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Details

Stereochemistry ACHIRAL
Molecular Formula C44H50N6O2.2Cl
Molecular Weight 765.813
Optical Activity NONE
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EXEPORFINIUM CHLORIDE

SMILES

[Cl-].[Cl-].C[N+](C)(C)CCCOC1=CC=C(C=C1)c2c3ccc(cc4ccc([nH]4)c(C5=CC=C(OCCC[N+](C)(C)C)C=C5)c6ccc(cc7ccc2[nH]7)n6)n3

InChI

InChIKey=KJLHJQGDBJNMPU-XRFOENPRSA-L
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-;;

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C44H52N6O2
Molecular Weight 696.9227
Charge 2
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
1912L54M2V
Record Status Validated (UNII)
Record Version