Tetracycline

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 aureomycin derivative.
Year first mentioned:	1953
Development status:	Approved, off-patent, not available in some countries

Chemical structure(s):
Canonical 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
Isomeric 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:	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
InChI Key:	NWXMGUDVXFXRIG-WESIUVDSSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/54675776

External links:
Guide to Pharmacology:	tetracycline
Main Source:	https://www.researchgate.net/publication/51907943_The_history_of_the_tetracyclines