Compound ID | 246

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Omadacycline

Synonym(s): Omadacycline tosylate  |  PTK-0796  |  Nuzyra

Class: Tetracycline

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor
Target Pathogen: Active against pathogens causing bacterial pneumonia, acute bacterial skin and skin structure infections, and complicated urinary tract infections
Description: Minocycline (aminomethylcycline) derivative; Flamm. R., Rhomberg. P., huband. M., Farrell. D. "Activity of Omadacycline Tested Against Streptococcus pneumoniae from a Global Surveillance Program (2014) " Abstracts of the Interscience Conference on Antimicrobial Agents and Chemotherapy. 2015.
Institute where first reported: Paratek Pharmaceuticals, USA
Year first mentioned: 2006
Highest development stage: Approved by FDA in 2018
Development status: Approved
Chemical structure(s):
Click here for structure editor
Molecular weight: 556.65
Iso. SMILES: CC(C)(C)CNCC1=CC(=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N(C)C)N(C)C
InChI Key: VJYKVCURWJGLPG-IQZGDKDPSA-N
Can. SMILES: CC(C)(C)CNCC1=CC(=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N(C)C)N(C)C
InChI: InChI=1S/C29H40N4O7/c1-28(2,3)12-31-11-14-10-17(32(4)5)15-8-13-9-16-21(33(6)7)24(36)20(27(30)39)26(38)29(16,40)25(37)18(13)23(35)19(15)22(14)34/h10,13,16,21,31,34-35,38,40H,8-9,11-12H2,1-7H3,(H2,30,39)/t13-,16-,21-,29-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54697325
Guide to Pharmacology: omadacycline
Citations:
  • http://aac.asm.org/content/58/3/1279.full
  • https://www.ncbi.nlm.nih.gov/pubmed/30726689
  • https://journals.asm.org/doi/10.1128/aac.01242-13
    • Patent: AU2021288202A1

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