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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H10N2O3S
Molecular Weight 214.242
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 7-AMINODESACETOXYCEPHALOSPORANIC ACID

SMILES

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

InChI

InChIKey=NVIAYEIXYQCDAN-CLZZGJSISA-N
InChI=1S/C8H10N2O3S/c1-3-2-14-7-4(9)6(11)10(7)5(3)8(12)13/h4,7H,2,9H2,1H3,(H,12,13)/t4-,7-/m1/s1

HIDE SMILES / InChI
Molecular Formula C8H10N2O3S
Molecular Weight 214.242
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://link.springer.com/chapter/10.1007/978-1-4615-9290-7_68 | https://www.ncbi.nlm.nih.gov/pubmed/10932155 | https://www.ncbi.nlm.nih.gov/pubmed/7764037

7-Aminodesacetoxycephalosporanic acid is a key intermediate for the synthesis of cephalosporins antibiotics and their intermediates. The current process for producing 7-ADCA involves a multistep chemical ring expansion of penicillin G to phenylacetyl-7-ADCA, from which the aromatic side chain is removed using a penicillin acylase.

Originator

Minka, A.F.
1
Sources: Farmatsevtichnii Zhurnal (Kiev) (1963), 18, (5), 32-5.

Approval Year

2017
422
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Environmentally safe production of 7-aminodeacetoxycephalosporanic acid (7-ADCA) using recombinant strains of Acremonium chrysogenum.
2000 Aug
Patents

Patents

GB944417
1

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 15:45:58 GMT 2023
Edited
by admin
on Fri Dec 15 15:45:58 GMT 2023
Record UNII
ANM3MSM8TN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
7-AMINODESACETOXYCEPHALOSPORANIC ACID
Common Name English
DEACETOXYCEPHALOSPORANIC ACID
Common Name English
7-AMINO-3-METHYL-3-CEPHEN-4-CARBOXYLIC ACID
Common Name English
7-AMINO-3-METHYL-.DELTA.3-CEPHAN-4-CARBOXYLIC ACID
Common Name English
7-.BETA.-AMINO-3-METHYL-3-CEPHEM-4-CARBOXYLIC ACID
Common Name English
7-ADCA
Common Name English
7-AMINO-3-DEACETOXYCEPHALOSPORANIC ACID
Common Name English
CEFRADINE IMPURITY A [EP IMPURITY]
Common Name English
(6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Systematic Name English
3-METHYL-7-AMINO-.DELTA.3-CEPHEM-4-CARBOXYLIC ACID
Common Name English
CEFADROXIL MONOHYDRATE IMPURITY B [EP IMPURITY]
Common Name English
3-METHYL-7-AMINOCEPH-3-EM-4-CARBOXYLIC ACID
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-AMINO-3-METHYL-8-OXO-, (6R,7R)-
Common Name English
CEPHALEXIN IMPURITY B
Common Name English
CEFADROXIL RELATED COMPOUND B [USP-RS]
Common Name English
7-AMINO-3-METHYL-.DELTA.3-CEPHEM-4-CARBOXYLIC ACID
Common Name English
7-AMINODEACETOXYCEPHALEXANIC ACID
Common Name English
7.BETA.-AMINO-3-METHYLCEPH-3-EM-4-CARBOXYLIC ACID
Common Name English
7-AMINODEACETOXYCEPHALOSPORANIC ACID
Common Name English
7-AMINO-3-METHYLCEPHALOSPORANIC ACID
Common Name English
7-AMINO-3-DESACETOXYCEPHALOSPORANIC ACID
Common Name English
7-AMINO-3-METHYL-3-CEPHEM-4-CARBOXYLIC ACID
Common Name English
CEFADROXIL RELATED COMPOUND B
USP-RS  
Common Name English
CEFADROXIL IMPURITY B [EP IMPURITY]
Common Name English
Code System Code Type Description
DRUG BANK
DB14107
Created by admin on Fri Dec 15 15:45:58 GMT 2023 , Edited by admin on Fri Dec 15 15:45:58 GMT 2023
PRIMARY
CHEBI
64984
Created by admin on Fri Dec 15 15:45:58 GMT 2023 , Edited by admin on Fri Dec 15 15:45:58 GMT 2023
PRIMARY
CAS
22252-43-3
Created by admin on Fri Dec 15 15:45:58 GMT 2023 , Edited by admin on Fri Dec 15 15:45:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
244-870-1
Created by admin on Fri Dec 15 15:45:58 GMT 2023 , Edited by admin on Fri Dec 15 15:45:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID4057687
Created by admin on Fri Dec 15 15:45:58 GMT 2023 , Edited by admin on Fri Dec 15 15:45:58 GMT 2023
PRIMARY
RXCUI
1990418
Created by admin on Fri Dec 15 15:45:58 GMT 2023 , Edited by admin on Fri Dec 15 15:45:58 GMT 2023
PRIMARY
PUBCHEM
33498
Created by admin on Fri Dec 15 15:45:58 GMT 2023 , Edited by admin on Fri Dec 15 15:45:58 GMT 2023
PRIMARY
FDA UNII
ANM3MSM8TN
Created by admin on Fri Dec 15 15:45:58 GMT 2023 , Edited by admin on Fri Dec 15 15:45:58 GMT 2023
PRIMARY
RS_ITEM_NUM
1097126
Created by admin on Fri Dec 15 15:45:58 GMT 2023 , Edited by admin on Fri Dec 15 15:45:58 GMT 2023
PRIMARY
DAILYMED
ANM3MSM8TN
Created by admin on Fri Dec 15 15:45:58 GMT 2023 , Edited by admin on Fri Dec 15 15:45:58 GMT 2023
PRIMARY
Related Record Type Details
Structure of CEPHALEXIN
PARENT -> IMPURITY
Structure of CEFADROXIL
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of CEPHRADINE ANHYDROUS
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
NIH
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