Afabicin | CAS#1518800-35-5 | Bacterial Inhibitor

Afabicin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 327001

CAS#: 1518800-35-5 (free acid)

Description: 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.

Chemical Structure

Afabicin

CAS# 1518800-35-5 (free acid)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 327001
Name: Afabicin
CAS#: 1518800-35-5 (free acid)
Chemical Formula: C23H24N3O7P
Exact Mass: 485.14
Molecular Weight: 485.433
Elemental Analysis: C, 56.91; H, 4.98; N, 8.66; O, 23.07; P, 6.38

Price and Availability

Size	Price	Availability
1mg	USD 150	Ready to ship
5mg	USD 450	Ready to ship
10mg	USD 750	Ready to ship
25mg	USD 1450	Ready to ship
50mg	USD 2450	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 1518800-40-2 (potassium) 1518800-35-5 (free acid) 1518800-53-7 (calcium) 1518800-29-7 (sodium) 1518800-36-6 (diolamine)

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

Appearance: Solid powder

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

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#YXM220720

QC Data:

View QC data: current batch, Lot#YXM220720

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

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 MedKoo Biosciences \|\| http://www.medkoo.com \|\| sales@medkoo.com 2500 Gateway Centre Blvd Suite 400, Morrisville, NC27560, USA. Tel: 919-636-5577, Fax: 919-980-4831 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/
In vivo activity:	TBD

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Soluble in DMSO	0.0	100.00

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.
In vivo protocol:	TBD

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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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.

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