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

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
Structure of 6-AMINOPENICILLANIC ACID

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

HIDE SMILES / InChI

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Some immunochemical properties of penicillenic acid. An antigenic determinant derived from penicillin.
1960 Dec 1
Hypersensitivity to penicillenic acid derivatives in human beings with penicillin allergy.
1962 Apr 1
Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy.
1990 Nov
Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity.
1992
Detection of specific IgE antibodies to major and minor antigenic determinants in sera of penicillin allergic patients.
2003 Dec
Continuous penicillin G hydrolysis in an electro-membrane reactor with immobilized penicillin G acylase.
2003 Mar
Study of nucleophile binding in the penicillin acylase active center. Kinetic analysis.
2003 Mar
Improving the industrial production of 6-APA: enzymatic hydrolysis of penicillin G in the presence of organic solvents.
2003 Nov-Dec
Isolation and characterization of a new strain of Achromobacter sp. with beta-lactam antibiotic acylase activity.
2003 Oct
Kinetics of enzyme acylation and deacylation in the penicillin acylase-catalyzed synthesis of beta-lactam antibiotics.
2003 Sep
Penicillin derivatives induce chemical structure-dependent root development, and application for plant transformation.
2004 Apr
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
UV irradiation and desiccation modulate the three-dimensional extracellular matrix of Nostoc commune (Cyanobacteria).
2005 Dec 2
[Disseminated actinomycosis].
2005 Jun
Penicillin acylase catalysis in the presence of ionic liquids.
2006 Dec
Immobilization of permeabilized whole cell penicillin G acylase from Alcaligenes faecalis using pore matrix crosslinked with glutaraldehyde.
2006 Jul
High yield recombinant penicillin G amidase production and export into the growth medium using Bacillus megaterium.
2006 Nov 28
In vivo transport of the intermediates of the penicillin biosynthetic pathway in tailored strains of Penicillium chrysogenum.
2007 Aug
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
Molecularly imprinted polymers as antibody mimics in automated on-line fluorescent competitive assays.
2007 Jul 1
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
Molecular cloning and characterization of thermostable beta-lactam acylase with broad substrate specificity from Bacillus badius.
2007 May
Comparative production of 6-aminopenicillanic acid by different E. coli strains and their acridine orange (AO) induced mutants.
2007 Nov 1
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
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
Poststreptococcal dystonia with bilateral striatal enlargement: MR imaging and spectroscopic findings.
2008 Aug
Saturation mutagenesis reveals the importance of residues alphaR145 and alphaF146 of penicillin acylase in the synthesis of beta-lactam antibiotics.
2008 Jan 1
Development of the semi-synthetic penicillins and cephalosporins.
2008 Mar
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
FT-IR, FT-Raman, ab initio and DFT structural and vibrational frequency analysis of 6-aminopenicillanic acid.
2010 Jan
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
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Sources: DOI: 10.1098/rspb.1961.0048
MIC of 6-APA agains Gram-positive and Gram-negative is in range 50-250 ug/ml.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:23:43 GMT 2023
Edited
by admin
on Fri Dec 15 15:23:43 GMT 2023
Record UNII
QR0C4R7XVN
Record Status Validated (UNII)
Record Version
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Name Type Language
6-AMINOPENICILLANIC ACID
MI  
Common Name English
CLOXACILLIN SODIUM IMPURITY C [EP IMPURITY]
Common Name English
(+)-6-AMINOPENICILLANIC ACID
Common Name English
PHENOXYMETHYLPENICILLIN (BENZATHINE) TETRAHYDRATE IMPURITY C [EP IMPURITY]
Common Name English
AMOXICILLIN TRIHYDRATE IMPURITY A [EP IMPURITY]
Common Name English
FLUCLOXACILLIN MAGNESIUM OCTAHYDRATE IMPURITY C [EP IMPURITY]
Common Name English
(2S,5R,6R)-6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
OXACILLIN SODIUM MONOHYDRATE IMPURITY A [EP IMPURITY]
Common Name English
DICLOXACILLIN SODIUM IMPURITY C [EP IMPURITY]
Common Name English
PIPERACILLIN SODIUM IMPURITY H [EP]
Common Name English
PHENOXYMETHYLPENICILLIN IMPURITY C [EP IMPURITY]
Common Name English
AMOXICILLIN SODIUM IMPURITY A [EP IMPURITY]
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-AMINO-3,3-DIMETHYL-7-OXO-, (2S,5R,6R)-
Systematic Name English
AMPICILLIN IMPURITY A [EP IMPURITY]
Common Name English
PHENOXYMETHYLPENICILLIN POTASSIUM IMPURITY C [EP IMPURITY]
Common Name English
6-AMINO-PENICILLANIC ACID
Common Name English
6-APA
Common Name English
BENZYLPENICILLIN POTASSIUM IMPURITY A [EP IMPURITY]
Common Name English
SULBACTAM SODIUM IMPURITY B [EP IMPURITY]
Common Name English
NSC-50071
Code English
AMPICILLIN TRIHYDRATE IMPURITY A [EP IMPURITY]
Common Name English
6-AMINOPENICILLANIC ACID [MI]
Common Name English
AMOXICILLIN RELATED COMPOUND A [USP-RS]
Common Name English
BENZYLPENICILLIN SODIUM IMPURITY A [EP IMPURITY]
Common Name English
FLUCLOXACILLIN SODIUM MONOHYDRATE IMPURITY C [EP IMPURITY]
Common Name English
AMOXICILLIN RELATED COMPOUND A [USP IMPURITY]
Common Name English
Code System Code Type Description
MERCK INDEX
m1724
Created by admin on Fri Dec 15 15:23:44 GMT 2023 , Edited by admin on Fri Dec 15 15:23:44 GMT 2023
PRIMARY Merck Index
CAS
551-16-6
Created by admin on Fri Dec 15 15:23:44 GMT 2023 , Edited by admin on Fri Dec 15 15:23:44 GMT 2023
PRIMARY
PUBCHEM
11082
Created by admin on Fri Dec 15 15:23:44 GMT 2023 , Edited by admin on Fri Dec 15 15:23:44 GMT 2023
PRIMARY
RS_ITEM_NUM
1031514
Created by admin on Fri Dec 15 15:23:44 GMT 2023 , Edited by admin on Fri Dec 15 15:23:44 GMT 2023
PRIMARY
FDA UNII
QR0C4R7XVN
Created by admin on Fri Dec 15 15:23:44 GMT 2023 , Edited by admin on Fri Dec 15 15:23:44 GMT 2023
PRIMARY
CHEBI
16705
Created by admin on Fri Dec 15 15:23:44 GMT 2023 , Edited by admin on Fri Dec 15 15:23:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-993-4
Created by admin on Fri Dec 15 15:23:44 GMT 2023 , Edited by admin on Fri Dec 15 15:23:44 GMT 2023
PRIMARY
NSC
50071
Created by admin on Fri Dec 15 15:23:44 GMT 2023 , Edited by admin on Fri Dec 15 15:23:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID7046097
Created by admin on Fri Dec 15 15:23:44 GMT 2023 , Edited by admin on Fri Dec 15 15:23:44 GMT 2023
PRIMARY
WIKIPEDIA
6-APA
Created by admin on Fri Dec 15 15:23:44 GMT 2023 , Edited by admin on Fri Dec 15 15:23:44 GMT 2023
PRIMARY
SMS_ID
100000178040
Created by admin on Fri Dec 15 15:23:44 GMT 2023 , Edited by admin on Fri Dec 15 15:23:44 GMT 2023
PRIMARY
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