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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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$135.00
25 MG
$462.00

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5 MG
$135.00
25 MG
$462.00

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

$135.00

In StockDetails

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Quality Level

100

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.[1]
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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Certificates of Analysis (COA)

Lot/Batch Number
0000381257
0000381257
0000219407
0000219406
032M4726V

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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
Felicia Klinger et al.
British journal of pharmacology, 166(5), 1631-1642 (2011-12-23)
Flupirtine is a non-opioid analgesic that has been in clinical use for more than 20 years. It is characterized as a selective neuronal potassium channel opener (SNEPCO). Nevertheless, its mechanisms of action remain controversial and are the purpose of this
Anton Kolosov et al.
Pain medicine (Malden, Mass.), 13(11), 1444-1456 (2012-10-20)
Current treatments for cancer pain are often inadequate, particularly when metastasis to bone is involved. The addition to the treatment regimen of another drug that has a complementary analgesic effect may increase the overall analgesia without the necessity to increase
Lioubov I Brueggemann et al.
American journal of physiology. Lung cellular and molecular physiology, 302(1), L120-L132 (2011-10-04)
Expression and function of Kv7 (KCNQ) voltage-activated potassium channels in guinea pig and human airway smooth muscle cells (ASMCs) were investigated by quantitative reverse transcriptase polymerase chain reaction (qRT-PCR), patch-clamp electrophysiology, and precision-cut lung slices. qRT-PCR revealed expression of multiple
S E Sander et al.
Neuropharmacology, 62(2), 1052-1061 (2011-11-15)
L-DOPA-induced dyskinesias (LID) represent a severe complication of long-time pharmacotherapy in Parkinson's disease that necessitates novel therapeutics. The acute and chronic effects of K(V)7.2-7.5 channel openers (retigabine, flupirtine) on the severity of LID and parkinsonian signs were examined in comparison
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