Imidocarb dipropionate
[CAS# 55750-06-6]

Identification

• Classification: Analytical chemistry >> Analytical reagent >> Ion chromatography reagent
• Name: Imidocarb dipropionate
• Synonyms: N,N'-Bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)urea dipropionate
• Molecular Formula: C₁₉H₂₀N₆O.2(C₃H₆O₂)
• Molecular Weight: 496.57
• CAS Registry Number: 55750-06-6
• EC Number: 259-791-8
• SMILES: CCC(=O)O.CCC(=O)O.C1CN=C(N1)C2=CC(=CC=C2)NC(=O)NC3=CC=CC(=C3)C4=NCCN4

Properties

• Melting point: 205 °C (Decomposes) (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Imidocarb dipropionate is a synthetic chemical compound widely used as an antiprotozoal agent, primarily in veterinary medicine for the treatment and prevention of diseases caused by protozoan parasites such as Babesia and Anaplasma species. It is a dipropionate ester derivative of imidocarb, with the molecular formula C₂₂H₂₈N₆O₄, designed to enhance the compound’s solubility and bioavailability.

Imidocarb was first developed in the mid-20th century as part of efforts to control hemoprotozoan infections in livestock, which cause significant economic losses in agriculture. The dipropionate form is commonly used due to its improved pharmacokinetic properties compared to the free base, allowing for effective systemic administration.

The mechanism of action of imidocarb dipropionate involves interference with the nucleic acid metabolism of protozoan parasites. It inhibits the synthesis of nucleotides and disrupts DNA replication, leading to the death of the parasites within the host’s red blood cells. This targeted action makes it effective against intracellular parasites responsible for diseases such as babesiosis and anaplasmosis.

Clinically, imidocarb dipropionate is administered by injection in animals such as cattle, sheep, and dogs. It is used both therapeutically to treat active infections and prophylactically to prevent the development of disease in endemic areas. The drug is effective in clearing parasitemia and reducing clinical signs such as anemia, fever, and lethargy associated with protozoal infections.

Pharmacokinetically, imidocarb dipropionate exhibits good absorption following intramuscular or subcutaneous administration, with distribution throughout the body, including intracellular compartments where parasites reside. It is metabolized primarily in the liver and excreted via the kidneys. The dipropionate ester prolongs the drug’s half-life, allowing sustained therapeutic levels.

Adverse effects of imidocarb dipropionate in treated animals may include transient pain at the injection site, cholinergic symptoms such as salivation and diarrhea, and in rare cases, toxicity manifesting as muscle tremors or respiratory distress. Proper dosing and veterinary supervision minimize these risks.

Analytically, imidocarb dipropionate can be identified and quantified in pharmaceutical formulations and biological samples using high-performance liquid chromatography (HPLC), mass spectrometry (MS), and ultraviolet-visible (UV-Vis) spectrophotometry. These techniques support quality control and pharmacokinetic studies.

In summary, imidocarb dipropionate is a veterinary antiprotozoal agent effective against intracellular parasites causing babesiosis and anaplasmosis. Its development has improved the management of hemoprotozoan diseases in livestock through targeted disruption of parasite nucleic acid synthesis, with enhanced pharmacokinetic properties provided by the dipropionate ester form.

References

2024. A 50-year-old question: Can imidocarb chemoprophylaxis ensure seroconversion for babesiosis in cattle under field conditions?. Veterinary Parasitology, 334.
DOI: 10.1016/j.vetpar.2024.110337

2021. Efficacy of long-acting oxytetracycline and imidocarb dipropionate for the chemosterilization of Anaplasma marginale in experimentally infected carrier cattle in Argentina. Veterinary Parasitology: Regional Studies and Reports, 23.
DOI: 10.1016/j.vprsr.2020.100513

1974. Imidocarb dipropionate therapy in Kenyan anaplasmosis and babesiosis. Tropical Animal Health and Production, 6(2).
DOI: 10.1007/bf02380540