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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

Description

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

Pfizer
420
Curator's Comment: # Pfizer & Co C

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[Thoughts on explaining cigarette smoking].
1987 Feb
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
Structure of cephalosporin acylase in complex with glutaryl-7-aminocephalosporanic acid and glutarate: insight into the basis of its substrate specificity.
2001 Dec
Active site residues of cephalosporin acylase are critical not only for enzymatic catalysis but also for post-translational modification.
2001 Dec 21
[Establishment of detective systems for GL-7ACA acylase expression].
2001 Nov
Modulation of penicillin acylase properties via immobilization techniques: one-pot chemoenzymatic synthesis of Cephamandole from Cephalosporin C.
2001 Sep 17
Cross-reactivity of cefotetan and ceftriaxone antibodies, associated with hemolytic anemia, with other: cephalosporins and penicillin.
2002 Aug
Structure-based prediction of modifications in glutarylamidase to allow single-step enzymatic production of 7-aminocephalosporanic acid from cephalosporin C.
2002 Jan
Expression of gene encoding GL-7ACA acylase in Escherichia coli.
2002 Jul
The crystal structure of Helicobacter pylori cysteine-rich protein B reveals a novel fold for a penicillin-binding protein.
2002 Mar 22
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
Industrial production of beta-lactam antibiotics.
2003 Jun
Immobilization of glutaryl-7-aminocephalosporanic acid acylase on silica gel and enhancement of its stability.
2003 Mar
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
Catalytic properties of D-amino acid oxidase in cephalosporin C bioconversion: a comparison between proteins from different sources.
2004 Mar-Apr
D-Amino acid oxidase: structure, catalytic mechanism, and practical application.
2005 Jan
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
Enzymatic modifications of cephalosporins by cephalosporin acylase and other enzymes.
2006 Apr-Jun
[Microspeciation of amphoteric molecules of unusual acid-base properties].
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
[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
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

Patents

JP1056682A
1
JP1090190A
1
JP2001507688A
24
JP2001525667A
12
JP2002000266A
1
JP2005198655A
1
JP2005348743A
1
JP3903392B2
18
JPH00453499A
1
JPH00568551A
1
JPH00584077A
1
JPH00584078A
1
JPH00898683A
1
JPH00898686A
1
JPH01131182A
1
JPH02160791A
1
JPH022396A
1
JPH0242085A
1
JPH02456A
1
JPH04104792A
1
JPH04198184A
1
JPH04211088A
1
JPH04230689A
1
JPH0453499A
1
JPH05211889A
1
JPH05211890A
1
JPH0568551A
1
JPH0584077A
1
JPH0584078A
1
JPH06141857A
1
JPH06184161A
1
JPH06225794A
1
JPH0646835A
1
JPH0680673A
1
JPH0690746A
1
JPH07145173A
1
JPH07165765A
1
JPH07222587A
1
JPH07303483A
1
JPH07313161A
1
JPH08224089A
1
JPH08242884A
1
JPH08256789A
1
JPH08301874A
1
JPH0898683A
1
JPH0898686A
1
JPH0948784A
1
JPH10291991A
1
JPH10291993A
1
JPH1160583A
1
JPS05238092A
4

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:01:59 UTC 2023
Edited
by admin
on Fri Dec 15 15:01:59 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 Fri Dec 15 15:01:59 UTC 2023 , Edited by admin on Fri Dec 15 15:01:59 UTC 2023
PRIMARY
ECHA (EC/EINECS)
213-485-0
Created by admin on Fri Dec 15 15:01:59 UTC 2023 , Edited by admin on Fri Dec 15 15:01:59 UTC 2023
PRIMARY
CHEBI
2255
Created by admin on Fri Dec 15 15:01:59 UTC 2023 , Edited by admin on Fri Dec 15 15:01:59 UTC 2023
PRIMARY
MERCK INDEX
m1699
Created by admin on Fri Dec 15 15:01:59 UTC 2023 , Edited by admin on Fri Dec 15 15:01:59 UTC 2023
PRIMARY Merck Index
PUBCHEM
441328
Created by admin on Fri Dec 15 15:01:59 UTC 2023 , Edited by admin on Fri Dec 15 15:01:59 UTC 2023
PRIMARY
CAS
957-68-6
Created by admin on Fri Dec 15 15:01:59 UTC 2023 , Edited by admin on Fri Dec 15 15:01:59 UTC 2023
PRIMARY
MESH
C030735
Created by admin on Fri Dec 15 15:01:59 UTC 2023 , Edited by admin on Fri Dec 15 15:01:59 UTC 2023
PRIMARY
WIKIPEDIA
7-ACA
Created by admin on Fri Dec 15 15:01:59 UTC 2023 , Edited by admin on Fri Dec 15 15:01:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID9045342
Created by admin on Fri Dec 15 15:01:59 UTC 2023 , Edited by admin on Fri Dec 15 15:01:59 UTC 2023
PRIMARY
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NIH
NCATS
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