Antibiotics having a β- lactam ring

types of fungi and bacteria. Usually they are used as

chemotherapy drugs.
There are antibiotics: antibacterial, antifungal, antineoplastic.
Depending on the method of obtaining: natural and semi-synthetic.

Erythromycin, Clarithromycin, Azithromycin;
Tetracyclines: Oxytetracycline, Doxycycline;
Nitrobenzene derivative: Chloramphenicol;
Aminoglycosides: Streptomycin, Gentamycin,

Amikacin, Neomycin;
Lincosamide antibiotics: Lincomycin, Clindamycin;
Glycopeptide antibiotics: Vancomycin.

from cell membranes: Polymyxins, Polyenes—Amphotericin B, Nystatin;
Inhibit protein synthesis: Tetracyclines,

Chloramphenicol, Erythromycin, Clindamycin,
Cause misreading of m-RNA code and affect permeability: Aminoglycosides;
Interfere with DNA function: Rifampicin

Bacteriostatic (stopping of the growth and division of bacterial cells)
Spectrum

of activity:
Narrow-spectrum: Penicillin G, Erythromycin
Broad-spectrum: Tetracyclines, Chloramphenicol

cephalosporins and chloramphenicol are irritant.
Systemic toxicity: Almost all AMAs produce

dose related and predictable organ toxicities. Some have a high therapeutic index—doses up to 100-fold range may be given without apparent damage to host cells. These include penicillins, some cephalosporins and erythromycin.
Others have a lower therapeutic index—doses have to be individualized and toxicity watched for, e.g.:
Aminoglycosides: 8th cranial nerve and kidney toxicity.
Tetracyclines: liver and kidney damage.
Chloramphenicol: bone marrow depression.

restricted to conditions where no suitable alternative is available (Polymyxin

B, Vancomycin, Amphotericin B)
Practically all AMAs are capable of causing hypersensitivity reactions. These are unpredictable and unrelated to dose.
Drug resistance (Natural resistance, Mutation, Gene transfer, Cross resistance)
Superinfection (Suprainfection).

1941.
Chemical structure of penicillins:
Thiazolidine ring;
β-lactam ring;

wall is composed of a polymer called peptidoglycan that consists

of glycan units joined to each other by peptide cross-links.
Ps. inhibit transpeptidase, but activate production of autolysins
Ps. interfere with the last step of bacterial cell wall synthesis (transpeptidation or cross-linkage). Cell lysis can then occur, either through osmotic pressure or through the activation of autolysins. The type of action is bactericidal.

Benzylpenicillin-benzatine (bicilline 1), Bicilline-5
For oral use (acid-stable): phenoxymethylpenicillin

and N. meningitidis;
B. anthracis, Corynebacterium diphtheriae,
Clostridia (tetani and others),
Listeria,

spirochetes (Treponema pallidum, Leptospira),
Actinomyces
Staph. Aureus produces penicillinase (a narrow spectrum β-lactamase which opens the β-lactam ring and inactivates Ps)

It penetrates well into the tissues, through BBB only in

inflammation. It is excreted by the kidneys in the active form.
Bicillins are poorly water soluble salts, they are administered only I.M. They are long-term acting drugs.
Phenoxymethylpenicillin is acid-stable, its bioavailability is 30-60%. It is less active. It is used for respiratory infections.

infections
Meningococcal infections (meningitis)
Gonorrhoea
Syphilis, Leptospirosis
Diphtheria
Tetanus and gas gangrene
Prophylactic uses (Benzathine penicillin

- bicillins): rheumatic fever, bacterial endocarditis

penicillins
a) Aminopenicillins: Ampicillin, Amoxicillin.
b) Act on Pseudomonas aeruginosa: Carbenicillin, Ticarcillin,

Piperacillin, Mezlocillin.
β-lactamase inhibitors: Clavulanic acid, Sulbactam, Tazobactam

against PnG sensitive organisms is weaker. They do not effect

on Treponema and Borrelia.
They are incompletely absorbed from oral route, especially if taken in empty stomach. Elimination occurs primarily by kidney, also partly by liver. They are administered 4-6 times a day p/o, IV, IM.
Uses: staphylococcal infections.

and Helicobacter pylori. They are active against all organisms sensitive

to PnG (except treponema). They are destroyed by penicillinase and inactive against staphylococci
They are absorbed from GIT (absorption of amoxicillin is better). They are eliminated by kidneys and they are partly excreted in bile and reabsorbed—enterohepatic circulation occurs.
Ampicillin is used 4-6 times a day,
Amoxicillin – 3 times a day.

dysentery;
Cholecystitis;
H. pylori-infections (ulcer)
Septicaemias and mixed infections

indole positive Proteus, Bacteroides, many Enterobacteriaceae, Klebsiella,.
They are neither penicillinase-resistant

nor acid resistant. They are inactive orally and are excreted rapidly in urine. They are used 4-6 times a day.
Uses: serious infections caused by Pseudomonas or Proteus, e.g. burns, urinary tract infection, septicaemia.

tazobactam): amoxicillin + clavulanic acid
Clavulanic acid has a structural similarity

with penicillins and it is subject to destruction. Antibiotic retains its structure.
Uses: skin and soft tissue infections, intraabdominal and gynaecological sepsis, urinary, biliary and respiratory tract infections.

dyspepsia, phlebitis, infiltrates)
Neurotoxicity (seizures)
Dysbacteriosis, superinfection
Resistance of microorganisms
Thrombosis and embolism (bicillin)
Carboxypenicillins

and Ureidopenicillins: violation of blood (leukopenia, thrombocytopenia), interstitial nephritis, disorders of coagulation

by the chemical attachment of side chains to 7-aminocephalosporanic acid.




They

act bactericidally; inhibit transpeptidase, disrupt the synthesis of peptidoglycan, violate the synthesis of the cell wall.

to the staphylococcal penicillinase and also have activity against Proteus

mirabilis, E. coli, and K. pneumoniae. These drugs are destroyed by cephalosporinase.
Cephalexin (p/o), cefazolin (IM,IV) pass into the tissues, go through the BBB poorly, they are excreted by the kidneys by tubular secretion, appointed 3-6 times a day.

organisms: H. influenzae, Enterobacter aerogenes, and some Neisseria species, whereas

activity against gram-positive organisms is weaker.
Cefuroxime, cefaclor pass through the BBB in inflammation. They are excreted by the kidneys by filtration. They are appointed 3 times a day.

potent than first-generation cephalosporins against MSSA, have enhanced activity against

gram-negative bacilli. They act on Pseudomonas aeruginosa, Bacteroides, they are resistant to cephalosporinase.
They distribute very well into body fluids.
Adequate therapeutic levels in the CSF, regardless of inflammation, are achieved.
They are administered 1-2 times a day.

gram-positive), they are resistant to β-lactamases, but do not act

on Bacteroides.
They are administered IM, IV 2-4 times a day. They do not pass through the BBB. They are excreted by kidneys.

for the treatment of serious infections. They are injected IV

2-3 times a day.

organisms, especially Klebsiella, Proteus, Enterobacter, Serratia;
Penicillinase producing staphylococcal infections;
Septicaemias caused

by gram-negative organisms;
Surgical prophylaxis;
Meningitis;
Gonorrhoea;
Mixed aerobic-anaerobic infections;
Infections of GIT

phlebitis, dyspeptic disorders;
Nephrotoxicity (1 generation);
Neurotoxicity (nystagmus, hallucinations, seizures);
Hematotoxicity (thrombocytopenia, neutropenia,

reduction of blood clotting);
Alcohol intolerance(diarrhea, nausea, tachycardia, redness of the face);
Dysbacteriosis. Diarrhoea.

resistant to the action of most β-lactamases.
It is administered IV

and IM.
Side effects: phlebitis, skin rash, abnormal liver function tests.
This drug may be a safe alternative for treating patients who are allergic to other penicillins, cephalosporins, or carbapenems.

fragilis., Cl.difficile.
They are resistant to most β-lactamases; inhibit penicillinase producing

staphylococci.
Uses: serious hospital-acquired respiratory, urinary, abdominal, pelvic, skin and soft tissue infections.
Side effects: nephrotoxicity, diarrhoea, vomiting, skin rashes and other hypersensitivity reactions.

lactone structure to which one or more sugars are attached.
1

generation - Erythromycin
2 generation - Clarithromycin, Roxithromycin, Spiramycin, Josamycin
3 generation (azalid) - Azithromycin (Sumamed)
Type of action – bacteriostatic.

subunit of the bacterial ribosome, thus inhibiting translocation steps of

protein synthesis. They may also interfere with other steps, such as transpeptidation.

gonorrhoeae, Str. viridans, N. meningitidis
Mycoplasma, H. influenzae, B. pertussis,

Clostridia, C. diphtheriae and Listeria,
Campylobacter, Legionella, Rickettsiae
Gardnerella vaginalis
Chlamydia trachomatis

also effective against Haemophilus influenzae, Helicobacter pylori, Moraxella, Legionella, Mycoplasma

pneumoniae, toxoplasms.
Azithromycin: H. influenzae, Mycoplasma, Chlamydia pneumoniae, Legionella, Moraxella, Campylobacter, Ch. trachomatis, Mycobacterium avium, N. gonorrhoeae.

the tissue. They do not pass through the BBB They

are excreted partially by the kidneys, partly by the liver (the bile).
They are used: Erythromycin 4-6 times a day.
2 generation-2 times a day.
Azithromycin is captured by leukocytes, passes with them into the focus of inflammation.
Its concentration is higher in the focus of inflammation than that in the blood.
It is eliminated slowly from the focus of inflammation and the body and used once a day.

mastitis),
Conjunctivitis,
Pneumonia caused by chlamydia, Mycoplasma, Legionella, Moraxella),
Sexually transmitted infections (syphilis,

gonorrhea),
Urogenital infection (prostatitis, adnexitis, urethritis, vaginitis).
Cholecystitis, cholangitis.
Ulcer.

Allergic reaction,
Arrhythmias,
Deafness.

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