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Carbenicillin

Catalog No. DB00578 Name DrugBank
CAS Number 4697-36-3 Website http://www.ualberta.ca/
M. F. C17H18N2O6S Telephone (780) 492-3111
M. W. 378.39962 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 460

SYNONYMS

IUPAC name
(2S,5R,6R)-6-(2-carboxy-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
IUPAC Traditional name
carbenicillin
Brand Name
Pyopen
Geopen
Synonyms
Carboxybenzylpenicillin acid
Carbenicilline [INN-French]
alpha-Carboxybenzylpencillin
Carboxybenzylpenicillin
Carbenicillinum [INN-Latin]
Carbenicillina [DCIT]
Carbenicilina [INN-Spanish]

DATABASE IDS

PubChem CID 20824
CAS Number 4697-36-3
PubChem SID 46505653

PROPERTIES

Hydrophobicity(logP) 1.8
Solubility 451 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved
Description Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function. [PubChem]
Indication For the treatment of acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of bacteria.
Pharmacology Carbenicillin is a semisynthetic penicillin. Though carbenicillin provides substantial in vitro activity against a variety of both gram-positive and gram-negative microorganisms, the most important aspect of its profile is in its antipseudomonal and antiproteal activity. Because of the high urine levels obtained following administration, carbenicillin has demonstrated clinical efficacy in urinary infections due to susceptible strains of: Escherichia coli, Proteus mirabilis, Proteus vulgaris, Morganella morganii, Pseudomonas species, Providencia rettgeri, Enterobacter species, and Enterococci (S. faecalis).
Toxicity Carbenicillin blood levels achievable are very low, and toxic reactions as a function of overdosage should not occur systematically. The oral LD50 in mice is 3,600 mg/kg, in rats 2,000 mg/kg, and in dogs is in excess of 500 mg/kg. The lethal human dose is not known. Symptoms of overdose include diarrhea, nausea, stomach upset, and vomiting.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Minimal.
Absorption Rapidly absorbed from the small intestine following oral administration. Oral bioavailability is 30 to 40%.
Half Life 1 hour
Protein Binding 30 to 60%
External Links
Wikipedia
RxList
Drugs.com

REFERENCES