Afabicin

Last updated

Afabicin
Afabicin.svg
Clinical data
Other namesAFN-1720; Debio1450
Legal status
Legal status
  • Investigational
Identifiers
  • [6-[(E)-3-[methyl-[(3-methyl-1-benzofuran-2-yl)methyl]amino]-3-oxoprop-1-enyl]-2-oxo-3,4-dihydro-1,8-naphthyridin-1-yl]methyl dihydrogen phosphate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C23H24N3O7P
Molar mass 485.433 g·mol−1
3D model (JSmol)
  • CC1=C(OC2=CC=CC=C12)CN(C)C(=O)/C=C/C3=CC4=C(N=C3)N(C(=O)CC4)COP(=O)(O)O
  • InChI=1S/C23H24N3O7P/c1-15-18-5-3-4-6-19(18)33-20(15)13-25(2)21(27)9-7-16-11-17-8-10-22(28)26(23(17)24-12-16)14-32-34(29,30)31/h3-7,9,11-12H,8,10,13-14H2,1-2H3,(H2,29,30,31)/b9-7+
  • Key:HFYMDQMXVPJNTH-VQHVLOKHSA-N

Afabicin (Debio 1450) is an experimental antibiotic developed by Debiopharm for the treatment of Staphylococcus aureus infections. It is a prodrug which is converted in vivo into the active form afabicin desphosphono (Debio 1452) which acts as an inhibitor of the staphylococcal enoyl-acyl carrier protein reductase (FabI) enzyme. It has shown similar efficacy in clinical trials to established drugs such as vancomycin, but has not yet been approved for clinical use. [1] [2] [3] [4] [5] [6]

See also

References

  1. ↑ Menetrey A, Janin A, Pullman J, Overcash JS, Haouala A, Leylavergne F, et al. (March 2019). "Bone and Joint Tissue Penetration of the Staphylococcus-Selective Antibiotic Afabicin in Patients Undergoing Elective Hip Replacement Surgery". Antimicrobial Agents and Chemotherapy. 63 (3). doi:10.1128/AAC.01669-18. PMC   6395911 . PMID   30559136.
  2. ↑ Bassetti M, Del Puente F, Magnasco L, Giacobbe DR (May 2020). "Innovative therapies for acute bacterial skin and skin-structure infections (ABSSSI) caused by methicillin-resistant Staphylococcus aureus: advances in phase I and II trials". Expert Opinion on Investigational Drugs. 29 (5): 495–506. doi:10.1080/13543784.2020.1750595. PMID   32242469.
  3. ↑ Wittke F, Vincent C, Chen J, Heller B, Kabler H, Overcash JS, et al. (September 2020). "Afabicin, a First-in-Class Antistaphylococcal Antibiotic, in the Treatment of Acute Bacterial Skin and Skin Structure Infections: Clinical Noninferiority to Vancomycin/Linezolid". Antimicrobial Agents and Chemotherapy. 64 (10). doi:10.1128/AAC.00250-20. PMC   7508579 . PMID   32747361.
  4. ↑ Ruggieri F, Compagne N, Antraygues K, Eveque M, Flipo M, Willand N (August 2023). "Antibiotics with novel mode of action as new weapons to fight antimicrobial resistance". European Journal of Medicinal Chemistry. 256 115413. doi:10.1016/j.ejmech.2023.115413. PMID   37150058.
  5. ↑ Bibens L, Becker JP, Dassonville-Klimpt A, Sonnet P (March 2023). "A Review of Fatty Acid Biosynthesis Enzyme Inhibitors as Promising Antimicrobial Drugs". Pharmaceuticals. 16 (3): 425. doi: 10.3390/ph16030425 . PMC   10054515 . PMID   36986522.
  6. ↑ Nowakowska J, Cameron DR, De Martino A, Kühn J, Le Fresne-Languille S, Leuillet S, et al. (August 2023). "Evaluation of the microbiota-sparing properties of the anti-staphylococcal antibiotic afabicin". The Journal of Antimicrobial Chemotherapy. 78 (8): 1900–1908. doi:10.1093/jac/dkad181. PMC   10393889 . PMID   37294305.
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