Structure via PubChem · Public domain (PubChem)
carbenicillin
Sign in to saveAlso known as CBPC, (2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, alpha-phenyl(carboxymethylpenicillin), N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamic acid, carboxybenzylpenicillin, alpha-carboxybenzylpenicillin
Carbenicillin is a bactericidal antibiotic belonging to the carboxypenicillin subgroup of the penicillins. It was discovered by scientists at Beecham and marketed as Pyopen. It has Gram-negative coverage which includes Pseudomonas aeruginosa but limited Gram-positive coverage. The carboxypenicillins are susceptible to degradation by beta-lactamase enzymes, although they are more resistant than ampicillin to degradation. Carbenicillin is also more stable at lower pH than ampicillin.
Chemical data
- Formula
- C17H18N2O6S
- Molecular weight
- 378.4 g/mol
- IUPAC name
- (2S,5R,6R)-6-[(2-carboxy-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-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)O)C(=O)O)C
- InChIKey
- FPPNZSSZRUTDAP-UWFZAAFLSA-N
- XLogP
- 1.1
- Polar surface area
- 149 Ų
- H-bond donors
- 3
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
3,421 papers- Carbenicillin and ticarcillin.The Medical clinics of North America · 1982
- Octenidine/carbenicillin GUMBOS as potential treatment for oropharyngeal gonorrhoea.The Journal of antimicrobial chemotherapy · 2020
- Carbenicillin--gentamicin.The New England journal of medicine · 1971
- Carbenicillin.Plastic and reconstructive surgery · 1983
- Carbenicillin.The Medical letter on drugs and therapeutics · 1970
via PubMed
~3 min read
Encyclopedic overview
4 sectionsContents
- Pharmacology
- Spectrum of bacterial susceptibility and resistance
- References
- Further reading
{{Drugbox | Verifiedfields = changed | verifiedrevid = 460017669 | IUPAC_name = (2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | image = Carbenicillin.svg | image_class = skin-invert-image | synonyms = CB
| tradename = Geocillin; Pyopen | Drugs.com = | pregnancy_US = B | pregnancy_category = Passes into breast milk | legal_status= Rx-only | routes_of_administration = Oral, parenteral
Excerpted from Wikipedia’s “carbenicillin” article, available under the CC BY-SA 4.0 licence.