Clavulaninsure

brl14151 · Clavulanate acid · 3008-b · C06662 · MM-14151 · Clavulansaeure · CLAVULANIC ACID · antibioticmm14151

https://huagongshe.com/de/chemical/5280980

Identifikatoren & physikalische Daten

CAS No.	58001-44-8
Summenformel	C8H9NO5
Durchschnittliche Molmasse	199,16 g/mol
Monoisotopische Masse	199,04807239 g/mol
SMILES	O=C(O)[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N21
InChIKey	HZZVJAQRINQKSD-PBFISZAISA-N
PubChem CID	5280980
ChEMBL	CHEMBL777
ChEBI	CHEBI:48947
EC No.	261-069-2
DTXSID	DTXSID2022830
Lokaler Name	Clavulaninsure

Chemische & physikalische Eigenschaften

XLogP	-1,2
Polarare Oberfläche (TPSA)	87,1
H-Brücken-Donoren	2
H-Brücken-Akzeptoren	5
Frei drehbare Bindungen	2
Schwere Atome	14
Formalladung	0
Komplexität	324
LogP (Verteilungskoeffizient)	-2.3-1.5
LogS	0.23
Löslichkeit	3.37e+02 g/LH2O : 50 mg/mL (251.05 mMNeed ultrasonic)
Siedepunkt	545.8545.8±50.0 °C(Predicted)
Schmelzpunkt	117.5-118117.5 - 118 °C
Physical Description	Solid
Dissociation Constants	2.7
Dichte	1.65±0.1 g/cm3(Predicted)
Lagerbedingungen	4°C, protect from light, stored under nitrogen
Aggregatzustand	Solid
pKa (Säurekonstante)	3.68±0.20(Predicted)
Farbe	Off-white to light yellow

Sicherheit & Vorschriften

Regulatorische Informationen	Clavulanic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Unerwünschte Wirkungen	Clavulanic acid, when administered with amoxicillin, can cause some mild gastrointestinal adverse effects. These include vomiting, nausea, loose stools, and discomfort. Antibiotic-associated diarrhea due to amoxicillin-clavulanic acid treatment is the most common adverse effect. There is a higher incidence of diarrhea when clavulanic acid is added to amoxicillin compared to amoxicillin alone. Diarrhea is more common in those taking a high dose of the extended-release form of clavulanic acid and amoxicillin. Drug-induced pancreatitis from clavulanic acid and amoxicillin has occurred in a few cases.When used for the treatment of urinary tract infections, this drug combination can cause candida vaginitis. Amoxicillin, in conjunction with clavulanic acid, is the most common cause of idiosyncratic drug-induced injury, specifically cholestatic liver injury, and this can lead to an increase in alkaline phosphatase and bilirubin levels. Since clavulanic acid administration is always in conjunction with amoxicillin, it is important to consider the adverse effects of amoxicillin alone as well. Hypersensitivity reactions to this drug combination, usually due to amoxicillin, can occur and result in dermatological reactions. Still, none of these allergic reactions are known to be due to clavulanic acid alone.
Toxizitätsübersicht	The toxicity of clavulanic acid alone is unknown. However, the toxic effects of amoxicillin/clavulanate have been reported. The most common toxic effect is an idiosyncratic drug-induced hepatic injury which leads to a mixed hepatocellular-cholestatic injury, and it is more common in older men. Amoxicillin-clavulanic acid is the most common cause of idiosyncratic drug-induced hepatic injury. Risk factors for hepatic injury include sex, cytochrome P450, and genetic polymorphisms. These risk factors should be examined before administering amoxicillin/clavulanate to reduce the risk of toxic and adverse effects. In addition to early diagnosis and discontinuation of the drug, N-acetylcysteine can be administered to minimize damage. Additionally, steroids can be given to decrease the time it takes to return hepatic enzymes and bilirubin levels to normal. Liver failure is also a rare but possible toxic effect of amoxicillin-clavulanic acid.
Alarmwort	Warnung
Gefahrenhinweise	Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Anwendungen & Verwendung

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