Decoquinate | CAS#18507-89-6 | coccidiostat

MedKoo Cat#: 561595 | Name: Decoquinate

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Description:

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

Decoquinate is a nonantibiotic coccidiostat.

Chemical Structure

Decoquinate

CAS#18507-89-6

Theoretical Analysis

MedKoo Cat#: 561595

Name: Decoquinate

CAS#: 18507-89-6

Chemical Formula: C24H35NO5

Exact Mass: 417.2515

Molecular Weight: 417.54

Elemental Analysis: C, 69.04; H, 8.45; N, 3.35; O, 19.16

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
5g	USD 450.00	2 Weeks
10g	USD 650.00	2 Weeks
25g	USD 1,150.00	2 Weeks

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Synonym

Decoquinate; Deccox; Decoxy; NSC 339057; NSC339057; NSC-339057

IUPAC/Chemical Name

Ethyl 6-(decyloxy)-7-ethoxy-4-hydroxyquinoline-3-carboxylate

InChi Key

JHAYEQICABJSTP-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H35NO5/c1-4-7-8-9-10-11-12-13-14-30-21-15-18-20(16-22(21)28-5-2)25-17-19(23(18)26)24(27)29-6-3/h15-17H,4-14H2,1-3H3,(H,25,26)

SMILES Code

O=C(C1=C(O)C2=CC(OCCCCCCCCCC)=C(OCC)C=C2N=C1)OCC

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Decoquinate is a quinolone derivative that can be used for research of coccidiosis in domestic ruminants and has potent activity against both Plasmodium hepatic development and red cell replication.

In vitro activity:

First, it was hypothesized that if cytochrome bc1 complex were the target, decoquinate, like atovaquone, would be active in hepatic stages of the parasite. Sporozoites were assayed for their ability to develop within human hepatocytes expressing murine CD81, an essential surface protein required by the parasite for successful invasion. Decoquinate showed a 10-fold increase in activity over atovaquone with an IC50 value of 177 pM (Figure 2, panel c) supporting the hypothesis that decoquinate shares properties with atovaquone, including inhibition of the cytochrome bc1 complex. In contrast, the DMSO control had no effect on parasite or hepatocyte proliferation. Additionally, a >180-fold shift in the IC50 of decoquinate was observed in the ScDHOD-D10attB line (Table 3) indicating that the primary mode of action for decoquinate is inhibition of the mitochondrial ETC. Reference: ACS Chem Biol. 2011 Nov 18; 6(11): 1214–1222. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3220786/

In vivo activity:

Decoquinate was used in an animal prophylaxis test in which mice are given a single 50 mg kg–1 oral dose at the same time as receiving 50,000 P. yoelii sporozoites injected intravenously. Four of five mice treated with decoquinate survived, whereas one developed delayed patent parasitemia on day 7 (Table 2). All five untreated mice developed patent parasitemia within 3 days and needed to be euthanized at day 7. Reference: ACS Chem Biol. 2011 Nov 18; 6(11): 1214–1222. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3220786/

	Solvent	mg/mL	mM
Solubility
	DMSO	1.0	2.39

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 417.54 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. Nam TG, McNamara CW, Bopp S, Dharia NV, Meister S, Bonamy GM, Plouffe DM, Kato N, McCormack S, Bursulaya B, Ke H, Vaidya AB, Schultz PG, Winzeler EA. A chemical genomic analysis of decoquinate, a Plasmodium falciparum cytochrome b inhibitor. ACS Chem Biol. 2011 Nov 18;6(11):1214-22. doi: 10.1021/cb200105d. Epub 2011 Sep 8. PMID: 21866942; PMCID: PMC3220786. 2. Lindsay DS, Woods KM, Upton SJ, Blagburn BL. Activity of decoquinate against Cryptosporidium parvum in cell cultures and neonatal mice. Vet Parasitol. 2000 May 17;89(4):307-11. doi: 10.1016/s0304-4017(00)00209-0. PMID: 10799844.

In vitro protocol:

In vivo protocol:

1: Souza TS, Moreira DRM, Marcelino HR. Chemical and Pharmacological Properties of Decoquinate: A Review of Its Pharmaceutical Potential and Future Perspectives. Pharmaceutics. 2022 Jun 30;14(7):1383. doi: 10.3390/pharmaceutics14071383. PMID: 35890280; PMCID: PMC9315532. 2: Zeng S, Wang H, Tao L, Ning X, Fan Y, Zhao S, Qin L, Chen X. Decoquinate liposomes: highly effective clearance of Plasmodium parasites causing severe malaria. Malar J. 2022 Jan 24;21(1):24. doi: 10.1186/s12936-022-04042-8. PMID: 35073922; PMCID: PMC8785525. 3: Taylor MA, Bartram DJ. The history of decoquinate in the control of coccidial infections in ruminants. J Vet Pharmacol Ther. 2012 Oct;35(5):417-27. doi: 10.1111/j.1365-2885.2012.01421.x. Epub 2012 Jun 24. PMID: 22724547. 4: EFSA Panel on Additives, Products or Substances used in Animal Feed (EFSA FEEDAP Panel); Bampidis V, Azimonti G, Bastos ML, Christensen H, Dusemund B, Kouba M, Kos Durjava M, López-Alonso M, López Puente S, Marcon F, Mayo B, Pechová A, Petkova M, Ramos F, Sanz Y, Villa RE, Woutersen R, Aquilina G, Bories G, Cocconcelli PS, Brantom P, Halle I, Kolar B, van Beelen P, Wester P, Holczknecht O, Vettori MV, Gropp J. Safety and efficacy of Deccox® (decoquinate) for chickens for fattening. EFSA J. 2019 Jan 14;17(1):e05541. doi: 10.2903/j.efsa.2019.5541. PMID: 32626086; PMCID: PMC7009050. 5: Lindsay DS, Nazir MM, Maqbool A, Ellison SP, Strobl JS. Efficacy of decoquinate against Sarcocystis neurona in cell cultures. Vet Parasitol. 2013 Sep 1;196(1-2):21-3. doi: 10.1016/j.vetpar.2013.02.008. Epub 2013 Feb 21. PMID: 23523012. 6: Olejnik M, Szprengier-Juszkiewicz T. Deposition and depletion of decoquinate in eggs after administration of cross-contaminated feed. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(7):1124-8. doi: 10.1080/19440049.2015.1045558. Epub 2015 May 26. PMID: 25952987. 7: Fan Y, Qin L, Huang Z, Liang S, Huang X, Zeng S, Liu Y, Wang H. Preliminary Assessment of Intramuscular Depot of Lipid-Based Decoquinate Formulation for Long-Term Chemoprophylaxis of Malaria. Pharmaceutics. 2022 Dec 15;14(12):2813. doi: 10.3390/pharmaceutics14122813. PMID: 36559304; PMCID: PMC9782194. 8: Wang H, Li Q, Reyes S, Zhang J, Zeng Q, Zhang P, Xie L, Lee PJ, Roncal N, Melendez V, Hickman M, Kozar MP. Nanoparticle formulations of decoquinate increase antimalarial efficacy against liver stage Plasmodium infections in mice. Nanomedicine. 2014 Jan;10(1):57-65. doi: 10.1016/j.nano.2013.07.010. Epub 2013 Jul 25. PMID: 23891618. 9: EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP); Bampidis V, Azimonti G, Bastos ML, Christensen H, Dusemund B, Durjava MF, Kouba M, López-Alonso M, López Puente S, Marcon F, Mayo B, Pechová A, Petkova M, Ramos F, Sanz Y, Villa RE, Woutersen R, Gropp J, Rychen G, Holczknecht O, Vettori MV. Efficacy of the feed additive consisting of decoquinate (Deccox®) for use in chickens for fattening (Zoetis Belgium SA). EFSA J. 2021 Mar 8;19(3):e06453. doi: 10.2903/j.efsa.2021.6453. PMID: 33732399; PMCID: PMC7938356. 10: Buxton D, Brebner J, Wright S, Maley SW, Thomson KM, Millard K. Decoquinate and the control of experimental ovine toxoplasmosis. Vet Rec. 1996 May 4;138(18):434-6. doi: 10.1136/vr.138.18.434. PMID: 8735260. 11: Fry M, Williams RB. Effects of decoquinate and clopidol on electron transport in mitochondria of Eimeria tenella (Apicomplexa: Coccidia). Biochem Pharmacol. 1984 Jan 15;33(2):229-40. doi: 10.1016/0006-2952(84)90480-5. PMID: 6704148. 12: Wang ZY, Cai CY, Chang XH, Fei CZ, Qiu MQ, Jiang SX, Xue FQ, Zhang LF. Residue depletion of decoquinate in chicken tissues after oral administration. J Vet Pharmacol Ther. 2013 Apr;36(2):116-21. doi: 10.1111/j.1365-2885.2012.01386.x. Epub 2012 Mar 1. PMID: 22380457. 13: Wang H, Fan Y, Qin L, Cheng Z, Chen X, Zeng S, Liang S, Tong Y, Tao Z, Liu Y, Liu X, Ning X, Chen P, Zhao S, Chen X. Preparation of Decoquinate Solid Dispersion by Hot-Melt Extrusion as an Oral Dosage Form Targeting Liver-Stage Plasmodium Infection. Antimicrob Agents Chemother. 2022 Jun 21;66(6):e0221821. doi: 10.1128/aac.02218-21. Epub 2022 Jun 6. PMID: 35658489; PMCID: PMC9211432. 14: Guo FC, Suo X, Zhang GZ, Shen JZ. Efficacy of decoquinate against drug sensitive laboratory strains of Eimeria tenella and field isolates of Eimeria spp. in broiler chickens in China. Vet Parasitol. 2007 Jul 20;147(3-4):239-45. doi: 10.1016/j.vetpar.2007.04.002. Epub 2007 May 7. PMID: 17485176. 15: Liu S, Tang Y, Lu Y, Guo Y, Xie K, Guan F, Gao P, Zhu Y, Dong Y, Zhang T, Zhang G, Dai G, Xie X. Qualitative and Quantitative Determination of Decoquinate in Chicken Tissues by Gas Chromatography Tandem Mass Spectrometry. Molecules. 2023 May 4;28(9):3875. doi: 10.3390/molecules28093875. PMID: 37175285; PMCID: PMC10180170. 16: Knoll KE, van der Walt MM, Loots DT. In Silico Drug Discovery Strategies Identified ADMET Properties of Decoquinate RMB041 and Its Potential Drug Targets against Mycobacterium tuberculosis. Microbiol Spectr. 2022 Apr 27;10(2):e0231521. doi: 10.1128/spectrum.02315-21. Epub 2022 Mar 30. PMID: 35352998; PMCID: PMC9045315. 17: Nam TG, McNamara CW, Bopp S, Dharia NV, Meister S, Bonamy GM, Plouffe DM, Kato N, McCormack S, Bursulaya B, Ke H, Vaidya AB, Schultz PG, Winzeler EA. A chemical genomic analysis of decoquinate, a Plasmodium falciparum cytochrome b inhibitor. ACS Chem Biol. 2011 Nov 18;6(11):1214-22. doi: 10.1021/cb200105d. Epub 2011 Sep 8. PMID: 21866942; PMCID: PMC3220786. 18: Hobson-Frohock A. Determination of decoquinate in poultry feed. Analyst. 1982 Oct;107(1279):1195-9. doi: 10.1039/an9820701195. PMID: 7181123. 19: Knoll KE, Lindeque Z, Adeniji AA, Oosthuizen CB, Lall N, Loots DT. Elucidating the Antimycobacterial Mechanism of Action of Decoquinate Derivative RMB041 Using Metabolomics. Antibiotics (Basel). 2021 Jun 10;10(6):693. doi: 10.3390/antibiotics10060693. PMID: 34200519; PMCID: PMC8228794. 20: Lindsay DS, Toivio-Kinnucan MA, Blagburn BL. Decoquinate induces tissue cyst formation by the RH strain of Toxoplasma gondii. Vet Parasitol. 1998 Jun 15;77(2-3):75-81. doi: 10.1016/s0304-4017(98)00099-5. PMID: 9746277.

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