Clavulanic acid is an antibiotic isolated in 1974 from a gram-positive bacterium, Streptomyces clavuligerus and is always used in combination with amoxicillin and in its saline form clavulanate potassium for the treatment of infections that affect

• lower respiratory tract
• urinary tract
• some skin infections
• sinusitis
• otitis media
• soft tissues caused by organisms such as H. influenzae, M. catarrhalise S. aureus

and is used in surgical antimicrobial prophylaxis and postoperative infections in urology as a beta-lactamase inhibitor (which can inhibit the activity of most penicillins) by preventing degradation of the β-lactam ring, thereby ensuring that these damaging microorganisms are eradicated. Clavulanic acid reduces the susceptibility of beta-lactamase-positive strains to beta-lactamase-negative strains.

Clavulanic acid, which is found in liquid or solid form, does not possess its own specific antibacterial effects, but must always be accompanied by amoxicillin.

Applications

This study collected and analyzed clinical, laboratory, and therapeutic data from children with acute hematogenous osteomyelitis admitted to an Italian children's hospital between 2010 and 2019. The results suggest that amoxicillin-clavulanic acid could be an option for oral antibiotic therapy in children with acute hematogenous osteomyelitis (1).

This study collected and analyzed clinical, laboratory, and therapeutic data from children with acute hematogenous osteomyelitis admitted to an Italian children's hospital between 2010 and 2019. The results suggest that amoxicillin-clavulanic acid could be an option for oral antibiotic therapy in children with acute hematogenous osteomyelitis (2).

The amoxicillin/clavulanic acid combination is a broad-spectrum antibacterial treatment in pediatric patients against penicillin-resistant S. pneumoniae intermedia and against beta-lactamase-producing strains of Haemophilus influenzae and Moraxella catarrhalis that cause acute otitis media (3).

Breastfeeding is considered the gold standard for infant nutrition.Data from this research suggest that amoxicillin/clavulanic acid and cefuroxime may be safe during breastfeeding. Larger studies are needed to confirm these findings (4).

For transrectal ultrasound-guided biopsy of the prostate (TRUBP) lacombination of pivmecillinam and amoxicillin/clavulanic acid has been shown to be clinically, bacteriologically, and ecologically attractive prophylaxis compared with ciprofloxacin (5).

This study evaluated the clinical and microbiological outcomes of amoxicillin/clavulanic acid administration in urinary tract infections, and the results confirmed the validity and efficacy of oral administration, although some strains may develop resistance during therapy (6).

Clavulanic acid studies

Typical optimal characteristics of the commercial product clavulanic acid

• Molecular Formula: C₈H₉NO₅
• Molecular Weight: 199.162 g·mol⁻¹
• CAS: 58001-44-8
• UNII 23521W1S24
• EC Number: 261-069-2
• DSSTox Substance ID: DTXSID2022830
• MDL number  
• PubChem Substance ID  5280980 
• InChl=1S/C8H9NO5/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)/b4-1-/t6-,7-/m1/s1
• InChI Key      HZZVJAQRINQKSD-PBFISZAISA-N
• SMILES    C1C2N(C1=O)C(C(=CCO)O2)C(=O)O
• IUPAC (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• ChEBI    48947

Synonyms: 

• BRL 14151
• Clavulanate
• Clavulanic Acid, Monosodium Salt
• Clavulanic Acid, Monopotassium Salt
• Clavulanate Potassium

References______________________________________________________________________

(1) Tonelli F, Mazzei T, Novelli A, Mazzoni P, Ficari F; Italian Cooperative Group. Amoxicillin/clavulanic acid versus cefotaxime for antimicrobial prophylaxis in abdominal surgery: a randomized trial. J Chemother. 2002 Aug;14(4):366-72. doi: 10.1179/joc.2002.14.4.366. 

(2) Serrano E, Ferri I, Galli L, Chiappini E. Amoxicillin-Clavulanic Acid Empirical Oral Therapy for the Management of Children with Acute Haematogenous Osteomyelitis. Antibiotics (Basel). 2020 Aug 18;9(8):525. doi: 10.3390/antibiotics9080525.

(3) Easton J, Noble S, Perry CM. Amoxicillin/clavulanic acid: a review of its use in the management of paediatric patients with acute otitis media. Drugs. 2003;63(3):311-40. doi: 10.2165/00003495-200363030-00005.

(4) Benyamini L, Merlob P, Stahl B, Braunstein R, Bortnik O, Bulkowstein M, Zimmerman D, Berkovitch M. The safety of amoxicillin/clavulanic acid and cefuroxime during lactation. Ther Drug Monit. 2005 Aug;27(4):499-502. doi: 10.1097/01.ftd.0000168294.25356.d0. 

(5) Antsupova V, Nørgaard N, Bisbjerg R, Nygaard Jensen J, Boel J, Jarløv JO, Arpi M. Antibiotic prophylaxis for transrectal prostate biopsy-a new strategy. J Antimicrob Chemother. 2014 Dec;69(12):3372-8. doi: 10.1093/jac/dku293.

(6) Beytur A, Yakupogullari Y, Oguz F, Otlu B, Kaysadu H. Oral amoxicillin-clavulanic Acid treatment in urinary tract infections caused by extended-spectrum Beta-lactamase-producing organisms. Jundishapur J Microbiol. 2014 Dec 6;8(1):e13792. doi: 10.5812/jjm.13792.