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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
Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity.
1992
[Studies on the immobilized penicillin acylase on polymer beads].
2001 Apr
A novel enzyme reactor using gluten membrane entrapping cell-associated enzyme.
2001 Dec
[Determination of degraded products of penicillin by high performance liquid chromatography].
2001 Jan
Immobilized penicillin G acylase as reactor and chiral selector in liquid chromatography.
2001 Jul 6
The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography.
2001 Oct
Contrasting fates for 6-alpha-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS).
2001 Sep 17
Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects.
2001 Sep-Oct
Biotransformations catalyzed by multimeric enzymes: stabilization of tetrameric ampicillin acylase permits the optimization of ampicillin synthesis under dissociation conditions.
2001 Spring
The role of hydrophobic active-site residues in substrate specificity and acyl transfer activity of penicillin acylase.
2002 Apr
Monitoring of enzymatic hydrolysis of penicillin G by pyrolysis-negative ion mass spectrometry.
2002 Jul 1
Equilibrium modeling of extractive enzymatic hydrolysis of penicillin G with concomitant 6-aminopenicillanic acid crystallization.
2002 May 20
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
Quantitative characterization of the nucleophile reactivity in penicillin acylase-catalyzed acyl transfer reactions.
2002 Sep 23
Inhibitory effects in the side reactions occurring during the enzymic synthesis of amoxicillin: p-hydroxyphenylglycine methyl ester and amoxicillin hydrolysis.
2003 Aug
Detection of specific IgE antibodies to major and minor antigenic determinants in sera of penicillin allergic patients.
2003 Dec
Biotechnological applications of penicillin acylases: state-of-the-art.
2003 Jan
A rapid and specific method to screen environmental microorganisms for cephalosporin acylase activity.
2003 Jul
Industrial production of beta-lactam antibiotics.
2003 Jun
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
Kinetics of enzyme acylation and deacylation in the penicillin acylase-catalyzed synthesis of beta-lactam antibiotics.
2003 Sep
Adsorption of components of enzymatic synthesis of ampicillin on different hydrophobic resins.
2003 Spring
Penicillin derivatives induce chemical structure-dependent root development, and application for plant transformation.
2004 Apr
Penicillin G acylase-based stationary phases: analytical applications.
2004 Apr 16
Penicillin acylase-catalyzed synthesis of beta-lactam antibiotics in highly condensed aqueous systems: beneficial impact of kinetic substrate supersaturation.
2004 Feb 5
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
Chromophoric spin-labeled beta-lactam antibiotics for ENDOR structural characterization of reaction intermediates of class A and class C beta-lactamases.
2004 May
Development of a novel and automated fluorescent immunoassay for the analysis of beta-lactam antibiotics.
2005 Aug 24
UV irradiation and desiccation modulate the three-dimensional extracellular matrix of Nostoc commune (Cyanobacteria).
2005 Dec 2
[Disseminated actinomycosis].
2005 Jun
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
Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays.
2006 Mar 15
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
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
Saturation mutagenesis reveals the importance of residues alphaR145 and alphaF146 of penicillin acylase in the synthesis of beta-lactam antibiotics.
2008 Jan 1
Small molecule inhibition of a Group II chaperonin: pinpointing a loop region within the equatorial domain as necessary for protein refolding.
2009 Jan 1
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
Improved A. faecalis penicillin amidase mutant retains the thermodynamic and pH stability of the wild type enzyme.
2010 Apr
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
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:23:43 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:23:44 UTC 2023
PRIMARY Merck Index
CAS
551-16-6
Created by admin on Fri Dec 15 15:23:44 UTC 2023 , Edited by admin on Fri Dec 15 15:23:44 UTC 2023
PRIMARY
PUBCHEM
11082
Created by admin on Fri Dec 15 15:23:44 UTC 2023 , Edited by admin on Fri Dec 15 15:23:44 UTC 2023
PRIMARY
RS_ITEM_NUM
1031514
Created by admin on Fri Dec 15 15:23:44 UTC 2023 , Edited by admin on Fri Dec 15 15:23:44 UTC 2023
PRIMARY
FDA UNII
QR0C4R7XVN
Created by admin on Fri Dec 15 15:23:44 UTC 2023 , Edited by admin on Fri Dec 15 15:23:44 UTC 2023
PRIMARY
CHEBI
16705
Created by admin on Fri Dec 15 15:23:44 UTC 2023 , Edited by admin on Fri Dec 15 15:23:44 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-993-4
Created by admin on Fri Dec 15 15:23:44 UTC 2023 , Edited by admin on Fri Dec 15 15:23:44 UTC 2023
PRIMARY
NSC
50071
Created by admin on Fri Dec 15 15:23:44 UTC 2023 , Edited by admin on Fri Dec 15 15:23:44 UTC 2023
PRIMARY
EPA CompTox
DTXSID7046097
Created by admin on Fri Dec 15 15:23:44 UTC 2023 , Edited by admin on Fri Dec 15 15:23:44 UTC 2023
PRIMARY
WIKIPEDIA
6-APA
Created by admin on Fri Dec 15 15:23:44 UTC 2023 , Edited by admin on Fri Dec 15 15:23:44 UTC 2023
PRIMARY
SMS_ID
100000178040
Created by admin on Fri Dec 15 15:23:44 UTC 2023 , Edited by admin on Fri Dec 15 15:23:44 UTC 2023
PRIMARY
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