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Structure via PubChem · Public domain (PubChem)
carbenicillin phenyl
Sign in to saveAlso known as carbenicillin phenyl ester, (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(3-oxo-3-phenoxy-2-phenylpropanoyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Carfecillin is a beta-lactam antibiotic. It is a phenyl derivative of carbenicillin, acting as a prodrug.
Chemical data
- Formula
- C23H22N2O6S
- Molecular weight
- 454.5 g/mol
- IUPAC name
- (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(3-oxo-3-phenoxy-2-phenylpropanoyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)OC4=CC=CC=C4)C(=O)O)C
- InChIKey
- NZDASSHFKWDBBU-KVMCETHSSA-N
- XLogP
- 3
- Polar surface area
- 138 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
16 papers- Carbenicillin Indanyl Disodium.2006
- Carbenicillin prodrugs: stability kinetics of alpha-phenyl and alpha-indanyl esters in aqueous solution.Journal of pharmaceutical sciences · 1979
- Absorption kinetics of carbenicillin phenyl sodium and carbenicillin indanyl sodium in man.Chemical & pharmaceutical bulletin · 1982
- Val-237 for Ala substitution in the TEM-2 beta-lactamase dramatically alters the catalytic efficiencies towards carbenicillin and ticarcillin.FEMS microbiology letters · 1994
- Choice among penicillins and cephalosporins.British medical journal · 1974
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 454.12
Show 4 more facts
- chemical formula
- C₂₃H₂₂N₂O₆S
- canonical SMILES
- CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)OC4=CC=CC=C4)C(=O)O)C
- isomeric SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)OC4=CC=CC=C4)C(=O)O)C
- subject has role
- antibiotic
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Carfecillin is a beta-lactam antibiotic. It is a phenyl derivative of carbenicillin, acting as a prodrug.
== References ==
Excerpted from Wikipedia’s “carbenicillin phenyl” article, available under the CC BY-SA 4.0 licence.