BUCETIN

Possibly Marketed Outside US

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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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 Bucetin was withdrawn from the market due to renal toxicity.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

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2,578
Unknown 2,578
Fever 23	Primary	Withdrawn	Betadid
Pain 614	Primary	Withdrawn	Betadid

PubMed

Show entries

Title	Date	PubMed
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

Showing 1 to 2 of 2 entries

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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.