Metacycline (Rondomycin)

Synonym(s): Methacycline  |  methamycin  |  andramycin  |  GS-2876

Class: Tetracycline

Spectrum of activity:	Gram-positive  &  Gram-negative
Details of activity:	Broad-spectrum activity; protein synthesis inhibitor (prevents access to aminoacyl-tRNA binding site)
Description:	Semi-synthetic compound derived from oxytetracycline; with reduced absorption (administered orally); reduced usefulness due to emergence of tetracycline resistance William, M., et al. "Comparison of two new tetracycline with tetracycline and demetyhlchlortetracycline."Program and Abstracts of the interscience science Conference on Antimicrobial Agents and Chemotherapy. 1961.
Institute where first reported:	Medpointe Pharmaceuticals; University of Washington
Year first mentioned:	1961
Highest developmental phase:	Approved
Development status:	Discontinued
Reason Dropped:	Small serum activity afer 24 hours compared with tetracycline

Chemical structure(s):
Canonical SMILES:	C=C1C2=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
Isomeric SMILES:	CN(C)[C@H]1[C@@H]2[C@H]([C@@H]3C(=C)C4=C(C(=CC=C4)O)C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O
InChI:	InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25-27,30,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1
InChI Key:	XIYOPDCBBDCGOE-IWVLMIASSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/54675785

External links:
Guide to Pharmacology:	metacycline
Main Source:	https://journals.sagepub.com/doi/abs/10.3181/00379727-110-27501
Citations:	https://academic.oup.com/jac/article/58/2/256/718565 https://journals.sagepub.com/doi/epdf/10.3181/00379727-110-27501
Patent:	US3966808A