Compound ID | 1974

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Clindamycin

Class: Lincosamide

Spectrum of activity: Gram-positive
Details of activity: Binds to the rRNA of the bacterial 50S ribosome subunit, overlapping with the binding sites of the oxazolidinone, pleuromutilin, and macrolide antibiotics, thus blocking ribosomal translocation. Bacteriostatic activity against Gram-positive bacteria including many MRSA strains.
Description: Semisynthetic lincosamide derived from lincomycin. Oral and parenteral application. Alternative treatment of protozoal diseases and anaerobic bacterial infections.
Year first mentioned: 1964
Development status: Approved, off-patent
Chemical structure(s):
Click here for structure editor
Molecular weight: 424.98
Iso. SMILES: CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl
InChI Key: KDLRVYVGXIQJDK-AWPVFWJPSA-N
Can. SMILES: CCC[C@@H]1C[C@@H](C(=O)N[C@H]([C@H](C)Cl)[C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)N(C)C1
InChI: InChI=1S/C18H33ClN2O5S/c1-5-6-10-7-11(21(3)8-10)17(25)20-12(9(2)19)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,22-24H,5-8H2,1-4H3,(H,20,25)/t9-,10+,11-,12+,13-,14+,15+,16+,18+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/446598
Guide to Pharmacology: clindamycin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/33278179/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9137603/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3250868/

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