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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/09/16 14:19:06」(JST)
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Azlocillin
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Systematic (IUPAC) name |
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
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Clinical data |
AHFS/Drugs.com |
International Drug Names |
Identifiers |
CAS Registry Number |
37091-66-0 Y |
ATC code |
J01CA09 |
PubChem |
CID: 6479523 |
DrugBank |
DB01061 Y |
ChemSpider |
4980416 Y |
UNII |
HUM6H389W0 Y |
KEGG |
D02339 Y |
ChEBI |
CHEBI:2956 Y |
ChEMBL |
CHEMBL1537 Y |
Chemical data |
Formula |
C20H23N5O6S |
Molecular mass |
461.491 g/mol |
SMILES
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O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)NC(=O)N2C(=O)NCC2)[C@H]4SC3(C)C
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InChI
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InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1 Y
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Key:JTWOMNBEOCYFNV-NFFDBFGFSA-N Y
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Y (what is this?) (verify) |
Azlocillin is an acylampicillin antibiotic with an extended spectrum of activity and greater in vitro potency than the carboxy penicillins. Azlocillin is similar to mezlocillin and piperacillin. It demonstrates antibacterial activity against a broad spectrum of bacteria, including Pseudomonas aeruginosa and, in contrast to most cephalosporins, exhibits activity against enterococci.
Contents
- 1 Spectrum of bacterial susceptibility
- 2 Synthesis
- 3 See also
- 4 References
Spectrum of bacterial susceptibility
Azlocillin is considered a broad spectrum antibiotic and can be used against a number of Gram positive and Gram negative bacteria. The following represents MIC susceptibility data for a few medically significant organisms.[1]
- Escherichia coli 1 μg/mL - 32 μg/mL
- Haemophilus spp. 0.03 μg/mL - 2 μg/mL
- Pseudomonas aeruginosa 4 μg/mL - 6.25 μg/mL
Synthesis
Azlocillin synthesis:
FR 2100682 eidem
U.S. Patent 3,933,795 [2]
Azlocillin synthesis 2:
[2][3]
An interesting alternative synthesis of azlocillin involves activation of the substituted phenylglycine analogue 1 with 1,3-dimethyl-2-chloro-1-imidazolinium chloride (2) and then condensation with 6-APA.
See also
References
- ^ http://www.toku-e.com/Assets/MIC/Azlocillin%20sodium%20salt.pdf
- ^ a b H. B. Konig et al., Eur. J. Med. Chem. - Chim. Ther. 17, 59 (1982).
- ^ doi:10.1021/jm00324a056
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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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Other |
- polymyxins/detergent
- depolarizing
- Hydrolyze NAM-NAG
- Gramicidin
- Isoniazid
- Teixobactin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of bacterial disease
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Description |
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Disease |
- Gram-positive firmicutes
- Gram-positive actinobacteria
- Gram-negative proteobacteria
- Gram-negative non-proteobacteria
- Cholera
- Tuberculosis
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Treatment |
- Antibiotics
- cell wall
- nucleic acid
- mycobacteria
- protein synthesis
- other
- Antibodies
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UpToDate Contents
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English Journal
- Phage lysin as a substitute for antibiotics to detect Mycobacterium tuberculosis from sputum samples with the BACTEC MGIT 960 system.
- Subramanyam B, Sivaramakrishnan GN, Dusthackeer A, Nagamiah S, Kumar V.SourceDepartment of Bacteriology, Tuberculosis Research Centre (Indian Council of Medical Research), Mayor V. R. Ramanathan Road,Chetput, Chennai, Tamil Nadu, India.
- Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases.Clin Microbiol Infect.2012 May;18(5):497-501. doi: 10.1111/j.1469-0691.2011.03601.x. Epub 2011 Aug 29.
- Phage lysin was evaluated as a substitute for antibiotics in sputum samples processed by a modified Petroff's method for the detection of Mycobacterium tuberculosis with the MGIT 960 system. One hundred and fifty sputum samples were processed, inoculated onto two slopes of Lowenstein-Jensen medium,
- PMID 21883661
- Direct drug susceptibility testing of Mycobacterium tuberculosis for rapid detection of multidrug resistance using the Bactec MGIT 960 system: a multicenter study.
- Siddiqi S, Ahmed A, Asif S, Behera D, Javaid M, Jani J, Jyoti A, Mahatre R, Mahto D, Richter E, Rodrigues C, Visalakshi P, Rüsch-Gerdes S.SourceBecton Dickinson, Sparks, Maryland, USA.
- Journal of clinical microbiology.J Clin Microbiol.2012 Feb;50(2):435-40. Epub 2011 Dec 7.
- Conventional indirect drug susceptibility testing of Mycobacterium tuberculosis with liquid medium is well established and offers time-saving and reliable results. This multicenter study was carried out to evaluate if drug susceptibility testing (DST) can be successfully carried out directly from pr
- PMID 22162558
Japanese Journal
- The Comparative Synergistic Activity of Amicacin,Gentamicin,Netilmicin and Azlocillin,Mezlocillin,Carbenicillin and Ticarcillin against Seratis Marcescens
- Fu Kwung-ping,Neu Harold C.
- Journal of Antibiotics 31(2), P135-140, 1978-02
- NAID 40005313651
Related Links
- azlocillin a ureidopenicillin with a broad spectrum of activity, but inactivated by β-lactamase. ... Disclaimer All content on this website, including dictionary, thesaurus, literature, geography, and other reference data is for informational ...
- az·lo·cil·lin sodium (ăz′lō-sĭl′ĭn) n. A derivative of penicillin used in treating infections caused by Pseudomonas aeruginosa, Escherichia coli, and Haemophilus influenzae. azlocillin sodium [az′lōsil′in] a semisynthetic penicillin antibiotic. ...
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