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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

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

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.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[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
Patents

Patents

JPH0717918A
3
JPS05296794A
1
JPS51133289A
1
JPS51148095A
1
JPS52110895A
1
JPS5382791A
1
JPS5671093A
1
JPS5732289A
1
JPS59187799A
1
JPS59219291A
1
JPS6034971A
1

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 Mon Mar 31 17:56:16 GMT 2025
Edited
by admin
on Mon Mar 31 17:56:16 GMT 2025
Record UNII
QR0C4R7XVN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
6-Aminopenicillanic acid
MI  
Common Name English
NSC-50071
Preferred 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
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 Mon Mar 31 17:56:17 GMT 2025 , Edited by admin on Mon Mar 31 17:56:17 GMT 2025
PRIMARY Merck Index
CAS
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
PUBCHEM
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
RS_ITEM_NUM
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
FDA UNII
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
CHEBI
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
ECHA (EC/EINECS)
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
NSC
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
EPA CompTox
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
WIKIPEDIA
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
SMS_ID
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
Structure of AMPICILLIN TRIHYDRATE
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Structure of FLUCLOXACILLIN MAGNESIUM OCTAHYDRATE
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Structure of DICLOXACILLIN SODIUM
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Structure of AMPICILLIN
PARENT -> IMPURITY
Structure of SULBACTAM SODIUM
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
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Structure of OXACILLIN SODIUM
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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Structure of PENICILLIN V
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NIH
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