Page last updated: 2024-11-06

flomoxef

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Description

Flomoxef, a synthetic, broad-spectrum cephalosporin antibiotic, was developed in the 1980s as a potential treatment for a wide range of bacterial infections. It is characterized by its unique chemical structure, which incorporates a 7-methoxy group and a 3-methylthiomethyl group, leading to its enhanced antibacterial activity. Flomoxef exhibits a wide spectrum of activity against gram-positive and gram-negative bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). It is particularly effective against anaerobic bacteria, which are often implicated in serious infections. The compound's mechanism of action involves inhibition of bacterial cell wall synthesis, leading to bacterial cell lysis and death. Flomoxef's effectiveness against a broad spectrum of bacteria and its ability to penetrate tissues make it a promising candidate for treating various infections, including pneumonia, skin infections, and urinary tract infections. Research on flomoxef has focused on understanding its pharmacokinetic properties, efficacy in treating infections, and potential for resistance development. Despite its initial promise, flomoxef has not been widely adopted in clinical practice due to factors such as the emergence of antibiotic resistance and the development of newer cephalosporin derivatives with broader activity and improved safety profiles. However, ongoing research continues to explore potential applications of flomoxef in specific clinical settings.'

flomoxef: structure given in first source; RN given refers to sodium salt [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

flomoxef : A second-generation oxacephem antibiotic in which the oxazine ring is substituted at C-3 with a hydroxyethyl-substituted tetrazolylthiomethyl group and the azetidinone ring carries 7alpha-methoxy and 7beta-{2-[(difluoromethyl)thiomethyl]acetamido} substituents. [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 CID65864
CHEMBL ID15413
CHEBI ID135813
SCHEMBL ID49438
MeSH IDM0132758

Synonyms (40)

Synonym
AC-15832
6315-s
flomoxef sodium
flomoxef
fmox
flomoxef [inn]
flomoxefum
(6r,7r)-7-{2-[(difluoromethyl)sulfanyl]acetamido}-3-({[1-(2-hydroxyethyl)-1h-tetrazol-5-yl]sulfanyl}methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CHEBI:135813
(6r,7r)-7-[[2-(difluoromethylsulfanyl)acetyl]amino]-3-[[1-(2-hydroxyethyl)tetrazol-5-yl]sulfanylmethyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CHEMBL15413
D07963
flomoxef (inn)
99665-00-6
(6r,7r)-7-[[2-(difluoromethylthio)-1-oxoethyl]amino]-3-[[[1-(2-hydroxyethyl)-5-tetrazolyl]thio]methyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
A846063
(6r,7r)-7-[2-[bis(fluoranyl)methylsulfanyl]ethanoylamino]-3-[[1-(2-hydroxyethyl)-1,2,3,4-tetrazol-5-yl]sulfanylmethyl]-7-methoxy-8-oxidanylidene-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
NCGC00182999-01
v9e5u5xf42 ,
flomoxefo [spanish]
(-)-(6r,7r)-7-(2-((difluoromethyl)thio)acetamido)-3-(((1-(2-hydroxyethyl)-1h-tetrazol-5-yl)thio)methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
unii-v9e5u5xf42
flomoxefum [latin]
dtxsid5048845 ,
flomoxefo
AKOS015896442
flomoxef [mi]
flomoxef [who-dd]
SCHEMBL49438
5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[[(difluoromethyl)thio]acetyl]amino]-3-[[[1-(2-hydroxyethyl)-1h-tetrazol-5-yl]thio]methyl]-7-methoxy-8-oxo-, (6r-cis)-
DB11935
(7r)-7-(2-(difluoromethylthio)acetamido)-3-((1-(2-hydroxyethyl)-1h-tetrazol-5-ylthio)methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
BCP20920
Q5459999
(6r,7r)-7-{2-[(difluoromethyl)sulfanyl]acetamido}-3-({[1-(2-hydroxyethyl)-1h-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
gtpl12251
HY-B0706
CS-0009596
5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[[(difluoromethyl)thio]acetyl]amino]-3-[[[1-(2-hydroxyethyl)-1h-tetrazol-5-yl]thio]methyl]-7-methoxy-8-oxo-, (6r,7r)-
uhrbtbzowwgkmk-domzbbrysa-n

Research Excerpts

Overview

Flomoxef (6315-S) is a new oxacephem antibiotic which differs from latamoxef because it has [1-(2-hydroxethyl)-1H-tetrazol-5-yl] thiomethyl (HTT) as a side chain at the 3'-position of cephem group instead of NMTT. It is an antibiotic with strong antibacterial activity against staphylococci including methicillin-resistant strains and streptococci.

ExcerptReferenceRelevance
"Flomoxef is an off-patent oxacephem β-lactam with stability against non-AmpC ESBLs, with potential for utility in these settings."( Flomoxef for neonates: extending options for treatment of neonatal sepsis caused by ESBL-producing Enterobacterales.
Darlow, CA; Hope, W, 2022
)
2.89
"Flomoxef is an oxacephem and has a potent and broad bactericidal spectrum against aerobes and anaerobes."( A comprehensive multi-institutional study of empiric therapy with flomoxef in surgical infections of the digestive organs. The Kyushu Research Group for Surgical Infection.
Shimada, M; Sugimachi, K; Takenaka, K, 1994
)
1.25
"Flomoxef (6315-S) is a new oxacephem antibiotic which differs from latamoxef because it has [1-(2-hydroxethyl)-1H-tetrazol-5-yl] thiomethyl (HTT) as a side chain at the 3'-position of cephem group instead of NMTT and an extensive modification of 7 beta-acylamino side chain."( Flomoxef, a new oxacephem antibiotic, does not cause hemostatic defects.
Brancaccio, V; Cazzola, M; De Giglio, C; Matera, MG; Paternò, E; Rossi, F, 1993
)
2.45
"Flomoxef is a fourth generation cephem which has the same activity against gram-negative bacteria as the third generation cephems, but is also active against gram-positive organisms, especially most methicillin resistant Staphylococcus aureus (MRSA). "( The meaning of the development of flomoxef and clinical experience in Japan.
Ishigami, T; Ito, M, 1991
)
2
"Flomoxef is an antibiotic with strong antibacterial activity against staphylococci including methicillin-resistant strains and streptococci with the exception of Enterococcus faecalis and Enterococcus faecium."( The in vitro activity of flomoxef compared to four other cephalosporins and imipenem.
Knothe, H; Shah, PM, 1991
)
1.31
"Flomoxef is a new oxacephem of broad antibacterial activity. "( Pharmacokinetics and hemostasis following administration of a new, injectable oxacephem (6315-S, flomoxef) in volunteers and in patients with renal insufficiency.
Andrassy, K; Gorges, K; Hirauchi, K; Koderisch, J; Sonntag, H, 1991
)
1.94

Effects

Flomoxef (FMOX) has a broad antibacterial spectrum against Gram-positive and Gram-negative bacteria. Its potent antibacterial activity against Staphylococcus aureus is a significant advantage.

ExcerptReferenceRelevance
"Flomoxef (FMOX) has a broad antibacterial spectrum against Gram-positive and Gram-negative bacteria; especially its potent antibacterial activity against Staphylococcus aureus is a significant advantage that may not be found with other cephem compounds. "( [Experimental and clinical studies of flomoxef in the field of obstetrics and gynecology. Representative Committee Members of the Research Team for Infections in the Field of Obstetrics and Gynecology].
Deguchi, K; Matsuda, S; Ninomiya, K; Noda, K; Okada, H; Shimizu, T, 1988
)
1.99
"flomoxef has no activity."( The in vitro activity of flomoxef compared to four other cephalosporins and imipenem.
Knothe, H; Shah, PM, 1991
)
1.31
"Flomoxef (FMOX) has a broad antibacterial spectrum against Gram-positive and Gram-negative bacteria; especially its potent antibacterial activity against Staphylococcus aureus is a significant advantage that may not be found with other cephem compounds. "( [Experimental and clinical studies of flomoxef in the field of obstetrics and gynecology. Representative Committee Members of the Research Team for Infections in the Field of Obstetrics and Gynecology].
Deguchi, K; Matsuda, S; Ninomiya, K; Noda, K; Okada, H; Shimizu, T, 1988
)
1.99

Toxicity

ExcerptReferenceRelevance
" Because VCM has the adverse reaction of nephrotoxicity, we are apprehensive about using VCM with other antibiotics, which might increase this problem."( [Nephrotoxicity and drug interaction of vancomycin (2)].
Nakagawa, Y; Toyoguchi, T, 1996
)
0.29

Pharmacokinetics

Flomoxef (FMOX, 6315-S), a new oxacephem parenteral antibiotic, was studied in the neonatal field. Pharmacokinetic analyses showed that the concentration of flomoxec in the mucosal tissue was over 1.

ExcerptReferenceRelevance
" Pharmacokinetic studies on FMOX with 20 mg/kg dose were done in 19 patients including 8 LBW infants."( [Flomoxef in neonates and young infants; clinical efficacy, pharmacokinetic evaluation and effect on the intestinal bacterial flora].
Fujita, K; Hiramoto, A; Inyaku, F; Kakuya, F; Maruyama, S; Murono, K; Saijyo, M; Sakata, H; Yoshioka, H, 1991
)
1.19
"Flomoxef (FMOX), a new broad spectrum oxacephem antibiotic, was studied in the neonatal field and the pharmacokinetic results obtained are summarized below."( [Pharmacokinetic studies of flomoxef in the neonatal field].
Kimura, K; Miyano, T; Shimomura, H, 1991
)
2.02
" High concentrations of FMOX were demonstrated in maternal serum, umbilical arterial serum and amniotic fluid with Cmax values of 48."( [Placental transfer and pharmacokinetic parameters of flomoxef during the perinatal period].
Fujimoto, S; Hanatani, K; Iwaki, M; Makinoda, S; Negishi, H; Tanaka, T; Tsuruta, H, 1991
)
0.53
" Furthermore, a new method was presented for the calculation of pharmacokinetic parameters from the data obtained by the microdialysis method."( Continuous monitoring of unbound flomoxef levels in rat blood using microdialysis and its new pharmacokinetic analysis.
Saisho, Y; Umeda, T, 1991
)
0.56
"Microbiological and pharmacokinetic studies were carried out on flomoxef (FMOX, 6315-S), a new oxacephem parenteral antibiotic, in the ophthalmologic field."( [Microbiological and pharmacokinetic studies on flomoxef in ophthalmologic field].
Ooishi, M; Oomomo, A; Sakaue, F; Tazawa, H, 1989
)
0.77
"0 micrograms/ml after 20 mg/kg of drip infusion for 30 minutes and the half-life was 17."( [Clinical and pharmacokinetics evaluation of flomoxef in pediatrics].
Adachi, Y; Araki, A; Hasui, M; Higashino, H; Kobayashi, T; Kobayashi, Y; Matsui, T; Nogi, S; Shuto, K; Sonoda, N, 1987
)
0.53
" Pharmacokinetic analyses were performed using a two compartment open model."( [Pharmacokinetics of flomoxef in children undergoing chronic hemodialysis].
Mito, Y; Nakano, T; Sasagawa, F; Sekine, O, 1993
)
0.6
" Mean Cmax values were clearly dose dependent, and mean T1/2 values tended to be longer in premature infants compared to neonates."( [Pharmacokinetics and clinical studies on flomoxef in neonates and premature infants. A study of flomoxef in the perinatal collaboration research group].
Fujii, R; Fujita, K; Hiramoto, A; Inyaku, F; Kakuya, F; Maruyama, S; Murono, K; Saijo, M; Sakata, H; Yoshioka, H, 1993
)
0.55
"Human pharmacokinetic parameters are often predicted prior to clinical study from in vivo preclinical pharmacokinetic data."( Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
Jolivette, LJ; Ward, KW, 2005
)
0.33
" The drug concentrations in plasma and PF were determined and analyzed using population pharmacokinetic modeling."( Development of breakpoints of cephems for intraabdominal infections based on pharmacokinetics and pharmacodynamics in the peritoneal fluid of patients.
Ikawa, K; Ikeda, K; Morikawa, N; Ohge, H; Sueda, T, 2008
)
0.35
" The drug concentrations in plasma and prostate tissue were analyzed pharmacokinetically and used for a stochastic simulation to predict the probability of attaining pharmacodynamic target in prostate tissue."( Clinical pharmacokinetics of flomoxef in prostate tissue and dosing considerations for prostatitis based on site-specific pharmacodynamic target attainment.
Ikawa, K; Kajikawa, K; Kanao, K; Kobayashi, I; Morikawa, N; Morinaga, S; Muramatsu, H; Nakamura, K; Nishikawa, G; Onita, T; Sugie, M; Tobiume, M; Watanabe, M, 2020
)
0.85
" Herein, pharmacokinetic analysis of flomoxef in the abdominal tissue was conducted to simulate dosing regimens for pharmacodynamic target attainment in abdominal sites."( Pharmacokinetics of flomoxef in plasma, peritoneal fluid, peritoneum, and subcutaneous adipose tissue of patients undergoing lower gastrointestinal surgery: Dosing considerations based on site-specific pharmacodynamic target attainment.
Hirano, T; Ikawa, K; Kaiki, Y; Kitagawa, H; Morikawa, N; Ohge, H; Shigemoto, N; Takahashi, S; Uegami, S; Watadani, Y; Yoshimura, K, 2023
)
1.51
" Accordingly, non-compartmental and compartmental pharmacokinetic parameters were calculated, and simulations were conducted to evaluate site-specific pharmacodynamic target values."( Pharmacokinetics of flomoxef in plasma, peritoneal fluid, peritoneum, and subcutaneous adipose tissue of patients undergoing lower gastrointestinal surgery: Dosing considerations based on site-specific pharmacodynamic target attainment.
Hirano, T; Ikawa, K; Kaiki, Y; Kitagawa, H; Morikawa, N; Ohge, H; Shigemoto, N; Takahashi, S; Uegami, S; Watadani, Y; Yoshimura, K, 2023
)
1.23

Compound-Compound Interactions

The in-vitro activity of ciprofloxacin alone and in combination with flomoxef against clinical Bacteroides fragilis strains was evaluated.

ExcerptReferenceRelevance
"207 clinical isolates from strains of patients from the University Children's Hospital of Kiel were investigated for their in vitro activity with the agar dilution method against flomoxef and cefazolin (alone and partially in combination with vancomycin)."( In vitro activity of flomoxef and cefazolin in combination with vancomycin.
Simon, C; Simon, M, 1991
)
0.79
" Therefore, the nephrotoxic effects and pharmacokinetics of VCM were examined in rabbits and compared with those in rabbits administered with VCM and other antibiotics."( [Nephrotoxicity and drug interaction of vancomycin (2)].
Nakagawa, Y; Toyoguchi, T, 1996
)
0.29
"Using checkerboard and time-kill assays, the in-vitro activity of ciprofloxacin alone and in combination with flomoxef against clinical Bacteroides fragilis strains was evaluated."( In-vitro activity of ciprofloxacin combined with flomoxef against Bacteroides fragilis, compared with that of ciprofloxacin combined with clindamycin.
Harada, T; Ito, Y; Iwai, S; Iwanaga, H; Kato, K; Nakagawa, Y; Sato, T; Takayama, T, 2002
)
0.78

Dosage Studied

The biliary excretion of flomoxef, an oxacephem antibiotic, was greater after dosing at 21:00 than at 09:00 h in diurnally active human subjects. Two dose finding studies in patients with various degrees of renal insufficiency revealed that the dosage of flmoxef has to be reduced exactly according to the renal function.

ExcerptRelevanceReference
" High plasma levels in proportion to dosage are seen with flomoxef, the transfer to various body fluids and tissue is good, and the half-life in the plasma is about 50 min."( The meaning of the development of flomoxef and clinical experience in Japan.
Ishigami, T; Ito, M, 1991
)
0.8
" Two dose finding studies in patients with various degrees of renal insufficiency revealed that the dosage of flomoxef has to be reduced exactly according to the renal function."( Pharmacokinetics and hemostasis following administration of a new, injectable oxacephem (6315-S, flomoxef) in volunteers and in patients with renal insufficiency.
Andrassy, K; Gorges, K; Hirauchi, K; Koderisch, J; Sonntag, H, 1991
)
0.71
" In these cases the daily dosage amounted to 41-119 mg/kg."( [The study of flomoxef in the pediatric field].
Mastumoto, K; Nakada, Y; Nakanishi, Y; Nakazawa, S; Narita, A; Niino, K; Sato, H; Suzuki, H, 1987
)
0.63
" FMOX was administered to 3 patients with pneumonia, 8 patients with bronchopneumonia, 2 patients with tonsillitis, 2 patients with pyelonephritis, one patient each with cervical lymphadenitis, and pustulosis associated with severe varicella at daily dosage levels of 61."( [Clinical studies of flomoxef in the field of pediatrics].
Ito, S; Mayumi, M; Mikawa, H, 1987
)
0.59
" Thus, a positive dose-response relationship was found among the 3 doses."( [Pharmacokinetics and clinical studies of flomoxef in the pediatric field].
Aramaki, M; Fujimoto, T; Kawakami, A; Koga, T; Motohiro, T; Oda, K; Sakata, Y; Shimada, Y; Tanaka, K; Tomita, S, 1987
)
0.54
"Bile flow and bile acid excretion for 6 h after dosing did not differ significantly between the 09."( Diurnal variation in the biliary excretion of flomoxef in patients with percutaneous transhepatic biliary drainage.
Fujimura, A; Hishikawa, S; Kobayashi, E; Miyata, M; Sugimoto , K, 2001
)
0.57
" However, as the difference was relatively small, flomoxef could be given at any time of day without any dosage adjustments."( Diurnal variation in the biliary excretion of flomoxef in patients with percutaneous transhepatic biliary drainage.
Fujimura, A; Hishikawa, S; Kobayashi, E; Miyata, M; Sugimoto , K, 2001
)
0.82
"We previously reported that the biliary excretion of flomoxef, an oxacephem antibiotic, was greater after dosing at 21:00 than at 09:00 h in diurnally active human subjects."( Dosing-time-dependent variation in biliary excretion of flomoxef in rats.
Fujimura, A; Hishikawa, S; Kobayashi, E; Kumagai, Y; Sugimoto, K, 2003
)
0.81
"Intraoperative repeated antimicrobial dosing is therefore recommended to prevent the surgical wound infection for prolonged colorectal surgery."( The significance of the intraoperative repeated dosing of antimicrobials for preventing surgical wound infection in colorectal surgery.
Fukushima, Y; Hiraoka, N; Morimoto, T; Morita, S; Nishisho, I; Nomura, T; Shibata, N, 2005
)
0.33
" Using the kinetic data from this study, the individualization of dosage regimens for prophylactic use of flomoxef might be possible."( Pharmacokinetic analysis of flomoxef in children undergoing cardiopulmonary bypass and modified ultrafiltration.
Ishino, K; Kurosaki, Y; Masuda, Z; Sano, S; Yamauchi, K, 2008
)
0.85
" The bacteriostatic and bactericidal breakpoints were determined as the highest MIC values at which the bacteriostatic and bactericidal probabilities in PF were > or =80%, which values varied with drug and dosing regimen."( Development of breakpoints of cephems for intraabdominal infections based on pharmacokinetics and pharmacodynamics in the peritoneal fluid of patients.
Ikawa, K; Ikeda, K; Morikawa, N; Ohge, H; Sueda, T, 2008
)
0.35
" In this study, the antibacterial activity of FMOX was investigated, and Monte Carlo Simulation was conducted to determine the appropriate dosing regimens of FMOX based on the probability of target attainment (TA%) at the critical drug exposure metric of time that drug concentrations remain above 40% (showing bacteriostatic effect) or 70% (showing bactericidal effect) of time during which plasma concentration above minimum inhibitory concentration (MIC) of the drug (T(>MIC)) against the ESBL producing Enterobacteriaceae."( Evaluation of antibacterial activities of flomoxef against ESBL producing Enterobacteriaceae analyzed by Monte Carlo simulation.
Ito, A; Nakamura, R; Tatsumi, YM; Tsuji, M; Wajima, T, 2013
)
0.65
" Herein, pharmacokinetic analysis of flomoxef in the abdominal tissue was conducted to simulate dosing regimens for pharmacodynamic target attainment in abdominal sites."( Pharmacokinetics of flomoxef in plasma, peritoneal fluid, peritoneum, and subcutaneous adipose tissue of patients undergoing lower gastrointestinal surgery: Dosing considerations based on site-specific pharmacodynamic target attainment.
Hirano, T; Ikawa, K; Kaiki, Y; Kitagawa, H; Morikawa, N; Ohge, H; Shigemoto, N; Takahashi, S; Uegami, S; Watadani, Y; Yoshimura, K, 2023
)
1.51
" The simulation based on these results showed the dosing regimens (q8h [3 g/day] and q6h [4 g/day]) achieved the bactericidal effect (% T > minimum inhibitory concentration [MIC] = 40%) in all tissues at an MIC of 1 mg/L."( Pharmacokinetics of flomoxef in plasma, peritoneal fluid, peritoneum, and subcutaneous adipose tissue of patients undergoing lower gastrointestinal surgery: Dosing considerations based on site-specific pharmacodynamic target attainment.
Hirano, T; Ikawa, K; Kaiki, Y; Kitagawa, H; Morikawa, N; Ohge, H; Shigemoto, N; Takahashi, S; Uegami, S; Watadani, Y; Yoshimura, K, 2023
)
1.23
" This study provides evidence concerning the use of optimal dosing regimens for treating abdominal infection caused by strains like ESBL-producing bacteria."( Pharmacokinetics of flomoxef in plasma, peritoneal fluid, peritoneum, and subcutaneous adipose tissue of patients undergoing lower gastrointestinal surgery: Dosing considerations based on site-specific pharmacodynamic target attainment.
Hirano, T; Ikawa, K; Kaiki, Y; Kitagawa, H; Morikawa, N; Ohge, H; Shigemoto, N; Takahashi, S; Uegami, S; Watadani, Y; Yoshimura, K, 2023
)
1.23
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
antibacterial drugA drug used to treat or prevent bacterial infections.
[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 (3)

ClassDescription
N-acyl-amino acidA carboxamide resulting from the formal condensation of a carboxylic acid with the amino group of an amino acid.
oxacephemAny member of the oxacephem sub-group of cephem antibiotics, in which the thiaazabicyclo moiety of the cephalosporins is replaced by an oxaazabicyclo moiety, and where R3 is -H or -OCH3.
organonitrogen heterocyclic antibiotic
[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 (74)

Assay IDTitleYearJournalArticle
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID206639In vitro antibacterial activity against clinical isolates methicillin-resistant Staphylococcus aureus was determined1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID534388Antibacterial activity against Escherichia coli JM109 harboring recombinant pKHM-1 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID67911In vitro antibacterial activity against clinical isolates Enterococcus faecalis was determined1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID67569In vivo efficacy was determined against Enterococcus faecalis C 00631995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID207480Antibacterial activity was determined against Methicillin-resistant Staphylococcus aureus (MRSA) 5038 (Gram-positive)1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID113436Antibacterial activity was determined against Escherichia coli 29 at a challenge dose of 1.35*10e6 (cells/mouse) administered subcutaneously1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID560773Antibacterial activity against Staphylococcus aureus TS2921 harboring ddlA Asp102Asn mutation after 20 hrs2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Evaluation of target specificity of antibacterial agents using Staphylococcus aureus ddlA mutants and D-cycloserine in a silkworm infection model.
AID534385Antibacterial activity against Escherichia coli K-12 W1895 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID543429Antimicrobial activity against Escherichia coli XL-1 Blue harboring plasmid CL1920 by disk diffusion method2009Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1
Novel chimeric beta-lactamase CTX-M-64, a hybrid of CTX-M-15-like and CTX-M-14 beta-lactamases, found in a Shigella sonnei strain resistant to various oxyimino-cephalosporins, including ceftazidime.
AID560774Antibacterial activity against Staphylococcus aureus TS5337 harboring ddlA Pro178Ser mutation after 20 hrs2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Evaluation of target specificity of antibacterial agents using Staphylococcus aureus ddlA mutants and D-cycloserine in a silkworm infection model.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID207379In vivo efficacy was determined against MRSA 51201995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID207482Antibacterial activity was determined against Staphylococcus aureus FDA 209P (Gram-positive)1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID534382Antibacterial activity against Escherichia coli K-12 W1895 transconjugant harboring pCF243 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID113444Antibacterial activity was determined against Streptococcus pneumoniae C 0096 at a challenge dose of 1.60*10e2 (cells/mouse) administered subcutaneously1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID113437Antibacterial activity was determined against Enterococcus faecalis C 0063 at a challenge dose of 7.00*10e7 (cells/mouse) administered subcutaneously1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID560772Antibacterial activity against Staphylococcus aureus RN4220 after 20 hrs2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Evaluation of target specificity of antibacterial agents using Staphylococcus aureus ddlA mutants and D-cycloserine in a silkworm infection model.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID69932Antibacterial activity was determined against Escherichia coli NIHJ JC-2 (Gram-negative)1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID540215Volume of distribution at steady state in rat after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID206644In vitro antibacterial activity against clinical isolates methicillin-resistant Staphylococcus aureus was determined1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID67904In vitro antibacterial activity against clinical isolates Enterococcus faecalis was determined1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID207381In vivo efficacy was determined against Staphylococcus aureus Smith1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID205572Antibacterial activity was determined against Staphylococcus epidermidis ATCC 12228 (Gram-positive)1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID540220Clearance in human after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID540216Clearance in dog after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID540219Volume of distribution at steady state in monkey after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID113439Antibacterial activity was determined against MRSA 5120 at a challenge dose of 7.6*10e7 (cells/mouse) administered subcutaneously1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID96071Antibacterial activity was determined against Klebsiella pneumoniae NCTC 9632 (Gram-negative)1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID69020In vivo efficacy was determined against Escherichia coli 291995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID540218Clearance in monkey after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID67902In vitro antibacterial activity against clinical isolates Enterococcus faecalis was determined1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID206783In vitro antibacterial activity against clinical isolates methicillin-resistant Staphylococcus aureus was determined1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID205382Antibacterial activity was determined against Serratia marcescens ATCC 12648 (Gram-negative)1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID67077Antibacterial activity was determined against Enterococcus faecalis ATCC 21212 (Gram-positive)1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID543417Antimicrobial activity against rifampicin-resistant Escherichia coli X1037 transconjugant by disk diffusion method2009Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1
Novel chimeric beta-lactamase CTX-M-64, a hybrid of CTX-M-15-like and CTX-M-14 beta-lactamases, found in a Shigella sonnei strain resistant to various oxyimino-cephalosporins, including ceftazidime.
AID534391Antibacterial activity against Escherichia coli JM109 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID208629In vitro antibacterial activity against clinical isolates Ampicillin-insensitive Streptococcus pneumoniae was determined1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID560779Antibacterial activity against Staphylococcus aureus TS2921 harboring ddlA Asp102Asn mutation in fifth-instar silkworm larva infection model assessed as compound concentration per gram of larva causing reduction in survival after 48 hrs post dose at 27 de2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Evaluation of target specificity of antibacterial agents using Staphylococcus aureus ddlA mutants and D-cycloserine in a silkworm infection model.
AID560776Antibacterial activity against Staphylococcus aureus TS2921 harboring ddlA Asp102Asn mutation and coexpressing pSddlA which complements temperature sensitivity after 20 hrs2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Evaluation of target specificity of antibacterial agents using Staphylococcus aureus ddlA mutants and D-cycloserine in a silkworm infection model.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID560777Antibacterial activity against Staphylococcus aureus TS2921 harboring ddlA Asp102Asn mutation in presence of 100 mM D-Ala-D-Ala, which complements temperature sensitivity after 20 hrs2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Evaluation of target specificity of antibacterial agents using Staphylococcus aureus ddlA mutants and D-cycloserine in a silkworm infection model.
AID543421Antimicrobial activity against rifampicin-resistant Escherichia coli X1037 by disk diffusion method2009Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1
Novel chimeric beta-lactamase CTX-M-64, a hybrid of CTX-M-15-like and CTX-M-14 beta-lactamases, found in a Shigella sonnei strain resistant to various oxyimino-cephalosporins, including ceftazidime.
AID540214Clearance in rat after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID164392Antibacterial activity was determined against Pseudomonas aeruginosa ATCC 10145 (Gram-negative)1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID560778Antibacterial activity against Staphylococcus aureus RN4220 in fifth-instar silkworm larva infection model assessed as compound concentration per gram of larva causing reduction in survival after 48 hrs post dose at 27 degC2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Evaluation of target specificity of antibacterial agents using Staphylococcus aureus ddlA mutants and D-cycloserine in a silkworm infection model.
AID208612In vitro antibacterial activity against clinical isolates Ampicillin-insensitive Streptococcus pneumoniae was determined1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID543413Antimicrobial activity against Shigella sonnei UIH-1 expressing beta-lactamase CTX-M-64 by disk diffusion method2009Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1
Novel chimeric beta-lactamase CTX-M-64, a hybrid of CTX-M-15-like and CTX-M-14 beta-lactamases, found in a Shigella sonnei strain resistant to various oxyimino-cephalosporins, including ceftazidime.
AID534379Antibacterial activity against Citrobacter freundii KHM243 clinical isolate by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID540221Volume of distribution at steady state in human after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID208622In vitro antibacterial activity against clinical isolates Ampicillin-insensitive Streptococcus pneumoniae was determined1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID560780Antibacterial activity against Staphylococcus aureus TS5337 harboring ddlA Pro178Ser mutation in fifth-instar silkworm larva infection model assessed as compound concentration per gram of larva causing reduction in survival after 48 hrs post dose at 27 de2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Evaluation of target specificity of antibacterial agents using Staphylococcus aureus ddlA mutants and D-cycloserine in a silkworm infection model.
AID543425Antimicrobial activity against Escherichia coli XL-1 Blue transconjugant harboring beta-lactamase CTX-M-64 by disk diffusion method2009Antimicrobial agents and chemotherapy, Jan, Volume: 53, Issue:1
Novel chimeric beta-lactamase CTX-M-64, a hybrid of CTX-M-15-like and CTX-M-14 beta-lactamases, found in a Shigella sonnei strain resistant to various oxyimino-cephalosporins, including ceftazidime.
AID560781Antibacterial activity against Staphylococcus aureus TS10007 harboring ddlA Asp39Asn mutation in fifth-instar silkworm larva infection model assessed as compound concentration per gram of larva causing reduction in survival after 48 hrs post dose at 27 de2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Evaluation of target specificity of antibacterial agents using Staphylococcus aureus ddlA mutants and D-cycloserine in a silkworm infection model.
AID540217Volume of distribution at steady state in dog after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID208146In vivo efficacy was determined against Streptococcus pneumoniae C 00961995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID560775Antibacterial activity against Staphylococcus aureus TS10007 harboring ddlA Asp39Asn mutation after 20 hrs2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Evaluation of target specificity of antibacterial agents using Staphylococcus aureus ddlA mutants and D-cycloserine in a silkworm infection model.
AID113443Antibacterial activity was determined against Staphylococcus aureus Smith at a challenge dose of 1.32*10e7 (cells/mouse) administered subcutaneously (value in parentheses indicates 95% CL)1995Journal of medicinal chemistry, Jun-09, Volume: 38, Issue:12
Synthesis and biological evaluation of a series of new parenteral optically active 3-[[(N-alkylpyridinium-4'-yl)thio]methyl]-2-oxaisocephems.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (202)

TimeframeStudies, This Drug (%)All Drugs %
pre-199042 (20.79)18.7374
1990's88 (43.56)18.2507
2000's35 (17.33)29.6817
2010's27 (13.37)24.3611
2020's10 (4.95)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 47.37

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 Index47.37 (24.57)
Research Supply Index5.46 (2.92)
Research Growth Index4.64 (4.65)
Search Engine Demand Index73.18 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (47.37)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials25 (11.90%)5.53%
Reviews3 (1.43%)6.00%
Case Studies33 (15.71%)4.05%
Observational0 (0.00%)0.25%
Other149 (70.95%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]