CHEBI:5098 - flucloxacillin

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ChEBI Name flucloxacillin
ChEBI ID CHEBI:5098
Definition A penicillin compound having a 6β-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido] side-chain.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H17ClFN3O5S
Net Charge 0
Average Mass 453.87200
Monoisotopic Mass 453.056
InChI InChI=1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1
InChIKey UIOFUWFRIANQPC-JKIFEVAISA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)c1c(C)onc1-c1c(F)cccc1Cl)C(O)=O
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): antibacterial drug
A drug used to treat or prevent bacterial infections.
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.
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ChEBI Ontology
Outgoing flucloxacillin (CHEBI:5098) has role antibacterial drug (CHEBI:36047)
flucloxacillin (CHEBI:5098) is a penicillin (CHEBI:17334)
flucloxacillin (CHEBI:5098) is conjugate acid of flucloxacillin(1−) (CHEBI:52037)
Incoming flucloxacilloyl-L-lysine (CHEBI:139365) has functional parent flucloxacillin (CHEBI:5098)
flucloxacillin(1−) (CHEBI:52037) is conjugate base of flucloxacillin (CHEBI:5098)
flucloxacilloyl group (CHEBI:59152) is substituent group from flucloxacillin (CHEBI:5098)
flucloxcillanyl group (CHEBI:61616) is substituent group from flucloxacillin (CHEBI:5098)
IUPAC Name
6β-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido]-2,2-dimethylpenam-3α-carboxylic acid
INNs Sources
flucloxacillin KEGG DRUG
flucloxacilline DrugBank
flucloxacillinum DrugBank
Synonyms Sources
(2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillin ChemIDplus
Floxacillin KEGG COMPOUND
flucloxacilina DrugBank
Flucloxacillin KEGG COMPOUND
Brand Name Source
Floxapen DrugBank
Manual Xrefs Databases
1183 DrugCentral
C11748 KEGG COMPOUND
D04196 KEGG DRUG
DB00301 DrugBank
Flucloxacillin Wikipedia
View more database links
Registry Numbers Types Sources
4771988 Beilstein Registry Number Beilstein
4771988 Reaxys Registry Number Reaxys
5250-39-5 CAS Registry Number KEGG COMPOUND
5250-39-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12569987 PubMed citation Europe PMC
15773973 PubMed citation Europe PMC
23032409 PubMed citation Europe PMC
23542420 PubMed citation Europe PMC
25998949 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
5481218 PubMed citation Europe PMC
Last Modified
15 March 2018