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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12N2O5S
Molecular Weight 272.278
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 7-AMINOCEPHALOSPORANIC ACID

SMILES

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2N)C(O)=O

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 272.278
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
D-amino-acid oxidase--an improved production of the enzyme by the yeast Trigonopsis variabilis in a laboratory fermentor.
2001
Improvement of the synthesis of diphenylmethyl 7beta-(o-hydroxy)benzylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate.
2001 Aug
Active site residues of cephalosporin acylase are critical not only for enzymatic catalysis but also for post-translational modification.
2001 Dec 21
Industrial production of beta-lactam antibiotics.
2003 Jun
Synthesis and preliminary antimicrobial evaluation of new 7-(N-pyrrolyl) derivatives of cephalosporins.
2004
Batch production of deacetyl 7-aminocephalosporanic acid by immobilized cephalosporin-C deacetylase.
2004 Aug
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
Evolution of an acylase active on cephalosporin C.
2005 Dec
D-Amino acid oxidase: structure, catalytic mechanism, and practical application.
2005 Jan
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
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
YesT: a new rhamnogalacturonan acetyl esterase from Bacillus subtilis.
2008 Apr
Development of the semi-synthetic penicillins and cephalosporins.
2008 Mar
A single Phe54Tyr substitution improves the catalytic activity and thermostability of Trigonopsis variabilis D-amino acid oxidase.
2010 Feb 28
Protein engineering of penicillin acylase.
2010 Jul
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 Wed Jul 05 22:34:03 UTC 2023
Edited
by admin
on Wed Jul 05 22:34:03 UTC 2023
Record UNII
9XI67897RG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
7-AMINOCEPHALOSPORANIC ACID
MI  
Common Name English
CEFTRIAXONE SODIUM IMPURITY E [IP]
Common Name English
CEFAZOLIN SODIUM IMPURITY H [EP IMPURITY]
Common Name English
7-ACA
Common Name English
3-(ACETOXYMETHYL)-7-AMINOCEPHEM-4-CARBOXYLIC ACID
Common Name English
CEFOPERAZONE SODIUM IMPURITY E [EP IMPURITY]
Common Name English
(7R)-7-AMINOCEPHALOSPORANIC ACID
Common Name English
7.BETA.-AMINO-3-ACETOXYMETHYLCEPHEMCARBOXYLIC ACID
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
3-ACETOXYMETHYL-7.BETA.-AMINOCEPH-3-EM-4-CARBOXYLIC ACID
Common Name English
7.BETA.-AMINOCEPHALOSPORANIC ACID
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-7-AMINO-8-OXO-, (6R,7R)-
Systematic Name English
7-AMINOCEPHALOSPORANIC ACID [MI]
Common Name English
7-Aminocephalosporanic acid [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
9XI67897RG
Created by admin on Wed Jul 05 22:34:03 UTC 2023 , Edited by admin on Wed Jul 05 22:34:03 UTC 2023
PRIMARY
ECHA (EC/EINECS)
213-485-0
Created by admin on Wed Jul 05 22:34:03 UTC 2023 , Edited by admin on Wed Jul 05 22:34:03 UTC 2023
PRIMARY
CHEBI
2255
Created by admin on Wed Jul 05 22:34:03 UTC 2023 , Edited by admin on Wed Jul 05 22:34:03 UTC 2023
PRIMARY
MERCK INDEX
M1699
Created by admin on Wed Jul 05 22:34:03 UTC 2023 , Edited by admin on Wed Jul 05 22:34:03 UTC 2023
PRIMARY Merck Index
PUBCHEM
441328
Created by admin on Wed Jul 05 22:34:03 UTC 2023 , Edited by admin on Wed Jul 05 22:34:03 UTC 2023
PRIMARY
CAS
957-68-6
Created by admin on Wed Jul 05 22:34:03 UTC 2023 , Edited by admin on Wed Jul 05 22:34:03 UTC 2023
PRIMARY
MESH
C030735
Created by admin on Wed Jul 05 22:34:03 UTC 2023 , Edited by admin on Wed Jul 05 22:34:03 UTC 2023
PRIMARY
WIKIPEDIA
7-ACA
Created by admin on Wed Jul 05 22:34:03 UTC 2023 , Edited by admin on Wed Jul 05 22:34:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID9045342
Created by admin on Wed Jul 05 22:34:03 UTC 2023 , Edited by admin on Wed Jul 05 22:34:03 UTC 2023
PRIMARY
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