Page last updated: 2024-12-06

carfecillin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Carfecillin: The phenyl ester of CARBENICILLIN that, upon oral administration, is broken down in the intestinal mucosa to the active antibacterial. It is used for urinary tract infections. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID33672
CHEMBL ID1095283
CHEBI ID3414
SCHEMBL ID150615
MeSH IDM0003482

Synonyms (35)

Synonym
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((1,3-dioxo-3-phenoxy-2-phenylpropyl)amino)-3,3-dimethyl-7-oxo-, (2s-(2alpha,5alpha,6beta))-
carbenicillin phenyl ester
einecs 248-171-2
brn 1095507
carfecillinum [inn-latin]
6-((1,3-dioxo-3-phenoxy-2-phenylpropyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid (2s-(2alpha,5alpha,6beta))-
malonamic acid, n-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenyl-, 1-phenyl ester
carfecilina [inn-spanish]
carfecilline [inn-french]
6-(2-phenoxycarbonyl-2-phenylacetamido)penicillansaeure
(2s,5r,6r)-3,3-dimethyl-7-oxo-6-((2-phenoxycarbonyl)-2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure
carbenicillin phenyl
27025-49-6
carfecillin
2,2-dimethyl-6beta-[(3-oxo-3-phenoxy-2-phenylpropanoyl)amino]penam-3alpha-carboxylic acid
CHEBI:3414 ,
carfecillinum
carfecilina
(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
carfecilline
CHEMBL1095283
9uu4xdb74x ,
unii-9uu4xdb74x
carfecillin [inn]
n-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamic acid 1-phenyl ester
carfecillin [who-dd]
carfecillin [jan]
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((1,3-dioxo-3-phenoxy-2-phenylpropyl)amino)-3,3-dimethyl-7-oxo-, (2s-(2.alpha.,5.alpha.,6.beta.))
SCHEMBL150615
carbenicillinphenylsodium
DTXSID10891704
Q5039237
DB13506
gtpl12288
(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

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Carfecillin treatment was successful in 20 out of 30 patients with UTI."( Pharmacokinetic and clinical studies with carfecillin.
Arr, M; Benesch, L; Graber, H; Magyar, T, 1978
)
1.24

Toxicity

ExcerptReferenceRelevance
"2-1590) mg/kg for oral and intraperitoneal administration respectively allowed the authors to consider the antibiotic as a low toxic substance under conditions of a single administration."( [Acute toxicity and the cumulative properties of carfecillin].
Berezina, EK; LidovskiÄ­, MZ; Zel'tser, IZ, 1978
)
0.51

Pharmacokinetics

ExcerptReferenceRelevance
"Following a review of the latest methods of treating infections of the urinary ways, the pharmacokinetic and clinical results of a new antibiotic, Carfecillin, are reported."( [Pharmacokinetic and clinical research of a new phenyl ester of carbecinillin: carfecillin].
Bosio, G; Bramato, C; Sachelariu, N; Salassa, B; Sattinger, M; Soranzo, ML, 1979
)
0.69

Bioavailability

ExcerptReferenceRelevance
" Unlike carbenicillin, carfecillin is well absorbed in mice after oral administration, producing significant carbenicillin blood concentrations and the compound is as effective by the oral route in the treatment of various experimental mouse infections as is parenteral carbenicillin."( Carfecillin: antibacterial activity in vitro and in vivo.
Basker, MJ; Comber, KR; Sutherland, R; Valler, GH, 1977
)
2.01
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
penicillinAny member of the group of substituted penams containing two methyl substituents at position 2, a carboxylate substituent at position 3 and a carboxamido group at position 6.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID476929Human intestinal absorption in po dosed human2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Neural computational prediction of oral drug absorption based on CODES 2D descriptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-199020 (90.91)18.7374
1990's1 (4.55)18.2507
2000's0 (0.00)29.6817
2010's1 (4.55)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.26

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index24.26 (24.57)
Research Supply Index3.22 (2.92)
Research Growth Index4.15 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (9.09%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]