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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 of BUCETIN

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
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 Bucetin was withdrawn from the market due to renal toxicity.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

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
Betadid

Approved Use

Unknown
Primary
Withdrawn
Betadid

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[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
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
Drug absorption, metabolism, and excretion. 3. Synthesis of the metabolites of bucetin (beta-hydroxybutyro-p-phenetidide).
1968 Nov
Drug absorption, metabolism, and excretion. II. Metabolism of bucetin (beta-hydroxybutyro-p-phenetidide) in rabbits.
1968 Sep
Carcinogenicity of bucetin in (C57BL/6 X C3H)F1 mice.
1987 Nov
Patents

Patents

JPS56115719A
3

Sample Use Guides

In Vivo Use Guide
Curator's Comment: The tablet contains bucetin 100 mg, ethoxybenzamide 100 mg, Al-acetylsalicylate 180 mg (https://www.jstage.jst.go.jp/article/cpb1958/15/7/15_7_1002/_pdf)
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
Curator's Comment: https://www.jstage.jst.go.jp/article/cpb1958/33/7/33_7_2877/_pdf
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 UTC 2023
Edited
by admin
on Fri Dec 15 16:30:22 UTC 2023
Record UNII
6M7CVQ8PF8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUCETIN
INN   JAN   MI   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
WHO-VATC QN02BE54
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
WHO-ATC N02BE54
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
WHO-VATC QN02BE04
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
NCI_THESAURUS C241
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
WHO-ATC N02BE04
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
WHO-VATC QN02BE74
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
Code System Code Type Description
INN
1283
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
214-109-8
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
NCI_THESAURUS
C72112
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
NSC
759243
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
DRUG CENTRAL
413
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
CAS
1083-57-4
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
EVMPD
SUB05942MIG
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
WIKIPEDIA
Bucetin
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID6020721
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
PUBCHEM
14130
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
NSC
320045
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
DRUG BANK
DB13278
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
SMS_ID
100000085843
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL1697856
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
MERCK INDEX
m2737
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY Merck Index
FDA UNII
6M7CVQ8PF8
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
MESH
C023637
Created by admin on Fri Dec 15 16:30:22 UTC 2023 , Edited by admin on Fri Dec 15 16:30:22 UTC 2023
PRIMARY
Related Record Type Details
Structure of BUCETIN, (-)-
ENANTIOMER -> RACEMATE
Structure of BUCETIN, (+)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of BUCETIN
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