Compound ID | 2010

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Oxytetracycline (terramycin)

Synonym(s): Geomycin

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: Natural product produced by Streptomyces.
Year first mentioned: 1952
Development status: Approved, off-patent, not available in most countries
Chemical structure(s):
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Molecular weight: 460.43
Iso. SMILES: C[C@@]1([C@H]2[C@@H]([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)O
InChI Key: OWFJMIVZYSDULZ-PXOLEDIWSA-N
Can. SMILES: C[C@]1(C2=CC=CC(=C2C(=C3[C@@H]1[C@@H]([C@H]4[C@@H](C(=O)C(=C([C@]4(C3=O)O)O)C(=O)N)N(C)C)O)O)O)O
InChI: InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25-26,28,30,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54675779
Guide to Pharmacology: oxytetracycline
Citation: https://www.researchgate.net/publication/51907943_The_history_of_the_tetracyclines

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