Page last updated: 2024-11-08

phenethicillin

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

Description

phenethicillin: minor descriptor (85); major descriptor (63-84); on-line search PENICILLIN, PHENOXYMETHYL/AA (66-85); Index Medicus search PHENETHICILLIN (63-84); RN given refers to (2S-(2alpha,5alpha,6beta))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

phenethicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-phenoxypropanamido group. [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]

Cross-References

ID SourceID
PubMed CID272833
CHEMBL ID1614637
CHEBI ID52427
SCHEMBL ID3862
MeSH IDM0263003

Synonyms (84)

Synonym
BRD-A66025870-237-05-1
KBIO1_000234
DIVK1C_000234
(2s,5r,6r)-3,3-dimethyl-7-oxo-6-{[2-(phenyloxy)propanoyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SPECTRUM_000736
PRESTWICK3_000723
PRESTWICK2_000723
BSPBIO_001782
SPECTRUM5_001431
BSPBIO_000646
IDI1_000234
pheneticillin
.alpha.-phenoxyethylpenicillin
phenethicillin
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3-dimethyl-7-oxo-6-[(1-oxo-2-phenoxypropyl)amino]-, [2s-(2.alpha.,5.alpha.,6.beta.)]-
phenoxy pc
1-phenoxyethylpenicillin
147-55-7
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3-dimethyl-7-oxo-6-(2-phenoxypropionamido)-
phenethicilin
nsc-117548
phenoxyethylpenicillin
nsc117548
einecs 205-691-4
nsc 117548
pheneticillinum [inn-latin]
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenoxypropionamido)-
feneticillina [dcit]
pheneticilline [inn-french]
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((1-oxo-2-phenoxypropyl)amino)-, (2s-(2alpha,5alpha,6beta))-
feneticilina [inn-spanish]
phenethicillinum
KBIO2_001216
KBIO2_003784
KBIO3_001282
KBIOGR_000945
KBIO2_006352
KBIOSS_001216
SPECTRUM4_000393
NINDS_000234
SPBIO_001493
PRESTWICK1_000723
SPECTRUM3_000281
SPBIO_002585
PRESTWICK0_000723
SPECTRUM2_001337
BPBIO1_000712
pheneticilline
6beta-(2-phenoxypropanamido)-2,2-dimethylpenam-3alpha-carboxylic acid
feneticilina
penicillin b
CHEBI:52427 ,
(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenoxypropanoyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
pheneticillinum
(2s,5r,6r)-3,3-dimethyl-7-oxo-6-(2-phenoxypropanoylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
D08350
pepc
pheneticillin (inn)
alfacilin
synthepen
feneticillin
CHEMBL1614637
efa30x554h ,
feneticillina
pheneticillin [inn]
unii-efa30x554h
EPITOPE ID:120370
pheneticillin [who-dd]
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((1-oxo-2-phenoxypropyl)amino)-, (2s,5r,6r)-
(2s,5r,6r)-3,3-dimethyl-7-oxo-6-(2-phenoxypropionamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
SCHEMBL3862
CS-4500
HY-B1003
DTXSID6023448
AKOS030526098
SBI-0051572.P002
NONJJLVGHLVQQM-JHXYUMNGSA-N
DB13337
Q7181338
(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[2-(phenoxy)propanoylamino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
gtpl12275
pheneticillin;-phenoxyethylpenicillin
(2s,5r,6r)-3,3-dimethyl-7-oxo-6-(2-phenoxypropanamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
EN300-19768158

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"In this study the antimicrobial effects of phenoxymethylpenicillin (PM) and pheneticillin (PE) in vitro and in an experimental animal infection model were compared as well as the pharmacokinetic properties of both drugs in patients."( Comparative pharmacodynamics and clinical pharmacokinetics of phenoxymethylpenicillin and pheneticillin.
Mattie, H; Overbosch, D; van Furth, R, 1985
)
0.27
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Bioavailability

ExcerptReferenceRelevance
" It is suggested that, if minimal impairment of bioavailability by ingesta is desired, then the penicillins commonly administered by mouth (amoxycillin, ampicillin, penicillin V, phenethicillin, cloxacillin) should be given to dogs that are fasting."( Effect of ingesta on systemic availability of penicillins administered orally in dogs.
Egerton, JR; Emslie, DR; Martin, IC; Watson, AD, 1986
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

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.
penicillin allergenAny penicillin which causes the onset of an allergic reaction.
[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]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)10.00000.11007.190310.0000AID1449628
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID409959Inhibition of bovine liver MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID540211Fraction unbound in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID409957Inhibition of bovine liver MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID781325pKa (acid-base dissociation constant) as determined by Liao ref: J Chem Info Model 20092014Pharmaceutical research, Apr, Volume: 31, Issue:4
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (132)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990116 (87.88)18.7374
1990's4 (3.03)18.2507
2000's7 (5.30)29.6817
2010's4 (3.03)24.3611
2020's1 (0.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (3.45%)5.53%
Reviews7 (4.83%)6.00%
Case Studies5 (3.45%)4.05%
Observational0 (0.00%)0.25%
Other128 (88.28%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]