Cyano-, Nitrile-

2-Chloro-4-fluorobenzonitrile is a drug that has been shown to have antitumor effects by binding to the CB2 receptor. It inhibits hydrogenation reduction of the molecule, which may be due to its ability to react with both functional groups. 2-Chloro-4-fluorobenzonitrile has also been shown to inhibit progesterone receptor, which may lead to an increase in progesterone levels and a decrease in estrogen levels. The pharmacokinetic properties of this compound are not yet known.

2-Cyanocinnamic acid is a fatty acid that has been shown to inhibit the synthesis of proteins. It binds to cytochrome c oxidase, inhibiting mitochondrial respiration and electron transport, leading to decreased ATP production. 2-Cyanocinnamic acid is not easily transported out of mitochondria, which leads to its accumulation in the mitochondrial matrix. This accumulation causes synergistic inhibition with glutamate, leading to a decrease in ATP production and an increase in intracellular levels of reactive oxygen species (ROS). The use of 2-cyanoacrylic acid as a mitochondrial transport inhibitor has been proposed for the treatment of obesity and diabetes.
2-Cyanocinnamic acid also inhibits fatty acid uptake by binding to the protein translocase at the outer membrane of cells. This binding prevents monomers from entering the cell, where they are broken down by beta oxidation and converted into acetyl-CoA, which can be used for energy production or stored as triglycer

4-Amino-2-cyanotoluene is a quinazoline compound that inhibits the synthesis of thymine, which is necessary for DNA replication. This compound binds to the enzyme thymidylate synthetase, thereby inhibiting the synthesis of thymine. The inhibitory effect has been shown in a study using calf thymus DNA. 4-Amino-2-cyanotoluene also inhibits the synthesis of other nucleic acids such as adenine and guanine.

3-Cyanoethylbenzoic acid is an anthropogenic compound that is produced by the Friedel-Crafts reaction between benzoyl chloride and acrylonitrile in the presence of a base. 3-Cyanoethylbenzoic acid is used as a solvent for chromatographic methods, such as gradient elution, ion exchange, and reversed phase. 3-Cyanoethylbenzoic acid has been used to determine the optical purity of benzoate salts and amides. This compound can be taken orally in solid oral dosage form or enterically in liquid oral dosage form. 3-Cyanoethylbenzoic acid interacts with other drugs that are metabolized by CYP3A4, such as erythromycin, to produce an active metabolite (N-desmethyldesipramide).