Page last updated: 2024-12-06

amdinocillin

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Description

Amdinocillin: An amidinopenicillanic acid derivative with broad spectrum antibacterial action. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

mecillinam : A penicillin in which the 6beta substituent is [(azepan-1-yl)methylidene]amino; an extended-spectrum penicillin antibiotic that binds specifically to penicillin binding protein 2 (PBP2), and is only considered to be active against Gram-negative bacteria. [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 CID36273
CHEMBL ID258646
CHEMBL ID530
CHEBI ID51208
SCHEMBL ID34387
SCHEMBL ID34388
MeSH IDM0000876

Synonyms (86)

Synonym
mecillinamum
CHEBI:51208 ,
mecilinamo
6beta-{[(azepan-1-yl)methylidene]amino}-2,2-dimethylpenam-3alpha-carboxylic acid
amdinocillin
(2s,5r,6r)-6-{[(1e)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
32887-01-7
amdinocillin (usan)
D02888
coactin (tn)
mecillinam (inn)
MLS001424041
MLS000759478
mecillinam
smr000466361
penicillin hx
DB01163
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, (2s-(2alpha,5alpha,6beta))-
(2s,5r,6r)-6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
selexidin
6-((hexahydro-1h-azepin-1-yl)methyleneamino)penicillanic acid
amdinocillin [usan]
fl 1060
ro 109070
mecilinamo [inn-spanish]
mecillinamum [inn-latin]
einecs 251-277-1
hexacillin
fl-1060
ro 10-9070
coactin
(2s,5r,6r)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
HMS2051E14
micillinam
CHEMBL258646
(2s,5r,6r)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
ro-10-9070
CHEMBL530
NCGC00188988-01
dtxcid202584
tox21_112209
dtxsid3022584 ,
cas-32887-01-7
CCG-100873
unii-v10579p3qz
v10579p3qz ,
mecillinam [inn]
amdinocillin [usan:usp]
S6584
BRD-K41051431-001-01-6
(2s,5r,6r)-6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid.
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, (2s-(2.alpha.,5.alpha.,6.beta.)0-
mecillinam [mart.]
amdinocillin [orange book]
mecillinam [jan]
mecillinam [who-dd]
selecidin
amdinocillin [mi]
AB01209740-01
AKOS022185296
NC00123
SCHEMBL34387
SCHEMBL34388
NCGC00164583-02
tox21_112209_1
79580-20-4
AC-32602
6beta-[(azepan-1-ylmethylidene)amino]-2,2-dimethylpenam-3alpha-carboxylic acid
C21545
mecillinam, vetranal(tm), analytical standard
mfcd00056869
(2s,5r,6r)-6-((e)-azepan-1-ylmethyleneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
gtpl12813
(2s,5r,6r)-6-(((e)-azepan-1-ylmethylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Q13019044
FS-4354
CS-0017618
HY-A0269
mecillinam;coactin;fl 1060
AKOS040744826
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, (2s-(2alpha,5alpha,6beta)0-
6beta-(((azepan-1-yl)methylidene)amino)-2,2-dimethylpenam-3alpha-carboxylic acid
j01ca11
mecilinam
(2s,5r,6r)-6-((azepan-1-ylmethylidene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
mecillinam (mart.)

Research Excerpts

Overview

Amminocillin is a beta-amidino penicillanic acid derivative that binds specifically to penicillin-binding protein 2. Amdinocillin has bactericidal activity against a broad spectrum of gram-negative bacteria.

ExcerptReferenceRelevance
"Amdinocillin (mecillinam) is a β-lactam antibiotic that is used mainly for the treatment of uncomplicated urinary tract infections. "( Amdinocillin (Mecillinam) resistance mutations in clinical isolates and laboratory-selected mutants of Escherichia coli.
Andersson, DI; Sundqvist, M; Thulin, E, 2015
)
3.3
"Amdinocillin is a beta-amidino penicillanic acid derivative that binds specifically to penicillin-binding protein 2."( Penicillin-binding proteins and role of amdinocillin in causing bacterial cell death.
Neu, HC, 1983
)
1.25
"Amdinocillin is a semisynthetic derivative of 6-beta-amidinopenicillanic acid, which has bactericidal activity against a broad spectrum of gram-negative bacteria. "( Systemic infections treated with amdinocillin in combination with other beta-lactam antibiotics.
Beam, TR; King, JW; Neu, HC; Smith, LG, 1983
)
1.99
"Amdinocillin is a novel penicillin whose antibacterial activity is derived from its ability to bind specifically and avidly to Penicillin Binding Protein-2 (PBP 2). "( Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use.
Neu, HC,
)
3.02

Effects

Amminocillin has a plasma half-life of about one hour in patients with grossly normal renal function. Amdinocillin was previously shown to be synergistic with other beta-lactam antibiotics against many gram-negative bacteria.

ExcerptReferenceRelevance
"Amdinocillin has a plasma half-life of about one hour in patients with grossly normal renal function."( Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use.
Neu, HC,
)
2.3
"Amdinocillin has been shown to have broad coverage in vitro against many strains of Enterobacteriaceae. "( Amdinocillin therapy of experimental animal infections.
Gordin, FM; Sande, MA, 1983
)
3.15
"Amdinocillin has previously been shown to be synergistic with other beta-lactam antibiotics against many gram-negative bacteria. "( Combination amdinocillin and cefoxitin therapy of multiply-resistant Serratia marcescens urinary tract infections.
Amon, MB; Krause, LK; Ward, TT, 1983
)
2.09
"Amdinocillin has a plasma half-life of about one hour in patients with grossly normal renal function."( Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use.
Neu, HC,
)
2.3

Toxicity

ExcerptReferenceRelevance
" Amdinocillin/penicillin proved to be a safe and effective alternative to gentamicin/penicillin; no adverse reactions were noted nor did the regimen adversely affect renal or hepatic function."( Efficacy, pharmacology, and safety of amdinocillin in treatment of neonates.
de Louvois, J; Mulhall, A, 1983
)
1.45

Pharmacokinetics

The pharmacokinetic disposition of amdinocillin and cephalothin was determined, when administered alone or in combination to healthy volunteers. The penetration of am dinocillin into human cerebrospinal fluid was also studied.

ExcerptReferenceRelevance
" In this thesis pharmacodynamic parameters have been studied after brief exposure of gram-positive bacteria to daptomycin, imipenem or vancomycin and after short exposure of gram-negative bacteria to amikacin, ampicillin, aztreonam, cefepime, cefotaxime, ceftazidime, ceftriaxone, cefuroxime, imipenem, mecillinam, or piperacillin."( Pharmacodynamic effects of antibiotics. Studies on bacterial morphology, initial killing, postantibiotic effect and effective regrowth time.
Hanberger, H, 1992
)
0.28
" In late pregnancy (39-40 weeks of gestation) the plasma mean peak concentration (Cmax = (29 +/- 14 micrograms ml-1) after parenteral administration of 200 mg mecillinam was slightly lower and the volume of distribution (V = 65 +/- 29."( The pharmacokinetics of mecillinam and pivmecillinam in pregnant and non-pregnant women.
Erkkola, R; Heikkilä, A; Iisalo, E; Pyykkö, K, 1992
)
0.28
" The pharmacokinetic parameters were obtained using an open, two-compartment model."( Pharmacokinetics of mecillinam after a single intravenous dose in patients with impaired renal function.
Moukhtar, I; Nawishy, S; Sabbour, M, 1987
)
0.27
" It was noted that in subjects with creatinine clearances of greater than 50 ml/min, the elimination half-life remained relatively constant; however, as the creatinine clearance decreased from 50 to 5 ml/min, there was a progressive rise in the elimination half-life."( Pharmacokinetics of intravenous amdinocillin in healthy subjects and patients with renal insufficiency.
Bornemann, LD; Brocks, VM; Fang, LS; Patel, IH; Rubin, RH; Tolkoff-Rubin, NE, 1985
)
0.55
" The purpose of this study was to determine the pharmacokinetic disposition of this antibiotic."( Pharmacokinetics of mecillinam in health subjects.
Barriere, SL; Conte, JE; Gambertoglio, JG; Lin, ET, 1980
)
0.26
" Mean peak plasma concentrations were approximately 50 micrograms/ml, and the plasma half-life was approximately 53 min."( Multiple-dose pharmacokinetics of amdinocillin in healthy volunteers.
Barriere, SL; Conte, JE; Gambertoglio, JG; Lin, ET, 1982
)
0.54
" The pharmacokinetic disposition of amdinocillin and cephalothin was determined, when administered alone or in combination to healthy volunteers, as well as the penetration of amdinocillin into human cerebrospinal fluid."( Amdinocillin pharmacokinetics. Simultaneous administration with cephalothin and cerebrospinal fluid penetration.
Barriere, SL; Conte, JE; Gambertoglio, JG; Lin, ET, 1983
)
1.98
"The pharmacokinetic parameters of amdinocillin and pivamdinocillin were studied in 12 normal volunteers."( Pharmacokinetics of amdinocillin and pivamdinocillin in normal volunteers.
Christenson, JG; Francke, EL; Neu, HC; Ortiz-Neu, C; Srinivasan, S, 1983
)
0.87
" 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
" Both methods were applied to a pharmacokinetic study of pivmecillinam and mecillinam after oral administration of 400 mg pivmecillinam hydrochloride tablets in healthy Chinese subjects."( LC-MS/MS methods for determination of unstable pivmecillinam and mecillinam in acidified human plasma: Application to a pharmacokinetic study.
Ding, L; Gao, HY; Qian, XP; Sun, LN; Sun, SY; Wang, Y; Wang, YQ; Yang, YL; Zhao, Y, 2022
)
0.72

Compound-Compound Interactions

Amdinocillin alone and in combination with other beta-lactam antibiotics was tested for in vitro activity against aminoglycoside-susceptible and resistant gram-negative bacteria. The findings indicate that antibiotic disks used routinely in the clinical laboratory can be used in a simple elution test to determine susceptibility of organisms.

ExcerptReferenceRelevance
" The combination of ampicillin or cefazolin with mecillinam leads to bactericidal acceleration; the effects are comparable to those of the combination with gentamycin."( [Effects of ampicillin and cefazolin combined with mecillinam (author's transl)].
Bischof-Léger, E; Helm, EB; Stille, W, 1978
)
0.26
"The synergic in-vitro post-antibiotic effect (PAE) of mecillinam, in combination with either ampicillin, aztreonam, ceftazidime or piperacillin, on a reference strain of Escherichia coli was evaluated by bioluminescence assay of bacterial ATP."( Synergic post-antibiotic effect of mecillinam, in combination with other beta-lactam antibiotics in relation to morphology and initial killing.
Hanberger, H; Maller, R; Nilsson, LE; Svensson, E, 1991
)
0.28
"The antibacterial activity of ampicillin against Enterobacteriaceae strongly increased when combined with 6 beta-bromopenicillanic acid (BPA) or clavulanic acid (CA)."( In vitro activity of ampicillin alone and in combination with different concentrations of 6 beta-bromopenicillanic acid, clavulanic acid and mecillinam.
Houben, AW; Stobberingh, EE; van Boven, CP, 1987
)
0.27
"Amdinocillin alone and in combination with other beta-lactam antibiotics was tested for in vitro activity against aminoglycoside-susceptible and resistant gram-negative bacteria."( In vitro activity of amdinocillin in combination with other beta-lactam antibiotics against aminoglycoside-susceptible and resistant gram-negative bacteria.
Gibson, G; Nachamkin, I; Samel, C; Sawyer, K; Skalina, D, 1988
)
2.04
" The findings indicate that antibiotic disks used routinely in the clinical laboratory can be used in a simple elution test to determine susceptibility of organisms to beta-lactam antibiotics alone and in combination with amdinocillin."( Collaborative clinical laboratory study of a broth-disk test for determination of bacterial susceptibility to beta-lactams in combination with amdinocillin.
Barry, AL; Beskid, G; Cleeland, R; Fallat, V; Isenberg, HD; Murray, PR; Pierson, C; Squires, E; Tilton, RC, 1987
)
0.66
"The beta-lactamase inhibitors clavulanic acid and sulbactam were combined with mecillinam."( Synergistic activity of mecillinam in combination with the beta-lactamase inhibitors clavulanic acid and sulbactam.
Neu, HC, 1982
)
0.26
" Although amdinocillin, alone or in combination with cefoxitin, appeared effective as second-line therapy in infections with organisms shown sensitive in vitro, the combination of amdinocillin and ticarcillin or carbenicillin was only moderately effective in initial therapy for neutropenic, febrile, cancer patients."( Amdinocillin: use alone or in combination with cefoxitin or carbenicillin-ticarcillin.
Bodey, GP; Estey, EH; Lawson, RD, 1983
)
2.11
"Scanning electron microscopy was used to study the morphologic effects of amdinocillin (mecillinam) when combined with several beta-lactam antibiotics in vitro (Escherichia coli, three isolates; Klebsiella pneumoniae, one isolate) and also in vivo (E."( Morphologic changes produced by amdinocillin alone and in combination with beta-lactam antibiotics: in vitro and in vivo.
Cleeland, R; Kramer, MJ; Mauriz, YR; Robertson, TL; Timmes, MD, 1983
)
0.78
" We report the results of a multicenter study evaluating the safety and efficacy of amdinocillin in combination with other beta-lactam antibiotics in the treatment of 120 serious gram-negative bacterial infections."( Systemic infections treated with amdinocillin in combination with other beta-lactam antibiotics.
Beam, TR; King, JW; Neu, HC; Smith, LG, 1983
)
0.77
"Amdinocillin in combination with another beta-lactam antibiotic (ampicillin, cephalothin, cefamandole or cefoxitin) was used to treat 25 patients with pyelonephritis (with or without bacteremia), pneumonia, bacteremia secondary to intravenous devices, and urinary tract infections (with catheter in place) due to gram-negative organisms."( Amdinocillin in combination with beta-lactam antibiotics for treatment of serious gram-negative infections.
Farrar, WE; Rotstein, C, 1983
)
3.15
"The phosphonopeptide alafosfalin (L-alanyl-L-1-aminoethylphosphonic acid) exhibited synergy in vitro and in animal studies against a range of bacterial genera when combined with cephalexin."( Antibacterial properties of alafosfalin combined with cephalexin.
Atherton, FR; Hall, MJ; Hassall, CH; Holmes, SW; Lambert, RW; Lloyd, WJ; Nisbet, LJ; Ringrose, PS; Westmacott, D, 1981
)
0.26

Bioavailability

ExcerptReferenceRelevance
"The bioavailability of amdinocillin was not altered when amdinocillin pivoxil was ingested 1 h before a standard breakfast, and it increased by 20% when amdinocillin pivoxil was ingested with or 1 h after a standard breakfast."( Influence of food on bioavailability of amdinocillin pivoxil.
Bornemann, LD; Castellano, S; Enthoven, D; Lin, AH; Patel, IH, 1988
)
0.85
" Bioavailability was 45 percent after the 250 mg dose and 38 percent after the 500 mg dose."( Pharmacokinetics of amdinocillin and pivamdinocillin in normal volunteers.
Christenson, JG; Francke, EL; Neu, HC; Ortiz-Neu, C; Srinivasan, S, 1983
)
0.59
" These "in combo" PAMPA data were used to predict the human absolute bioavailability of the ampholytes."( The permeation of amphoteric drugs through artificial membranes--an in combo absorption model based on paracellular and transmembrane permeability.
Avdeef, A; Sun, N; Tam, KY; Tsinman, O, 2010
)
0.36
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

The dosage of pivamdinocillin in adults was 400 to 800 mg, every 6 hours, for 10 to 16 days; dosage in children was half this amount for 11 to 15 days. Although the clearance from plasma and the half-life of amdinOCillin were altered up to fourfold in patients with creatinine clearances of less than 15 ml/min, the amdinocisin dosage per se may not need to be reduced for these patients.

ExcerptRelevanceReference
" Dosage reductions of these drugs may be appropriate in certain situations."( Therapeutic considerations in using combinations of newer beta-lactam antibiotics.
Barriere, SL, 1986
)
0.27
" Although the clearance from plasma and the half-life of amdinocillin were altered up to fourfold in patients with creatinine clearances of less than 15 ml/min, the amdinocillin dosage per se may not need to be reduced for these patients if the frequency of dosing is reduced from six to three or four times daily."( Pharmacokinetics of intravenous amdinocillin in healthy subjects and patients with renal insufficiency.
Bornemann, LD; Brocks, VM; Fang, LS; Patel, IH; Rubin, RH; Tolkoff-Rubin, NE, 1985
)
0.8
" Based on the relationship between creatinine clearance and plasma clearance of mecillinam, and considering that the drug is a relatively non-toxic bactericidal antibiotic, the following dosage adjustment scheme is proposed: glomerular filtration rate over 30 ml/min: normal dosage; 10-30 ml/min: 50% of normal dosage; under 10 ml/min: 25% of normal dosage."( Single-dose kinetics and dosage of mecillinam in renal failure and haemodialysis.
Schapira, A,
)
0.13
" The dosage of pivamdinocillin in adults was 400 to 800 mg, every 6 hours, for 10 to 16 days; dosage in children was half this amount for 11 to 15 days."( Management of enteric fever with amdinocillin.
Ball, AP; Geddes, AM, 1983
)
0.88
"In a multi-centre study in general practice, 292 female patients with acute urinary tract infection received a 5-day course of pivmecillinam at a dosage of either 200 mg or 400 mg twice-daily."( A general practice evaluation of pivmecillinam given twice daily as a treatment for acute urinary tract infection.
Sheldon, MG; Skinner, JL; Venables, TL, 1984
)
0.27
" coli, with emphasis on optimal dosing and combination therapy with β-lactamase inhibitors, are warranted."( High rate of per oral mecillinam treatment failure in community-acquired urinary tract infections caused by ESBL-producing Escherichia coli.
Jenum, PA; Jørgensen, SB; Liestøl, K; Sundsfjord, A; Søraas, A, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antibacterial drugA drug used to treat or prevent bacterial infections.
antiinfective agentA substance used in the prophylaxis or therapy of infectious diseases.
[role 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]

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]

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency33.49150.006038.004119,952.5996AID1159521
AR proteinHomo sapiens (human)Potency24.34140.000221.22318,912.5098AID743040; AID743054
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency22.16390.000214.376460.0339AID720691; AID720719
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency11.88320.001723.839378.1014AID743083
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (74)

Assay IDTitleYearJournalArticle
AID93996Minimum inhibitory concentration against Klebsiella aerogenes X5L (inoculum, 10e4 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID660265Antimicrobial activity against wild type Escherichia coli expressing AcrAB-TolC efflux pump2012European journal of medicinal chemistry, Jun, Volume: 52Computational analysis of structure-based interactions and ligand properties can predict efflux effects on antibiotics.
AID63907Minimum inhibitory concentration against Enterobacter cloacae A13 (inoculum, 10e5 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID197866Minimum inhibitory concentration against Staphylococcus aureus A4 (inoculum, 10e5 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID64224Minimum inhibitory concentration against Escherichia coli DC2 (inoculum, 10e4 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID198158Minimum inhibitory concentration against Serratia marcescens A16 (inoculum, 10e5 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID64247Minimum inhibitory concentration against Escherichia coli TEM X3 (inoculum, 10e5 cfu per spot)(TEM I type lactamase producer)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID151382Minimum inhibitory concentration against Proteus vulgaris Pv9 (inoculum, 10e5 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
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.
AID64225Minimum inhibitory concentration against Escherichia coli DCO (inoculum, 10e4 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID660261Ratio of MIC for wild type Escherichia coli JC7623 to MIC for acrAB-deficient Escherichia coli JZM1202012European journal of medicinal chemistry, Jun, Volume: 52Computational analysis of structure-based interactions and ligand properties can predict efflux effects on antibiotics.
AID70152Minimum inhibitory concentration against 30 strains of Escherichia coli1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Synthesis and beta-lactamase inhibitory properties of 2 beta-[(1,2,3-triazol-1-yl)methyl]-2 alpha-methylpenam-3 alpha-carboxylic acid 1,1-dioxide and related triazolyl derivatives.
AID519740Antibacterial activity against Escherichia coli DH5alpha expressing Klebsiella pneumoniae beta-lactamase SHV-72 by agar dilution method2008Antimicrobial agents and chemotherapy, May, Volume: 52, Issue:5
The Lys234Arg substitution in the enzyme SHV-72 is a determinant for resistance to clavulanic acid inhibition.
AID93999Minimum inhibitory concentration against Klebsiella pneumoniae A24 (inoculum, 10e5 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID151370Minimum inhibitory concentration against Proteus mirabilis A18 (inoculum, 10e5 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID198311Minimum inhibitory concentration against Streptococcus pyogenes (inoculum, 10e5 cfu per spot) A11991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID63910Minimum inhibitory concentration against Enterobacter cloacae P99 (inoculum, 10e4 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
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.
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.
AID150913Minimum inhibitory concentration against Pseudomonas aeruginosa A21 (inoculum, 10e5 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID519734Antibacterial activity against Escherichia coli DH5alpha with deltaampC by agar dilution method2008Antimicrobial agents and chemotherapy, May, Volume: 52, Issue:5
The Lys234Arg substitution in the enzyme SHV-72 is a determinant for resistance to clavulanic acid inhibition.
AID70153Minimum inhibitory concentration against 30 strains of Escherichia coli1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Synthesis and beta-lactamase inhibitory properties of 2 beta-[(1,2,3-triazol-1-yl)methyl]-2 alpha-methylpenam-3 alpha-carboxylic acid 1,1-dioxide and related triazolyl derivatives.
AID64042Minimum inhibitory concentration against Enterobacter cloacae P99 (inoculum, 10e4 cfu per spot)(type I lactamase producer)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID445445Permeability at pH 6.5 by PAMPA method2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
The permeation of amphoteric drugs through artificial membranes--an in combo absorption model based on paracellular and transmembrane permeability.
AID563598Antimicrobial activity against ESBL producing Escherichia coli assessed as susceptible isolates by Etest2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
Foreign travel is a major risk factor for colonization with Escherichia coli producing CTX-M-type extended-spectrum beta-lactamases: a prospective study with Swedish volunteers.
AID64249Minimum inhibitory concentration against Escherichia coli X4 (inoculum, 10e5 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID64082Minimum inhibitory concentration against Escherichia coli A8 (inoculum, 10e5 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID519743Antibacterial activity against Klebsiella pneumoniae INSRA1229 harboring SHV-72 Ile8Phe, Ala146Val, and Lys234Arg mutations by agar dilution method2008Antimicrobial agents and chemotherapy, May, Volume: 52, Issue:5
The Lys234Arg substitution in the enzyme SHV-72 is a determinant for resistance to clavulanic acid inhibition.
AID519737Antibacterial activity against Escherichia coli DH5alpha expressing Klebsiella pneumoniae beta-lactamase SHV-1 by agar dilution method2008Antimicrobial agents and chemotherapy, May, Volume: 52, Issue:5
The Lys234Arg substitution in the enzyme SHV-72 is a determinant for resistance to clavulanic acid inhibition.
AID93997Minimum inhibitory concentration against Klebsiella aerogenes X6 (inoculum, 10e4 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID445446Oral bioavailability in human2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
The permeation of amphoteric drugs through artificial membranes--an in combo absorption model based on paracellular and transmembrane permeability.
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.
AID197871Minimum inhibitory concentration against Staphylococcus aureus A6 (inoculum, 10e5 cfu per spot)1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and beta-lactamase stability on the pKa of the C-7 heterocycle.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347424RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347425Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347407qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID322319Antibacterial activity against Escherichia coli DH5 alpha isolates by agar dilution method2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Spread of extended-spectrum beta-lactamase CTX-M-producing escherichia coli clinical isolates in community and nosocomial environments in Portugal.
AID322325Antibacterial activity against Escherichia coli DH5 alpha-URA5924 isolates expressing CTX-M-32 by agar dilution method2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Spread of extended-spectrum beta-lactamase CTX-M-producing escherichia coli clinical isolates in community and nosocomial environments in Portugal.
AID322324Antibacterial activity against Escherichia coli INSRA5924 isolates expressing CTX-M-32 and TEM-1B enzymes by agar dilution method2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Spread of extended-spectrum beta-lactamase CTX-M-producing escherichia coli clinical isolates in community and nosocomial environments in Portugal.
AID322323Antibacterial activity against Escherichia coli DH5 alpha-URA5905 isolates expressing CTX-M-15 and TEM-1B enzymes by agar dilution method2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Spread of extended-spectrum beta-lactamase CTX-M-producing escherichia coli clinical isolates in community and nosocomial environments in Portugal.
AID322322Antibacterial activity against Escherichia coli INSRA5905 isolates expressing CTX-M-15 and TEM-1B enzymes by agar dilution method2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Spread of extended-spectrum beta-lactamase CTX-M-producing escherichia coli clinical isolates in community and nosocomial environments in Portugal.
AID322320Antibacterial activity against Escherichia coli INSRA5776 isolates expressing CTX-M-14 and TEM-1B enzymes by agar dilution method2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Spread of extended-spectrum beta-lactamase CTX-M-producing escherichia coli clinical isolates in community and nosocomial environments in Portugal.
AID322321Antibacterial activity against Escherichia coli DH5 alpha-URA5776 isolates expressing CTX-M-14 enzyme by agar dilution method2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Spread of extended-spectrum beta-lactamase CTX-M-producing escherichia coli clinical isolates in community and nosocomial environments in Portugal.
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 (419)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990257 (61.34)18.7374
1990's45 (10.74)18.2507
2000's45 (10.74)29.6817
2010's49 (11.69)24.3611
2020's23 (5.49)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 26.65

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 Index26.65 (24.57)
Research Supply Index6.20 (2.92)
Research Growth Index4.50 (4.65)
Search Engine Demand Index36.71 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (26.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials54 (12.30%)5.53%
Reviews12 (2.73%)6.00%
Case Studies2 (0.46%)4.05%
Observational0 (0.00%)0.25%
Other371 (84.51%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Ibuprofen Versus Mecillinam for Uncomplicated Cystitis in Adult, Non-pregnant Women [NCT01849926]Phase 4383 participants (Actual)Interventional2013-04-30Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]