BUCETIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H17NO3
Molecular Weight	223.2683
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=CC=C(NC(=O)CC(C)O)C=C1

InChI

InChIKey=LIAWQASKBFCRNR-UHFFFAOYSA-N

InChI=1S/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)

HIDE SMILES / InChI

Molecular Formula	C12H17NO3
Molecular Weight	223.2683
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3479641https://www.ncbi.nlm.nih.gov/pubmed/3479641
Curator's Comment: Description was created based on several sources, including http://www.waters.com/webassets/cms/library/docs/720004141en.pdf | http://www.waters.com/webassets/cms/library/docs/720005475en.pdf | http://journals.sagepub.com/doi/abs/10.1177/009286150103500134

Bucetin (3-hydroxy-p-butyrophenetidide) is an antipyretic analgesic drug with cancerogenic potential. Bucetin was withdrawn from the market due to renal toxicity. The compound has the chiral center. Pharmacological activity of enantiomers is unknown. The racemic mixture is used as a model compound to demostrate effectivity of the chiral supercritical fluid chromatography purification.

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2578
Unknown 2578
Fever 23 Sources: http://www.genome.jp/dbget-bin/www_bget?D01116	Primary	Withdrawn	Betadid Approved Use Unknown
Pain 614 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3479641	Primary	Withdrawn	Betadid Approved Use Unknown

PubMed

Title	Date	PubMed
[Study on Butylon, a new combined analgesic, with special reference to the analgesic potentiation between o-ethoxybenzamide and 3-hydroxy-p-burtyrophenetidide (Bucetin)].	1966 May 20	5951694
Studies on absorption and excretion of drug. 8. The release rate in vivo of antipyretic and analgesic drugs from commercial sugar coated tablets.	1967 Jul	5583134
Drug absorption, metabolism, and excretion. 3. Synthesis of the metabolites of bucetin (beta-hydroxybutyro-p-phenetidide).	1968 Nov	5719020
Drug absorption, metabolism, and excretion. II. Metabolism of bucetin (beta-hydroxybutyro-p-phenetidide) in rabbits.	1968 Sep	5709240
Carcinogenicity of bucetin in (C57BL/6 X C3H)F1 mice.	1987 Nov	3479641

Patents

Sample Use Guides

In Vivo Use Guide

The tablet contains bucetin 100 mg. The tablets are given to male adults with 200 ml of water on a fasting stomach.

Route of Administration: Oral

In Vitro Use Guide

Bucetin was found to be mutagenic to Salmonella typhimurum TA100 in the presence of liver 9000g supernatant fraction (S9) prepared from polychlorinated biphenyl (PCB)-treated hamsters and a reduced NADPH-generating system.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:30:22 GMT 2023` Edited by `admin` on `Fri Dec 15 16:30:22 GMT 2023`
Record UNII	6M7CVQ8PF8
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BUCETIN

Official Name

English

P-BUTYROPHENETIDIDE, 3-HYDROXY-

Systematic Name

English

BETADID

Brand Name

English

BUCETIN [MI]

Common Name

English

(±)-BUCETIN

Common Name

English

.BETA.-HYDROXYBUTYRIC ACID P-PHENETIDIDE

Common Name

English

3-HYDROXY-P-BUTYROPHENETIDIDE

Common Name

English

bucetin [INN]

Common Name

English

Bucetin [WHO-DD]

Common Name

English

BUCETIN [JAN]

Common Name

English

NSC-759243

Code

English

3-HYDROXY-4-BUTYROPHENETIDIDE

Common Name

English

NSC-320045

Code

English

BUTANAMIDE, N-(4-ETHOXYPHENYL)-3-HYDROXY-

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

N02BE74