Home Carboxys 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7S)-

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7S)-

CAS No.:
56796-20-4
Catalog Number:
AG01CCIB
Molecular Formula:
Molecular Weight:
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%(HPLC)
In Stock USA
United States
$58
- +
10mg
98%(HPLC)
In Stock USA
United States
$82
- +
25mg
98%(HPLC)
In Stock USA
United States
$144
- +
Product Description
Catalog Number:
AG01CCIB
Chemical Name:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7S)-
CAS Number:
56796-20-4
MDL Number:
MFCD00865068
IUPAC Name:
(6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChI:
InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
InChI Key:
SNBUBQHDYVFSQF-HIFRSBDPSA-N
EC Number:
260-384-2
UNII:
3J962UJT8H
Properties
Complexity:
818  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
471.045g/mol
Formal Charge:
0
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
471.525g/mol
Monoisotopic Mass:
471.045g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
239A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.6  
Literature
Title Journal
A systematic toxicity evaluation of cephalosporins via transcriptomics in zebrafish and in silico ADMET studies. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20180601
Post-operative infection and prophylactic antibiotic administration after radical cystectomy with orthotopic neobladder urinary diversion. Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20120801
Oral availability of cefadroxil depends on ABCC3 and ABCC4. Drug metabolism and disposition: the biological fate of chemicals 20120301
In vivo biliary clearance should be predicted by intrinsic biliary clearance in sandwich-cultured hepatocytes. Drug metabolism and disposition: the biological fate of chemicals 20120301
Association between antimicrobial consumption and clinical isolates of methicillin-resistant Staphylococcus aureus: a 14-year study. Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20120201
Validated stability-indicating high-performance thin-layer chromatographic method for estimation of cefpodoxime proxetil in bulk and in pharmaceutical formulation according to International conference on harmonization guidelines. Journal of pharmacy & bioallied sciences 20120101
Acute fulminant pseudomembranous colitis which developed after ileostomy closure and required emergent total colectomy: a case report. Journal of medical case reports 20120101
Fever-based antibiotic therapy for acute cholangitis following successful endoscopic biliary drainage. Journal of gastroenterology 20111201
Correlation between cephamycin consumption and the incidence of antimicrobial resistance in Acinetobacter baumannii at a university hospital in China from 2001 to 2009. International journal of clinical pharmacology and therapeutics 20111201
Pyogenic cervical spondylitis caused by Pasteurella haemolytica attributed to excessive contact with dogs. Orthopedics 20111109
Different clinical characteristics among Aeromonas hydrophila, Aeromonas veronii biovar sobria and Aeromonas caviae monomicrobial bacteremia. Journal of Korean medical science 20111101
6-Mercaptopurine transport by equilibrative nucleoside transporters in conditionally immortalized rat syncytiotrophoblast cell lines TR-TBTs. Journal of pharmaceutical sciences 20110901
Fragmental modeling of hPepT2 and analysis of its binding features by docking studies and pharmacophore mapping. Bioorganic & medicinal chemistry 20110801
Miliary tuberculosis following transrectal ultrasonography (TRUS)-guided prostate biopsy. Korean journal of urology 20110601
Simultaneous determination of eight β-lactam antibiotics in human serum by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110501
[The clinical efficacy and safety of intravenous cefmetazole in treatment of 1,522 patients with aspiration pneumonia]. Zhonghua nei ke za zhi 20110401
Migrating motor complex changes after side-to-side ileal bypass in mouse ileum ex-vivo: mechanism underlying the blind loop syndrome? Journal of the Korean Surgical Society 20110401
Emerging knowledge of regulatory roles of D-amino acids in bacteria. Cellular and molecular life sciences : CMLS 20110301
Risk factors and outcomes of Escherichia coli bacteremia caused by strains that produce CTX-M or non-CTX-M extended-spectrum-beta-lactamases. European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 20110101
Staphylococcus aureus requires cardiolipin for survival under conditions of high salinity. BMC microbiology 20110101
Screening of antibiotics that interact with organic anion-transporting polypeptides 1B1 and 1B3 using fluorescent probes. Biological & pharmaceutical bulletin 20110101
Occupational asthma in antibiotic manufacturing workers: case reports and systematic review. Journal of allergy 20110101
Role of pirenoxine in the effects of catalin on in vitro ultraviolet-induced lens protein turbidity and selenite-induced cataractogenesis in vivo. Molecular vision 20110101
Attenuation of prostaglandin E2 elimination across the mouse blood-brain barrier in lipopolysaccharide-induced inflammation and additive inhibitory effect of cefmetazole. Fluids and barriers of the CNS 20110101
Multicenter prospective randomized phase II study of antimicrobial prophylaxis in low-risk patients undergoing colon surgery. Surgery today 20101001
Clostridium difficile bacteremia, Taiwan. Emerging infectious diseases 20100801
Involvement of multidrug resistance-associated protein 4 in efflux transport of prostaglandin E(2) across mouse blood-brain barrier and its inhibition by intravenous administration of cephalosporins. The Journal of pharmacology and experimental therapeutics 20100601
Implementing a standard protocol to decrease the incidence of surgical site infections in rectal cancer surgery. Surgery today 20100401
Virtual Screening of potential drug-like inhibitors against Lysine/DAP pathway of Mycobacterium tuberculosis. BMC bioinformatics 20100101
The use of tacrolimus for recurrent lupus enteritis: a case report. Journal of medical case reports 20100101
Risk factors for complications after laparoscopic surgery in colorectal cancer patients: experience of 401 cases at a single institution. World journal of surgery 20090801
A human hepatocyte-bearing mouse: an animal model to predict drug metabolism and effectiveness in humans. PPAR research 20090101
Pneumomediastinum as first manifestation of emphysematous pyelonephritis in a patient who is non-diabetic. BMJ case reports 20090101
Xanthogranulomatous pyelonephritis successfully treated with antibiotics only. Journal of the Chinese Medical Association : JCMA 20081201
Successful treatment of gastric perforation with thyrotoxic crisis. The American journal of emergency medicine 20081101
Effect of plasma protein binding on in vitro-in vivo correlation of biliary excretion of drugs evaluated by sandwich-cultured rat hepatocytes. Drug metabolism and disposition: the biological fate of chemicals 20080701
Simultaneous Klebsiella pneumoniae and amoebic liver abscess in an immunocompetent patient. The American journal of the medical sciences 20080501
Chimeric mice with humanized liver. Toxicology 20080403
Predominant contribution of rat organic anion transporting polypeptide-2 (Oatp2) to hepatic uptake of beta-lactam antibiotics. Pharmaceutical research 20080301
In vitro antimicrobial susceptibility of Mycobacterium abscessus in Korea. Journal of Korean medical science 20080201
Klebsiella oxytoca bacteremia causing septic shock in recipients of hematopoietic stem cell transplant: Two case reports. Cases journal 20080101
Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter. Pharmaceutical research 20071201
Specific antibiotic prophylaxis based on bile cultures is required to prevent postoperative infectious complications in pancreatoduodenectomy patients who have undergone preoperative biliary drainage. World journal of surgery 20071101
Lemierre syndrome: a case of postanginal sepsis. The Korean journal of internal medicine 20070901
Change of drug excretory pathway by CCl4-induced liver dysfunction in rat. Biochemical pharmacology 20070801
[Fundamental study on the selection of antimicrobial prophylactic agents in abdominal surgery]. The Japanese journal of antibiotics 20070801
Randomized, multicenter trial of antibiotic prophylaxis in elective colorectal surgery: single dose vs 3 doses of a second-generation cephalosporin without metronidazole and oral antibiotics. Archives of surgery (Chicago, Ill. : 1960) 20070701
Humanization of excretory pathway in chimeric mice with humanized liver. Toxicological sciences : an official journal of the Society of Toxicology 20070601
Involvement of MRP4 (ABCC4) in the luminal efflux of ceftizoxime and cefazolin in the kidney. Molecular pharmacology 20070601
[Pyometra as a cause of fever; report on two cases]. Kansenshogaku zasshi. The Journal of the Japanese Association for Infectious Diseases 20070501
Characterization of antimicrobial resistance patterns and class 1 integrons in Escherichia coli O26 isolated from humans and animals. International journal of antimicrobial agents 20070301
[Clinical and bacterial analysis of pediatric urinary tract infection]. Kansenshogaku zasshi. The Journal of the Japanese Association for Infectious Diseases 20070101
Application of chimeric mice with humanized liver for predictive ADME. Drug metabolism reviews 20070101
Gemella morbillorum liver abscess. Scandinavian journal of infectious diseases 20070101
Effects of air tourniquet on the antibiotics concentration, in bone marrow, injected just before the start of operation. Modern rheumatology 20070101
[Prophylactic effect of fosfomycin on postoperative infection in gastroenterological surgery]. The Japanese journal of antibiotics 20061201
Verification of cefmetazole and cefpodoxime proxetil contamination to other pharmaceuticals by liquid chromatography-tandem mass spectrometry. Chemical & pharmaceutical bulletin 20061001
Prediction of pharmacokinetics of antibiotics in patients with end-stage renal disease. Biological & pharmaceutical bulletin 20060701
LC/MS/MS method for the determination of trace amounts of cefmetazole and cefpodoxime proxetil contaminants in pharmaceutical manufacturing environments. Journal of pharmaceutical and biomedical analysis 20060616
Emergence and prevalence of beta-lactamase-producing Klebsiella pneumoniae resistant to cephems in Japan. International journal of antimicrobial agents 20060601
Determination of cefmetazole residue at pharmaceutical manufacturing facilities by chemiluminescence flow injection analysis. Journal of pharmaceutical and biomedical analysis 20060503
In vitro activities of 16 antimicrobial agents against clinical isolates of extended-spectrum beta-lactamase-producing Escherichia coli and Klebsiella pneumoniae in two regional hospitals in Taiwan. Journal of microbiology, immunology, and infection = Wei mian yu gan ran za zhi 20060201
[A case of multiple recurrence of Clostridium difficile-associated diarrhea--analysis of isolates from the patient using PCR ribotyping]. Nihon Shokakibyo Gakkai zasshi = The Japanese journal of gastro-enterology 20060201
Beta-lactam antibiotic-induced release of lipoteichoic acid from Staphylococcus aureus leads to activation of neutrophil granulocytes. Annals of clinical microbiology and antimicrobials 20060101
Case report: infective endocarditis caused by Brevundimonas vesicularis. BMC infectious diseases 20060101
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure. Journal of pharmaceutical sciences 20050701
Antimicrobial activity of antibiotics in combination with natural flavonoids against clinical extended-spectrum beta-lactamase (ESBL)-producing Klebsiella pneumoniae. Phytotherapy research : PTR 20050701
Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1. Journal of medicinal chemistry 20050630
[Surveillance of susceptibility of clinical isolates to cefmetazole between 2000 and 2003]. The Japanese journal of antibiotics 20050601
Infections of cefotaxime-resistant and cefmetazole-susceptible Escherichia coli and Klebsiella pneumoniae in children. Journal of microbiology, immunology, and infection = Wei mian yu gan ran za zhi 20050401
[Antimicrobial activity of fosfomycin under various conditions against standard strains, beta-lactam resistant strains, and multidrug efflux system mutants]. The Japanese journal of antibiotics 20050401
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20050101
Fluoroquinolone-resistant Salmonella Paratyphi A. Emerging infectious diseases 20050101
The significance of the intraoperative repeated dosing of antimicrobials for preventing surgical wound infection in colorectal surgery. Surgery today 20050101
Unmasking hypotension by beta lactam during dextran sulfate low-density lipoprotein apheresis. American journal of kidney diseases : the official journal of the National Kidney Foundation 20041201
[Feasibility of short-term antibiotic prophylaxis after pulmonary resection]. Kyobu geka. The Japanese journal of thoracic surgery 20041201
Influence of various antimicrobial agents on the intestinal flora in an intestinal MRSA-carrying rat model. Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20041201
Mycobacterium goodii infections associated with surgical implants at Colorado hospital. Emerging infectious diseases 20041001
[A case of radiofrequency ablation therapy for recurrent hepatomas with tumor fever--efficacy of hepatic arterial infusion therapy with antibiotics and anticancer drugs]. Gan to kagaku ryoho. Cancer & chemotherapy 20041001
[A case of probable bacterial translocation-associated sepsis in healthy adult]. Kansenshogaku zasshi. The Journal of the Japanese Association for Infectious Diseases 20040301
Development and validation of a MEKC method for the direct determination of cefozopran in human serum. Journal of pharmaceutical and biomedical analysis 20040204
Escherichia coli producing CTX-M-2 beta-lactamase in cattle, Japan. Emerging infectious diseases 20040101
[Study of resistance mechanism on cefotaxime resistant Proteus mirabilis isolated from clinical specimens and its clinical background]. Kansenshogaku zasshi. The Journal of the Japanese Association for Infectious Diseases 20040101
In vitro antibiotic susceptibility of lactobacilli isolated from commercial products containing active lactobacilli. Acta paediatrica Taiwanica = Taiwan er ke yi xue hui za zhi 20040101
Molecular and epidemiologic analysis of a county-wide outbreak caused by Salmonella enterica subsp. enterica serovar Enteritidis traced to a bakery. BMC infectious diseases 20040101
Enhancement of antimicrobial effects of various antibiotics against methicillin-resistant Staphylococcus aureus (MRSA) by combination with fosfomycin. Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20031201
Meningitis caused by Enterococcus gallinarum in patients with ventriculoperitoneal shunts. Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20031201
[Surveillance of susceptibility of clinical isolates to cefmetazole between 2000 and 2002]. The Japanese journal of antibiotics 20031201
[Application of the MIC breakpoints based on pharmacokinetics and pharmacodynamics parameter in the clinical laboratory]. The Japanese journal of antibiotics 20031201
Intracystic hemorrhage with spontaneous rupture of liver cyst complicated by infection: a case report. Osaka city medical journal 20031201
[Post-marketing surveillance of antibacterial activities of cefozopran against various clinical isolates--I. Gram-positive bacteria]. The Japanese journal of antibiotics 20031001
[Antimicrobial activity of fosfomycin against beta-lactamase-producing methicillin-sensitive Staphylococcus aureus and methicillin-sensitive coagulase-negative staphylococci]. The Japanese journal of antibiotics 20030401
[Detection of novel nucleotide substitutions resulting amino acid substitutions in TEM type beta-lactamase gene isolated from a clinically isolated extended spectrum beta-lactamases (ESBLs) productive Escherichia coli]. Rinsho byori. The Japanese journal of clinical pathology 20030301
[Antibiotic susceptibility of Neisseria gonorrhoeae epidemic strains in Changsha]. Hunan yi ke da xue xue bao = Hunan yike daxue xuebao = Bulletin of Hunan Medical University 20030227
[Successful combination therapy of teicoplanin with cefmetazole on postoperative cardiovascular MRSA infections: clinical report on two cases]. The Japanese journal of antibiotics 20030201
[Antibacterial activities of fosfomycin against several fresh clinical isolates--comparison of the test methods for antibacterial activity]. The Japanese journal of antibiotics 20021201
[Extended-spectrum beta-lactamase in Klebsiella pneumoniae and Escherichia coli isolates]. Zhonghua yi xue za zhi 20021110
Antimicrobial susceptibility of major pathogens of orofacial odontogenic infections to 11 beta-lactam antibiotics. Oral microbiology and immunology 20021001
Investigation of extended-spectrum beta-lactamase in Klebsiellae pneumoniae and Escherichia coli from China. Diagnostic microbiology and infectious disease 20021001
[beta-lactamase-producing activity and antimicrobial susceptibility of major pathogenic bacteria isolated from clinical samples. Japan beta-lactamase Research Group]. The Japanese journal of antibiotics 20020901
Cefpirome sulphate for gynaecological infections and prophylaxis of non-laparotomy surgery in patients with benign disease. International journal of antimicrobial agents 20020501
[A three-year review of acute respiratory tract infections caused by Streptococcus milleri group]. Kansenshogaku zasshi. The Journal of the Japanese Association for Infectious Diseases 20020301
[Post-marketing surveillance of antibacterial activities of cefozopran against various clinical isolates--I. Gram-positive bacteria]. The Japanese journal of antibiotics 20020201
Significance of SIRS score in therapeutic strategy for acute appendicitis. Hepato-gastroenterology 20020101
Clinical review: bacteremia caused by anaerobic bacteria in children. Critical care (London, England) 20020101
Epigallocatechin gallate synergy with ampicillin/sulbactam against 28 clinical isolates of methicillin-resistant Staphylococcus aureus. The Journal of antimicrobial chemotherapy 20010901
[Clinical analysis of nosocomial infection of extended spectrum beta-lactamase-producing bacteria]. Zhonghua nei ke za zhi 20010901
[Immunological properties of S-1090, cefmatilen hydrochloride hydrate]. The Journal of toxicological sciences 20010501
[A questionnaire survey on the theory of postoperative infection prophylaxis in gynecology]. Kansenshogaku zasshi. The Journal of the Japanese Association for Infectious Diseases 20010501
Incidence of beta-lactamase production and antimicrobial susceptibility of anaerobic gram-negative rods isolated from pus specimens of orofacial odontogenic infections. Oral microbiology and immunology 20010201
MRSA meningitis in postoperative patients. Report of 4 cases. The Japanese journal of antibiotics 19900601
[A successful treatment of an infective endocarditis caused by methicillin-resistant Staphylococcus aureus with a combination of cefmetazole with fosfomycin]. The Japanese journal of antibiotics 19890901
[Nephrotoxicity of cefodizime sodium in rats--single and 14-day repeated intravenous administration]. The Journal of toxicological sciences 19880601
Myoclonic activity associated with cefmetazole, with a review of neurotoxicity of cephalosporins. Clinical neurology and neurosurgery 19880101
Induction of IgG1 and IgE responses to protein-conjugated and unconjugated beta-lactam antibiotics in the mouse--efficacy of Freund's complete adjuvant. Experientia 19851215
In vitro susceptibility of Mycobacterium fortuitum to N-formimidoyl thienamycin and several cephamycins. Antimicrobial agents and chemotherapy 19821201
Properties