Clavulaninsure

Clavulanic acid Struktur
58001-44-8
CAS-Nr.
58001-44-8
Bezeichnung:
Clavulaninsure
Englisch Name:
Clavulanic acid
Synonyma:
brl14151;Clavulanate acid;3008-b;C06662;MM-14151;Clavulansaeure;CLAVULANIC ACID;antibioticmm14151;Clavulanic acid USP/EP/BP;(2r-(2-alpha,3z,5-alpha))-xo
CBNumber:
CB9722501
Summenformel:
C8H9NO5
Molgewicht:
199.16
MOL-Datei:
58001-44-8.mol

Clavulaninsure Eigenschaften

Siedepunkt:
545.8±50.0 °C(Predicted)
Dichte
1.65±0.1 g/cm3(Predicted)
storage temp. 
4°C, protect from light, stored under nitrogen
Löslichkeit
H2O : 50 mg/mL (251.05 mM; Need ultrasonic)
pka
3.68±0.20(Predicted)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" />
Sicherheit
P261 Einatmen von Staub vermeiden.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Clavulaninsure Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

Clavulanic acid is a mold product with only weak intrinsic antibacterial activity, but it is an excellent irreversible inhibitor of most β-lactamases. It is believed to acylate the active site serine by mimicking the normal substrate. Hydrolysis occurs with some β-lactamases, but in many cases, subsequent reactions occur that inhibit the enzyme irreversibly. This leads to its classification as a mechanism-based inhibitor (or so-called suicide substrate). The precise chemistry is not well understood, but when clavulanic acid is added to ampicillin and amoxicillin preparations, the potency against β-lactamase–producing strains is markedly enhanced.

Verwenden

beta-lactamase inhibitor

Definition

ChEBI: Antibiotic isolated from Streptomyces clavuligerus. It acts as a suicide inhibitor of bacterial beta-lactamase enzymes.

Weltgesundheitsorganisation (WHO)

The amoxicillin/clavulanic acid combination should be reserved for infections likely or known to be caused by amoxicillin- resistant beta-lactamase producing strains. Amoxicillin/clavulanic acid is listed in the WHO Model List of Essential Drugs.

Antimicrobial activity

It exhibits broad-spectrum but low intrinsic activity, most MICs being in the range 16–128 mg/L. Enterobacteriaceae and Staph. aureus are among the more sensitive and Ps. aeruginosa the most resistant organisms. MICs of 8 mg/L against H. influenzae and 0.1–4 mg/L for penicillinase-producing N. gonorrhoeae are notable.

Allgemeine Beschreibung

Clavulanic acid was found in the culture broth of Streptomyces clavuligerus by Beecham Research Laboratories in 1976. It was the first β-lactamase inhibitor. This antibiotic shows weak antibacterial activity against grampositive and gram-negative organisms but strong inhibitory activity against the β-lactamase produced by ampicillin-resistant bacteria. Clavulanic acid is used orally in combination with amoxicillin and with ticarcillin by injection to enhance the activities of these antibiotics against resistant infections.

Pharmakokinetik

It exhibits broad-spectrum but low intrinsic activity, most MICs being in the range 16–128 mg/L. Enterobacteriaceae and Staph. aureus are among the more sensitive and Ps. aeruginosa the most resistant organisms. MICs of 8 mg/L against H. influenzae and 0.1–4 mg/L for penicillinase-producing N. gonorrhoeae are notable.

Clinical Use

Clavulanic acid is an antibiotic isolated from Streptomycesclavuligeris. Structurally, it is a 1-oxopenam lacking the6-acylamino side chain of penicillins but possessing a 2-hydroxyethylidene moiety at C-2. Clavulanic acid exhibitsvery weak antibacterial activity, comparable with that of6-APA and, therefore, is not useful as an antibiotic. Itis, however, a potent inhibitor of S. aureus β-lactamaseand plasmid-mediated β-lactamases elaborated by Gramnegativebacilli.
Combinations of amoxicillin and the potassium saltof clavulanic acid are available (Augmentin) in variousfixed-dose oral dosage forms intended for the treatment ofskin, respiratory, ear, and urinary tract infections causedby -lactamase–producing bacterial strains. These combinationsare effective against β-lactamase–producingstrains of S. aureus, E. coli, K. pneumoniae, Enterobacter,H. influenzae, Moraxella catarrhalis, and Haemophilusducreyi, which are resistant to amoxicillin alone. The oral bioavailability of amoxicillin and potassium clavulanate issimilar. Clavulanic acid is acid-stable. It cannot undergo penicillanicacid formation because it lacks an amide side chain.Potassium clavulanate and the extended-spectrum penicillinticarcillin have been combined in a fixed-dose, injectableform for the control of serious infections caused byβ-lactamase–producing bacterial strains. This combinationhas been recommended for septicemia, lower respiratory tractinfections, and urinary tract infections caused by β-lactamase–producing Klebsiella spp., E. coli, P. aeruginosa,and other Pseudomonas spp., Citrobacter spp., Enterobacterspp., S. marcescens, and S. aureus. It also is used in bone andjoint infections caused by these organisms. The combinationcontains 3 g of ticarcillin disodium and 100 mg of potassiumclavulanate in a sterile powder for injection (Timentin).

Clavulaninsure Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Clavulaninsure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 84)Lieferanten
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58001-44-8(Clavulaninsure)Verwandte Suche:


  • 4-Oxa-1-azabicyclo3.2.0heptane-2-carboxylic acid, 3-(2-hydroxyethylidene)-7-oxo-, (2R,3Z,5R)-
  • (2r-(2-alpha,3z,5-alpha))-xo
  • 3008-b
  • 4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,3-(2-hydroxyethylidene)-7-o
  • antibioticmm14151
  • 4,7-DIOXO-[3-(2-HYDROXYETHYLIDENE)]-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID
  • CLAVULANIC ACID
  • (2R,3Z,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabi-cyclo[3.2.0]heptane-2-carboxylic acid
  • (2R,3Z,5β)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • MM-14151
  • C06662
  • Clavulanic acid USP/EP/BP
  • brl14151
  • Clavulanate acid
  • Clavulansaeure
  • 58001-44-8
  • antibiotic
  • Antibiotics
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