Antifebrin

Antifebrin

Antifebrin, also known as acetanilide, is an organic compound with the chemical formula C₆H₅NH(COCH₃). It is a white, odorless solid that was historically used as a fever-reducing agent and pain reliever. Antifebrin was one of the first synthetic drugs used in medicine, marking a significant development in the field of pharmaceuticals.

History

Antifebrin was first synthesized in 1866 by the French chemist Charles Gerhardt. However, it was not until 1886 that its antipyretic (fever-reducing) properties were discovered by Cahn and Hepp. The compound was marketed under the trade name Antifebrin and became widely used as a treatment for fever and pain.

Chemical Properties

Antifebrin is an aromatic amide and is structurally related to aniline and acetic acid. It is slightly soluble in water but more soluble in organic solvents such as ethanol and ether. The compound is stable under normal conditions but can decompose upon exposure to strong acids or bases.

Mechanism of Action

Antifebrin works by inhibiting the enzyme cyclooxygenase (COX), which is involved in the synthesis of prostaglandins. Prostaglandins are compounds that mediate inflammation and pain in the body. By reducing the production of prostaglandins, Antifebrin helps to lower fever and alleviate pain.

Medical Use and Side Effects

While Antifebrin was effective as an antipyretic and analgesic, it was found to have significant side effects, including methemoglobinemia, a condition where hemoglobin is converted to methemoglobin, reducing its ability to carry oxygen. This led to symptoms such as cyanosis and shortness of breath. Due to these adverse effects, Antifebrin was largely replaced by safer alternatives such as paracetamol (acetaminophen) and aspirin.

Synthesis

Antifebrin can be synthesized by the acetylation of aniline using acetic anhydride or acetyl chloride. The reaction involves the substitution of the hydrogen atom in the amino group of aniline with an acetyl group, forming acetanilide.

Also see

• Paracetamol
• Aspirin
• Nonsteroidal anti-inflammatory drug
• Aniline