Compound ID | 2012

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Tigecycline

Synonym(s): GAR-936

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. Active against Gram-positive bacteria and some Gram-negative bacteria (e.g. E. coli, Klebsiella, Acinetobacter)
Description: Semisynthetic minocycline derivative
Year first mentioned: 1999
Development status: Approved, off-patent
Chemical structure(s):
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Molecular weight: 585.65
Iso. SMILES: CC(C)(C)NCC(=O)NC1=CC(=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N(C)C)N(C)C
InChI Key: SOVUOXKZCCAWOJ-HJYUBDRYSA-N
Can. SMILES: CC(C)(C)NCC(=O)NC1=CC(=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N(C)C)N(C)C
InChI: InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36-37,40,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54686904
Guide to Pharmacology: tigecycline
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9258068/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9225766/

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