Synonym
XF-73; XF 73; XF73; Exeporfinium chloride
IUPAC/Chemical Name
3,3'-((porphyrin-5,15-diylbis(4,1-phenylene))bis(oxy))bis(N,N,N-trimethylpropan-1-aminium) chloride
InChi Key
KJLHJQGDBJNMPU-XRFOENPRSA-L
InChi Code
InChI=1S/C44H50N6O2.2ClH/c1-49(2,3)25-7-27-51-37-17-9-31(10-18-37)43-39-21-13-33(45-39)29-35-15-23-41(47-35)44(42-24-16-36(48-42)30-34-14-22-40(43)46-34)32-11-19-38(20-12-32)52-28-8-26-50(4,5)6;;/h9-24,29-30,45,48H,7-8,25-28H2,1-6H3;2*1H/q+2;;/p-2/b33-29-,34-30-,35-29-,36-30-,43-39-,43-40-,44-41-,44-42-;;
SMILES Code
C[N+](C)(C)CCCOC(C=C1)=CC=C1/C2=C(N/3)\C=CC3=C\C4=N/C(C=C4)=C(C5=CC=C(OCCC[N+](C)(C)C)C=C5)\C(N6)=CC=C6/C=C7C=CC2=N/7.[Cl-].[Cl-]
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, not in water
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
Biological target:
XF-73 is a synthetic dicationic porphyrin derivative with antibacterial activity.
In vitro activity:
The effects of XF-73 on the growth and survival of S. aureus SH1000 were investigated by viable count and culture absorbance techniques. XF-73 was rapidly bactericidal against S. aureus SH1000 and demonstrated more rapid killing kinetics than all other comparator agents when tested at an equivalent multiple (4x) of the MIC. Exposure of S. aureus to XF-73 for 10 min completely inhibited DNA, RNA and protein synthesis. XF-73 had no effect on transcription and translation in vitro. Cells exposed to XF-73 gave a positive response in the BacLight assay, which detects membrane damage. The drug also caused substantial loss of K(+) and ATP from the cell, but did not promote bacterial lysis.
Reference: J Antimicrob Chemother. 2009 Oct;64(4):735-40. https://pubmed.ncbi.nlm.nih.gov/19689976/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
0.0 |
0.00 |
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
765.82
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. Farrell DJ, Robbins M, Rhys-Williams W, Love WG. In vitro activity of XF-73, a novel antibacterial agent, against antibiotic-sensitive and -resistant Gram-positive and Gram-negative bacterial species. Int J Antimicrob Agents. 2010 Jun;35(6):531-6. doi: 10.1016/j.ijantimicag.2010.02.008. Epub 2010 Mar 25. PMID: 20346634.
2. Ooi N, Miller K, Hobbs J, Rhys-Williams W, Love W, Chopra I. XF-73, a novel antistaphylococcal membrane-active agent with rapid bactericidal activity. J Antimicrob Chemother. 2009 Oct;64(4):735-40. doi: 10.1093/jac/dkp299. Epub 2009 Aug 18. PMID: 19689976.
In vitro protocol:
1. Farrell DJ, Robbins M, Rhys-Williams W, Love WG. In vitro activity of XF-73, a novel antibacterial agent, against antibiotic-sensitive and -resistant Gram-positive and Gram-negative bacterial species. Int J Antimicrob Agents. 2010 Jun;35(6):531-6. doi: 10.1016/j.ijantimicag.2010.02.008. Epub 2010 Mar 25. PMID: 20346634.
2. Ooi N, Miller K, Hobbs J, Rhys-Williams W, Love W, Chopra I. XF-73, a novel antistaphylococcal membrane-active agent with rapid bactericidal activity. J Antimicrob Chemother. 2009 Oct;64(4):735-40. doi: 10.1093/jac/dkp299. Epub 2009 Aug 18. PMID: 19689976.
1: Gonzales FP, Felgenträger A, Bäumler W, Maisch T. Fungicidal photodynamic effect of a twofold positively charged porphyrin against Candida albicans planktonic cells and biofilms. Future Microbiol. 2013 Jun;8(6):785-97. doi: 10.2217/fmb.13.44. PubMed PMID: 23701333.
2: Farrell DJ, Robbins M, Rhys-Williams W, Love WG. Investigation of the potential for mutational resistance to XF-73, retapamulin, mupirocin, fusidic acid, daptomycin, and vancomycin in methicillin-resistant Staphylococcus aureus isolates during a 55-passage study. Antimicrob Agents Chemother. 2011 Mar;55(3):1177-81. doi: 10.1128/AAC.01285-10. Epub 2010 Dec 13. PubMed PMID: 21149626; PubMed Central PMCID: PMC3067113.
3: Walker K. Interscience Conference on Antimicrobial Agents and Chemotherapy - 50th Annual Meeting - Research on Promising New Agents: Part 1. IDrugs. 2010 Nov;13(11):743-5. PubMed PMID: 21046515.
4: Schmitz J, Holzgrabe U. [XF-73 - a new antibacterial lead compound]. Pharm Unserer Zeit. 2010 Sep;39(5):335-6. doi: 10.1002/pauz.201090075. German. PubMed PMID: 20818680.
5: Farrell DJ, Robbins M, Rhys-Williams W, Love WG. In vitro activity of XF-73, a novel antibacterial agent, against antibiotic-sensitive and -resistant Gram-positive and Gram-negative bacterial species. Int J Antimicrob Agents. 2010 Jun;35(6):531-6. doi: 10.1016/j.ijantimicag.2010.02.008. Epub 2010 Mar 25. PubMed PMID: 20346634.
6: Ooi N, Miller K, Randall C, Rhys-Williams W, Love W, Chopra I. XF-70 and XF-73, novel antibacterial agents active against slow-growing and non-dividing cultures of Staphylococcus aureus including biofilms. J Antimicrob Chemother. 2010 Jan;65(1):72-8. doi: 10.1093/jac/dkp409. Epub . PubMed PMID: 19889790.
7: Ooi N, Miller K, Hobbs J, Rhys-Williams W, Love W, Chopra I. XF-73, a novel antistaphylococcal membrane-active agent with rapid bactericidal activity. J Antimicrob Chemother. 2009 Oct;64(4):735-40. doi: 10.1093/jac/dkp299. Epub 2009 Aug 18. PubMed PMID: 19689976.
