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Details

Stereochemistry ACHIRAL
Molecular Formula C44H50N6O2
Molecular Weight 694.9068
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of EXEPORFINIUM

SMILES

C[N+](C)(C)CCCOC1=CC=C(C=C1)C2=C3C=CC(C=C4NC(C=C4)=C(C5=NC(C=C5)=CC6=CC=C2N6)C7=CC=C(OCCC[N+](C)(C)C)C=C7)=N3

InChI

InChIKey=KZTXNPVFWHWJSH-OPFFBBNOSA-N
InChI=1S/C44H50N6O2/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/q+2/b33-29-,34-30-,35-29-,36-30-,43-39-,43-40-,44-41-,44-42-

HIDE SMILES / InChI

Molecular Formula C44H52N6O2
Molecular Weight 696.9227
Charge 2
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Exeporfinium (XF-73), a dicationic porphyrin derivative, is an antibacterial drug. Exeporfinium acts via a bacterial cell-surface mechanism that affects membrane permeability and integrity, leading to release of intracellular components and bacterial cell death, without lysis. Exeporfinium represents a broad-spectrum Gram-positive antibacterial drug. It also has activity against a number of Gram-negative bacteria. Exeporfinium has been granted Fast Track designation by the US FDA for the prevention of post-surgical staphylococcal infections such as Methicillin Resistant Staphylococcus aureus.

Approval Year

PubMed

PubMed

TitleDatePubMed
[XF-73 - a new antibacterial lead compound].
2010 Sep
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.
2011 Mar
Fungicidal photodynamic effect of a twofold positively charged porphyrin against Candida albicans planktonic cells and biofilms.
2013 Jun
Patents

Sample Use Guides

Phase 2 study: 0.3 mL applications in each naris of 0.2% w/w exeporfinium (XF-73) nasal gel for a cumulative dose of 6.0 mg of XF-73.
Route of Administration: Nasal
XF-73 was active [minimum inhibitory concentration (MIC) 0.25-4 mg/L] against all of the Gram-positive bacteria tested, irrespective of the antibiotic resistance profile of the isolates, suggesting that the mechanism of action of XF-73 is unique compared with the major antibiotic classes. Gram-negative activity was lower (MIC 1 mg/L to > 64 mg/L).
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:13:13 GMT 2023
Edited
by admin
on Sat Dec 16 05:13:13 GMT 2023
Record UNII
R41ECT47G6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EXEPORFINIUM
Common Name English
1-PROPANAMINIUM, 3,3'-(21H,23H-PORPHINE-5,15-DIYLBIS(4,1-PHENYLENEOXY))BIS(N,N,N-TRIMETHYL-
Common Name English
EXEPORFINIUM CATION
Common Name English
EXEPORFINIUM ION
Common Name English
3,3'-(21H,23H-PORPHYRIN-5,15-DIYLBIS(((4,1-PHENYLENE)OXY)-N,N,N-TRIMETHYLPROPAN-1-AMINIUM))
Common Name English
Code System Code Type Description
FDA UNII
R41ECT47G6
Created by admin on Sat Dec 16 05:13:14 GMT 2023 , Edited by admin on Sat Dec 16 05:13:14 GMT 2023
PRIMARY
PUBCHEM
9918583
Created by admin on Sat Dec 16 05:13:14 GMT 2023 , Edited by admin on Sat Dec 16 05:13:14 GMT 2023
PRIMARY
CAS
756818-36-7
Created by admin on Sat Dec 16 05:13:14 GMT 2023 , Edited by admin on Sat Dec 16 05:13:14 GMT 2023
PRIMARY
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