CHEBI:3534 - cephalexin

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ChEBI Name cephalexin
ChEBI ID CHEBI:3534
Definition A semisynthetic first-generation cephalosporin antibiotic having methyl and β-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and Gram-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C16H17N3O4S
Net Charge 0
Average Mass 347.38900
Monoisotopic Mass 347.094
InChI InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
InChIKey ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
SMILES [H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1)C(O)=O
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cephalexin (CHEBI:3534) has role antibacterial drug (CHEBI:36047)
cephalexin (CHEBI:3534) is a cephalosporin (CHEBI:23066)
cephalexin (CHEBI:3534) is a semisynthetic derivative (CHEBI:72588)
cephalexin (CHEBI:3534) is conjugate acid of cephalexin(1−) (CHEBI:59392)
Incoming cefalexin pivoxil (CHEBI:135750) has functional parent cephalexin (CHEBI:3534)
cephalexin monohydrate (CHEBI:3535) has part cephalexin (CHEBI:3534)
cephalexin(1−) (CHEBI:59392) is conjugate base of cephalexin (CHEBI:3534)
IUPAC Name
7β-[(2R)-2-amino-2-phenylacetamido]-3-methyl-3,4-didehydrocepham-4-carboxylic acid
INNs Sources
cefalexina ChemIDplus
cefalexine ChemIDplus
cefalexinum ChemIDplus
Synonyms Sources
(6R,7R)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid IUPAC
7-(D-α-Aminophenylacetamido)desacetoxycephalosporanic acid ChemIDplus
7-β-(D-alpha-Amino-alpha-phenylacetylamino)-3-methyl-3-cephem-4-carboxylic acid ChemIDplus
Cefalexin KEGG COMPOUND
Celexin ChemIDplus
Cepastar ChemIDplus
Cepexin ChemIDplus
Cephacillin ChemIDplus
Ceporexin ChemIDplus
CEX KEGG DRUG
Manual Xrefs Databases
1791 VSDB
571 DrugCentral
C06895 KEGG COMPOUND
Cefalexin Wikipedia
D00263 KEGG DRUG
DB00567 DrugBank
HMDB0014707 HMDB
LSM-5957 LINCS
US3275626 Patent
US3507861 Patent
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Registry Numbers Types Sources
15686-71-2 CAS Registry Number KEGG COMPOUND
15686-71-2 CAS Registry Number ChemIDplus
4238892 Reaxys Registry Number Reaxys
965503 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
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Last Modified
09 February 2018