Amoxicillin is a drug , a semi-synthetic broad-spectrum antibiotic of the penicillin group. In its pharmacological properties, it is close to ampicillin , but, in contrast to it, has better oral bioavailability. Amoxicillin, like many other beta-lactam antibiotics, is subject to degradation by beta-lactamases produced by certain bacteria, so it is often used in combination with clavulanic acid , which acts as an inhibitor of such enzymes.
| Amoxicillin | |
|---|---|
| Amoxicillin | |
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| Chemical compound | |
| IUPAC | [2S- [2alpha, 5alpha, 6beta (S *)]] - 6 - [[Amino (4-hydroxyphenyl) acetyl] amino] -3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [ 3.2.0] heptane-2-carboxylic acid (including in the form of trihydrate or sodium salt). |
| Gross formula | C 16 H 19 N 3 O 5 S |
| Molar mass | 365.4 g / mol |
| Cas | |
| PubChem | |
| Drugbank | |
| Classification | |
| Farmakol. Group | Penicillins |
| ATX | |
| ICD-10 | |
| Pharmacokinetics | |
| Bioavailable | 95% |
| Plasma Protein Binding | 17-20% |
| Metabolism | Liver |
| The half-life. | 1-1.5 hours |
| Excretion | Kidneys : 50-78% |
| Dosage Forms | |
| granules for suspension for oral administration; capsules; powder for the preparation of a solution for intravenous and intramuscular administration (Amoxisar); powder for the preparation of a suspension for oral administration (Amosin, Gramox-D, Ospamox); powder substance (amoxicillin trihydrate); pills; dispersible tablets (Flemoxin Solutab); coated tablets | |
| Route of administration | |
| and | |
| Other names | |
| Amoxisar, Amoxicillin Sandoz, Amoxil, Amoxicillin Trihydrate, Amoxicillin DS, Amoxicillin-ratiopharm, Amoxicillin Sodium Sterile, Amosin, Amofast, Gonoform, Grunamoxm , “Gramox-D”, “Danemox”, “Moxipen”, “Ospamox”, “Purimox”, “Flemoxin Solutab”, “Hikontsil”, “Ecobol”. | |
History
The drug was developed by Beecham in 1972 and began to be sold by GlaxoSmithKline (the Beecham successor ) under the name Amoxil, however, the patent for the drug has already expired, and other manufacturers are selling it under several other names.
Properties
Amoxicillin belongs to the penicillin class. They are organic compounds, the basis of which is 6-aminopenicillanic acid , which is obtained from the cultures of the mold fungus Penicillium chrysogenum .
| 6-aminopenicillanic acid | ||
| Benzylpenicillin | Ampicillin | Amoxicillin |
As can be seen, amoxicillin differs from ampicillin in the presence of a hydroxyl group. This molecular change increases the absorption rate of the drug, due to which there is less destruction of the β-lactam ring and the creation of high concentrations in the blood in less time. Due to this, amoxicillin tablets can be prescribed instead of the injectable form of ampicillin, which provides economic benefits and ease of use.
In turn, ampicillin and amoxicillin differ from benzylpenicillin by the presence of an amino group, and therefore they are often referred to as a subgroup of aminopenicillins. Both drugs differ from benzylpenicillin by resistance to gastric juice, and, accordingly, by the presence of oral dosage forms, as well as a wider spectrum of action. The range of activity of aminopenicillins is expanded due to the action on some representatives of the enterobacteriaceae family: Escherichia coli , Shigella , Salmonella and proteus mirabilis , which are characterized by a low level of production of chromosomal β-lactamases. In this case, ampicillin is slightly superior to amoxicillin in activity against shigella. [one]
Pharmacology
Antibacterial bactericidal acid-resistant agent of a wide spectrum of action from the group of semisynthetic penicillins . It inhibits transpeptidase, disrupts the synthesis of peptidoglycan (a component of the bacterial cell wall ) during the period of division and growth, and causes lysis of bacteria. Active against aerobic gram - positive bacteria: Staphylococcus spp. (with the exception of penicillinase producing strains), Streptococcus spp. ; and aerobic gram - negative bacteria: Neisseria gonorrhoeae , Neisseria meningitidis , Escherichia coli , Shigella spp. Salmonella spp. Klebsiella spp. Penicillinase-producing microorganisms are resistant to amoxicillin. In a combination of amoxicillin with clavulanic acid , the resistance of beta-lactamases is neutralized. The action develops 15-30 minutes after administration and lasts 8 hours.
Absorption is fast, high (93%), food intake does not affect absorption, does not break down in the acidic environment of the stomach . When taken orally at a dose of 125 and 250 mg, the maximum concentration is 1.5-3 μg / ml and 3.5-5 μg / ml, respectively. The time to reach maximum concentration after oral administration is 1-2 hours. It has a large distribution volume - high concentrations are found in plasma , sputum, bronchial secretion (in the purulent bronchial secretion, the distribution is weak), pleural and peritoneal fluid, urine, the contents of skin blisters, lung tissue, intestinal mucosa , female genital organs, prostate gland, fluid middle ear , bone, adipose tissue, gall bladder (with normal liver function), fetal tissues. With an increase in the dose by 2 times, the concentration also increases by 2 times. The concentration in bile exceeds the concentration in plasma by 2-4 times. In amniotic fluid and vessels of the umbilical cord, the concentration of amoxicillin is 25-30% of the plasma level of a pregnant woman. It penetrates poorly through the blood-brain barrier , with inflammation of the meninges ( meningitis ), the concentration in the cerebrospinal fluid is about 20%. Communication with plasma proteins - 17%.
Partially metabolized to form inactive metabolites . The elimination half-life is 1-1.5 hours. It is excreted by 50–70% by the kidneys unchanged by tubular excretion (80%) and glomerular filtration (20%), by the liver 10–20%. A small amount is excreted in breast milk . The elimination half-life in premature infants and infants up to 6 months is 3-4 hours. In case of impaired renal function ( creatinine clearance less than or equal to 15 ml / min), the elimination half-life increases to 8.5 hours. Amoxicillin is removed by hemodialysis .
Indications
Bacterial infections caused by sensitive microflora: infections of the respiratory tract and ENT organs ( sinusitis [2] , pharyngitis , tonsillitis , acute otitis media ; bronchitis , pneumonia ), the genitourinary system ( pyelonephritis , pyelitis , cystitis , urethritis , gonorrhea , endometritis , cervicitis ) , the gastrointestinal tract ( peritonitis , enterocolitis , typhoid , cholangitis , cholecystitis , caused by H. pylori infections gastritis ), skin and soft tissue infections ( erysipelas , impetigo , secondarily infected dermatoses ), leptospirosis , listeriosis , Lyme disease ( Borrelia s ), dysentery , salmonellosis , salmonellonositelstvo , meningitis , endocarditis ( prophylaxis ), sepsis .
Contraindications
Hypersensitivity (including to other penicillins , cephalosporins , carbapenems ), allergic diathesis , bronchial asthma , hay fever , infectious mononucleosis , lymphocytic leukemia , liver failure , a history of gastrointestinal tract diseases (especially colitis associated with the use of antibiotics), lacquer period children and old age.
With caution - pregnancy , renal failure , a history of bleeding.
Application
Inside, before or after a meal.
As prescribed by the doctor.
Overdose
Symptoms: nausea , vomiting , diarrhea , impaired water-electrolyte balance (as a result of vomiting and diarrhea).
Treatment: gastric lavage, activated charcoal , saline laxatives, drugs to maintain water-electrolyte balance; hemodialysis .
Side effects
Allergic reactions: urticaria , flushing of the skin , erythema , angioedema , rhinitis , conjunctivitis ; rarely - fever , joint pain , eosinophilia , exfoliative dermatitis , erythema multiforme exudative , Stevens-Johnson syndrome ; reactions similar to serum sickness; in isolated cases - anaphylactic shock .
From the digestive system : dysbiosis , taste change, vomiting, nausea, diarrhea, stomatitis , glossitis , impaired liver function, a moderate increase in the activity of “liver” transaminases , pseudomembranous enterocolitis .
From the side of the nervous system : agitation, anxiety, insomnia , ataxia , confusion , behavior change, depression , peripheral neuropathy , headache , dizziness , convulsive reactions.
Laboratory indicators: leukopenia , neutropenia , thrombocytopenic purpura , anemia .
Other: shortness of breath , tachycardia , intertitial nephritis , vaginal candidiasis , superinfection (especially in patients with chronic diseases or low body resistance ).
Interactions
Antacids , glucosamine , laxatives, food, aminoglycosides - slow down and reduce absorption; ascorbic acid enhances absorption.
Bactericidal antibiotics (including aminoglycosides , cephalosporins , cycloserine , vancomycin , rifampicin ) - a synergistic effect; bacteriostatic drugs ( macrolides , chloramphenicol , lincosamides , tetracyclines , sulfonamides ) - antagonistic.
Increases the effectiveness of indirect anticoagulants (suppressing the intestinal microflora, reduces the synthesis of vitamin K and the prothrombin index ); reduces the effectiveness of estrogen-containing oral contraceptives , drugs, in the process of metabolism of which para-aminobenzoic acid is formed, ethinyl estradiol - the risk of bleeding "breakthrough".
Diuretics , allopurinol , oxyphenbutazone , phenylbutazone , non-steroidal anti-inflammatory drugs; drugs that block tubular secretion - reducing tubular secretion, increase concentration. Allopurinol increases the risk of developing a skin rash. Reduces clearance and increases the toxicity of methotrexate . Enhances the absorption of digoxin .
Instructions
With the course of treatment, it is necessary to monitor the state of the function of the blood, liver and kidneys.
The development of superinfection is possible due to the growth of microflora insensitive to amoxicillin, which requires a corresponding change in antibiotic therapy.
In the treatment of patients with bacteremia, the development of a bacteriolysis reaction ( Jarisch-Herxheimer reaction ) is possible. In patients with hypersensitivity to penicillins , cross-allergic reactions with cephalosporin antibiotics are possible.
When treating mild diarrhea with a course of treatment, antidiarrheal drugs that reduce intestinal motility should be avoided; kaolin or attapulgite-containing antidiarrheal agents may be used. For severe diarrhea, consult a doctor.
Treatment necessarily continues for another 48-72 hours after the disappearance of the clinical signs of the disease. With the simultaneous use of estrogen-containing oral contraceptives and amoxicillin, other or additional methods of contraception should be used if possible.
See also
Notes
- ↑ Belousov Yu. B. Group of penicillins . A Practical Guide to Anti-Infectious Chemotherapy . NIIAH SGMA (09/10/2002). Date of treatment November 2, 2015.
- ↑ Alekseeva N.S., Aznabaeva L.F., Antoniv V.F. et al. Otorhinolaryngology: nat. hands. / ed. V.T. Palchun. - GEOTAR-Media, 2009 .-- S. 469. - 954 p. - ISBN 9785970413586 .