Chlortetracycline, Aureomycin

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. First drug of the tetracycline class. Still used for topical treatment.
Year first mentioned:	1945
Development status:	Approved, off-patent, not available in most countries

Chemical structure(s):
Canonical 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)Cl)O)O)O)C(=O)N)N(C)C)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=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O
InChI:	InChI=1S/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26-27,30,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1
InChI Key:	DHPRQBPJLMKORJ-XRNKAMNCSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/54675777

External links:
Guide to Pharmacology:	chlortetracycline
Main Source:	https://www.nature.com/articles/163159a0
Citation:	https://www.nejm.org/doi/10.1056/NEJM194902172400701