Decoquinate
[CAS# 18507-89-6]

Identification

• Classification: API >> Veterinary drug raw materials
• Name: Decoquinate
• Synonyms: Deccox; Ethyl 6-decyloxy-7-ethoxy-4-hydroxy-3-quinolinate
• Molecular Formula: C₂₄H₃₅NO₅
• Molecular Weight: 417.54
• CAS Registry Number: 18507-89-6
• EC Number: 242-389-1
• SMILES: CCCCCCCCCCOC1=C(C=C2C(=C1)C(=O)C(=CN2)C(=O)OCC)OCC

Properties

• Solubility: 10 mM (DMSO)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Decoquinate is a compound belonging to the class of hydroxynaphthoquinones, used primarily as anticoccidial agents in livestock. Decoquinate was discovered in the 1960s during efforts to develop effective treatments for coccidiosis, a parasitic disease caused by various protozoa of the genus Eimeria. Decoquinate was synthesized and evaluated as having potent activity against coccidia in poultry and other livestock.

Chemically, decoquinate is a hydroxynaphthoquinone derivative with the molecular formula C21H25NO3. It is typically a yellow to brownish-yellow crystalline powder that is slightly soluble in water but soluble in organic solvents such as ethanol and acetone. This solubility characteristic affects its formulation and administration in veterinary medicine.

Decoquinate acts by disrupting the electron transport chain in the mitochondria of coccidia, specifically inhibiting the function of the cytochrome b complex. This disturbance results in a blockage in the production of adenosine triphosphate (ATP), the cellular energy unit, ultimately leading to metabolic dysfunction and parasite death. Importantly, decoquinate selectively targets coccidia while sparing host cells, making it a safe and effective treatment for coccidiosis in livestock.

Decoquinate is widely used in the poultry industry to prevent and treat coccidiosis, a disease that causes economic losses due to reduced growth rates, poor feed conversion, and mortality of infected animals. Decoquinate is also effective against coccidiosis infections in other livestock species, such as cattle, sheep, and goats, helping to improve productivity and animal welfare.

Commercial formulations of decoquinate include feed additives, premixes, and oral solutions designed to be added to animal feed or drinking water. These formulations ensure that the compound is evenly distributed and effectively delivered to livestock, thereby optimizing its effectiveness in treating coccidiosis.

Decoquinate is well tolerated by livestock when used according to recommended dosing guidelines. Regulatory agencies, such as the U.S. Food and Drug Administration (FDA) and the European Medicines Agency (EMA), have established guidelines for its use in veterinary medicine to ensure it is safe for animal consumption and to minimize impact on the environment.

Ongoing research focuses on: investigating the mechanisms of coccidial resistance development and optimizing treatment strategies to prevent or delay resistance to decoquinate and other anticoccidial drugs; and developing new formulations and delivery systems to improve bioavailability, efficacy, and ease of use in livestock production systems.

References

2022. Preparation of Decoquinate Solid Dispersion by Hot-Melt Extrusion as an Oral Dosage Form Targeting Liver-Stage Plasmodium Infection. Antimicrobial Agents and Chemotherapy.
DOI: 10.1128/aac.02218-21

2018. Formulation of Natural Oil Nano-Emulsions for the Topical Delivery of Clofazimine, Artemisone and Decoquinate. Pharmaceutical Research.
DOI: 10.1007/s11095-018-2471-9

2016. Straightforward conversion of decoquinate into inexpensive tractable new derivatives with significant antimalarial activities. Bioorganic & Medicinal Chemistry Letters.
DOI: 10.1016/j.bmcl.2016.05.024