Compound ID | 2008

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Tetracycline

Class: Tetracycline

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor. Binds reversibly to the bacterial 30S ribosomal subunit preventing the aminoacyl tRNA from binding to the A site
Description: Semisynthetic derivative of the natural product aureomycin from Streptomyces aureofaciens which exhibited higher potency, favourable pharmacological profile, and better solubility
Year first mentioned: 1953
Highest development stage: Approved by FDA in 1954
Development status: Approved
Chemical structure(s):
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Molecular weight: 444.44
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)N)N(C)C)O
InChI Key: NWXMGUDVXFXRIG-WESIUVDSSA-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)N)N(C)C)O)O)O
InChI: InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54675776
Guide to Pharmacology: tetracycline
Citation: https://doi.org/10.1111/j.1749-6632.2011.06354.x

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