Oleandomycin

From WikiMD's medical encyclopedia

Oleandomycin is an antibiotic that belongs to the macrolide class of antibiotics. It was first isolated from the bacterium Streptomyces antibioticus in the 1950s. Oleandomycin is primarily used in the treatment of bacterial infections caused by susceptible organisms.

History

Oleandomycin was discovered in 1955 by scientists at the pharmaceutical company Pfizer. It was one of the first macrolide antibiotics to be discovered, following the discovery of erythromycin in 1952.

Mechanism of Action

Like other macrolide antibiotics, oleandomycin works by inhibiting protein synthesis in bacteria. It binds to the 50S subunit of the bacterial ribosome, preventing the addition of new amino acids to the growing peptide chain.

Medical Uses

Oleandomycin is used to treat a variety of bacterial infections, including respiratory tract infections, skin infections, and sexually transmitted infections. It is particularly effective against Streptococcus pneumoniae and Staphylococcus aureus.

Side Effects

Common side effects of oleandomycin include nausea, vomiting, diarrhea, and abdominal pain. In rare cases, it can cause allergic reactions or liver damage.

Resistance

Resistance to oleandomycin can occur through several mechanisms, including modification of the antibiotic target, efflux of the antibiotic from the bacterial cell, and enzyme-mediated inactivation of the antibiotic.

See Also

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Types of antibacterials
Antibacterials that inhibit protein synthesis (J01A, J01B, J01F, J01G, QJ01XQ)
30S
50S
Oxazolidinone (initiation inhibitors)
Peptidyl transferase
MLS (transpeptidation/translocation)
Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams)
Narrow
spectrum
Extended
spectrum
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Monobactams
β-lactamase inhibitors
Polypeptides
Lipopeptides
- Insert into bacterial cell wall causing perforation and depolarization: Daptomycin - Surfactin
Other
- Inhibits PG elongation and crosslinking: Ramoplanin§
Intracellular
- Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)

- DADAL/AR inhibitors (Cycloserine)

- bactoprenol inhibitors (Bacitracin)
Other
- Hydrolyze NAM-NAG

- - lysozyme - Tyrothricin - - Gramicidin - - Tyrocidine - Isoniazid#

- Teixobactin


Antibacterials that inhibit nucleic acid (J01E, J01M)
Antifolates
(inhibit bacterial
purine metabolism,
inhibiting DNA/RNA synthesis)

DHFR inhibitors - 2,4-Diaminopyrimidine (Brodimoprim - Iclaprim - Ormetoprim - Pyrimethamine - Tetroxoprim - Trimethoprim)
Sulfonamides (DHPS inhibitors)
Short-acting - Sulfisomidine - Sulfamethizole - Sulfadimidine (Sulfamethazine - Sulfadimerazine - Sulfadimezine) - Sulfapyridine (Sulfasalazine) - Sulfafurazole (Acetyl sulfisoxazole) - Sulfanilamide (Prontosil) - Sulfathiazole (Phthalylsulfathiazole - Succinylsulfathiazole) - Sulfathiourea

Intermediate-acting - Sulfamethoxazole - Sulfadiazine - Sulfamoxole

Long-acting - Sulfadimethoxine - Sulfadoxine - Sulfalene - Sulfametomidine - Sulfametoxydiazine - Sulfamethoxypyridazine - Sulfaperin - Sulfamerazine - Sulfaphenazole - Sulfamazone

Other/ungrouped - Mafenide - Sulfacetamide - Sulfaclozine - Sulfadicramide - Sulfaguanidine - Sulfametrole - Sulfanitran

Combinations - Trimethoprim/sulfamethoxazole - Ormetoprim/sulfadimethoxine - Pyrimethamine/dapsone - Pyrimethamine/sulfadoxine

Other DHPS inhibitors - Acediasulfone - Dapsone - Solasulfone - Sulfoxone

Quinolones
(inhibit topoisomerase/DNA gyrase)

1st Generation - Cinoxacin - Flumequine - Nalidixic acid - Oxolinic acid - Pipemidic acid - Piromidic acid - Rosoxacin

Fluoroquinolones
2nd Gen - Ciprofloxacin - Ofloxacin - Enoxacin - Fleroxacin - Lomefloxacin - Nadifloxacin - Levonadifloxacin - Alalevonadifloxacin - Norfloxacin - Pefloxacin - Rufloxacin

3rd Gen - Levofloxacin - Balofloxacin - Grepafloxacin - Pazufloxacin - Sparfloxacin - Temafloxacin - Tosufloxacin

4th Gen - Besifloxacin - Delafloxacin - Gatifloxacin - Finafloxacin - Gemifloxacin - Moxifloxacin - Clinafloxacin - Garenoxacin - Prulifloxacin - Sitafloxacin - Trovafloxacin - Alatrofloxacin

Veterinary use - Danofloxacin - Difloxacin - Enrofloxacin - Ibafloxacin - Marbofloxacin - Orbifloxacin - Pradofloxacin - Sarafloxacin

Newer non-fluorinated - Nemonoxacin - Ozenoxacin Related (DNA gyrase) - Aminocoumarins (Novobiocin)

Anaerobic DNA inhibitors

Nitroimidazole derivatives - Secnidazole

RNA synthesis inhibitors

Rifamycins - Rifampicin - Rifabutin - Rifapentine - Rifaximin - Rifalazil
Lipiarmycins - Fidaxomicin


Antibacterials: others (J01X, D06AX)
Other/ungrouped


  • Oleandomycin chemical structure

  • Oleandomycin synthesis step 1

  • Oleandomycin synthesis step 2

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Contributors: Prab R. Tumpati, MD