Ramoplanin

From Food & Medicine Encyclopedia

Ramoplanin is a lipoglycodepsipeptide antibiotic that is produced by the bacterium Actinoplanes sp. ATCC 33076. It is a potent inhibitor of bacterial cell wall synthesis and has been investigated for the treatment of Clostridium difficile infection and methicillin-resistant Staphylococcus aureus (MRSA) infections.

History[edit]

Ramoplanin was first isolated in 1984 from the fermentation broth of Actinoplanes sp. ATCC 33076. The compound was named after the RAmo group of the SAnofi pharmaceutical company, which discovered it.

Mechanism of action[edit]

Ramoplanin inhibits the final stages of peptidoglycan synthesis, which is essential for bacterial cell wall formation. It binds to the lipid intermediate Lipid II, preventing the transglycosylation and transpeptidation steps in peptidoglycan synthesis. This results in the inhibition of bacterial cell wall synthesis and ultimately leads to cell death.

Clinical use[edit]

Ramoplanin has been investigated for the treatment of infections caused by Gram-positive bacteria, including MRSA and C. difficile. It is not absorbed from the gastrointestinal tract and is therefore used for the treatment of gastrointestinal infections.

Resistance[edit]

Resistance to ramoplanin is rare. The main mechanism of resistance is the modification of the target Lipid II, which reduces the binding affinity of ramoplanin.

Safety and side effects[edit]

The most common side effects of ramoplanin are gastrointestinal disturbances, including nausea, vomiting, and diarrhea. Rare side effects include allergic reactions and changes in liver function tests.

See also[edit]

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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


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    Ramoplanin
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    Synthesis of Hpg3-Phe9 Subunit
  • Fmoc-L-HAsn(Trt)-Obn Preparation
    Fmoc-L-HAsn(Trt)-Obn Preparation
  • Synthesis of Depsipeptide Subunit
    Synthesis of Depsipeptide Subunit
  • Synthesis of Orn10-Gly14 Subunit
    Synthesis of Orn10-Gly14 Subunit
  • Preparation of Acyl Group
    Preparation of Acyl Group
  • Deprotection
    Deprotection

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