Generated by DeepSeek V3.2| Augmentin | |
|---|---|
| IUPAC name | (2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; potassium |
| Tradename | Augmentin, Co-amoxiclav, others |
| Drugs.com | Monograph |
| MedlinePlus | a685024 |
| Licence US | Augmentin |
| Routes of administration | By mouth, intravenous |
| CAS number | 74469-00-4 |
| ATC prefix | J01 |
| ATC suffix | CR02 |
| PubChem | 6435923 |
| ChemSpiderID | 10482160 |
| UNII | 8X42RQ089J |
| ChEBI | 61031 |
| Chemical formula | C₁₆H₁₉N₃O₅S·C₈H₉NO₅·K |
| Molar mass | 699.95 g·mol⁻¹ |
Augmentin. It is a combination antibiotic medication used to treat a variety of bacterial infections. The drug combines the broad-spectrum penicillin amoxicillin with the beta-lactamase inhibitor clavulanic acid, which protects the amoxicillin from enzymatic degradation by resistant bacteria. This formulation extends its effectiveness against many pathogens that would otherwise be resistant to amoxicillin alone, making it a common choice for infections in areas like the respiratory tract, skin, and urinary system.
Augmentin is indicated for the treatment of infections caused by susceptible strains of bacteria. Common uses include sinusitis, otitis media, community-acquired pneumonia, and cellulitis. It is also effective against certain urinary tract infections and animal bite wounds, where organisms like Pasteurella multocida may be present. The combination is particularly valuable in treating infections where beta-lactamase-producing organisms such as Staphylococcus aureus or Haemophilus influenzae are suspected, as documented in guidelines from institutions like the World Health Organization and the Infectious Diseases Society of America.
The most common adverse effects are related to the gastrointestinal tract, including diarrhea, nausea, and vomiting. A specific concern is the development of Clostridioides difficile-associated diarrhea, which can range from mild to severe colitis. Allergic reactions, ranging from skin rash to rare but serious anaphylaxis, can occur, particularly in individuals with a known hypersensitivity to penicillin. Less frequently, abnormalities in liver function tests and jaundice have been reported, typically with prolonged use.
Pharmacologically, the amoxicillin component works by inhibiting bacterial cell wall synthesis, binding to penicillin-binding proteins. The clavulanic acid component is a beta-lactam compound with minimal intrinsic antibacterial activity but potent inhibitory action against many beta-lactamase enzymes produced by bacteria, including those encoded by the TEM-1 gene. This inhibition prevents the degradation of amoxicillin. The combination is well-absorbed orally, with peak concentrations occurring approximately one to two hours after administration, and is excreted largely unchanged by the kidney.
The development of Augmentin was a direct response to the growing problem of bacterial antibiotic resistance mediated by beta-lactamase enzymes. Researchers at the British pharmaceutical company Beecham Group pioneered the combination in the late 1970s. The key innovation was the discovery and isolation of clavulanic acid from the soil bacterium Streptomyces clavuligerus. This work led to the drug's introduction to the United Kingdom market in 1981 and subsequent approval by the United States Food and Drug Administration in 1984, marking a significant advance in antimicrobial chemotherapy.
Augmentin is available under many brand names globally, including Co-amoxiclav. It is on the World Health Organization's List of Essential Medicines. Its widespread use has been a subject of stewardship programs aimed at curbing antimicrobial resistance, promoted by bodies like the Centers for Disease Control and Prevention. The drug has been involved in notable legal cases, such as patent disputes between GlaxoSmithKline and generic manufacturers. Furthermore, its role in treating common childhood infections has made it a familiar medication in many households, influencing public perception of antibiotic treatment.
Category:World Health Organization essential medicines Category:Combination drugs Category:Beta-lactam antibiotics