Meclocycline

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 tetracycline derivative. Was used topically.
Year first mentioned:	1964
Development status:	Discontinued
Reason Dropped:	Toxic if given systemically

Chemical structure(s):
Canonical SMILES:	C=C1C2=C(C(=CC=C2Cl)O)C(=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
Isomeric SMILES:	CN(C)[C@H]1[C@@H]2[C@H]([C@@H]3C(=C)C4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O
InChI:	InChI=1S/C22H21ClN2O8/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30/h4-5,10,14-15,17,26-28,31,33H,1H2,2-3H3,(H2,24,32)/t10-,14-,15+,17+,22+/m1/s1
InChI Key:	RNIADBXQDMCFEN-IWVLMIASSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/54676539

External links:
Guide to Pharmacology:	meclocycline
Main Source:	https://www.researchgate.net/publication/51907943_The_history_of_the_tetracyclines
Citation:	https://pubmed.ncbi.nlm.nih.gov/1675534/