CHEBI:49566 - cloxacillin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name cloxacillin
ChEBI ID CHEBI:49566
Definition A semisynthetic penicillin antibiotic carrying a 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido group at position 6.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:49565, CHEBI:3765
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Formula C19H18ClN3O5S
Net Charge 0
Average Mass 435.88214
Monoisotopic Mass 435.066
InChI InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
InChIKey LQOLIRLGBULYKD-JKIFEVAISA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)c1c(C)onc1-c1ccccc1Cl)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.
antibacterial agent
A substance that kills or slows the growth of bacteria.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cloxacillin (CHEBI:49566) has functional parent oxacillin (CHEBI:7809)
cloxacillin (CHEBI:49566) has role antibacterial agent (CHEBI:33282)
cloxacillin (CHEBI:49566) has role antibacterial drug (CHEBI:36047)
cloxacillin (CHEBI:49566) is a penicillin (CHEBI:17334)
cloxacillin (CHEBI:49566) is a semisynthetic derivative (CHEBI:72588)
cloxacillin (CHEBI:49566) is conjugate acid of cloxacillin(1−) (CHEBI:51350)
Incoming cloxacillin(1−) (CHEBI:51350) is conjugate base of cloxacillin (CHEBI:49566)
IUPAC Name
2,2-dimethyl-6β-({[5-methyl-3-(2-chlorophenyl)isoxazol-4-yl]carbonyl}amino)penam-3α-carboxylic acid
INNs Sources
cloxacilina ChemIDplus
cloxacillin KEGG DRUG
cloxacilline ChemIDplus
cloxacillinum ChemIDplus
Synonyms Sources
(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
(3-(o-chlorophenyl)-5-methyl-4-isoxazolyl)penicillin ChemIDplus
6-(3-(o-chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid ChemIDplus
Cloxacillin KEGG COMPOUND
CLOXACILLIN PDBeChem
Manual Xrefs Databases
1859 VSDB
720 DrugCentral
C06923 KEGG COMPOUND
Cloxacillin Wikipedia
CXN PDBeChem
D07733 KEGG DRUG
DB01147 DrugBank
HMDB0015278 HMDB
LSM-15183 LINCS
US2996501 Patent
View more database links
Registry Numbers Types Sources
1232834 Beilstein Registry Number Beilstein
1232834 Reaxys Registry Number Reaxys
61-72-3 CAS Registry Number KEGG COMPOUND
61-72-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16540070 PubMed citation Europe PMC
16853954 PubMed citation Europe PMC
1701026 PubMed citation Europe PMC
24858821 PubMed citation Europe PMC
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25582344 PubMed citation Europe PMC
26365730 PubMed citation Europe PMC
27446834 PubMed citation Europe PMC
27889744 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
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8566082 PubMed citation Europe PMC
Last Modified
15 March 2018