Amoxicillin/clavulanic acid: Difference between revisions

Amoxicillin/clavulanic acid

Combination of
Amoxicillin	Penicillin antibiotic
Clavulanic acid	Beta-lactamase inhibitor
Clinical data
Trade names	Augmentin, Clavulin, Amoclan, others[1]
Other names	co-amoxiclav, amox-clav
AHFS/Drugs.com	Monograph
MedlinePlus	a685024
License data	US DailyMed: Amoxicillin clavulanate
Pregnancy category	AU: B1
Routes of administration	By mouth, intravenous[2]
ATC code	J01CR02 (WHO) QJ01CR02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)[3] CA: ℞-only[4] UK: POM (Prescription only) US: ℞-only
Identifiers
CAS Number	74469-00-4 74428-36-7
PubChem CID	6435924
ChemSpider	4940608
KEGG	D06485
ChEMBL	ChEMBL1697738
CompTox Dashboard (EPA)	DTXSID40225477
Chemical and physical data
Formula	C24H27KN4O10S
Molar mass	602.66 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C.C1C2N(C1=O)C(C(=CCO)O2)C(=O)[O-].[K+]
InChI InChI=DWHGNUUWCJZQHO-ZVDZYBSKSA-M Key:1S/C16H19N3O5S.C8H9NO5.K/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7;10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4;/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24);1,6-7,10H,2-3H2,(H,12,13);/q;;+1/p-1/b;4-1-;/t9-,10-,11+,14-;6-,7-;/m11./s1
NY (what is this?)  (verify)

Amoxicillin/clavulanic acid, also known as co-amoxiclav or amox-clav, sold under the brand name Augmentin, among others, is an antibiotic medication used for the treatment of a number of bacterial infections.^[5] It is a combination consisting of amoxicillin, a β-lactam antibiotic, and potassium clavulanate, a β-lactamase inhibitor.^[5] It is specifically used for otitis media, streptococcal pharyngitis, pneumonia, cellulitis, urinary tract infections, and animal bites.^[5] It is taken by mouth or by injection into a vein.^[2]

Common side effects include diarrhea, vomiting, and allergic reactions.^[5] It also increases the risk of yeast infections, headaches, and blood clotting problems.^[2][6] It is not recommended in people with a history of a penicillin allergy.^[2] It is relatively safe for use during pregnancy.^[5]

Amoxicillin/clavulanic acid was approved for medical use in the United States in 1984.^[5] It is on the World Health Organization's List of Essential Medicines.^[7][8] The World Health Organization classifies amoxicillin/clavulanic-acid as critically important for human medicine.^[9] It is available as a generic medication.^[5] In 2021, it was the 115th most commonly prescribed medication in the United States, with more than 5 million prescriptions.^[10][11]

Amoxicillin/clavulanic acid is widely used to treat or prevent many infections caused by susceptible bacteria, such as:

• urinary tract infections
• respiratory tract infections
• skin and soft tissue infections
• sinus infections
• tonsillitis
• cat scratches
• infections caused by the bacterial flora of the mouth, such as:
  • dental infections
  • infected animal bites
  • infected human bites (including uncomplicated "clenched-fist" or "reverse-bite" injuries)^[12][13]

It is also used for tuberculosis that is resistant to other treatments.^[5] The World Health Organization recommends giving amoxicillin-clavulanate along with meropenem as one of the therapeutic options in drug resistant tuberculosis.^[14] However, across the spectrum of dosage of amoxicillin-clavulanate combination, the dose of clavulanate is constant at 125 mg, whereas the dose of amoxicillin varies at 250 mg, 500 mg and 875 mg. Thus the use of low dose amoxicillin-clavulanate in combination with meropenem may be used in part of treatment regime for drug resistant TB and this has been demonstrated in a clinical setting also. Its efficacy is attributed not to the amoxicillin component, but to the protective action of clavulanic acid over meropenem against beta-lactamase produced by the mycobacteria. Therefore, the minimum dosage of amoxicillin (250 mg) is recommended.^[15]

Possible side effects include diarrhea, vomiting, nausea, thrush, and skin rash. These do not usually require medical attention. As with all antimicrobial agents, antibiotic-associated diarrhea due to Clostridium difficile infection—sometimes leading to pseudomembranous colitis—may occur during or after treatment with amoxicillin/clavulanic acid.^[13]

Rarely, cholestatic jaundice (also referred to as cholestatic hepatitis, a form of liver toxicity) has been associated with amoxicillin/clavulanic acid. The reaction may occur up to several weeks after treatment has stopped, and usually takes weeks to resolve. It is more frequent in men, older people, and those who have taken long courses of treatment; the estimated overall incidence is one in 100,000 exposures.^[13] In the United Kingdom, co-amoxiclav carries a warning from the Committee on Safety of Medicines to this effect.^[12]

As all aminopenicillins, amoxicillin has been associated with Stevens–Johnson syndrome/toxic epidermal necrolysis, although these reactions are very rare.^[13][16]

British scientists working at Beecham (now part of GlaxoSmithKline), filed for patent protection for the drug combination in 1977, which was granted in 1982.^[17] It was sold under the brand name Augmentin.^[12][18]

Amoxicillin/clavulanic acid is the International Nonproprietary Name (INN) and co-amoxiclav is the British Approved Name (BAN).^{[citation needed]}

Many branded products indicate their strengths as the quantity of amoxicillin. Augmentin 250, for example, contains 250 mg of amoxicillin and 125 mg of clavulanic acid.^[12][19]

An intravenous preparation has been available in the UK since 1985,^[20] but no parenteral preparation is available in the US;^{[citation needed]} the nearest equivalent is ampicillin/sulbactam.^{[citation needed]}

Suspensions of amoxicillin/clavulanic acid are available for use in children. They must be refrigerated to maintain effectiveness.^{[citation needed]}

Amoxicillin/clavulanic acid is used in numerous animals for a variety of conditions:

• Dogs: Skin and soft tissue infections such as wounds, abscesses, cellulitis, superficial/juvenile and deep pyoderma due to susceptible strains of the following organisms: β-lactamase-producing Staphylococcus aureus, non-β-lactamase-producing Staphylococcus aureus, Staphylococcus spp., Streptococcus spp., and E. coli; and periodontal infections due to susceptible strains of both aerobic and anaerobic bacteria.^[21]

• Cats: Skin and soft tissue infections such as wounds, abscesses, and cellulitis/dermatitis due to susceptible strains of the following organisms: β-lactamase-producing Staphylococcus aureus, non-β-lactamase-producing Staphylococcus aureus, Staphylococcus spp., Streptococcus spp., E. coli, and Pasteurella spp; urinary tract infections (cystitis) due to susceptible strains of E. coli.^[21]

Bacterial antibiotic resistance is a growing problem in veterinary medicine. Amoxicillin/clavulanic acid is reported to be effective against clinical Klebsiella infections, but is not efficacious against Pseudomonas infections.^[22]