Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H12N2O3S |
Molecular Weight | 216.257 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O
InChI
InChIKey=NGHVIOIJCVXTGV-ALEPSDHESA-N
InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
Molecular Formula | C8H12N2O3S |
Molecular Weight | 216.257 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2844714Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/13622762
https://www.ncbi.nlm.nih.gov/pubmed/13742935
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2844714
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/13622762
https://www.ncbi.nlm.nih.gov/pubmed/13742935
6-amino-penicillanic acid is a common parent amine of various penicillins. 6-amino-penicillinic acid possesses definite antibacterial properties but these are much lower order than these of benzylpenicillin. It is destroyed by penicillinase (Beta-lactamase). The first penicillins to appear as derivatives of 6-APA were in fact phenethicillin and propicillin.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14448514 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
[Determination of degraded products of penicillin by high performance liquid chromatography]. | 2001 Jan |
|
Enzymatic synthesis of amoxicillin: avoiding limitations of the mechanistic approach for reaction kinetics. | 2002 Dec 20 |
|
Role of alphaArg145 and betaArg263 in the active site of penicillin acylase of Escherichia coli. | 2002 Jul 1 |
|
Monitoring of enzymatic hydrolysis of penicillin G by pyrolysis-negative ion mass spectrometry. | 2002 Jul 1 |
|
Penicillin acylase-catalyzed ampicillin synthesis using a pH gradient: a new approach to optimization. | 2002 Jun 5 |
|
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin. | 2002 Nov |
|
Monitoring of ampicillin and its related substances by NMR. | 2002 Nov 7 |
|
Quantitative characterization of the nucleophile reactivity in penicillin acylase-catalyzed acyl transfer reactions. | 2002 Sep 23 |
|
Inoculum studies in production of penicillin G acylase by Bacillus megaterium ATCC 14945. | 2002 Spring |
|
Industrial production of beta-lactam antibiotics. | 2003 Jun |
|
Continuous penicillin G hydrolysis in an electro-membrane reactor with immobilized penicillin G acylase. | 2003 Mar |
|
Adsorption of components of enzymatic synthesis of ampicillin on different hydrophobic resins. | 2003 Spring |
|
Penicillin G acylase-based stationary phases: analytical applications. | 2004 Apr 16 |
|
Purification, substrate specificity, and N-terminal amino acid sequence analysis of a beta-lactamase-free penicillin amidase from Alcaligenes sp. | 2004 Aug |
|
Production of 6-aminopenicillanic acid in aqueous two-phase systems by recombinant Escherichia coli with intracellular penicillin acylase. | 2004 Jan |
|
Increasing the synthetic performance of penicillin acylase PAS2 by structure-inspired semi-random mutagenesis. | 2004 Jul |
|
[Treatment mostly not in line with current knowledge. New guidelines for sinusitis therapy]. | 2004 Jun 10 |
|
Modifying the substrate specificity of penicillin G acylase to cephalosporin acylase by mutating active-site residues. | 2004 Jun 25 |
|
Chromophoric spin-labeled beta-lactam antibiotics for ENDOR structural characterization of reaction intermediates of class A and class C beta-lactamases. | 2004 May |
|
Evidence for the involvement of arginyl residue at the active site of penicillin G acylase from Kluyvera citrophila. | 2004 Oct |
|
Reactions of pyrazolylborate-zinc-hydroxide complexes related to beta-lactamase activity. | 2005 Jun 13 |
|
Purification and characterization of inducible cephalexin synthesizing enzyme in Gluconobacter oxydans. | 2005 Mar |
|
Penicillin acylase catalysis in the presence of ionic liquids. | 2006 Dec |
|
High yield recombinant penicillin G amidase production and export into the growth medium using Bacillus megaterium. | 2006 Nov 28 |
|
[Microspeciation of amphoteric molecules of unusual acid-base properties]. | 2007 |
|
Antibacterial and toxicological evaluation of beta-lactams synthesized by immobilized beta-lactamase-free penicillin amidase produced by Alcaligenes sp. | 2007 Dec |
|
Application of cross-linked enzyme aggregates of Bacillus badius penicillin G acylase for the production of 6-aminopenicillanic acid. | 2007 Jan |
|
The 50th anniversary of the discovery of 6-aminopenicillanic acid (6-APA). | 2007 Jan |
|
Enzymatic hydrolysis of penicillin in mixed ionic liquids/water two-phase system. | 2007 Jul-Aug |
|
Association of IL-10 level and IL-10 promoter SNPs with specific antibodies in penicillin-allergic patients. | 2007 Mar |
|
Comparative production of 6-aminopenicillanic acid by different E. coli strains and their acridine orange (AO) induced mutants. | 2007 Nov 1 |
|
Site-specific protonation microequilibria of penicillin and cephalosporin beta-lactam core molecules. | 2007 Sep |
|
6-aminopenicillanic acid production by intact cells of E. coli containing penicillin G acylase (PGA). | 2007 Sep 15 |
|
[Etiology of urinary tract infections and antimicrobial susceptibility: a study conducted on a population of children hospitalized in the Department of Pediatrics at Warsaw Bielany Hospital; 2004-2006]. | 2008 Apr-Jun |
|
Enzymatic hydrolysis of penicillin for 6-APA production in three-liquid-phase system. | 2008 Feb |
|
Development of the semi-synthetic penicillins and cephalosporins. | 2008 Mar |
|
Fluorophore-labeled beta-lactamase as a biosensor for beta-lactam antibiotics: a study of the biosensing process. | 2008 May 21 |
|
Small molecule inhibition of a Group II chaperonin: pinpointing a loop region within the equatorial domain as necessary for protein refolding. | 2009 Jan 1 |
|
Synthesis and biological evaluation of penem inhibitors of bacterial signal peptidase. | 2009 Jul 15 |
|
Hypersensitivity reactions to penicillins: studies in a group of patients with negative benzylpenicillin G skin test. | 2009 Jun |
|
Human health risk assessment of penicillin/aminopenicillin resistance in enterococci due to penicillin use in food animals. | 2009 Jun |
|
Molecular characterization of a fungal gene paralogue of the penicillin penDE gene of Penicillium chrysogenum. | 2009 May 26 |
|
Rhodotorula aurantiaca penicillin V acylase: active site characterization and fluorometric studies. | 2009 Nov 9 |
|
Enhanced production of 6-aminopenicillanic acid in aqueous methyl isobutyl ketone system with immobilized penicillin G acylase. | 2010 |
|
Improved A. faecalis penicillin amidase mutant retains the thermodynamic and pH stability of the wild type enzyme. | 2010 Apr |
|
A process to produce penicillin G acylase by surface-adhesion fermentation using Mucor griseocyanus to obtain 6-aminopenicillanic acid by penicillin G hydrolysis. | 2010 Apr |
|
Covalent anchoring of chloroperoxidase and glucose oxidase on the mesoporous molecular sieve SBA-15. | 2010 Feb 24 |
|
Heterologous expression of leader-less pga gene in Pichia pastoris: intracellular production of prokaryotic enzyme. | 2010 Feb 3 |
|
Immobilized aculeacin A acylase from Actinoplanes utahensis: characterization of a novel biocatalyst. | 2010 Jun |
|
Monitoring bioreactors using principal component analysis: production of penicillin G acylase as a case study. | 2010 Jun |
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:56:16 GMT 2025
by
admin
on
Mon Mar 31 17:56:16 GMT 2025
|
Record UNII |
QR0C4R7XVN
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
m1724
Created by
admin on Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
|
PRIMARY | Merck Index | ||
|
551-16-6
Created by
admin on Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
|
PRIMARY | |||
|
11082
Created by
admin on Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
|
PRIMARY | |||
|
1031514
Created by
admin on Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
|
PRIMARY | |||
|
QR0C4R7XVN
Created by
admin on Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
|
PRIMARY | |||
|
16705
Created by
admin on Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
|
PRIMARY | |||
|
208-993-4
Created by
admin on Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
|
PRIMARY | |||
|
50071
Created by
admin on Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
|
PRIMARY | |||
|
DTXSID7046097
Created by
admin on Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
|
PRIMARY | |||
|
6-APA
Created by
admin on Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
|
PRIMARY | |||
|
100000178040
Created by
admin on Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
|
||
|
PARENT -> IMPURITY |
|
||
|
PARENT -> IMPURITY |
|
||
|
PARENT -> IMPURITY |
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
PARENT -> IMPURITY |
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|