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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
Immobilized aculeacin A acylase from Actinoplanes utahensis: characterization of a novel biocatalyst.
2010-06
Monitoring bioreactors using principal component analysis: production of penicillin G acylase as a case study.
2010-06
Improved A. faecalis penicillin amidase mutant retains the thermodynamic and pH stability of the wild type enzyme.
2010-04
Enzymatic synthesis of amoxicillin via a one-pot enzymatic hydrolysis and condensation cascade process in the presence of organic co-solvents.
2010-04
A process to produce penicillin G acylase by surface-adhesion fermentation using Mucor griseocyanus to obtain 6-aminopenicillanic acid by penicillin G hydrolysis.
2010-04
Covalent anchoring of chloroperoxidase and glucose oxidase on the mesoporous molecular sieve SBA-15.
2010-02-24
Heterologous expression of leader-less pga gene in Pichia pastoris: intracellular production of prokaryotic enzyme.
2010-02-03
FT-IR, FT-Raman, ab initio and DFT structural and vibrational frequency analysis of 6-aminopenicillanic acid.
2010-01
Enhanced production of 6-aminopenicillanic acid in aqueous methyl isobutyl ketone system with immobilized penicillin G acylase.
2010
An engineered yeast efficiently secreting penicillin.
2009-12-15
Rhodotorula aurantiaca penicillin V acylase: active site characterization and fluorometric studies.
2009-11-09
Synthesis and biological evaluation of penem inhibitors of bacterial signal peptidase.
2009-07-15
Hypersensitivity reactions to penicillins: studies in a group of patients with negative benzylpenicillin G skin test.
2009-06
Human health risk assessment of penicillin/aminopenicillin resistance in enterococci due to penicillin use in food animals.
2009-06
Molecular characterization of a fungal gene paralogue of the penicillin penDE gene of Penicillium chrysogenum.
2009-05-26
[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].
2009-05-08
Small molecule inhibition of a Group II chaperonin: pinpointing a loop region within the equatorial domain as necessary for protein refolding.
2009-01-01
Free-radical destruction of beta-lactam antibiotics in aqueous solution.
2008-08-14
Poststreptococcal dystonia with bilateral striatal enlargement: MR imaging and spectroscopic findings.
2008-08
Hydrogel coated monoliths for enzymatic hydrolysis of penicillin G.
2008-08
Fluorophore-labeled beta-lactamase as a biosensor for beta-lactam antibiotics: a study of the biosensing process.
2008-05-21
Quantitative analysis of metabolites in complex biological samples using ion-pair reversed-phase liquid chromatography-isotope dilution tandem mass spectrometry.
2008-04-11
[Phase transfer catalyzed bioconversion of penicillin G to 6-APA by immobilized penicillin acylase in recyclable aqueous two-phase systems with light/pH sensitive copolymers].
2008-03
Development of the semi-synthetic penicillins and cephalosporins.
2008-03
Enzymatic hydrolysis of penicillin for 6-APA production in three-liquid-phase system.
2008-02
Saturation mutagenesis reveals the importance of residues alphaR145 and alphaF146 of penicillin acylase in the synthesis of beta-lactam antibiotics.
2008-01-01
Antibacterial and toxicological evaluation of beta-lactams synthesized by immobilized beta-lactamase-free penicillin amidase produced by Alcaligenes sp.
2007-12
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.
2007-11-22
Comparative production of 6-aminopenicillanic acid by different E. coli strains and their acridine orange (AO) induced mutants.
2007-11-01
6-aminopenicillanic acid production by intact cells of E. coli containing penicillin G acylase (PGA).
2007-09-15
Site-specific protonation microequilibria of penicillin and cephalosporin beta-lactam core molecules.
2007-09
In vivo transport of the intermediates of the penicillin biosynthetic pathway in tailored strains of Penicillium chrysogenum.
2007-08
Molecularly imprinted polymers as antibody mimics in automated on-line fluorescent competitive assays.
2007-07-01
Enzymatic hydrolysis of penicillin in mixed ionic liquids/water two-phase system.
2007-06-26
Molecular cloning and characterization of thermostable beta-lactam acylase with broad substrate specificity from Bacillus badius.
2007-05
Association of IL-10 level and IL-10 promoter SNPs with specific antibodies in penicillin-allergic patients.
2007-03
Application of cross-linked enzyme aggregates of Bacillus badius penicillin G acylase for the production of 6-aminopenicillanic acid.
2007-01
The 50th anniversary of the discovery of 6-aminopenicillanic acid (6-APA).
2007-01
[Microspeciation of amphoteric molecules of unusual acid-base properties].
2007
Penicillin acylase catalysis in the presence of ionic liquids.
2006-12
High yield recombinant penicillin G amidase production and export into the growth medium using Bacillus megaterium.
2006-11-28
Immobilization of permeabilized whole cell penicillin G acylase from Alcaligenes faecalis using pore matrix crosslinked with glutaraldehyde.
2006-07
Erythema multiforme to amoxicillin with concurrent infection by Epstein-Barr virus.
2006-04-12
Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays.
2006-03-15
[Modulatory effect of antimicrobial agents or aminoacids on the oxidative burst of polymorphonuclear neutrophils triggered by formylmethionyl-leucyl-phenylalanine (fMLP)].
2006-02
UV irradiation and desiccation modulate the three-dimensional extracellular matrix of Nostoc commune (Cyanobacteria).
2005-12-02
Development of a novel and automated fluorescent immunoassay for the analysis of beta-lactam antibiotics.
2005-08-24
[Disseminated actinomycosis].
2005-06
Recent biotechnological interventions for developing improved penicillin G acylases.
2004
Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy.
1990-11
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
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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
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NIH
NCATS
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