モキサラクタム
- 関
- latamoxef
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/10/14 02:41:40」(JST)
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Latamoxef
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| Systematic (IUPAC) name |
| (6R,7R)-7-{[carboxy(4-hydroxyphenyl)acetyl]amino}-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Clinical data |
| AHFS/Drugs.com |
International Drug Names |
| Legal status |
?
|
| Routes |
Intramuscular, intravenous |
| Pharmacokinetic data |
| Protein binding |
35 to 50% |
| Metabolism |
Nil |
| Half-life |
2 hours |
| Excretion |
Mostly renal, unchanged; also biliary |
| Identifiers |
| CAS number |
64952-97-2 Y |
| ATC code |
J01DD06 |
| PubChem |
CID 47499 |
| DrugBank |
DB04570 |
| ChemSpider |
43215 Y |
| UNII |
VUF6C936Z3 Y |
| KEGG |
D08109 Y |
| ChEBI |
CHEBI:599928 N |
| ChEMBL |
CHEMBL74632 Y |
| Chemical data |
| Formula |
C20H20N6O9S |
| Mol. mass |
520.474 g/mol |
SMILES
- O=C2N1/C(=C(\CO[C@@H]1[C@]2(OC)NC(=O)C(c3ccc(O)cc3)C(=O)O)CSc4nnnn4C)C(=O)O
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InChI
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InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1 Y
Key:JWCSIUVGFCSJCK-CAVRMKNVSA-N Y
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| N (what is this?) (verify) |
Latamoxef (or moxalactam) is an oxacephem antibiotic usually grouped with the cephalosporins. In oxacephems such as latamoxef, the sulfur atom of the cephalosporin core is replaced with an oxygen atom.
Latamoxef has been associated with prolonged bleeding time, and several cases of coagulopathy, some fatal, were reported during the 1980s.[1][2] Latamoxef is no longer available in the United States. As with other cephalosporins with a methylthiotetrazole side chain, latamoxef causes an antabuse reaction when mixed with alcohol. Additionally, the methylthiotetrazole side chain inhibits γ-carboxylation of glutamic acid; this can interfere with the actions of vitamin K.
It has been described as a third-generation cephalosporin.[3]
References
- ^ Weitekamp MR, Aber RC (1983). "Prolonged bleeding times and bleeding diathesis associated with moxalactam administration". JAMA 249 (1): 69–71. doi:10.1001/jama.249.1.69. PMID 6217353.
- ^ Brown RB, Klar J, Lemeshow S, Teres D, Pastides H, Sands M (1986). "Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients". Arch Intern Med 146 (11): 2159–64. doi:10.1001/archinte.146.11.2159. PMID 3778044.
- ^ Salem RR, McIndoe A, Matkin JA, Lidou AC, Clarke A, Wood CB (June 1987). "The hematologic effects of latamoxef sodium when used as a prophylaxis during surgical treatment". Surg Gynecol Obstet 164 (6): 525–9. PMID 3296254.
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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) |
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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
|
- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
|
|
|
β-lactamase resistant
|
- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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|
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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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|
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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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|
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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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|
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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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|
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4th (antipseudomonal)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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|
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5th
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- Ceftobiprole
- Ceftaroline fosamil
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Veterinary
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- 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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|
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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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|
|
| 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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|
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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
- IMP-51, a novel IMP-type metallo-β-lactamase with increased doripenem and meropenem hydrolyzing activities, in a carbapenem-resistant Pseudomonas aeruginosa clinical isolate.
- Tada T1, Nhung PH2, Miyoshi-Akiyama T3, Shimada K1, Phuong DM4, Anh NQ4, Ohmagari N5, Kirikae T6.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2015 Aug 17. pii: AAC.01611-15. [Epub ahead of print]
- A meropenem-resistant Pseudomonas aeruginosa isolate was obtained from a patient in a medical setting in Hanoi, Vietnam. The isolate was found to have a novel IMP-type metallo-β-lactamase, IMP-51, with an amino acid substitution (Ser262Gly) when compared with IMP-7. Escherichia coli expressing blaI
- PMID 26282421
- Mechanism of resistance and antibacterial susceptibility in extended-spectrum β-lactamase phenotype Klebsiella pneumoniae and Klebsiella oxytoca isolated between 2000 and 2010 in Japan.
- Sato T1, Hara T2, Horiyama T2, Kanazawa S2, Yamaguchi T2, Maki H2.
- Journal of medical microbiology.J Med Microbiol.2015 May;64(Pt 5):538-43. doi: 10.1099/jmm.0.000057. Epub 2015 Mar 26.
- Clinical isolates of Klebsiella pneumoniae and Klebsiella oxytoca collected from 20 Japanese medical facilities between 2000 and 2010 were analysed to evaluate the mechanisms of resistance and antibacterial susceptibilities to 14 antimicrobials. Overall, eight of 484 (1.6%) K. pneumoniae and 19 of 3
- PMID 25813819
- Prevalence and molecular characterization of CTX-M extended-spectrum β-lactamase-producing Escherichia coli from 2000 to 2010 in Japan.
- Hara T, Sato T, Horiyama T, Kanazawa S, Yamaguchi T, Maki H.
- The Japanese journal of antibiotics.Jpn J Antibiot.2015 Apr;68(2):75-84.
- The prevalence of extended-spectrum β-lactamase (ESBL) in Enterobacteriaceae has been increasing worldwide. The aims of this study were to determine the prevalence of ESBLs among clinical isolates of Escherichia coli obtained from 2000 to 2010 in Japan, and to characterize the sequence type (ST) an
- PMID 26182812
Japanese Journal
- Meropenem and moxalactam : Novel β-lactam antibiotics for efficient Agrobacterium-mediated transformation
- A Theoretical Study on the Substrate Deacylation Mechanism of Class C beta-Lactamase
- 畑 昌之,ハタ マサユキ,Hata Masayuki,Tanaka Yoshikazu,タナカ ヨシカズ,Fujii Yasuyuki,フジイ ヤスユキ,根矢 三郎,ネヤ サブロウ,Neya Saburo,星野 忠次,ホシノ チュウジ,Hoshino Chuji
- Journal of Physical Chemistry B 109(33), 16153-16160, 2005-08-25
- … In this study, the x-ray crystallographic structure of the inhibitor moxalactam-bound class C beta-lactamase (Patera et al., J. … 2000, 122, 10504-10512.) was utilized and moxalactam was changed into the substrate cefaclor. …
- NAID 80017590006
- メロペネムおよびモキサラクタムはアグロバクテリウム法によるタバコの形質転換効率を向上させる
Related Links
- Latamoxef (or moxalactam) is an oxacephem antibiotic usually grouped with the cephalosporins. In oxacephems such as ... "Prolonged bleeding times and bleeding diathesis associated with moxalactam administration". JAMA 249 (1): 69 –71.
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