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2-Phenylpropan-1,3-diyldicarbamat

Felbamate Struktur
25451-15-4
CAS-Nr.
25451-15-4
Bezeichnung:
2-Phenylpropan-1,3-diyldicarbamat
Englisch Name:
Felbamate
Synonyma:
W-554;Talox;Taloxa;Felbamyl;felbatol;felbamato;ADD-03055;FELBAMATE;Sch-54388;Felbanmate
CBNumber:
CB6689427
Summenformel:
C11H14N2O4
Molgewicht:
238.24
MOL-Datei:
25451-15-4.mol

2-Phenylpropan-1,3-diyldicarbamat Eigenschaften

Schmelzpunkt:
148-1500C
Siedepunkt:
511.9±50.0 °C(Predicted)
Dichte
1.275±0.06 g/cm3(Predicted)
Flammpunkt:
9℃
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
L?slichkeit
alcohol: soluble
pka
12.99±0.50(Predicted)
Aggregatzustand
Solid
Farbe
White
BCS Class
2
CAS Datenbank
25451-15-4(CAS DataBase Reference)
NIST chemische Informationen
Felbamate(25451-15-4)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
RIDADR  UN1230 - class 3 - PG 2 - Methanol
WGK Germany  2
RTECS-Nr. TZ1070000
HS Code  2924296000
Giftige Stoffe Daten 25451-15-4(Hazardous Substances Data)
Toxizit?t LD50 i.p. in mice: 4000 mg/kg (Ludwig et al.)
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H225 Flüssigkeit und Dampf leicht entzündbar. Entzündbare Flüssigkeiten Kategorie 2 Achtung GHS hazard pictogramssrc="/GHS02.jpg" width="20" height="20" /> P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H370 Sch?digt die Organe. Spezifische Zielorgan-Toxizit?t (einmalige Exposition) Kategorie 1 Achtung GHS hazard pictogramssrc="/GHS08.jpg" width="20" height="20" /> P260, P264, P270, P307+P311, P321,P405, P501
Sicherheit
P210 Von Hitze, hei?en Oberfl?chen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P260 Dampf/Aerosol/Nebel nicht einatmen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P301+P310 BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P311 GIFTINFORMATIONSZENTRUM/Arzt anrufen.

2-Phenylpropan-1,3-diyldicarbamat Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

Felbamate, characterized by its low toxicity and wide margin of safety, is efficacious in treating refractory patients with generalized tonic-clonic and complex partial seizures as monotherapy and adjunctive therapy.It has also been demonstrated to have a neuroprotective effect in cerebral ischemia and hypoxia. It has been suggested that the mechanism of its anticonvulsant activity is possibly through an interaction with the strychnineinsensitive receptor site on the NMDA receptor complex.

Chemische Eigenschaften

White Powder. Solubility in water 0.33 mg/mL, in ethanol 5.0 mg/mL, and in DMF 333.4 mg/mL.

Definition

ChEBI: The bis(carbamate ester) of 2-phenylpropane-1,3-diol. An anticonvulsant, it is used in the treatment of epilepsy.

Biologische Funktion

Felbamate (Felbatol) was introduced with the expectation that it would become a major drug in the treatment of epilepsy. Felbamate exhibited few manifestations of serious toxicity in early clinical trials. Soon after its introduction, however, it became apparent that its use was associated with a high incidence of aplastic anemia. Consequently, felbamate is indicated only for patients whose epilepsy is so severe that the risk of aplastic anemia is considered acceptable.
While its mechanism of action has not been clearly established, felbamate shows some activity as an inhibitor of voltage-dependent sodium channels in a manner similar to that of phenytoin and carbamazepine. Felbamate also interacts at the strychnine-insensitive glycine recognition site on the NMDA receptor– ionophore complex.Whether this effect is important to its anticonvulsant activity is not clear.

Hazard

Low toxicity by ingestion. Human systemic effects.

Biologische Aktivit?t

Anticonvulsant, acting as an antagonist at the NMDA-associated glycine binding site.

Mechanism of action

Gabapentin is a water-soluble amino acid originally designed to be a GABA-mimetic analogue capable of penetrating the CNS. Surprisingly, it has no direct GABA-mimetic activity, nor is it active on sodium channels. The mechanism of action remains unknown, although it has been suggested that gabapentin may alter the metabolism or release of GABA. Gabapentin raises brain GABA levels in patients with epilepsy. Recent studies have demonstrated gabapentin binding to calcium channels in a manner that can be allosterically modulated.
Gabapentin is indicated as an adjunct for use against partial seizures with or without secondary generalization, in patients older than 12 years, and as adjunct for the treatment of partial seizures in children 3 to 12 years of age. It also is approved for the treatment of postherpetic neuralgia.

Pharmakokinetik

The pharmacokinetic properties for gabapentin generally are favorable, with a bioavailability of 60% when given in low doses and somewhat less when given at higher doses because of saturable intestinal uptake by the L-amino-acid transporter. The L-amino-acid transporter is very susceptible to substrate saturation (low Km value). Its absorption and distribution into the CNS appears to be dependent on this amino acid transporter. Following the administration of an oral dose, gabapentin reaches peak plasma concentration in 2 to 3 hours. Additionally, it exhibits linear pharmacokinetics. Moreover, it is not extensively metabolized, nor is it an inducer of hepatic metabolizing enzymes. The elimination of unmetabolized gabapentin occurs by the renal route. Although its therapeutic range is not well characterized, gabapentin has a broad therapeutic index. This implies that a wide range of doses can be used, based on individual patient needs, without significant limitation because of dose-dependent side effects. Protein binding is negligible. Its elimination half-life of 5 to 7 hours is not affected by the dose or by other drugs, and its short half-life necessitates multiple daily administration.

Clinical Use

Felbamate is a dicarbamate that is structurally similar to the antianxiety drug meprobamate. It was approved by the U.S. FDA for antiseizure use in 1993. Following the occurrence of rare cases of aplastic anemia and of severe hepatotoxicity associated with the use of felbamate during early 1994, however, a black box warning was added to the drug's package insert). Despite this, felbamate continues to be used in many patients, although not as a first-line treatment. These toxicity effects may be attributed to the formation of toxic metabolites. Although felbamate use is now uncommon, it is used for severe refractory seizures, either partial, myoclonic, or atonic, or in Lennox-Gastaut syndrome

Nebenwirkungen

Adverse effects of gabapentin are uncommon and not serious. The CNS effects include mild to moderate sedation, fatigue, ataxia, headache, dizziness, and diplopia. Gabapentin may exacerbate myoclonus, but the effect is mild and does not require discontinuance of the drug. It has been associated with the development of neuropsychiatric adverse events in children.
Drug interactions are infrequent with gabapentin. It does not induce hepatic metabolizing enzymes, nor do other AEDs affect its metabolism and elimination. Antacids may decrease absorption. Gabapentin dosage may need to be decreased in patients with renal disease or in the elderly.

Stoffwechsel

Although the metabolism of felbamate has not been fully characterized, felbamate is esterase hydrolyzed to its monocarbamate metabolite, 2-phenyl-1,3-propanediol monocarbamate, which subsequently is oxidized via aldehyde dehydrogenase to its major human metabolite 3-carbamoyl-2-phenylpropionic acid. Other metabolites include the p-hydroxy and mercapturic acid metabolites of felbamate, which have been identified in human urine. Felbamate is a substrate for CYP2C19, with minor activity for CYP3A4 and CYP2E1. Thompson et al. has provided evidence for the formation of the reactive metabolite, 3-carbamoyl-2-phenylpropionaldehyde (CBMA), from the alcohol oxidation of 2-phenyl-1,3-propanediol monocarbamate. CBMA then undergoes spontaneous elimination to another reactive intermediate, 2-phenylpropenal (more commonly known as atropaldehyde), which is proposed to play a role in the development of toxicity during felbamate therapy. CBMA or a further product has been shown to provoke an immune response in mice. Evidence for in vivo atropaldehyde formation was confirmed with the identification of its mercapturic acid conjugates in human urine after felbamate administration. This is consistent with the hypothesis that atropaldehyde reacts rapidly with thiol nucleophiles, such as glutathione, to form mercapturates. More recently, a fluorine analogue of felbamate was synthesized in which the benzylic C2 hydrogen of the propane chain was replaced with fluorine, preventing the formation of atropaldehyde and confirming that the acidic benzylic hydrogen plays a pivotal role in its formation. This analogue is presently undergoing drug development. Felbamate administration exhibited linear kinetics, with a half-life of 20 to 23 hours in the absence of enzyme-inducing AEDs. Approximately 50% of an oral dose of felbamate is excreted unchanged.

2-Phenylpropan-1,3-diyldicarbamat Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


2-Phenylpropan-1,3-diyldicarbamat Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 205)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Shaanxi Dideu Medichem Co. Ltd
+86-29-81148696 +86-15536356810
1022@dideu.com China 3882 58
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795
ivan@atkchemical.com China 32957 60
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29880 58
Xiamen AmoyChem Co., Ltd
+86-86-5926051114 +8618959220845
sales@amoychem.com China 6383 58
Chongqing Chemdad Co., Ltd
+86-023-6139-8061 +86-86-13650506873
sales@chemdad.com China 39894 58
Alchem Pharmtech,Inc.
8485655694
sales@alchempharmtech.com United States 63687 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000
marketing@targetmol.com United States 32161 58
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418671 +8618949823763
sales@tnjchem.com China 34563 58
AFINE CHEMICALS LIMITED
+86-0571-85134551
sales@afinechem.com China 15352 58
Zhejiang J&C Biological Technology Co.,Limited
+1-2135480471 +1-2135480471
sales@sarms4muscle.com China 10473 58

25451-15-4(2-Phenylpropan-1,3-diyldicarbamat)Verwandte Suche:


  • 1,3-Propanediol, 2-phenyl-, dicarbamate
  • (3-aminocarbonyloxy-2-phenyl-propyl) carbamate
  • (3-carbamoyloxy-2-phenylpropyl) carbamate
  • carbamic acid (3-carbamoyloxy-2-phenyl-propyl) ester
  • Felbamate (250 mg)
  • 3-propanediol,2-phenyl-dicarbamate
  • ADD-03055
  • carbamicacid,2-phenyltrimethyleneester
  • felbamato
  • 1,3-Propanediol,2-phenyl-, 1,3-dicarbaMate
  • 1,3-Propanediol, 2-phenyl-, dicarbamate (8CI,9CI)
  • Felbamyl
  • Taloxa
  • W-554
  • FELBAMATE
  • felbatol
  • Felbanmate
  • FELBAMATE (2-PHENYL-1,3-PROPANEDIOL DICA
  • FELBAMATE 99.0%
  • 2-PhenyltrimethyleneEster
  • Talox
  • 2-phenylpropane-1,3-diyl dicarbamate
  • 2-PHENYL-1,3-PROPANEDIOL DICARBAMATE
  • Dicarbamic acid 2-phenyltrimethylene ester
  • Sch-54388
  • Felbamate solution
  • Felbamate, 98.0+ % (HPLC)
  • Felbamate USP/EP/BP
  • Felbamate (W-554
  • FelbamateQ: What is Felbamate Q: What is the CAS Number of Felbamate Q: What is the storage condition of Felbamate Q: What are the applications of Felbamate
  • Felbamate (1269312)
  • R)-Daurisoline
  • Felbamate (3-carbamoyloxy-2-phenylpropyl) carbamate
  • Felbamate in methanol
  • 25451-15-4
  • 23824
  • Heterocyclic Compounds
  • Glutamate receptor
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Inhibitors
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