Abstract
Nafamostat dimesylate {systematic name: [amino({6-[(4-{[amino(iminiumyl)methyl]amino}phenyl)carbonyloxy]naphthalen-2-yl})methylidene]azanium bis(methanesulfonate)}, C19H19N5O2 2+·2CH3O3S-, is a broad-spectrum serine protease inhibitor and has been applied clinically as an anti-coagulant agent during hemodialysis and for treatment of severe acute pancreatitis (SAP). Since nafamostat contains flexible moieties, it is necessary to determine the conformation to understand the structure-activity relationships. The divalent cation has a screw-like motif. The guanidinium group is approximately perpendicular to the naphthyl ring system, subtending a dihedral angle of 84.30 (14)°. In the crystal, the nafamostat mol-ecules form columnar structures surrounded by a hydro-philic region.
Highlights
Nafamostat dimesylate {systematic name: [amino({6-[(4-{[amino(iminiumyl)methyl]amino}phenyl)carbonyloxy]naphthalen-2-yl})methylidene]azanium bis(methanesulfonate)}, C19H19N5O22+Á2CH3O3SÀ, is a broad-spectrum serine protease inhibitor and has been applied clinically as an anticoagulant agent during hemodialysis and for treatment of severe acute pancreatitis (SAP)
The guanidinium group is approximately perpendicular to the naphthyl ring system, subtending a dihedral angle of 84.30 (14)
The dihedral angles between the amidino and naphthyl groups, the naphthyl group and ring C, and ring C and guanidinium group are 11.35 (13), 44.66 (10) and 51.11 (15), respectively
Summary
Nafamostat mesylate (I) is the bismethanesulfonic salt of 6amidino-2-naphthyl-4-guanidinobenzoate. It shows broadspectrum serine protease inhibition effect, and is a reversible competitive inhibitor as camostat mesylate (II) (Tamura et al, 1977; Fujii & Hitomi, 1981; Matsumoto et al, 1989). Nafamostat mesylate has been applied clinically with success as an effective anticoagulant and antiinflammatory agent during hemodialysis and for treatment of severe acute pancreatitis (Takeda et al, 1989), the crystal structure has not previously been reported. The crystal structure of nafamostat mesylate (I) is reported . The phenylguanidine groups in nafamostat and camostat are essentially similar except for the direction of residual groups
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