Flupirtine-d4 hydrochloride  (Synonyms: D 9998-d4 hydrochloride)

Flupirtine-d₄ (D 9998-d₄) hydrochloride is the deuterium labeled Flupirtine hydrochloride (HY-W709349). Flupirtine hydrochloride is an orally active, blood-brain barrier-crossing non-opioid analgesic and neuroprotective agent. Flupirtine hydrochloride is a neuronal potassium channel opener (Kv7 activator), a NMDA receptor antagonist and a GABA receptor activator. Flupirtine hydrochloride stabilizes blood-brain-barrier integrity, reduces oxidative stress and brain leukocyte infiltration, enhances angioneurogenesis, suppresses calcium influx, stabilizes neuronal resting membrane potential, and counteracts focal cerebral ischemia. Flupirtine hydrochloride exhibits analgesic, muscle relaxant properties, protects neurons from excitotoxic, ischemic, or cytokine-mediated death. Flupirtine hydrochloride functions as a non-opioid analgesic without antipyretic or antiphlogistic properties, shows no relevant affinity to opiate receptor. Flupirtine hydrochloride can be used for the research of focal cerebral ischemia, pain, Alzheimer’s disease, or multiple sclerosis^[1][2].

1. This compound can be used as a tracer.
2. This compound can be used as an internal standard for quantitative analysis by NMR, GC-MS, or LC-MS.

Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

344.81

C₁₅H₁₄D₄ClFN₄O₂

1324717-75-0

75507-68-5

Solid

White to off-white

Cl[H].CCOC(NC1=C(N=C(NCC2=C([2H])C([2H])=C(F)C([2H])=C2[2H])C=C1)N)=O

Room temperature in continental US; may vary elsewhere.

• [1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53(2):211-216.  [Content Brief]

  [2]. Kornhuber J, et al. Flupirtine shows functional NMDA receptor antagonism by enhancing Mg2+ block via activation of voltageindependent potassium channels. Rapid communication. J Neural Transm. 1999;106(9-10):857-67.;Klinger F, et al. Concomitant facilitation of GABAA receptors and KV7 channels by the non-opioid analgesic flupirtine. Br J Pharmacol. 2012 Jul;166(5):1631-42.;Swedberg MD, et al. Pharmacological mechanisms of action of flupirtine: a novel, centrally acting, nonopioid analgesic evaluated by its discriminative effects in the rat. J Pharmacol Exp Ther. 1988 Sep;246(3):1067-74.;Wu SN, et al. Evidence for inhibitory effects of flupirtine, a centrally acting analgesic, on delayed rectifier k(+) currents in motor neuron-like cells. Evid Based Complement Alternat Med. 2012;2012:148403.;Kolosov A, et al. Flupirtine enhances the anti-hyperalgesic effects of morphine in a rat model of prostate bone metastasis. Pain Med. 2012 Nov;13(11):1444-56.;Michel MC, et al. Unexpected frequent hepatotoxicity of a prescription drug, flupirtine, marketed for about 30 years. Br J Clin Pharmacol. 2012 May;73(5):821-5.  [Content Brief]