CAS Number75507-68-5
SynonymsKatadolon; Ethyl {2-amino-6-[(4-fluorobenzyl)amino]pyridin-3-yl}carbamate (2Z)-but-2-enedioate (1:1); 2-Amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-carbamic acid ethyl ester maleate; (Z)-but-2-enedioic acid,ethyl N-[2-amino-6-[(4-fluorophenyl)methylamino]pyridin-3-yl]carbamate; Ethyl {2-amino-6-[(4-fluorobenzyl)amino]-3-pyridinyl}carbamate (2Z)-2-butenedioate (1:1); Flupirtine maleate; Flupirtine (Maleate)
Molecular FormulaC19H21FN4O6
Molecular Weight420.39
Purity≥98 (HPLC)%
Density1.35 g/cm3
Boiling Point434.9ºC at 760 mmHg
Melting Point186-188ºC
Appearancesolid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 75507-68-5 |
| Catalog No. | 2A-9010575 |
| Chinese Name | 马来酸氟吡汀 |
| Synonyms | Katadolon; Ethyl {2-amino-6-[(4-fluorobenzyl)amino]pyridin-3-yl}carbamate (2Z)-but-2-enedioate (1:1); 2-Amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-carbamic acid ethyl ester maleate; (Z)-but-2-enedioic acid,ethyl N-[2-amino-6-[(4-fluorophenyl)methylamino]pyridin-3-yl]carbamate; Ethyl {2-amino-6-[(4-fluorobenzyl)amino]-3-pyridinyl}carbamate (2Z)-2-butenedioate (1:1); Flupirtine maleate; Flupirtine (Maleate) |
| Molecular Formula | C19H21FN4O6 |
| Molecular Weight | 420.39 |
| Purity | ≥98 (HPLC) |
| Density | 1.35 g/cm3 |
| Boiling Point | 434.9ºC at 760 mmHg |
| Melting Point | 186-188ºC |
| Appearance | solid |
| Water Solubility | DMSO: soluble >20mg/mL |
| Storage Condition | 2-8°C |
| Application | Flupirtine (D 9998) maleate is a neuronal potassium channel opener and has NMDA receptor antagonist properties. |
| HTC | 2942000000 |
| PubChem ID | 24278445 |
| MDL Number | MFCD00941415 |
| SMILES | 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 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | Transport |
| MSDS | msds/10575_1_75507_68_5.pdf |
| Bioactivity | Flupirtine Maleate(D 9998) is a selective neuronal potassium channel opener that also has NMDA receptor antagonist properties.IC50 Value: Target: Potassium channel; NMDA receptorin vitro: High concentrations of flupirtine antagonized inward currents to NMDA(200 microM) at -70 mV with an lC50 against steady-state responses of 182.1±12.1 microM. The effects of flupirtine were voltage-independent and not associated with receptor desensitization making actions within the NMDA receptor channel or at the glycine modulatory site unlikely. NMDA receptor antagonism probably has little relevance for the clinical efficacy of flupirtine as the concentrations needed were far higher than those achieved in clinical practice. However, the activation of a G-protein-regulated inwardly rectifying K+ channel was identified as an interesting molecular target site of flupirtine. In the next stage, the central nervous spectrum of action of experimental K+ channel openers (PCO) was considered. As far as they have been studied, experimental K+ channel openers display a spectrum of action comparable to that of flupirtine [1]. Therapeutic flupirtine concentrations (≤10 μM) did not affect voltage-gated Na(+) or Ca(2+) channels, inward rectifier K(+) channels, nicotinic acetylcholine receptors, glycine or ionotropic glutamate receptors. Flupirtine shifted the gating of K(V)7 K(+) channels to more negative potentials and the gating of GABA(A) receptors to lower GABA concentrations [2]. Cell exposure to flupirtine decreased the amplitude of delayed rectifier K(+) current (I(K(DR))) with a concomitant raise in current inactivation in NSC-34 neuronal cells [4].in vivo: Rats were trained to discriminate the novel analgesic flupirtine (10.0 mg/kg i.p., 10 min) from no drug under a two-choice fixed-ratio 5 shock-termination schedule. Flupirtine yielded a dose-response curve with an ED50 of 3.87 mg/kg. The opioid analgesics pentazocine, codeine and tramadol failed to produce flupirtine appropriate responding. The opioid antagonist naltrexone did not antagonize the discriminative effects of flupirtine [3]. Both morphine (ED50=0.74 mg/kg) and flupirtine (ED50=3.32 mg/kg) caused dose-related anti-hyperalgesia at doses that did not cause sedation [5]. Toxicity: Based on study-end data, hepatotoxicity was detected in 31% of patients receiving flupirtine for ≥ 6 weeks [6]. Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR Signaling Pathways >> Neuronal Signaling >> iGluR Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel Research Areas >> Neurological Disease References [1]. Yeung et al (2007) Molecular expression and pharmacological identification of a role for Kv7 channels in murine vascular reactivity. Br.J.Pharmacol. 151 758. [2]. Gordon R, Sofia RD, Diamantis W.Effect of flupirtine maleate on the nociceptive pathway, EEG, evoked potentials and polysynaptic reflexes in laboratory animals.Postgrad Med J. 1987;63 Suppl 3:49-55. [3]. Hedges A, Warrington SJ, Turner P, Niebch G.Flupirtine maleate and antipyrine half-life.Eur J Clin Pharmacol. 1987;33(4):437. [4]. Powell-Jackson P, Williams R.Use of flupirtine maleate as an analgesic in patients with liver disease.Br J Clin Pract. 1985 Feb;39(2):63-6. [5]. Diamantis W, Gordon R, Sofia RD.Analgesic activity following combined oral administration of flupirtine maleate and peripherally acting analgesics in mice and rats.Postgrad Med J. 1987;63 Suppl 3:29-34. Chemical & Physical Properties Density 1.35 g/cm3 Boiling Point 434.9ºC at 760 mmHg Melting Point 186-188ºC Molecular Formula C19H21FN4O6 Molecular Weight 420.392 Flash Point 216.8ºC Exact Mass 420.144501 PSA 170.59000 LogP 2.71190 InChIKey DPYIXBFZUMCMJM-BTJKTKAUSA-N SMILES CCOC(=O)Nc1ccc(NCc2ccc(F)cc2)nc1N.O=C(O)C=CC(=O)O Storage condition 2-8°C Water Solubility DMSO: soluble >20mg/mL |
| Use of | Properties Articles27 Name Flupirtine Maleate Salt Synonym More Synonyms Flupirtine maleate Biological Activity Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR Signaling Pathways >> Neuronal Signaling >> iGluR Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel Research Areas >> Neurological Disease References [2]. Gordon R, Sofia RD, Diamantis W.Effect of flupirtine maleate on the nociceptive pathway, EEG, evoked potentials and polysynaptic reflexes in laboratory animals.Postgrad Med J. 1987;63 Suppl 3:49-55. [3]. Hedges A, Warrington SJ, Turner P, Niebch G.Flupirtine maleate and antipyrine half-life.Eur J Clin Pharmacol. 1987;33(4):437. [4]. Powell-Jackson P, Williams R.Use of flupirtine maleate as an analgesic in patients with liver disease.Br J Clin Pract. 1985 Feb;39(2):63-6. [5]. Diamantis W, Gordon R, Sofia RD.Analgesic activity following combined oral administration of flupirtine maleate and peripherally acting analgesics in mice and rats.Postgrad Med J. 1987;63 Suppl 3:29-34. Chemical & Physical Properties Molecular Formula C19H21FN4O6 Exact Mass 420.144501 PSA 170.59000 LogP 2.71190 InChIKey DPYIXBFZUMCMJM-BTJKTKAUSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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