61177-45-5 Usage
Description
Potassium clavulanate is a semi-synthetic beta-lactamase inhibitor derived from Streptomyces. It contains a beta-lactam ring and acts as a potent inhibitor of beta-lactamases, protecting other beta-lactam antibiotics such as amoxicillin from enzymatic degradation. Although it has weak antibiotic activity when administered alone, it is commonly used in combination with other penicillin-based antibiotics to enhance their effectiveness against bacterial infections.
Uses
Used in Medicine:
Potassium clavulanate is used as an A -Lactamase inhibitor for increasing the effectiveness of amoxicillin and other penicillin-based antibiotics. It is particularly effective against Ambler class A β-lactamases, with IC50 values ranging from 12 to 60 nM. The combination of potassium clavulanate and amoxicillin, available under the trade name Augmentin, is used to treat various bacterial infections, including pneumonia, sinusitis, ear infections, urinary tract infections, bronchitis, and skin infections.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, potassium clavulanate is used as a potent synergistic agent when combined with penicillin and cephalosporins. It acts as a suicide inhibitor, covalently binding to a serine residue in the active site of the beta-lactamase, thus preventing antibiotic inactivation by microbial lactamases. This combination enhances the therapeutic outcomes and bioavailability of the antibiotics, making it a valuable component in the development of new drug formulations.
Chemical Properties:
Potassium clavulanate is a pale yellowish solid with potent inhibitory effects on beta-lactamases, making it an essential component in the fight against antibiotic-resistant bacteria.
Cautions
Before taking a combination of potassium clavulanate with any other penicillin-based antibiotic, one should discuss with medical providers and let them know whether they have severe kidney disease, jaundice or liver problems. In addition, it is important to inform the physician if an individual is allergic to penicillin or cephalosporin antibiotic, such as Amoxil, Levaquin, omnicef, and cefzil.
Although it is not clear with this drug may harm an unborn baby, it is important to inform the physician if one is pregnant or intending to become pregnant. In addition, studies have indicated that pass into breast milk, thus may affect a nursing infant. As such, it is important to inform the doctor if one is breast-feeding. Children should never be given potassium clavulanate without consulting a physician.
Administration
The drug should be take according to the prescription given by the doctor. Potassium clavulanate is taken orally every 12 hours at the start of a meal to minimize side effects such as stomach upset.
The extended release of the potassium clavulanate tablet must never been chewed or crushed. The medicine should be swallowed as a whole while the chewable tablet must be chewed before swallowing it. Before measuring a dose, the liquid medicine must be shaken well. The medicine should be only used for the full length of prescribed time. It is important not to skip any doses as it may lead to further infection that is resistant to antibiotics.
The medicine should never be taken with or just after ingesting a high-fat meal as it will make it harder for the body to absorb the drug.
Side Effects
Potassium clavulanate may cause diarrhea that is bloody or watery when taken in combination with amoxicillin. It may also lead to severe stomach pain, swelling of the face or tongue, loss of appetite, fever, dark color urine, weakness, or confusion. The medicine may cause jaundice or yellowing of skin as well as vaginal itching or discharge.
Originator
Clavulanate
,potassium
Lek
Manufacturing Process
Clavulanic acid may be obtained by aerobic cultivation of Streptomyces
clavuligerus in conventional nutrient media at, for example, about 25°-30°C
under roughly neutral conditions.
Cultivation of Streptomyces clavuligeru:
Streptomyces clavuligerus was cultivated at 26°C on agar slopes containing
1% Yeatex (yeast extract) ("Yeatex" is a Registered Trade mark), 1% glucose
and 2% Oxoid agar No. 3, pH 6.8. A sterile loop was used to transfer
mycelium and spores from the slope into 100 ml of a liquid medium in a 500
ml Ehrlenmeyer flask. The liquid medium had the following composition: Oxoid
Malt Extract 10g/L, Oxoid Bacteriological Peptone 10g/L, Glycerol 20 g/L, Tap
water 1 L.
The medium was adjusted to pH 7.0 with sodium hydroxide solution and 100
ml volumes dispensed into flasks which were closed with foam plugs prior to
autoclaving at 15 lb/sq.in. for 20 min. An inoculated seed flask was shaken for
3 days at 26°C on a rotary shaker with a 2 inch throw and a speed of 240
r.p.m.
Production stage flasks containing the liquid medium described above were
inoculated with 5% vegetative inoculum and grown under the same conditions
as the seed flask.
Clavulanic acid may be extracted from the culture medium. Normally the cells
of the Streptomyces clavuligerus are first removed from culture medium by
filtration or centrifugation. Then clavulanic acid is extracted into an organic
solvent, for example, n-butanol or ethyl acetate, or n-butyl acetate, or methyl
isobutyl ketone. Then n-butanol fraction are treated with new aqueous phase
using potassium hydrogen carbonate and then this aqueous phase is washed
with n-butanol. This aqueous extract, after separation of the phases, is
concentrated under reduced pressure. Freeze-drying at -20°C may also beemployed to provide a solid crude preparation of the potassium Z-(2R,5R)-3-
(β-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3,2,0]heptane-2-carboxylate
(clavulanate potassium).
Therapeutic Function
Beta-lactamase inhibitor
Check Digit Verification of cas no
The CAS Registry Mumber 61177-45-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,1,1,7 and 7 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 61177-45:
(7*6)+(6*1)+(5*1)+(4*7)+(3*7)+(2*4)+(1*5)=115
115 % 10 = 5
So 61177-45-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO5.K/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4;/h1,6-7,10H,2-3H2,(H,12,13);/q;+1/p-1/b4-1-;/t6-,7-;/m1./s1
61177-45-5Relevant articles and documents
Preparation of clavulanate salts
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Page column 5, (2008/06/13)
Provided is a process for purification of clavulanic acid or a pharmaceutically acceptable salt or ester thereof, including adding an additional solvent to a solution of clavulanic acid in water immiscible solvent; contacting the solution with an amine; isolating the amine salt of the clavulanic acid formed; and converting the amine into clavulanic acid or a pharmaceutically acceptable salt or ester thereof.
