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ChEBI
> Main
CHEBI:49566 - cloxacillin
Main
ChEBI Ontology
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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
Supplier Information
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Molfile
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Wikipedia
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Read full article at Wikipedia
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 (Br
o
nsted 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.
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
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
(2
S
,5
R
,6
R
)-
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
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
7417768
PubMed citation
Europe PMC
8566082
PubMed citation
Europe PMC
Last Modified
08 March 2019