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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
413
Curator's Comment: # Pfizer & Co C

Approval Year

Unknown
127998
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
643
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
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
A rapid and specific method to screen environmental microorganisms for cephalosporin acylase activity.
2003 Jul
An alternative procedure for preparation of cefdinir.
2003 Jun
An improved method for preparation of cefpodoxime proxetil.
2003 May
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
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
Evolution of an acylase active on cephalosporin C.
2005 Dec
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
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
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
Environmentally safe production of 7-ACA by recombinant Acremonium chrysogenum.
2010 Dec
Biosynthesis of cephalosporin-C acylase enzyme: optimal media design, purification, and characterization.
2010 Oct
Patents

Patents

JP1056682A
1
JP1090190A
1
JP2001507688A
19
JP2001525667A
12
JP2002000266A
1
JP2005198655A
1
JP2005348743A
1
JP3903392B2
13
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 16 15:58:10 UTC 2022
Edited
by admin
on Fri Dec 16 15:58:10 UTC 2022
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 16 15:58:10 UTC 2022 , Edited by admin on Fri Dec 16 15:58:10 UTC 2022
PRIMARY
ECHA (EC/EINECS)
213-485-0
Created by admin on Fri Dec 16 15:58:10 UTC 2022 , Edited by admin on Fri Dec 16 15:58:10 UTC 2022
PRIMARY
CHEBI
2255
Created by admin on Fri Dec 16 15:58:10 UTC 2022 , Edited by admin on Fri Dec 16 15:58:10 UTC 2022
PRIMARY
MERCK INDEX
M1699
Created by admin on Fri Dec 16 15:58:10 UTC 2022 , Edited by admin on Fri Dec 16 15:58:10 UTC 2022
PRIMARY Merck Index
PUBCHEM
441328
Created by admin on Fri Dec 16 15:58:10 UTC 2022 , Edited by admin on Fri Dec 16 15:58:10 UTC 2022
PRIMARY
CAS
957-68-6
Created by admin on Fri Dec 16 15:58:10 UTC 2022 , Edited by admin on Fri Dec 16 15:58:10 UTC 2022
PRIMARY
MESH
C030735
Created by admin on Fri Dec 16 15:58:10 UTC 2022 , Edited by admin on Fri Dec 16 15:58:10 UTC 2022
PRIMARY
WIKIPEDIA
7-ACA
Created by admin on Fri Dec 16 15:58:10 UTC 2022 , Edited by admin on Fri Dec 16 15:58:10 UTC 2022
PRIMARY
EPA CompTox
DTXSID9045342
Created by admin on Fri Dec 16 15:58:10 UTC 2022 , Edited by admin on Fri Dec 16 15:58:10 UTC 2022
PRIMARY
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NIH
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