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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12N2O5S
Molecular Weight 272.2792
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 7-AMINOCEPHALOSPORANIC ACID

SMILES

CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@]([H])([C@@]2([H])SC1)N

InChI

InChIKey=HSHGZXNAXBPPDL-HZGVNTEJSA-N
InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1

HIDE SMILES / InChI

Molecular Formula C10H12N2O5S
Molecular Weight 272.2792
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

7-aminocephalosporanicacid (7-ACA) is convenient starting material for the industrial production of various kinds of semisynthetic cephalosporin antibiotics. In many cases, chemical modifications at the C-7 position is required. Industrially, 7-ACA is derived by chemical or enzymatic deacylation from cephalosporin C, which is fermentatively produced by Acremonium chrysogenum. 7-ACA is a stable only at neutral pHs, enzymatic manipulations are desirable for chemical modifications in the production of cephalosporin related compounds.

Originator

Curator's Comment:: # Pfizer & Co C

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[Thoughts on explaining cigarette smoking].
1987 Feb
Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity.
1992
A rapid and specific method to screen environmental microorganisms for cephalosporin acylase activity.
2003 Jul
Multivariate analysis and classification of the chemical quality of 7-aminocephalosporanic acid using near-infrared reflectance spectroscopy.
2003 Jul 15
The kinetic properties of the carboxy terminal domain of the Bacillus licheniformis 749/I BlaR penicillin-receptor shed a new light on the derepression of beta-lactamase synthesis.
2003 Jun
An alternative procedure for preparation of cefdinir.
2003 Jun
An improved method for preparation of cefpodoxime proxetil.
2003 May
Deacylation activity of cephalosporin acylase to cephalosporin C is improved by changing the side-chain conformations of active-site residues.
2003 Oct 10
Industrial enzymatic production of cephalosporin-based beta-lactams.
2004
Synthesis and preliminary antimicrobial evaluation of new 7-(N-pyrrolyl) derivatives of cephalosporins.
2004
Occupational asthma and IgE sensitization to 7-aminocephalosporanic acid.
2004 Apr
Batch production of deacetyl 7-aminocephalosporanic acid by immobilized cephalosporin-C deacetylase.
2004 Aug
Affinity labeled glutaryl-7-amino cephalosporanic acid acylase C130 can hydrolyze the inhibitor during crystallization.
2004 Jan 16
[Compared D-amino acid oxidase expression in different Pichia pastoris host strains].
2004 Jul
Construction and application of fusion proteins of D-amino acid oxidase and glutaryl-7-aminocephalosporanic acid acylase for direct bioconversion of cephalosporin C to 7-aminocephalosporanic acid.
2004 Jun
Modifying the substrate specificity of penicillin G acylase to cephalosporin acylase by mutating active-site residues.
2004 Jun 25
Catalytic properties of D-amino acid oxidase in cephalosporin C bioconversion: a comparison between proteins from different sources.
2004 Mar-Apr
Toward the development of a cephalosporin-based dual-release prodrug for use in ADEPT.
2004 Nov 12
Evolution of an acylase active on cephalosporin C.
2005 Dec
D-Amino acid oxidase: structure, catalytic mechanism, and practical application.
2005 Jan
Single-step conversion of cephalosporin-C to 7-aminocephalosporanic acid by free and immobilized cells of Pseudomonas diminuta.
2005 Jul
Reactions of pyrazolylborate-zinc-hydroxide complexes related to beta-lactamase activity.
2005 Jun 13
1H and 13 C spectral assignments of 7beta-(cinnamoyl-substituted)amino-3-acetoxymethyl-cephalosporins.
2005 Mar
Purification and characterization of a novel aminoacylase from Streptomyces mobaraensis.
2005 Oct
Enzymatic modifications of cephalosporins by cephalosporin acylase and other enzymes.
2006 Apr-Jun
Thermal inactivation of D-amino acid oxidase from Trigonopsis variabilis occurs via three parallel paths of irreversible denaturation.
2006 Jul 5
Spectrophotometric assay for quantitative determination of 7-aminocephalosporanic acid from direct hydrolysis of cephalosporin C.
2006 Mar 15
[Microspeciation of amphoteric molecules of unusual acid-base properties].
2007
Microbial production of 7-amino-cephalosporanic acid and new generation cephalosporins (cephalothin) by different processing strategies.
2007
Reusability of entrapped cells of Pseudomonas diminuta for production of 7-aminocephalosporanic acid.
2007 Apr
Enzymatic synthesis of cephalosporins. The immobilized acylase from Arthrobacter viscosus: a new useful biocatalyst.
2007 Dec
Construction of recombinant Escherichia coli D11/pMSTO and its use in enzymatic preparation of 7-aminocephalosporanic acid in one pot.
2007 May 1
[7-aminocephalosporanic acid induced bronchial asthma in two patients].
2007 Oct
A colorimetric assay for the determination of acetyl xylan esterase or cephalosporin C acetyl esterase activities using 7-amino cephalosporanic acid, cephalosporin C, or acetylated xylan as substrate.
2007 Oct 15
Site-specific protonation microequilibria of penicillin and cephalosporin beta-lactam core molecules.
2007 Sep
New active site oriented glyoxyl-agarose derivatives of Escherichia coli penicillin G acylase.
2007 Sep 10
YesT: a new rhamnogalacturonan acetyl esterase from Bacillus subtilis.
2008 Apr
Properties and applications of microbial D-amino acid oxidases: current state and perspectives.
2008 Feb
Development of the semi-synthetic penicillins and cephalosporins.
2008 Mar
Optimization of glutaryl-7-aminocephalosporanic acid acylase expression in E. coli.
2008 Oct
The stabilizing effects of immobilization in D-amino acid oxidase from Trigonopsis variabilis.
2008 Sep 17
Stepwise engineering of a Pichia pastoris D-amino acid oxidase whole cell catalyst.
2010 Apr 26
Enhancement of glutaryl-7-aminocephalosporanic acid acylase activity of gamma-glutamyltranspeptidase of Bacillus subtilis.
2010 Aug
Occupational asthma in Korea.
2010 Dec
Environmentally safe production of 7-ACA by recombinant Acremonium chrysogenum.
2010 Dec
A single Phe54Tyr substitution improves the catalytic activity and thermostability of Trigonopsis variabilis D-amino acid oxidase.
2010 Feb 28
Improved cross-linked enzyme aggregates for the production of desacetyl beta-lactam antibiotics intermediates.
2010 Jan
Protein engineering of penicillin acylase.
2010 Jul
Biosynthesis of cephalosporin-C acylase enzyme: optimal media design, purification, and characterization.
2010 Oct
Gene expressions changes in bronchial epithelial cells: markers for respiratory sensitizers and exploration of the NRF2 pathway.
2014 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:39:34 UTC 2021
Edited
by admin
on Sat Jun 26 11:39:34 UTC 2021
Record UNII
9XI67897RG
Record Status Validated (UNII)
Record Version
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Name Type Language
7-AMINOCEPHALOSPORANIC ACID
MI  
Common Name English
CEFTRIAXONE SODIUM IMPURITY E [IP]
Common Name English
7-ACA
Common Name English
7-AMINOCEPHALO SPORANIC ACID [USP]
Common Name English
3-ACETOXYMETHYL-7-AMINOCEPH-3-EM-4-OIC ACID
Common Name English
7-AMINOCEPHALOSPORANIC ACID [MI]
Common Name English
7-AMINOCEPHALOSPORANIC ACID [WHO-DD]
Common Name English
(6R,7R)-3-((ACETYLOXY)METHYL)-7-AMINO-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
Code System Code Type Description
FDA UNII
9XI67897RG
Created by admin on Sat Jun 26 11:39:35 UTC 2021 , Edited by admin on Sat Jun 26 11:39:35 UTC 2021
PRIMARY
ECHA (EC/EINECS)
213-485-0
Created by admin on Sat Jun 26 11:39:35 UTC 2021 , Edited by admin on Sat Jun 26 11:39:35 UTC 2021
PRIMARY
MERCK INDEX
M1699
Created by admin on Sat Jun 26 11:39:35 UTC 2021 , Edited by admin on Sat Jun 26 11:39:35 UTC 2021
PRIMARY Merck Index
PUBCHEM
441328
Created by admin on Sat Jun 26 11:39:35 UTC 2021 , Edited by admin on Sat Jun 26 11:39:35 UTC 2021
PRIMARY
CAS
957-68-6
Created by admin on Sat Jun 26 11:39:35 UTC 2021 , Edited by admin on Sat Jun 26 11:39:35 UTC 2021
PRIMARY
MESH
C030735
Created by admin on Sat Jun 26 11:39:35 UTC 2021 , Edited by admin on Sat Jun 26 11:39:35 UTC 2021
PRIMARY
WIKIPEDIA
7-ACA
Created by admin on Sat Jun 26 11:39:35 UTC 2021 , Edited by admin on Sat Jun 26 11:39:35 UTC 2021
PRIMARY
EPA CompTox
957-68-6
Created by admin on Sat Jun 26 11:39:35 UTC 2021 , Edited by admin on Sat Jun 26 11:39:35 UTC 2021
PRIMARY
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