CHEBI:209807 - cefoxitin

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ChEBI Name cefoxitin
ChEBI ID CHEBI:209807
Definition A semisynthetic cephamycin antibiotic which, in addition to the methoxy group at the 7α position, has 2-thienylacetamido and carbamoyloxymethyl side-groups. It is resistant to β-lactamase.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41436, CHEBI:471714, CHEBI:3500, CHEBI:658070
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Formula C16H17N3O7S2
Net Charge 0
Average Mass 427.45200
Monoisotopic Mass 427.051
InChI InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1
InChIKey WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
SMILES [H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@]2(NC(=O)Cc1cccs1)OC)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 cefoxitin (CHEBI:209807) has role antibacterial drug (CHEBI:36047)
cefoxitin (CHEBI:209807) is a cephalosporin (CHEBI:23066)
cefoxitin (CHEBI:209807) is a cephamycin (CHEBI:55429)
cefoxitin (CHEBI:209807) is a semisynthetic derivative (CHEBI:72588)
cefoxitin (CHEBI:209807) is conjugate acid of cefoxitin(1−) (CHEBI:53655)
Incoming cefoxitin(1−) (CHEBI:53655) is conjugate base of cefoxitin (CHEBI:209807)
IUPAC Names
(6R,7S)-4-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(thiophen-2-enyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
3-[(carbamoyloxy)methyl]-7α-methoxy-7β-[(thiophen-2-yl)acetamido]-3,4-didehydrocepham-4-carboxylic acid
INNs Sources
cefoxitin KEGG DRUG
cefoxitina ChemIDplus
cefoxitine ChemIDplus
cefoxitinum ChemIDplus
ceftoxitin ChemIDplus
Synonyms Sources
(6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid IUPAC
Cefoxitin ChemIDplus
Cephoxitin ChemIDplus
CFX KEGG DRUG
Rephoxitin ChemIDplus
Manual Xrefs Databases
550 DrugCentral
C06887 KEGG COMPOUND
Cefoxitin Wikipedia
CFX PDBeChem
D02345 KEGG DRUG
DB01331 DrugBank
DE2129675 Patent
DE2203653 Patent
HMDB0015426 HMDB
LSM-5786 LINCS
US4297488 Patent
View more database links
Registry Numbers Types Sources
35607-66-0 CAS Registry Number KEGG COMPOUND
35607-66-0 CAS Registry Number ChemIDplus
4216947 Beilstein Registry Number Beilstein
4216947 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12569987 PubMed citation Europe PMC
17043131 PubMed citation ChEMBL
17178800 PubMed citation ChEMBL
17220412 PubMed citation ChEMBL
17353248 PubMed citation ChEMBL
17387156 PubMed citation ChEMBL
17923492 PubMed citation ChEMBL
18056283 PubMed citation ChEMBL
18070972 PubMed citation ChEMBL
2083978 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
8360877 PubMed citation ChEMBL
Last Modified
13 February 2018