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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/10/19 08:42:16」(JST)
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Cefsulodin
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Systematic (IUPAC) name |
4-(aminocarbonyl)-1-[((6R,7R)-2-carboxy-8-oxo-7-{[phenyl(sulfo)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]pyridinium |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Legal status |
?
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Identifiers |
CAS number |
52152-93-9 Y |
ATC code |
J01DD03 |
PubChem |
CID 5284530 |
ChemSpider |
4447588 Y |
UNII |
OV42LHE42B Y |
KEGG |
D02005 Y |
ChEMBL |
CHEMBL1617285 N |
Chemical data |
Formula |
C22H21N4O8S2+ |
Mol. mass |
533.556 g/mol |
SMILES
- O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(c3ccccc3)S(=O)(=O)O)C[n+]4ccc(C(=O)N)cc4)C([O-])=O
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InChI
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InChI=1S/C22H20N4O8S2/c23-18(27)13-6-8-25(9-7-13)10-14-11-35-21-15(20(29)26(21)16(14)22(30)31)24-19(28)17(36(32,33)34)12-4-2-1-3-5-12/h1-9,15,17,21H,10-11H2,(H4-,23,24,27,28,30,31,32,33,34)/t15-,17?,21-/m1/s1 Y
Key:SYLKGLMBLAAGSC-IKZMBGHXSA-N Y
|
N (what is this?) (verify) |
Cefsulodin is a third-generation cephalosporin antibiotic with specific activity against Pseudomonas aeruginosa. It has no significant activity against other Gram-negative bacteria and very limited activity against Gram-positive bacteria and anaerobic bacteria. Cefsulodin was first synthesized and patented by the Takeda Pharmaceutical Company in 1977. In 2002, Takeda stopped production of cefsulodin. Many years of low-stability cefsulodin production has led to a widespread reduction of laboratory and research uses. Current attempts (i.e. IDEXX Laboratories) of increasing purity and stability of cefsulodin center around recrystallization. Typically, the process entails: Cefsulodin is dissolved in an organic solvent, sodium ions, water, or any mixture thereof, then subsequently recrystallized through separation of the unwanted fraction. Recently, TOKU-E has found the main cause of cefsulodin instability stems from one key impurity in 7-aminocephalosporanic acid, a raw material used in the synthesis of cefsulodin. To produce high-purity, high-stability cefsulodin, TOKU-E uses industrial HPLC to remove significant quantities of this impurity in 7-ACA and thus produces ultrapure, ultrastable, and ultrapotent cefsulodin.[1]
General use
Cefuslodin is most commonly used in cefsulodin-irgasan-novobiocin agar to select for Yersinia microorganisms.[2] This agar is most often used in water and beverage testing.
Susceptibility data
The following represents MIC susceptibility data for various P. aeruginosa strains.
- Pseudomonas aeruginosa PA13 (resistant strain): 32 μg/ml
- Pseudomonas aeruginosa (wild-type, susceptible): 4 - 8 μg/ml
[3]
References
- ^ [1], TOKU-E Technical Application Sheet.
- ^ "BAM Media M35: Cefsulodin-Irgasan Novobiocin Agar or Yersinia Selective Agar". Retrieved 2 September 2012.
- ^ http://antibiotics.toku-e.com/antimicrobial_474.html
Antibacterials: cell envelope antibiotics (J01C-J01D)
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Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
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Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
Penicillins
(penams)
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Extended sp.
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- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
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|
β-lactamase resistant
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- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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|
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Penems
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|
|
Carbapenems
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- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
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|
Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
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2nd (HEN)
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- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
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3rd
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- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
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4th (antipseudomonal)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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5th
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- Ceftobiprole
- Ceftaroline fosamil
|
|
Veterinary
|
- Ceftiofur
- Cefquinome
- Cefovecin
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|
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Monobactams
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- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
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β-lactamase inh.
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- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
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Combinations
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- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
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|
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Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (lysozyme)
- Gramicidin
- Isoniazid
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
|
|
|
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UpToDate Contents
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English Journal
- Detection, enumeration and characterization of Yersinia enterocolitica 4/O:3 in pig tonsils at slaughter in Northern Italy.
- Bonardi S1, Alpigiani I2, Pongolini S3, Morganti M3, Tagliabue S4, Bacci C2, Brindani F2.Author information 1Department of Veterinary Science, Unit of Food Hygiene, University of Parma, Via del Taglio 10, 43126 Parma, Italy. Electronic address: silvia.bonardi@unipr.it.2Department of Veterinary Science, Unit of Food Hygiene, University of Parma, Via del Taglio 10, 43126 Parma, Italy.3Istituto Zooprofilattico Sperimentale della Lombardia e dell'Emilia-Romagna, Via dei Mercati 13/A, 43126 Parma, Italy.4Istituto Zooprofilattico Sperimentale della Lombardia e dell'Emilia-Romagna, Via Bianchi 9, 25124 Brescia, Italy.AbstractTonsils from 150 pigs slaughtered at 270days or older were tested for Yersinia enterocolitica with different cultural methods. Samples were collected in three different abattoirs of Northern Italy between April and November 2012 and were analysed by direct plating on cefsulodin-irgasan-novobiocin (CIN) agar and by enrichment procedures following the ISO 10273:2003 reference method. Twenty-three (15.3%) samples were positive: 22 tonsils (14.7%) were positive for human pathogenic Y. enterocolitica bio-serotype 4/O:3 and one tonsil (0.7%) for Y. enterocolitica bio-serotype 1A/7,8-8,8,19. Seventeen samples out of 23 (73.9%) were positive by direct plating method. Among the enrichment procedures, the best recovery rate (8 positives out of 23; 34.8%) was obtained by the two-day enrichment in peptone-sorbitol-bile (PSB) broth followed by plating on CIN agar plates. The two-day enrichment in PSB followed by potassium hydroxide (KOH) treatment before plating onto CIN agar gave 7 positives out of 23 (30.4%), decreasing to 3 positives (13.0%) without KOH treatment. The worst results were obtained by prolonged (five days) enrichment in PSB, with or without KOH treatment, followed by plating on CIN agar: 4.3% (1 out of 23) and 0.0% recovery rates, respectively. The mean concentration was 1.9×10(4)CFU/g, with a minimum of 1.0×10(2)CFU/g and a maximum of 5.8×10(4)CFU/g, thus demonstrating that tonsils may play an important role in contamination of pluck sets, carcasses, and slaughterhouse environment. Prevalence of virulence genes among the Y. enterocolitica 4/O:3 isolates was as follows: 12/22 (54.5%) for yadA, 21/22 (95.5%) for ail, 21/22 (95.5%) for inv and 22/22 (100%) for ystA. All Y. enterocolitica 4/O:3 isolates were sensitive to amoxicillin/clavulanic acid, ciprofloxacin and ceftazidime and resistant to ampicillin and cephalotin. High proportions of 4/O:3 isolates (95%) were sensitive to cefotaxime, gentamicin, kanamicin and nalidixic acid. High levels of resistance were observed to sulphonamide compounds (91%), streptomycin (64%) and chloramphenicol (55%). Multi-resistant isolates were very common; resistance to three or more antimicrobials was observed in 91% (20/22) of 4/O:3 isolates. High level of resistance to chloramphenicol was possibly due to coresistance to tiamphenicol, which was detected in 100% of the isolates. XbaI-PFGE detected four clusters among the 22 Y. enterocolitica 4/O:3 isolates. The most represented accounted for 77% (17/22) of the isolates, the second most common was found in 14% (3/22) of the isolates and the two other profiles were observed in single isolates. The comparison with a selection of human isolates supported the role of the pig as reservoir of 4/O:3 Y. enterocolitica.
- International journal of food microbiology.Int J Food Microbiol.2014 May 2;177:9-15. doi: 10.1016/j.ijfoodmicro.2014.02.005. Epub 2014 Feb 19.
- Tonsils from 150 pigs slaughtered at 270days or older were tested for Yersinia enterocolitica with different cultural methods. Samples were collected in three different abattoirs of Northern Italy between April and November 2012 and were analysed by direct plating on cefsulodin-irgasan-novobiocin (C
- PMID 24598512
- Within-batch prevalence and quantification of human pathogenic Yersinia enterocolitica and Y. pseudotuberculosis in tonsils of pigs at slaughter.
- Vanantwerpen G1, Van Damme I2, De Zutter L3, Houf K4.Author information 1Department Veterinary Public Health and Food Safety, Faculty Veterinary Medicine, Ghent University, Salisburylaan 133, B-9820 Merelbeke, Belgium. Electronic address: Gerty.Vanantwerpen@ugent.be.2Department Veterinary Public Health and Food Safety, Faculty Veterinary Medicine, Ghent University, Salisburylaan 133, B-9820 Merelbeke, Belgium. Electronic address: Inge.Vandamme@ugent.be.3Department Veterinary Public Health and Food Safety, Faculty Veterinary Medicine, Ghent University, Salisburylaan 133, B-9820 Merelbeke, Belgium. Electronic address: Lieven.Dezutter@ugent.be.4Department Veterinary Public Health and Food Safety, Faculty Veterinary Medicine, Ghent University, Salisburylaan 133, B-9820 Merelbeke, Belgium. Electronic address: Kurt.Houf@ugent.be.AbstractYersiniosis is a common bacterial zoonosis in Europe and healthy pigs are known to be the primary reservoir of human pathogenic Yersinia enterocolitica and Y. pseudotuberculosis. However, little information is available about the prevalence of these pathogens within pig batches at time of slaughter. The tonsils of 7047 fattening pigs, belonging to 100 farms, were aseptically collected immediately after evisceration in two Belgian slaughterhouses. The batch size varied between 70 and 930 pigs. On average, 70 pigs were sampled per batch. The tonsils were examined by direct plating on cefsulodin-irgasan-novobiocin (CIN) agar plates and the number of suspect Yersinia colonies was counted. Pathogenic Y. enterocolitica serotype O:3 were found in tonsils of 2009 pigs (28.5%), originating from 85 farms. The within-batch prevalence in positive farms ranged from 5.1 to 64.4%. The number of Y. enterocolitica in positive pigs varied between 2.01 and 5.98 log10 CFU g(-1) tonsil, with an average of 4.00 log10 CFU g(-1) tonsil. Y. pseudotuberculosis was found in seven farms, for which the within-batch prevalence varied from 2 to 10%. In five of these farms, both Y. enterocolitica and Y. pseudotuberculosis were simultaneously present. Human pathogenic Yersinia spp. are widespread in slaughter pig batches in Belgium as 87% of the tested batches were infected with these pathogens at the time of slaughter. The large variation of the prevalence between batches may lead to different levels of contamination of carcasses and risks for public health.
- Veterinary microbiology.Vet Microbiol.2014 Mar 14;169(3-4):223-7. doi: 10.1016/j.vetmic.2013.12.019. Epub 2014 Jan 10.
- Yersiniosis is a common bacterial zoonosis in Europe and healthy pigs are known to be the primary reservoir of human pathogenic Yersinia enterocolitica and Y. pseudotuberculosis. However, little information is available about the prevalence of these pathogens within pig batches at time of slaughter.
- PMID 24472227
- Transit effects on fecal Escherichia coli O157 prevalence and coliform concentrations in feedlot cattle.
- Aperce CC1, Alvarado CA, Miller KA, Van Bibber-Krueger CL, Drouillard JS.Author information 1Department of Animal Sciences and Industry, Kansas State University, Manhattan 66506-1600.AbstractOur objectives were to evaluate the effects of transportation and lairage on fecal shedding of Escherichia coli O157 (E. coli O157), total Escherichia coli, and total coliforms in feedlot cattle, and the relationships between E. coli O157 prevalence and total E. coli population. The study was a randomized complete block design with a split-plot including 2 treatments: a nontransported group, which remained in its pen at all times, and a transported group, which was transported for 1 h in a trailer and subsequently unloaded in a different pen. The experiment was repeated on 3 different days (blocking factor) with 20 steers/d (10 steers/treatment, 60 total). Fecal samples were taken pretransport (h 0) and after 4 and 28 h, lairage from freshly voided fecal pats were taken from each animal. One gram of feces was transferred to a PBS tube, serially diluted, and plated onto Petrifilm for enumeration of total coliforms. Another sample (1 g) was added to gram-negative broth containing cefixime, cefsulodin, and vancomycin, and subjected to immunomagnetic separation. Resulting beads were plated onto MacConkey agar with sorbitol, cefixime, and tellurite. Nonsorbitol fermenting colonies were selected and tested for indole production and O157 antigen agglutination. Results were confirmed using an API 20E kit. Prevalence of E. coli O157 was transient across blocks. E. coli O157 prevalence revealed no treatment × sampling time interaction (P = 0.179) or sampling time effect (P = 0.937), but a tendency for a treatment effect (P = 0.092). Numbers of E. coli and other coliforms did not change across blocks. No effect of treatment (P > 0.7) was observed on total E. coli concentrations or total coliforms. However, tendencies for treatment × sampling time interactions were observed on both populations (P < 0.08), as well as a tendency for a sampling time effect on total E. coli (P = 0.087) and an effect on total coliforms (P = 0.004). Prevalence of E. coli O157 was not correlated with the concentration of total E. coli (P = 0.954). Results suggest that shedding of E. coli O157 and coliforms can vary within a period of 29 h. Greater statistical power and pathogen quantification, as well as hide sampling and stress-related measurements, are needed to be able to conclude on the effects of transport stress on E. coli O157 prevalence and the changes undergone in pathogen shedding patterns after transportation.
- Journal of animal science.J Anim Sci.2014 Feb;92(2):676-82. doi: 10.2527/jas.2013-6712. Epub 2013 Dec 18.
- Our objectives were to evaluate the effects of transportation and lairage on fecal shedding of Escherichia coli O157 (E. coli O157), total Escherichia coli, and total coliforms in feedlot cattle, and the relationships between E. coli O157 prevalence and total E. coli population. The study was a rand
- PMID 24352970
Japanese Journal
- 近藤 千晶,林 芳樹,福田 麻里子 [他]
- 日本防菌防黴学会誌 = Journal of Antibacterial and Antifungal Agents 41(3), 125-132, 2013-03
- NAID 40019620660
- β-ラクタマーゼ非産生・アンピシリン耐性 Haemophilus influenzae のディスク拡散法を用いた簡易同定 : Cephalexin, Cefsulodin および Cefaclor ディスクの有効性
- 遠藤 隆一,山根 誠久,玉寄 美也子 [他],内堀 京子,仲宗根 勇
- 臨床病理 58(10), 963-971, 2010-10-25
- NAID 10029426324
- 免疫磁気ビーズ法と寒天重層法の併用による損傷したYersinia enterocolitica O:8の検出(公衆衛生学)
- 糀谷 英子,堀坂 知子,野村 義宏 [他],工藤 由起子,オカタニ アレシャンドレ トモミツ,岩田 剛敏,熊谷 進,林谷 秀樹
- The journal of veterinary medical science 68(3), 195-199, 2006-03
- … 損傷したYersinia enterocolitica O:8を河川水から効率的に検出するために,Y.enterocolitica O:8に対する抗体を用いた免疫磁気ビーズ法(IMS法)により,凍結により損傷させたO:8菌ならびに非損傷のO:8菌の検出率を比較した.cefsulodin-irgasan-novobiocin (CIN)寒天培地とVirulent Yersinia enterocolitica (VYE)寒天培地での寒天重層法は,損傷したO:8菌の検出率を向上させた.また,一般的にYersiniaの分離の際に用いられることの多いアルカリ処理法は,凍結損傷 …
- NAID 110004675724
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- forum Join the Word of the Day Mailing List For webmasters TheFreeDictionary Google Bing? Word / Article Starts with Ends with Text ... cefsulodin a second generation cephalosporin antibiotic with a narrow range of activity.
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★リンクテーブル★
[★]
- 英
- cefsulodin、cefsulodin sodium
- 関
- セフスロジンナトリウム
[★]
- 関
- cefsulodin