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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
Active site residues of cephalosporin acylase are critical not only for enzymatic catalysis but also for post-translational modification.
2001 Dec 21
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
An alternative procedure for preparation of cefdinir.
2003 Jun
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
Industrial enzymatic production of cephalosporin-based beta-lactams.
2004
Catalytic properties of D-amino acid oxidase in cephalosporin C bioconversion: a comparison between proteins from different sources.
2004 Mar-Apr
Single-step conversion of cephalosporin-C to 7-aminocephalosporanic acid by free and immobilized cells of Pseudomonas diminuta.
2005 Jul
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
Site-specific protonation microequilibria of penicillin and cephalosporin beta-lactam core molecules.
2007 Sep
YesT: a new rhamnogalacturonan acetyl esterase from Bacillus subtilis.
2008 Apr
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
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:01:59 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY
ECHA (EC/EINECS)
213-485-0
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY
CHEBI
2255
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY
MERCK INDEX
m1699
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY Merck Index
PUBCHEM
441328
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY
CAS
957-68-6
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY
MESH
C030735
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY
WIKIPEDIA
7-ACA
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID9045342
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY
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NIH
NCATS
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