Synonym
Afabicin diolamine; Afabicin; Debio 1450; Debio-1450; Debio1450; AFN-1720; AFN 1720; AFN1720;
IUPAC/Chemical Name
2-Propenamide, N-methyl-N-((3-methyl-2-benzofuranyl)methyl)-3-(5,6,7,8-tetrahydro-7-oxo-8-((phosphonooxy)methyl)-1,8-naphthyridin-3-yl)-, (2E)-, compd. with 2-aminoethanol (1:2)
InChi Key
RLXLAXQJCXOHNX-OJYIHNBOSA-N
InChi Code
1S/C23H24N3O7P.2C2H7NO/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;2*3-1-2-4/h3-7,9,11-12H,8,10,13-14H2,1-2H3,(H2,29,30,31);2*4H,1-3H2/b9-7+;;
SMILES Code
O=C(N(C)CC1=C(C)C2=CC=CC=C2O1)/C=C/C3=CC(CC4)=C(N=C3)N(COP(O)(O)=O)C4=O.NCCO.NCCO
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
>3 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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
607.60
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 |
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.
