Potassium Clavulanate

(BANM, rINNM)
Synonyms: BRL-14151K; Clavulanate de Potassium; Clavulanate Potassium Kaliumklavulanaatti; Kaliumklavulanat; Kálium-klavulanát; Kaliumklavulanát; Potassium, clavulanate de; Potasu klawulanian.
Cyrillic synonym: Калия Клавуланат.

💊 Chemical information

Chemical formula: C8H8KNO5 = 237.3.
CAS — 61177-45-5.

Pharmacopoeias.

In Chin., Eur., Jpn, and US. Eur. also includes Diluted Potassium Clavulanate.

Ph. Eur. 6.2 (Potassium Clavulanate). The potassium salt of a substance produced by the growth of certain strains of Streptomyces clavuligerus or by any other means. A white or almost white, hygroscopic, crystalline powder. Freely soluble in water; slightly soluble in alcohol; very slightly soluble in acetone. A 1% solution in water has a pH of 5.5 to 8.0. Store in airtight containers at a temperature of 2° to 8°.

Ph. Eur. 6.2 (Potassium Clavulanate, Diluted; Kalii Clavulanas Dilutus). A dry mixture of potassium clavulanate and microcrystalline cellulose or anhydrous or hydrated colloidal silicon dioxide. A white or almost white, hygroscopic, powder. A suspension corresponding to 1% of potassium clavulanate in water has a pH of 4.8 to 8.0. Store in airtight containers.

USP 31

(Clavulanate Potassium). A white to off-white powder. Freely soluble in water; soluble in methyl alcohol with decomposition. Stability in aqueous solutions is not good, optimum stability at a pH of 6.0 to 6.3. pH of a 1% solution in water is between 5.5 and 8.0. Store in airtight containers.

💊 Profile

Clavulanic acid is produced by cultures of Streptomyces clavuligerus. It has a beta-lactam structure resembling that of the penicillin nucleus, except that the fused thiazolidine ring of the penicillins is replaced by an oxazolidine ring. In general, clavulanic acid has only weak antibacterial activity. It is a potent progressive inhibitor of plasmid-mediated and some chromosomal beta-lactamases produced by Gram-negative bacteria including Haemophilus ducreyi, H. influenzae, Neisseria gonorrhoeae, Moraxella catarrhalis (Branhamella catarrhalis), Bacteroides fragilis, and some Enterobacteriaceae. It is also an inhibitor of the beta-lactamases produced by Staphylococcus aureus. Clavulanic acid can permeate bacterial cell walls and can therefore inactivate both extracellular enzymes and those that are bound to the cell. Its mode of action depends on the particular enzyme inhibited, but it generally acts as a competitive, and often irreversible, inhibitor. Clavulanic acid consequently enhances the activity of penicillin and cephalosporin antibacterials against many resistant strains of bacteria. However, it is generally less effective against chromosomally mediated type 1 beta-lactamases; therefore, many Citrobacter, Enterobacter, Morganella, and Serratia spp., and Pseudomonas aeruginosa remain resistant. Some plasmid-mediated extended-spectrum beta-lactamases in Klebsiella pneumoniae, some other Enterobacteriaceae, and Ps. aeruginosa are also not inhibited by beta-lactamase inhibitors. Clavulanic acid is given as potassium clavulanate orally and by injection with amoxicillin (co-amoxiclav), and by injection with ticarcillin. Use of clavulanate with penicillins has been associated with the development of cholestatic jaundice and hepatitis and therefore the use of coamoxiclav has declined (see below). The UK CSM1 recommended that it should be reserved for bacterial infections likely to be caused by amoxicillin-resistant beta-lactamase-producing strains and that treatment should not usually exceed 14 days. It may be considered for the following main indications:
sinusitis, otitis media, recurrent tonsillitis
acute exacerbations of chronic bronchitis
bronchopneumonia
urinary-tract infections, especially when recurrent or complicated, but not prostatitis
septic abortion, pelvic or puerperal sepsis, and intra-abdominal sepsis
cellulitis, animal bites, and severe dental abscess with spreading cellulitis.
1. Committee on Safety of Medicines/Medicines Control Agency. Revised indications for co-amoxiclav (Augmentin). Current Problems 1997; 23: 8. Also available at: http:// www.mhra.gov.uk/home/idcplg?IdcService=GET_FILE& dDocName=CON2023230&RevisionSelectionMethod= LatestReleased (accessed 11/07/06)

💊 Preparations

BP 2008: Co-amoxiclav Injection; Co-amoxiclav Tablets; USP 31: Amoxicillin and Clavulanate Potassium for Oral Suspension; Amoxicillin and Clavulanate Potassium Tablets; Ticarcillin and Clavulanic Acid for Injection; Ticarcillin and Clavulanic Acid Injection.

Proprietary Preparations

Arg.: Optamox; Indon.: Aclam; Turk.: Amoksilav. Multi-ingredient: Arg.: Aclav; Amixen Clavulanico; Amoclav; Amoxi Plus; Amoxigrand Compuesto; Amoxitenk Plus; Bi Moxal; Bi Moxal Duo; Bioclavid; Bioxilina Plus; Clavulox; Clavulox Duo; Cloximar Duo; Darzitil Plus; Dibional; Fullcilina Plus†; Grinsil Clavulanico; Klonalmox; Austral.: Augmentin; Ausclav†; Clamohexal; Clamoxyl; Clavulin; Curam; Timentin; Austria: Amoclan; Amoxicillin comp; AmoxiClavulan; Amoxicomp; Amoxiplus; Amoxistad plus; Augmentin; Benclav; Benomox; Betamoclav; Clavamox; Clavex; Clavolek; Clavoplus; Clavulanex; CombAmox; Curam; Lanoclav; Lekamoxiclav; Oxyclav; Xiclav; Belg.: Amoclane; Augmentin; Clavucid; CoAmoxi; Co-Amoxilan†; Docamoclaf; Timentin; Braz.: Augmentin; Betaclav; Clav-Air†; Clavoxil†; Clavulin; Novamox; Policlavumoxil; Sigma Clav; Timentin; Canad.: Apo-Amoxi Clav; Clavulin; Novo-Clavamoxin; ratio-Aclavulanate; Timentin; Chile: Ambilan; Ambilan Bid; Amolex; Augmentin; Augmentin Bid; Clavinex; Clavinex Duo; Clavoxilina Bid; Cz.: Amoksiklav; Augmentin; Augmentin-Duo; Betaklav; Curam; Enhancin; Forcid; Klamoxin†; Megamox; Timentin; Denm.: Bioclavid; Spektramox; Fin.: Amoxin Comp; Augmentin; Bioclavid; Clapharin Comp; Clavurion; Clavuxal; Forcid; Spektramox†; Fr.: Augmentin; Ciblor; Claventin; Ger.: Abiclav; Amoclav; Amoxclav; Amoxi-Clavulan; Amoxi-saar plus; Amoxicillin comp; Amoxiclav; Amoxidura Plus; Amoxillat-Clav†; Amuclan†; Augmentan; Gr.: Augmentin; Bioclavid; Forcid; Frolicin; Fugentin; Moxiclav; Tenervan; Timentin; Hong Kong: Amoksiklav; Augmentin; Clamovid; Curam; Fleming; Moxiclav; QualiMentin; Timentin; Hung.: Aktil; Amoclan†; Amoclav; Augmentin; Augmentin-Duo; Augmentin-Extra; Clavumox†; Co-Amoxi; Curam; Enhancin; Forcid; India: Augmentin; Boostim; Novaclav; Nuclav; Rapiclav†; Timentin; Indon.: Amocomb; Ancla; Augmentin; Auspilic; Bellamox; Betaclav; Biditin; Capsinat; Clabat; Claneksi; Clavamox; Comsikla; Danoclav; Daxet; Dexyclav; Improvox; Lansiclav; Nufaclav; Nuvoclav; Prafamoc; Protamox; Surpas; Syneclav; Viaclav; Vulamox; Zumafen; Irl.: Augmentin; Clavamel; Germentin; Pinaclav; Timentin†; Israel: Amoxiclav; Augmentin; Clavamox; Timentin; Ital.: Abba; Anival; Augmentin; Clavucar†; Clavulin; Neoduplamox; Timentin; Xinamod; Malaysia: Augmentin; Cavumox; Clamovid; Curam; Enhancin; Moxiclav; Vestaclav†; Mex.: Acarbixin; Acimox AC; Alvi-Tec; Amobay CL; Amoxiclav; Amoxiclide; Apoclavox; Augmentin; Avuxilan; Clambusil; Clamoxin; Clavant; Clavucyd; Clavulin; Clavuser; Enhancin; Gramaxin; Maxint†; Moxlin CLV; Riclasip; Servamox CLV; Sinufin; Timentin; Valclan; Neth.: Amoclan; Amuclan; Augmentin; Bioclavid; Forcid; Timentin; Norw.: Bremide†; NZ: Alpha-Amoxyclav; Augmentin; Synermox; Timentin; Philipp.: Amoclav; Augmentin; Augmex; Augurcin; Bactiv; Bactoclav; Bioclavid; Clamovid; Claneksi; Claventin; Clavoxel; Clovimax; Enhancin; Exten; Klavic; Natravox; Proxiclav; Sullivan; Suplentin; Timentin; Valmocel; Xilanic; Pol.: Amoksiklav; Augmentin; Curam; Forcid; Ramoclav; Taromentin; Timentin; Port.: Amoclavam; Amplamox Plus; Augmentin; Betamox; Clavamox; Clavepen; Forcid; Noprilam; Penilan; Rus.: Amoclan (Амоклан); Amoksiklav (Амоксиклав); Augmentin (Аугментин); Flemoclav (Флемоклав); Medoclav (Медоклав); Panklav (Панклав); Rapiclav (Рапиклав); Timentin (Тиментин); S.Afr.: Adco-Amoclav; Augmaxcil; Augmentin; Bio-Amoksiclav; Clamentin; Clavumox; Co-Amoxyclav; Curam; Forcid; Moxyclav†; Ranclav; Rolab-Amoclav; Singapore: Amocla; Augmentin; Augmex†; Clamonex; Clamovid; Curam; Enhancin; Fugentin; Moxiclav; Spain: Amoclave; Amoxyplus; Ardineclav; Augmentine; Bigpen†; Burmicin; Clavepen; Clavucid; Clavumox; Duonasa; Eupeclanic†; Inmupen†; Kelsopen; Swed.: Bioclavid; Spektramox; Switz.: Amicosol; Augmentin; Aziclav; Clavamox; clavu-basan†; Co-Amoxi; Co-Amoxicilline; Timenten†; Thai.: Amocla; Amoksiklav; Augclav; Augmentin; Augpen; Cavumox; Curam; Klamoks; Moxiclav; Moxicle; Pencla; Ranclav; Turk.: Amoklavin; Augmentin; Bioment; Croxilex; Klamoks; Klavunat; Klavupen; UAE: Julmentin; UK: Amiclav†; Augmentin; Augmentin-Duo; Timentin; USA: Amoclan; Augmentin; Timentin; Venez.: Augmentin; Augmentin Bid†; Clavumox; Curam; Fulgram.
Published January 24, 2019.