Synonym
Afabicin; Debio 1450; Debio-1450; Debio1450; AFN-1720; AFN 1720; AFN1720;
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
InChi Key
HFYMDQMXVPJNTH-VQHVLOKHSA-N
InChi Code
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+
SMILES Code
O=P(O)(OCN1C(CCC2=CC(/C=C/C(N(C)CC(O3)=C(C)C4=C3C=CC=C4)=O)=CN=C12)=O)O
Purity
>98% (or refer to the Certificate of Analysis)
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.
Storage Condition
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
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Related CAS#
Afabicin diolamine, CAS#1518800-36-6
Afabicin, CAS#1518800-35-5
Biological target:
Afabicin (Debio 1450) is the prodrug of Debio1452, specifically targeting staphylococci without significant activity against other
Gram-positive or Gram-negative species. Debio1452 is an inhibitor FabI, an enzyme critical to fatty acid biosynthesis in
staphylococci.
In vitro activity:
Afabicin desphosphono (Debio 1452, the active form of afabicin [Debio 1450]) is an inhibitor of FabI enoyl-Acyl carrier protein
reductase and has specific and extremely potent activity against Staphylococci, including strains resistant to current antistaphylococcal
Product data sheet
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agents. Using mouse J774 macrophages and human THP-1 monocytes, this study showed that afabicin desphosphono: (i) accumulates
rapidly in cells, reaching stable cellular-to-extracellular concentration ratios of about 30; (ii) is recovered entirely and free in the cellsoluble fraction (no evidence of stable association with proteins or other macromolecules).
Reference: Int J Antimicrob Agents. 2020 Feb;55(2):105848. https://pubmed.ncbi.nlm.nih.gov/31770623/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Soluble in DMSO |
0.0 |
100.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
485.43
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. 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.
In vitro protocol:
1. 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.
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: 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.
3: 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.
4: 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.
5: 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.
6: Ruggieri F, Compagne N, Antraygues K, Eveque M, Flipo M, Willand N. Antibiotics with novel mode of action as new weapons to fight antimicrobial resistance. Eur J Med Chem. 2023 Aug 5;256:115413. doi: 10.1016/j.ejmech.2023.115413. Epub 2023 Apr 26. PMID: 37150058.
7: Bibens L, Becker JP, Dassonville-Klimpt A, Sonnet P. A Review of Fatty Acid Biosynthesis Enzyme Inhibitors as Promising Antimicrobial Drugs. Pharmaceuticals (Basel). 2023 Mar 10;16(3):425. doi: 10.3390/ph16030425. PMID: 36986522; PMCID: PMC10054515.
8: 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.
