CHEBI:124991 - cefalotin

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ChEBI Name cefalotin
ChEBI ID CHEBI:124991
Definition A semisynthetic, first-generation cephalosporin antibiotic with acetoxymethyl and (2-thienylacetyl)nitrilo moieties at positions 3 and 7, respectively, of the core structure. Administered parenterally during surgery and to treat a wide spectrum of blood infections.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41547, CHEBI:50895
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Formula C16H16N2O6S2
Net Charge 0
Average Mass 396.43800
Monoisotopic Mass 396.045
InChI InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1
InChIKey XIURVHNZVLADCM-IUODEOHRSA-N
SMILES [H][C@@]1(NC(=O)Cc2cccs2)C(=O)N2C(C(O)=O)=C(COC(C)=O)CS[C@]12[H]
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
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 )
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 cefalotin (CHEBI:124991) has role antibacterial drug (CHEBI:36047)
cefalotin (CHEBI:124991) has role antimicrobial agent (CHEBI:33281)
cefalotin (CHEBI:124991) is a azabicycloalkene (CHEBI:50896)
cefalotin (CHEBI:124991) is a carboxylic acid (CHEBI:33575)
cefalotin (CHEBI:124991) is a cephalosporin (CHEBI:23066)
cefalotin (CHEBI:124991) is a semisynthetic derivative (CHEBI:72588)
cefalotin (CHEBI:124991) is a thiophenes (CHEBI:26961)
cefalotin (CHEBI:124991) is conjugate acid of cefalotin(1−) (CHEBI:50897)
Incoming cephalothin sodium (CHEBI:3542) has part cefalotin (CHEBI:124991)
cefalotin(1−) (CHEBI:50897) is conjugate base of cefalotin (CHEBI:124991)
IUPAC Names
(6R,7R)-3-(acetoxymethyl)-8-oxo-7-(thiophen-2-ylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7β-(thiophen-2-ylacetamido)-3-acetoxymethyl-3,4-didehydrocepham-4-carboxylic acid
INNs Sources
cefalotin ChEBI
cefalotina ChEBI
céfalotine ChEBI
cefalotinum ChEBI
Synonyms Sources
3-Acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid ChemIDplus
7-(2'-thienylacetamido)cephalosporanic acid ChEBI
7-(2-Thienylacetamido)cephalosporanic acid ChemIDplus
7-(Thiophene-2-acetamido)cephalosporin ChemIDplus
Cefalothin DrugBank
Cefalotin KEGG COMPOUND
Cephalothin DrugBank
CEPHALOTHIN PDBeChem
Cephalotin DrugBank
CET ChEBI
Manual Xrefs Databases
574 DrugCentral
C07761 KEGG COMPOUND
Cephalothin Wikipedia
CLS PDBeChem
D07635 KEGG DRUG
DB00456 DrugBank
FR1384197 Patent
HMDB0014599 HMDB
LSM-15184 LINCS
US3218318 Patent
View more database links
Registry Numbers Types Sources
153-61-7 CAS Registry Number ChemIDplus
945586 Beilstein Registry Number Beilstein
945586 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10930630 PubMed citation Europe PMC
12569987 PubMed citation Europe PMC
12833570 PubMed citation Europe PMC
1384868 PubMed citation Europe PMC
13963283 PubMed citation Europe PMC
1701026 PubMed citation Europe PMC
2083978 PubMed citation Europe PMC
23472927 PubMed citation Europe PMC
23680238 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
6176550 PubMed citation Europe PMC
Last Modified
13 February 2018