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
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N)C(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 |
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PubMed
Title | Date | PubMed |
---|---|---|
Some immunochemical properties of penicillenic acid. An antigenic determinant derived from penicillin. | 1960 Dec 1 |
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Hypersensitivity to penicillenic acid derivatives in human beings with penicillin allergy. | 1962 Apr 1 |
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A novel enzyme reactor using gluten membrane entrapping cell-associated enzyme. | 2001 Dec |
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Immobilized penicillin G acylase as reactor and chiral selector in liquid chromatography. | 2001 Jul 6 |
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The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography. | 2001 Oct |
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Contrasting fates for 6-alpha-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS). | 2001 Sep 17 |
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Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects. | 2001 Sep-Oct |
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Enzymatic synthesis of amoxicillin: avoiding limitations of the mechanistic approach for reaction kinetics. | 2002 Dec 20 |
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Role of alphaArg145 and betaArg263 in the active site of penicillin acylase of Escherichia coli. | 2002 Jul 1 |
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Monitoring of enzymatic hydrolysis of penicillin G by pyrolysis-negative ion mass spectrometry. | 2002 Jul 1 |
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Monitoring of ampicillin and its related substances by NMR. | 2002 Nov 7 |
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Inhibitory effects in the side reactions occurring during the enzymic synthesis of amoxicillin: p-hydroxyphenylglycine methyl ester and amoxicillin hydrolysis. | 2003 Aug |
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Detection of specific IgE antibodies to major and minor antigenic determinants in sera of penicillin allergic patients. | 2003 Dec |
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A rapid and specific method to screen environmental microorganisms for cephalosporin acylase activity. | 2003 Jul |
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Improving the industrial production of 6-APA: enzymatic hydrolysis of penicillin G in the presence of organic solvents. | 2003 Nov-Dec |
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Adsorption of components of enzymatic synthesis of ampicillin on different hydrophobic resins. | 2003 Spring |
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Recent biotechnological interventions for developing improved penicillin G acylases. | 2004 |
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Penicillin derivatives induce chemical structure-dependent root development, and application for plant transformation. | 2004 Apr |
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Purification, substrate specificity, and N-terminal amino acid sequence analysis of a beta-lactamase-free penicillin amidase from Alcaligenes sp. | 2004 Aug |
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Immobilization of permeabilized whole cell penicillin G acylase from Alcaligenes faecalis using pore matrix crosslinked with glutaraldehyde. | 2006 Jul |
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Erythema multiforme to amoxicillin with concurrent infection by Epstein-Barr virus. | 2006 Mar-Apr |
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Antibacterial and toxicological evaluation of beta-lactams synthesized by immobilized beta-lactamase-free penicillin amidase produced by Alcaligenes sp. | 2007 Dec |
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The 50th anniversary of the discovery of 6-aminopenicillanic acid (6-APA). | 2007 Jan |
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Comparative production of 6-aminopenicillanic acid by different E. coli strains and their acridine orange (AO) induced mutants. | 2007 Nov 1 |
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Calixarenes in a membrane environment: a monolayer study on the miscibility of three p-tert-butylcalix[4]arene beta-lactam derivatives with 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine. | 2007 Nov 22 |
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6-aminopenicillanic acid production by intact cells of E. coli containing penicillin G acylase (PGA). | 2007 Sep 15 |
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[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 |
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Enzymatic hydrolysis of penicillin for 6-APA production in three-liquid-phase system. | 2008 Feb |
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Saturation mutagenesis reveals the importance of residues alphaR145 and alphaF146 of penicillin acylase in the synthesis of beta-lactam antibiotics. | 2008 Jan 1 |
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Development of the semi-synthetic penicillins and cephalosporins. | 2008 Mar |
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Enhanced production of 6-aminopenicillanic acid in aqueous methyl isobutyl ketone system with immobilized penicillin G acylase. | 2010 |
|
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 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:58:58 UTC 2022
by
admin
on
Fri Dec 16 16:58:58 UTC 2022
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Record UNII |
QR0C4R7XVN
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Record Status |
Validated (UNII)
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6-APA
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