3-HYDROXY-P-BUTYROPHENETIDINE

Originator

Bucetin,ZYF Pharm Chemical

The Uses of 3-HYDROXY-P-BUTYROPHENETIDINE

3-Hydroxy-p-butyrophenetidine is an antipyretic and analgesic drug that is chemically similar to phenacetin (P294580). The use of 3-Hydroxy-p-butyrophenetidine has been withdrawn due to renal toxicity.

The Uses of 3-HYDROXY-P-BUTYROPHENETIDINE

Bucetin is an antipyretic and analgesic drug that is chemically similar to phenacetin. The use of Bucetin has been withdrawn due to renal toxicity.

What are the applications of Application

Bucetin is an antipyretic and analgesic drug that is chemically similar to phenacetin.

Background

Bucetin is an analgesic and antipyretic medication which was approved for use in Germany but was withdrawn from the market in 1986 due to renal toxicity caused by the medication.

Definition

ChEBI: Bucetin is an organic molecular entity.

Manufacturing Process

Bucetin may be prepared from acetoacetic acid p-phenetidide as follows: 5.5 parts of acetoacetic acid p-phenetidide, suspended in 600 parts by volume of methanol, are hydrogenated at 80°-85°C with a nickel catalyst supported on kiesel-guhr. When the theoretical quantity of hydrogen has been absorbed, the solution is cooled, then filtered, and the filtrate is concentrated. The solid residue is recrystallized from six times its weight of isopropanol. β- Hydroxybutyric acid p-phenetidide is obtained in an almost quantitative yield in the form of white crystals which melt at 160°C.
55 parts of acetoacetic acid p-phenetidide, suspended in 500 parts by volume of methanol, are hydrogenated with Raney nickel at 70°C. When the theoretical quantity of hydrogen has been absorbed, the solution is cooled, then filtered, and the filtrate is concentrated. The solid residue is recrystallized from six times its weight of isopropanol. 51 parts (93 % of the theoretical yield) of β-hydroxybutyric acid p-phenetidide are obtained in the form of white crystals, which are sparingly soluble in water and melt at 160°C.
A mixture of 5 g of aluminum amalgam, 5 g of acetoacetic acid p-phenetidide and 50 ml of ethanol are gently heated for 30 minutes. After filtering off the reducing agent with suction, water is added to the filtrate, and the latter is then acidified with 2 N hydrochloric acid. β-Hydroxybutyric acid p-phenetidide melting at 160°C crystallizes in almost quantitative yield in the form of white crystals.

brand name

Beelin;Bonanza;Haitmin;Hoe 15239;New isomidon;Ringl-s.

Therapeutic Function

Analgesic

World Health Organization (WHO)

Bucetin is an analogue of phenacetin. See WHO comment for phenacetin.

Metabolism

Not Available