Compound ID | 2611

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Metacycline (Rondomycin)

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

Class: Tetracycline

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor. Prevents access to aminoacyl-tRNA binding site
Target Pathogen: Broad-spectrum activity
Description: Semisynthetic 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):
Click here for structure editor
Molecular weight: 442.42
Iso. 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 Key: XIYOPDCBBDCGOE-IWVLMIASSA-N
Can. 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
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54675785
Guide to Pharmacology: metacycline
Citations:
  • https://academic.oup.com/jac/article/58/2/256/718565
  • https://journals.sagepub.com/doi/epdf/10.3181/00379727-110-27501
  • https://journals.sagepub.com/doi/abs/10.3181/00379727-110-27501
    • Patent: US3966808A

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