1083-57-4 Usage
Description
3-HYDROXY-P-BUTYROPHENETIDINE, also known as Bucetin, is an antipyretic and analgesic drug that is chemically similar to phenacetin. It was used for its fever-reducing and pain-relieving properties. However, its use has been withdrawn due to renal toxicity.
Uses
Used in Pharmaceutical Industry:
3-HYDROXY-P-BUTYROPHENETIDINE was used as an antipyretic and analgesic agent for the treatment of fever and pain relief. It was utilized to reduce high body temperature and alleviate pain in patients. However, its use has been discontinued due to the risk of renal toxicity.
Brand names associated with 3-HYDROXY-P-BUTYROPHENETIDINE include Beelin, Bonanza, Haitmin, Hoe 15239, New isomidon, and Ringl-s.
Originator
Bucetin,ZYF Pharm Chemical
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.
Therapeutic Function
Analgesic
World Health Organization (WHO)
Bucetin is an analogue of phenacetin. See WHO comment for
phenacetin.
Check Digit Verification of cas no
The CAS Registry Mumber 1083-57-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,8 and 3 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1083-57:
(6*1)+(5*0)+(4*8)+(3*3)+(2*5)+(1*7)=64
64 % 10 = 4
So 1083-57-4 is a valid CAS Registry Number.
InChI:InChI=1/C12H17NO3/c1-3-16-11-6-4-10(5-7-11)13-12(15)8-9(2)14/h4-7,9,14H,3,8H2,1-2H3,(H,13,15)
1083-57-4Relevant articles and documents
Hydroxy Group Directed Catalytic Hydrosilylation of Amides
Ni, Jizhi,Oguro, Tsubasa,Sawazaki, Taka,Sohma, Youhei,Kanai, Motomu
supporting information, p. 7371 - 7374 (2018/11/25)
Chemo- and site-selective hydrosilylation of α- or β-hydroxy amides using organocatalyst B(C6F5)3 and commercially available hydrosilanes is described. This transformation is operative under mild conditions and tolerates a wide range of functional groups. The reaction was applied for selective reduction of a specific amide group of the therapeutically important cyclic peptide cyclosporin A, demonstrating the potential usefulness of this catalytic method in late-stage structural transformations of drug lead molecules.