Afabicin
Afabicin (formerly Debio 1450, AFN-1720) is a prodrug of afabicin desphosphono, an enoyl-acyl carrier protein reductase (FabI) inhibitor, and is a first-in-class antibiotic with a novel mode of action to specifically target fatty acid synthesis in Staphylococcus spp.
For research use only. We do not sell to patients.
Chemical Information
| Name | Afabicin |
|---|---|
| Iupac Chemical Name | (E)-(6-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-en-1-yl)-2-oxo-3,4-dihydro-1,8-naphthyridin-1(2H)-yl)methyl dihydrogen phosphate |
| Synonyms | Afabicin; Debio 1450; Debio-1450; Debio1450; AFN-1720; AFN 1720; AFN1720; |
| Molecular Formula | C23H24N3O7P |
| Molecular Weight | 485.43 |
| Smile | O=P(O)(OCN1C(CCC2=CC(/C=C/C(N(C)CC(O3)=C(C)C4=C3C=CC=C4)=O)=CN=C12)=O)O |
| InChiKey | HFYMDQMXVPJNTH-VQHVLOKHSA-N |
| InChi | 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+ |
| CAS Number | 1518800-35-5 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Solubility | Soluble in DMSO |
| Handling | |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| HS Code |
| Targets | |
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| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
1: Wittke F, Vincent C, Chen J, Heller B, Kabler H, Overcash JS, Leylavergne F, Dieppois G. Afabicin, a First-in-Class Antistaphylococcal Antibiotic, in the Treatment of Acute Bacterial Skin and Skin Structure Infections: Clinical Noninferiority to Vancomycin/Linezolid. Antimicrob Agents Chemother. 2020 Sep 21;64(10):e00250-20. doi: 10.1128/AAC.00250-20. PMID: 32747361; PMCID: PMC7508579.
2: Menetrey A, Janin A, Pullman J, Overcash JS, Haouala A, Leylavergne F, Turbe L, Wittke F, Nicolas-Métral V. Bone and Joint Tissue Penetration of the Staphylococcus-Selective Antibiotic Afabicin in Patients Undergoing Elective Hip Replacement Surgery. Antimicrob Agents Chemother. 2019 Feb 26;63(3):e01669-18. doi: 10.1128/AAC.01669-18. PMID: 30559136; PMCID: PMC6395911.
3: Peyrusson F, Van Wessem A, Dieppois G, Van Bambeke F, Tulkens PM. Cellular pharmacokinetics and intracellular activity of the bacterial fatty acid synthesis inhibitor, afabicin desphosphono against different resistance phenotypes of Staphylococcus aureus in models of cultured phagocytic cells. Int J Antimicrob Agents. 2020 Feb;55(2):105848. doi: 10.1016/j.ijantimicag.2019.11.005. Epub 2019 Nov 23. PMID: 31770623.
4: Matos de Opitz CL, Sass P. Tackling antimicrobial resistance by exploring new mechanisms of antibiotic action. Future Microbiol. 2020 Jun;15:703-708. doi: 10.2217/fmb-2020-0048. Epub 2020 Jul 10. PMID: 32648783.
5: Bassetti M, Del Puente F, Magnasco L, Giacobbe DR. 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 Opin Investig Drugs. 2020 May;29(5):495-506. doi: 10.1080/13543784.2020.1750595. Epub 2020 Apr 19. PMID: 32242469.
6: Dyon-Tafani V, Josse J, Dieppois G, Ferry T, Laurent F. Antimicrobial activity of the new FabI inhibitor afabicin desphosphono against intraosteoblastic Staphylococcus aureus. Int J Antimicrob Agents. 2021 May;57(5):106321. doi: 10.1016/j.ijantimicag.2021.106321. Epub 2021 Mar 11. PMID: 33716179.
Chemical Structure
