U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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: http://www.genome.jp/dbget-bin/www_bget?D01116 http://www.drugfuture.com/chemdata/bucetin.html

Bucetin [(3-hydroxy-p-butyrophenetidide) CAS: 1083-57-4) is a homologue to phenacetin and is used instead of phenacetin as an analgesic drug because of its lower toxicity than that of phenacetin, despite having equivalent analgesic activity when used at an appropriate dose. Dysplastic lesions of the proximal tubules were frequently seen in the males given bucetin in a dose-related fashion.

Approval Year

Unknown
127998
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Withdrawn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Withdrawn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)
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: https://www.jstage.jst.go.jp/article/cpb1958/33/7/33_7_2877/_pdf
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 16 20:20:51 UTC 2022
Edited
by admin
on Fri Dec 16 20:20:51 UTC 2022
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 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
WHO-VATC QN02BE54
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
WHO-ATC N02BE54
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
WHO-VATC QN02BE04
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
NCI_THESAURUS C241
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
WHO-ATC N02BE04
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
WHO-VATC QN02BE74
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
Code System Code Type Description
INN
1283
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
ECHA (EC/EINECS)
214-109-8
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
NCI_THESAURUS
C72112
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
NSC
759243
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
DRUG CENTRAL
413
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
CAS
1083-57-4
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
EVMPD
SUB05942MIG
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
WIKIPEDIA
Bucetin
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
EPA CompTox
DTXSID6020721
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
PUBCHEM
14130
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
NSC
320045
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
DRUG BANK
DB13278
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
ChEMBL
CHEMBL1697856
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
MERCK INDEX
M2737
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY Merck Index
FDA UNII
6M7CVQ8PF8
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
MESH
C023637
Created by admin on Fri Dec 16 20:20:51 UTC 2022 , Edited by admin on Fri Dec 16 20:20:51 UTC 2022
PRIMARY
Related Record Type Details
Structure of BUCETIN, (-)-
ENANTIOMER -> RACEMATE
Structure of BUCETIN, (+)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of BUCETIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966