Exeporfinium chloride
new
featured

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

Hodoodo CAT#: H319746

CAS#: 718638-68-7 (Cl)

Description: Exeporfinium, also known as XF-73, is an anti-microbial which works via weakening bacteria cell walls. Exeporfinium chloride is a potential treatment for methicillin-resistant Staphylococcus aureus (MRSA) and possibly Clostridium difficile. Exeporfinium chloride has completed a phase I clinical trial for nasal decolonisation of MRSA—being tested against 5 bacterial strains. It seems unlikely to cause MRSA to develop resistance to it. Structurally it is a dicationic porphyrin.


Chemical Structure

img
Exeporfinium chloride
CAS# 718638-68-7 (Cl)

Theoretical Analysis

Hodoodo Cat#: H319746
Name: Exeporfinium chloride
CAS#: 718638-68-7 (Cl)
Chemical Formula: C44H50Cl2N6O2
Exact Mass: 0.00
Molecular Weight: 765.824
Elemental Analysis: C, 69.01; H, 6.58; Cl, 9.26; N, 10.97; O, 4.18

Price and Availability

Size Price Availability Quantity
1mg USD 190 Ready to ship
5mg USD 650 Ready to ship
10mg USD 1150 Ready to ship
25mg USD 1950 Ready to ship
50mg USD 2950 Ready to ship
100mg USD 4950 Ready to ship
Bulk inquiry

Related CAS #: 756818-36-7 (cation)   718638-68-7 (Cl)   943326-71-4 (bromide)    

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-]

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, 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

More Info:

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/
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.0 0.00

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.

Recalculate based on batch purity %
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.
In vivo protocol: TBD

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

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

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.