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carbenicillin

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EntityQ1050019· pop 22· linked from 209 articles

carbenicillin

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Also 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

via PubMed

Wikidata facts

Mass
378.088557
Has use
medication
Show 6 more facts
chemical formula
C₁₇H₁₈N₂O₆S
defined daily dose
12
subject has role
penicillin
isomeric 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
canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)O)C(=O)O)C
World Health Organisation international non-proprietary name
carbenicillin
Sources (5)

via Wikidata · CC0

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Encyclopedic overview

4 sections
Contents
  • 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.