Potassium clavulanate, from Streptomyces clavuligerus

Base Information

• Chemical Name: Potassium clavulanate, from Streptomyces clavuligerus
• CAS No.: 61177-45-5
• Molecular Formula: C8H8KNO5
• Molecular Weight: 237.254
• Hs Code.: 2942000000
• Mol file: 61177-45-5.mol

Synonyms:SCHEMBL5789008;SCHEMBL5789010;Potassium clavulanate, from Streptomyces clavuligerus;Potassium clavulanate, VETRANAL(TM), analytical standard;4-Oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3-(2-hydroxyethylidene)-7-oxo-, potassium salt (1:1), (2R,3Z,5R)-

Chemical Property of Potassium clavulanate, from Streptomyces clavuligerus

Chemical Property:

• Appearance/Colour: Pale yellowish solid
• Vapor Pressure: 3.45E-14mmHg at 25°C
• Melting Point: >160 °C
• Boiling Point: 545.8 °C at 760 mmHg
• Flash Point: 283.9 °C
• PSA: 89.90000
• LogP: -2.49240
• Storage Temp.: 2-8°C
• Solubility.: Freely soluble in water, slightly soluble in ethanol (96 per cent), very slightly soluble in acetone.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 238.01177887
• Heavy Atom Count: 15
• Complexity: 324

Purity/Quality:

99% ^*data from raw suppliers

Clavulanic Acid, Potassium Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,Xi
• Hazard Codes: F,Xn,Xi
• Statements: 11-42/43-44-36-14
• Safety Statements: 8-16-22-36/37-45-43-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2N(C1=O)C(C(=CCO)O2)C(=O)O.[K]
• Isomeric SMILES: C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O.[K]
• Description: Potassium clavulanate is a semi-synthetic beta-lactamase inhibitor isolated from Streptomyces. The compound contains a beta-lactam ring and strongly binds to beta-lactamase at their new active site, which protects other beta-lactam antibiotics such as amoxicillin from beta-lactamase catalysis. Clavulanate is a β-lactamase inhibitor that is effective against Ambler class A β-lactamases (IC50 values range from 12 to 60 nM). While it is not an effective antibiotic by itself, clavulanate is commonly used with other antibiotics that would be inactivated by β-lactamases secreted by bacteria. It is often combined with amoxicillin and other penicillin-based antibiotics.
• Uses: Combination of potassium clavulanate and amoxicillin is normally used in medicine to treat numerous different infections caused by bacteria, for instance, pneumonia, sinusitis, ear infections, urinary tract infections, bronchitis, and skin infections. Potassium clavulanate can also combined with other penicillin-based antibiotics. A -Lactamase inhibitor, typically added to amoxicillin to increase its effectiveness Clavulanic Acid is a β-lactamase inhibitor, typically added to amoxicillin to increase its effectiveness. Clavulanic acid is a β-lactam antibiotic produced by several species of Streptomyces. The free acid degrades and is isolated and maintained as either the sodium or potassium salt. Clavulanate is a weak antibiotic, but is a potent inhibitor of β-lactamases. In combination with penicillin and cephalosporins, it shows potent synergistic activity. Clavulanic acid is a suicide inhibitor, covalently binding to a serine residue in the active site of the β-lactamase.
• Therapeutic Function: Beta-lactamase inhibitor

Technology Process of Potassium clavulanate, from Streptomyces clavuligerus

There total 2 articles about Potassium clavulanate, from Streptomyces clavuligerus which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

N,N'-diisopropylethylenediammonium diclavulanate → potassium clavulanate (61177-45-5)

Guidance literature:

With potassium 2-ethylhexanoate; In water; isopropyl alcohol; at 0 - 10 ℃; for 1h;

Reference yield: 75.0%

N,N,N',N'-tetramethylethylenediammonium diclavulanate → potassium clavulanate (61177-45-5)

Guidance literature:

With potassium 2-ethylhexanoate; In water; isopropyl alcohol; at 20 ℃; for 0.5h;

Reference yield: 10.0%

potassium clavulanate (61177-45-5) → 2,5-bis(2-hydroxyethyl)pyrazine (4744-51-8) + 3-ethyl-2,5-di-(2-hydroxyethyl)-pyrazine (86917-74-0)

Guidance literature:

With water; at 40 ℃; for 72h; pH 6.9;

Downstream raw materials:

(2R,3S,5R)-benzyl-1-aza-3-(2'-hydroxyethyl)-4-oxa-7-oxobicyclo<3,2,0>heptane-2-carboxylate

(2R,3R,5R)-benzyl-1-aza-3-(2'-hydroxyethyl)-4-oxa-7-oxobicyclo<3,2,0>heptane-2-carboxylate

2,5-bis(2-hydroxyethyl)pyrazine

3-ethyl-2,5-di-(2-hydroxyethyl)-pyrazine

Refernces