Compound ID | 2016

Update compound information

Lymecycline

Class: Tetracycline

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Inhibits protein synthesis by binding reversibly to the bacterial 30S ribosomal subunit and preventing the aminoacyl tRNA from binding to the A site of the ribosome. Wide spectrum including protozoae, e.g. Plasmodium
Description: Semisynthetic tetracycline derivative. Used for topical treatment of acne vulgaris.
Year first mentioned: 1961
Development status: Approved, off-patent, not available in most countries
Chemical structure(s):
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Molecular weight: 602.63
Iso. SMILES: C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)NCNCCCC[C@@H](C(=O)O)N)N(C)C)O
InChI Key: PZTCVADFMACKLU-UEPZRUIBSA-N
Can. SMILES: C[C@]1(C2=CC=CC(=C2C(=C3[C@@H]1C[C@H]4[C@@H](C(=O)C(=C([C@]4(C3=O)O)O)C(=O)NCNCCCC[C@@H](C(=O)O)N)N(C)C)O)O)O
InChI: InChI=1S/C29H38N4O10/c1-28(42)13-7-6-9-17(34)18(13)22(35)19-14(28)11-15-21(33(2)3)23(36)20(25(38)29(15,43)24(19)37)26(39)32-12-31-10-5-4-8-16(30)27(40)41/h6-7,9,14-16,21,31,34-35,38,42-43H,4-5,8,10-12,30H2,1-3H3,(H,32,39)(H,40,41)/t14-,15-,16-,21-,28+,29-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54707177
Guide to Pharmacology: lymecycline
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1817106/pdf/brmedj02580-0039.pdf
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8459281/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8510691/

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