CHEBI:49566 - cloxacillin

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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 435.06557
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 (or active part thereof) that kills or slows the growth of bacteria.
allergen
A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
(via penicillin allergen )
(via penicillin )
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 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 penicillin allergen (CHEBI:88187)
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
25305230 PubMed citation Europe PMC
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
08 March 2019