Structure via PubChem · Public domain (PubChem)
cloxacillin
Sign in to saveAlso known as (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, [3-(o-chlorophenyl)-5-methyl-4-isoxazolyl]penicillin, 6-[3-(o-chlorophenyl)-5-methyl-4-isoxazolecarboxamido]penicillanic acid
Cloxacillin is an antibiotic useful for the treatment of several bacterial infections. This includes impetigo, cellulitis, pneumonia, septic arthritis, and otitis externa. It is not effective for methicillin-resistant Staphylococcus aureus (MRSA). It can be used by mouth and by injection.
Chemical data
- Formula
- C19H18ClN3O5S
- Molecular weight
- 435.9 g/mol
- IUPAC name
- (2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
- InChIKey
- LQOLIRLGBULYKD-JKIFEVAISA-N
- XLogP
- 2.4
- Polar surface area
- 138 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
4,251 papers- Cloxacillin-induced acute vanishing bile duct syndrome: A case study and literature review.British journal of clinical pharmacology · 2022
- Cloxacillin-induced cholestasis.Clinical infectious diseases : an official publication of the Infectious Diseases Society of America · 1994
- Cloxacillin-induced neutropenia.The Journal of infectious diseases · 1986
- Cloxacillin-induced skin eruption.Clinical and experimental dermatology · 2009
- Cloxacillin-induced leukopenia.Archives of internal medicine · 1985
via PubMed
Wikidata facts
- Mass
- 435.066
Show 5 more facts
- chemical formula
- C₁₉H₁₈ClN₃O₅S
- Commons category
- Cloxacillin
- isomeric SMILES
- CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
- canonical SMILES
- CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
- World Health Organisation international non-proprietary name
- cloxacillin
via Wikidata · CC0
~3 min read
Article
5 sectionsContents
- Mechanism of action
- Society and culture
- See also
- References
- External links
{{Drugbox | verifiedrevid = 460045783 | IUPAC_name = (2S,5R,6R)-6-{[3-(2-chlorophenyl)-5-methyl-oxazole-4-carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid or 5 methyl 3(2 chlorophenyl)4 isoxazoyl penicillin | image = Cloxacillin.svg | image_class = skin-invert-image | image2 = Cloxacillin-based-on-xtal-3D-bs-17.png | image_class2 = bg-transparent
| tradename = Cloxapen, others | Drugs.com = | pregnancy_US = B | legal_status = | routes_of_administration = By mouth, IM