Compound ID | 245

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Eravacycline

Synonym(s): TP-434  |  Xerava

Class: Tetracycline

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor
Target Pathogen: Broad spectrum activity including multidrug-resistant strains
Description: A tetracycline derivative (fluorocycline)
Institute where first reported: Tetraphase Pharmaceuticals, USA
Year first mentioned: 2010
Highest development stage: Approved by FDA in 2018
Development status: Approved
Chemical structure(s):
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Molecular weight: 558.56
Iso. SMILES: CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=C(C(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)NC(=O)CN5CCCC5)F
InChI Key: AKLMFDDQCHURPW-ISIOAQNYSA-N
Can. SMILES: CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=C(C(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)NC(=O)CN5CCCC5)F
InChI: InChI=1S/C27H31FN4O8/c1-31(2)20-13-8-11-7-12-14(28)9-15(30-16(33)10-32-5-3-4-6-32)21(34)18(12)22(35)17(11)24(37)27(13,40)25(38)19(23(20)36)26(29)39/h9,11,13,20,34-35,38,40H,3-8,10H2,1-2H3,(H2,29,39)(H,30,33)/t11-,13-,20-,27-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54726192
Guide to Pharmacology: eravacycline
Citations:
  • http://aac.asm.org/content/57/11/5548.full
  • https://journals.asm.org/doi/10.1128/spectrum.02351-23
  • https://journals.asm.org/doi/10.1128/aac.06187-11
  • https://pubs.acs.org/doi/10.1021/jm201467r
  • https://pubs.acs.org/doi/10.1021/jm201465w

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