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F8927

Sigma-Aldrich

Flupirtine maleate salt

≥98% (HPLC)

Synonym(s):

2-Amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-carbamic acid ethyl ester maleate salt

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About This Item

Empirical Formula (Hill Notation):
C15H17FN4O2 · C4H4O4
CAS Number:
75507-68-5
Molecular Weight:
420.39
MDL number:
MFCD00941415
UNSPSC Code:
12352200
PubChem Substance ID:
24278445
NACRES:
NA.77

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: soluble >20 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

OC(=O)\C=C/C(O)=O.CCOC(=O)Nc1ccc(NCc2ccc(F)cc2)nc1N

InChI

1S/C15H17FN4O2.C4H4O4/c1-2-22-15(21)19-12-7-8-13(20-14(12)17)18-9-10-3-5-11(16)6-4-10;5-3(6)1-2-4(7)8/h3-8H,2,9H2,1H3,(H,19,21)(H3,17,18,20);1-2H,(H,5,6)(H,7,8)/b;2-1-

InChI key

DPYIXBFZUMCMJM-BTJKTKAUSA-N

Biochem/physiol Actions

Flupirtine is commercially available as maleate salt. It exists in two polymorphs : flupirtine maleate A and B. Flupirtine is useful in treating muscular spasm, muscle tension and muscle stiffness. It is known to be effective in relieving back pain. Along with cytoprotection, flupirtine also offers protection against neurodegenerative disorders such as multiple sclerosis, amyotrophic lateral sclerosis, Alzheimer′s disease, Parkinson′s disease, Huntington′s chorea and AID (acquired immunodeficiency) associated encephalopathy. Flupirtine is found to be a potential drug for eye-related problems like maculopathy including diabetic retinopathy, retinitis pigmentosa and glaucoma. It is also proved to be helpful in preventing cardiac associated disorders such as myocardial ischemia and infarction, cerebral ischemia and infarction. Hepatitis is also prevented by the use of flupirtine.
Non-opioid analgesic; cytoprotective versus PrP fragment 106-126

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Martin C Michel et al.
British journal of clinical pharmacology, 73(5), 821-825 (2011-11-03)
To determine efficacy of the analgesic flupirtine in the treatment of overactive bladder syndrome in a proof-of-concept study. Double-blind, double-dummy, three-armed comparison of flupirtine extended release (400 mg/day, titrated to 600 mg/day), tolterodine extended release (4 mg/day) and placebo for
Syed Mohammed Naser et al.
Journal of the Indian Medical Association, 110(3), 158-160 (2012-10-04)
The study was conducted to evaluate the efficacy and safety of flupirtine maleate 100 mg thrice daily compared to tramadol hydrochloride 50 mg thrice daily as postoperative pain management for 5 days. A total of 113 postoperative patients were recruited
M A Ueberall et al.
International journal of clinical pharmacology and therapeutics, 49(11), 637-647 (2011-10-21)
Flupirtine, a nonopioid analgesic without antipyretic or antiphlogistic properties, constitutes a unique class within the group of WHO-I analgesics. First approved in Germany on a national level in 1989, this selective neuronal potassium channel opener evolved rapidly into one of
Fritz Klein et al.
Experimental and clinical transplantation : official journal of the Middle East Society for Organ Transplantation, 9(4), 270-272 (2011-08-09)
We present the case of a 48-year-old otherwise healthy man who required an urgent liver transplant owing to acute liver failure after flupirtine treatment. After 3 months of daily flupirtine intake as treatment for pseudoradicular pain syndrome, he presented at
Michael A Uberall et al.
Current medical research and opinion, 28(10), 1617-1634 (2012-09-14)
To demonstrate non-inferior/superior efficacy of flupirtine modified release (MR) compared with tramadol/placebo for the management of moderate to severe chronic low back pain (LBP). Randomized, double-blind, active-/placebo-controlled double-dummy multicenter study, performed in 31 German study centers. LBP patients (n = 363) with
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