, Cabaret J, Cortet J, Peineau N, Abongwa M, Courtot E, Robertson AP, Martin RJ. Investigation of acetylcholine receptor diversity in a nematode parasite leads to characterization of tribendimidine- and derquantel-sensitive nAChRs. PLoS Pathog. 2014 Jan 30;10(1):e1003870. doi: 10.1371/journal.ppat.1003870. PMID: 24497826; PMCID: PMC3907359. 16: Bartram DJ, Noé L, Krautmann MJ, Lane S, Geurden T. Clinical safety of rapid sequential administration of moxidectin injection and oral derquantel-abamectin as a quarantine treatment for introduced sheep. Vet Rec. 2013 Apr 20;172(16):426. doi: 10.1136/vr.101442. Epub 2013 Mar 23. PMID: 23525484. 17: Puttachary S, Trailovic SM, Robertson AP, Thompson DP, Woods DJ, Martin RJ. Derquantel and abamectin: effects and interactions on isolated tissues of Ascaris suum. Mol Biochem Parasitol. 2013 Apr;188(2):79-86. doi: 10.1016/j.molbiopara.2013.02.004. Epub 2013 Mar 21. PMID: 23523993; PMCID: PMC3864555. 18: Epe C, Kaminsky R. New advancement in anthelmintic drugs in veterinary medicine. Trends Parasitol. 2013 Mar;29(3):129-34. doi: 10.1016/j.pt.2013.01.001. Epub 2013 Feb 1. PMID: 23376212. 19: World Health Organization. Evaluation of certain veterinary drug residues in food. World Health Organ Tech Rep Ser. 2012;(969):i-vii, 1-101. PMID: 22953379. 20: 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. PMID: 22576857.