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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.

Originator

Approval Year

Unknown
127998
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
643
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
A novel enzyme reactor using gluten membrane entrapping cell-associated enzyme.
2001 Dec
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
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
Monitoring of ampicillin and its related substances by NMR.
2002 Nov 7
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
A rapid and specific method to screen environmental microorganisms for cephalosporin acylase activity.
2003 Jul
Improving the industrial production of 6-APA: enzymatic hydrolysis of penicillin G in the presence of organic solvents.
2003 Nov-Dec
Adsorption of components of enzymatic synthesis of ampicillin on different hydrophobic resins.
2003 Spring
Recent biotechnological interventions for developing improved penicillin G acylases.
2004
Penicillin derivatives induce chemical structure-dependent root development, and application for plant transformation.
2004 Apr
Purification, substrate specificity, and N-terminal amino acid sequence analysis of a beta-lactamase-free penicillin amidase from Alcaligenes sp.
2004 Aug
Immobilization of permeabilized whole cell penicillin G acylase from Alcaligenes faecalis using pore matrix crosslinked with glutaraldehyde.
2006 Jul
Erythema multiforme to amoxicillin with concurrent infection by Epstein-Barr virus.
2006 Mar-Apr
Antibacterial and toxicological evaluation of beta-lactams synthesized by immobilized beta-lactamase-free penicillin amidase produced by Alcaligenes sp.
2007 Dec
The 50th anniversary of the discovery of 6-aminopenicillanic acid (6-APA).
2007 Jan
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
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
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
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
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 Fri Dec 16 16:58:58 UTC 2022
Edited
by admin
on Fri Dec 16 16:58:58 UTC 2022
Record UNII
QR0C4R7XVN
Record Status Validated (UNII)
Record Version
  • Download
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
AMOXICILLIN TRIHYDRATE IMPURITY A [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
AMOXICILLIN RELATED COMPOUND A [USP IMPURITY]
Common Name English
Code System Code Type Description
MERCK INDEX
M1724
Created by admin on Fri Dec 16 16:58:58 UTC 2022 , Edited by admin on Fri Dec 16 16:58:58 UTC 2022
PRIMARY Merck Index
CAS
551-16-6
Created by admin on Fri Dec 16 16:58:58 UTC 2022 , Edited by admin on Fri Dec 16 16:58:58 UTC 2022
PRIMARY
PUBCHEM
11082
Created by admin on Fri Dec 16 16:58:58 UTC 2022 , Edited by admin on Fri Dec 16 16:58:58 UTC 2022
PRIMARY
RS_ITEM_NUM
1031514
Created by admin on Fri Dec 16 16:58:58 UTC 2022 , Edited by admin on Fri Dec 16 16:58:58 UTC 2022
PRIMARY
FDA UNII
QR0C4R7XVN
Created by admin on Fri Dec 16 16:58:58 UTC 2022 , Edited by admin on Fri Dec 16 16:58:58 UTC 2022
PRIMARY
DAILYMED
QR0C4R7XVN
Created by admin on Fri Dec 16 16:58:58 UTC 2022 , Edited by admin on Fri Dec 16 16:58:58 UTC 2022
PRIMARY
CHEBI
16705
Created by admin on Fri Dec 16 16:58:58 UTC 2022 , Edited by admin on Fri Dec 16 16:58:58 UTC 2022
PRIMARY
ECHA (EC/EINECS)
208-993-4
Created by admin on Fri Dec 16 16:58:58 UTC 2022 , Edited by admin on Fri Dec 16 16:58:58 UTC 2022
PRIMARY
NSC
50071
Created by admin on Fri Dec 16 16:58:58 UTC 2022 , Edited by admin on Fri Dec 16 16:58:58 UTC 2022
PRIMARY
EPA CompTox
DTXSID7046097
Created by admin on Fri Dec 16 16:58:58 UTC 2022 , Edited by admin on Fri Dec 16 16:58:58 UTC 2022
PRIMARY
WIKIPEDIA
6-APA
Created by admin on Fri Dec 16 16:58:58 UTC 2022 , Edited by admin on Fri Dec 16 16:58:58 UTC 2022
PRIMARY
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