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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27N5O7S
Molecular Weight 493.533
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASPOXICILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)[C@H](N)CC(=O)NC)C3=CC=C(O)C=C3)C(O)=O

InChI

InChIKey=BHELIUBJHYAEDK-OAIUPTLZSA-N
InChI=1S/C21H27N5O7S/c1-21(2)15(20(32)33)26-18(31)14(19(26)34-21)25-17(30)13(9-4-6-10(27)7-5-9)24-16(29)11(22)8-12(28)23-3/h4-7,11,13-15,19,27H,8,22H2,1-3H3,(H,23,28)(H,24,29)(H,25,30)(H,32,33)/t11-,13-,14-,15+,19-/m1/s1

HIDE SMILES / InChI

Description
Sources: DOI: 10.1016/S0065-7743(08)60861-1
Curator's Comment: description was created based on several sources, including: http://www.drugfuture.com/chemdata/ASPOXICILLIN.html http://www.120ty.net/bencandy.php?fid=232&id=36758 http://www.229877.com/article/2012/1209/31983.html

Aspoxicillin is an injectable, amino acid-type penicillin highly active against Gram-positive ad Gram-negative bacteria, including the beta-lactamase producing Bacillus fragilis. It is reportedly effective in the treatment of peritonitis, pneumonia and bronchitis. Adverse reactions are: rash, urticaria, skin itching, vomiting, abdominal pain.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Sources: http://www.229877.com/article/2012/1209/31983.html DOI: 10.1016/S0065-7743(08)60861-1
Curative
Doyle

Approved Use

It is reportedly effective in the treatment of peritonitis
Sources: DOI: 10.1016/S0065-7743(08)60861-1 http://www.229877.com/article/2012/1209/31983.html
Curative
Doyle

Approved Use

It is used for treatment of pneumonia
Sources: DOI: 10.1016/S0065-7743(08)60861-1 http://www.229877.com/article/2012/1209/31983.html
Curative
Doyle

Approved Use

It is used for treatment of chronic and acute bronchitis
PubMed

PubMed

TitleDatePubMed
Aspoxicillin versus piperacillin in severe abdominal infections--a comparative phase III study.
1994 Nov
Morphological changes and lysis induced by beta-lactams associated with the characteristic profiles of affinities of penicillin-binding proteins in actinobacillus pleuropneumoniae.
2000 Jun
Antimicrobial susceptibility of Pasteurella multocida isolated from cattle and pigs.
2001 Sep
Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae.
2002 Jan
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: For children: 40-80 mg/kg; in severe cases – 60 mg/kg, 2-4 injections per day
1-2 g twice a day, in severe infections – 6-8 g per day
Route of Administration: Intravenous
In Vitro Use Guide
The MIC90 values of aspoxicillin was 0.05 ug/ml for Actinobacillus pleuropneumoniae.
Name Type Language
ASPOXICILLIN
INN   MART.   MI   WHO-DD  
INN  
Official Name English
ASPOXICILLIN [MI]
Common Name English
ASPOXICILLIN [MART.]
Common Name English
aspoxicillin [INN]
Common Name English
DOYLE
Brand Name English
(2S,5R,6R)-6-((2R)-2-((2R)-2-AMINO-3-(METHYLCARBAMOYL)PROPIONAMIDO)-2-(P-HYDROXYPHENYL)ACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Common Name English
Aspoxicillin [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01CA19
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
WHO-ATC J01CA19
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
Code System Code Type Description
INN
5350
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY
NCI_THESAURUS
C72706
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY
FDA UNII
0745KNO26J
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY
EVMPD
SUB05585MIG
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID6046921
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY
MESH
C037485
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY
CAS
63358-49-6
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY
SMS_ID
100000086609
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY
PUBCHEM
71961
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY
ChEMBL
CHEMBL1318150
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY
MERCK INDEX
m2112
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB13816
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY
DRUG CENTRAL
248
Created by admin on Fri Dec 15 15:40:13 GMT 2023 , Edited by admin on Fri Dec 15 15:40:13 GMT 2023
PRIMARY