Page last updated: 2024-11-08

thienamycin

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

Description

thienamycin: beta-lactam antibiotic; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID441128
CHEMBL ID278773
CHEBI ID9542
MeSH IDM0064884

Synonyms (34)

Synonym
1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-aminoethyl)thio)-6-(1-hydroxyethyl)-7-oxo-, (5r-(5-alpha,6-alpha(r*)))-
59995-64-1
thienamycin
C06664
chebi:9542 ,
CHEMBL278773
(5r,6s)-3-(2-aminoethylsulfanyl)-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
A832563
thienpenem
unii-wmw5i5964p
wmw5i5964p ,
5-22-07-00446 (beilstein handbook reference)
1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-aminoethyl)thio)-6-((1r)-1-hydroxyethyl)-7-oxo-, (5r,6s)-rel-
unii-ewr2gdb37h
1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-aminoethyl)thio)-6-(1-hydroxyethyl)-7-oxo-, (5alpha,6alpha(r*))-
thienamycin, (+/-)-
65750-57-4
(+/-)-thienamycin
ewr2gdb37h ,
imipenem monohydrate impurity a [ep impurity]
1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-aminoethyl)thio)-6-((1r)-1-hydroxyethyl)-7-oxo-, (5r,6s)-
1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-aminoethyl)thio)-6-(1-hydroxyethyl)-7-oxo-, (5r-(5.alpha.,6.alpha.(r*)))-
thienamycin [mi]
(+)-thienamycin
(5r,6s)-3-((2-aminoethyl)sulfanyl)-6-((r)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene- 2-carboxylic acid
1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-aminoethyl)thio)-6-(1-hydroxyethyl)-7-oxo-, (5.alpha.,6.alpha.(r*))-
WKDDRNSBRWANNC-ATRFCDNQSA-N
Q3524791
(5r,6s)-3-(2-aminoethylthio)-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
DTXSID10975412
imipenem impurity a
thienamycin (>80%)
(5r,6s)-3-[(2-aminoethyl)sulfanyl]-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
(5r,6s)-3-[(2-aminoethyl)thio]-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;[5r-[5alpha,6alpha(r*)]]-3-[(2-aminoethyl)thio]-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Research Excerpts

Overview

Thienamycin was shown to be a more potent inhibitor than ampicillin of the enzyme peptidoglycan transpeptidase.

ExcerptReferenceRelevance
"Thienamycin was shown to be a more potent inhibitor than ampicillin of the enzyme peptidoglycan transpeptidase from Escherichia coli."( Inhibition of transpeptidase activity in Escherichia coli by thienamycin.
Brammer, KW; Jevons, S; Moore, BA, 1979
)
1.94

Dosage Studied

ExcerptRelevanceReference
" When administering combinations of antibiotics non-simultaneous dosing is superior to simultaneous administration."( [The kinetics of bacterial killing by fluctuating concentrations of antibiotics].
Allerberger, F; Bonatti, H; Dierich, MP; Guggenbichler, JP; Semenitz, E, 1989
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
carbapenemsThe class of beta-lactam antibiotics that whose members have a carbapenem skeleton which is variously substituted at positions 3, 4, and 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 (31)

Assay IDTitleYearJournalArticle
AID1124641Antibacterial activity against penicillin-resistant Pseudomonas aeruginosa MB3350 at 25 ug/disk1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
N-Acetimidoyl- and N-formimidoylthienamycin derivatives: antipseudomonal beta-lactam antibiotics.
AID66399Antibiotic activity was determined against Enterobacter species (6)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationships in the 2-arylcarbapenem series: synthesis of 1-methyl-2-arylcarbapenems.
AID64043In vitro minimal inhibitory concentration (MIC) in brain-heart infusion broth in the presence of hog liver esterase(1:1.5) in Escherichia coli 2661990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.
AID1124634Antibacterial activity against penicillin-sensitive Staphylococcus aureus MB2985 at 25 ug/disk1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
N-Acetimidoyl- and N-formimidoylthienamycin derivatives: antipseudomonal beta-lactam antibiotics.
AID103831In vitro minimal inhibitory concentration (MIC) in brain-heart infusion broth in the presence of hog liver esterase(1:1.5) in Morganella morganii 0011990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.
AID64044In vitro minimal inhibitory concentration (MIC) in brain-heart infusion broth in the presence of hog liver esterase(1:1.5) in Escherichia coli 1291990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.
AID203332Antibiotic activity was determined against Serratia species (2)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationships in the 2-arylcarbapenem series: synthesis of 1-methyl-2-arylcarbapenems.
AID1124640Antibacterial activity against penicillin-sensitive Pseudomonas aeruginosa MB2835 at 25 ug/disk1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
N-Acetimidoyl- and N-formimidoylthienamycin derivatives: antipseudomonal beta-lactam antibiotics.
AID1124635Antibacterial activity against penicillin-resistant Staphylococcus aureus MB2314 at 25 ug/disk1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
N-Acetimidoyl- and N-formimidoylthienamycin derivatives: antipseudomonal beta-lactam antibiotics.
AID1124637Antibacterial activity against penicillin-resistant Escherichia coli MB2964 at 25 ug/disk1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
N-Acetimidoyl- and N-formimidoylthienamycin derivatives: antipseudomonal beta-lactam antibiotics.
AID206717Tested for antibacterial activity against Staphylococcus aureus by disc-diffusion antibacterial assay1981Journal of medicinal chemistry, May, Volume: 24, Issue:5
Preparation and antibacterial activity of delta 1-thienamycin.
AID1124636Antibacterial activity against penicillin-sensitive Escherichia coli MB2482 at 25 ug/disk1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
N-Acetimidoyl- and N-formimidoylthienamycin derivatives: antipseudomonal beta-lactam antibiotics.
AID1124630Stability of the compound in amorphous form assessed as compound remaining after 1 month at 60 mg/ml at 23 degC in presence of 0.1 equiv of NaHCO31979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
N-Acetimidoyl- and N-formimidoylthienamycin derivatives: antipseudomonal beta-lactam antibiotics.
AID56110Susceptibility to mammalian dehydropeptidase DHP-1 relative to thienamycin1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationships in the 2-arylcarbapenem series: synthesis of 1-methyl-2-arylcarbapenems.
AID207488Antibiotic activity was determined against Staphylococcus aureus (5)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationships in the 2-arylcarbapenem series: synthesis of 1-methyl-2-arylcarbapenems.
AID1124639Antibacterial activity against penicillin-resistant Enterobacter cloacae MB2646 at 25 ug/disk1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
N-Acetimidoyl- and N-formimidoylthienamycin derivatives: antipseudomonal beta-lactam antibiotics.
AID209617In vitro minimal inhibitory concentration (MIC) in brain-heart infusion broth in the presence of hog liver esterase(1:1.5) in Streptococcus pyogenes 2031990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.
AID163913Antibiotic activity was determined against Pseudomonas aeruginosa (5)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationships in the 2-arylcarbapenem series: synthesis of 1-methyl-2-arylcarbapenems.
AID163776In vitro minimal inhibitory concentration (MIC) in brain-heart infusion broth in the presence of hog liver esterase(1:1.5) in Pseudomonas aeruginosa 1041990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.
AID66585Antibiotic activity was determined against Enterococcus (3)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationships in the 2-arylcarbapenem series: synthesis of 1-methyl-2-arylcarbapenems.
AID66738In vitro minimal inhibitory concentration (MIC) in brain-heart infusion broth in the presence of hog liver esterase(1:1.5) in Enterococcus cloacae 0091990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.
AID163070Antibiotic activity was determined against Proteus species (5)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationships in the 2-arylcarbapenem series: synthesis of 1-methyl-2-arylcarbapenems.
AID200255In vitro minimal inhibitory concentration (MIC) in brain-heart infusion broth in the presence of hog liver esterase(1:1.5) in Staphylococcus aureus 0051990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.
AID69936Antibiotic activity was determined against Escherichia coli(5)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationships in the 2-arylcarbapenem series: synthesis of 1-methyl-2-arylcarbapenems.
AID1124629Stability of the compound in amorphous form in 1 M PO4 assessed as time at which 90% of initial UV-absorbance remains at 60 mg/ml at pH 7 at 23 degC1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
N-Acetimidoyl- and N-formimidoylthienamycin derivatives: antipseudomonal beta-lactam antibiotics.
AID1124628Stability of the compound in amorphous form in deionized water assessed as time at which 90% of initial UV-absorbance remains at 60 mg/ml at 23 degC1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
N-Acetimidoyl- and N-formimidoylthienamycin derivatives: antipseudomonal beta-lactam antibiotics.
AID79397In vitro minimal inhibitory concentration (MIC) in brain-heart infusion broth in the presence of hog liver esterase(1:1.5) in Haemophilus influenzae 1021990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.
AID94126In vitro minimal inhibitory concentration (MIC) in brain-heart infusion broth in the presence of hog liver esterase(1:1.5) in Klebsiella pneumoniae 0091990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.
AID200256In vitro minimal inhibitory concentration (MIC) in brain-heart infusion broth in the presence of hog liver esterase(1:1.5) in Staphylococcus aureus 4001990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.
AID1124638Antibacterial activity against penicillin-sensitive Enterobacter cloacae MB2647 at 25 ug/disk1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
N-Acetimidoyl- and N-formimidoylthienamycin derivatives: antipseudomonal beta-lactam antibiotics.
AID94382Antibiotic activity was determined against Klebsiella species (5)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationships in the 2-arylcarbapenem series: synthesis of 1-methyl-2-arylcarbapenems.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (66)

TimeframeStudies, This Drug (%)All Drugs %
pre-199043 (65.15)18.7374
1990's6 (9.09)18.2507
2000's6 (9.09)29.6817
2010's10 (15.15)24.3611
2020's1 (1.52)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 37.00

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index37.00 (24.57)
Research Supply Index4.25 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index53.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (37.00)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.47%)5.53%
Reviews3 (4.41%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other64 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]