Pregabalin

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H336：Kann Schläfrigkeit und Benommenheit verursachen.

  H361：Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen.

• Sicherheit

  P201：Vor Gebrauch besondere Anweisungen einholen.

  P202：Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.

  P261：Einatmen von Staub vermeiden.

  P271：Nur im Freien oder in gut belüfteten Räumen verwenden.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P308+P313：BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

Pregabalin Chemische Eigenschaften,Einsatz,Produktion Methoden

• Beschreibung

  Pregabalin (Lyrica), a derivative of GABA that is closely related to gabapentin, has undergone extensive research for its efficacy in treating conditions such as generalized anxiety disorder (GAD), fibromyalgia, neuropathic pain, and partial complex seizures. It seems to have a more targeted effect on the a2-δ subunit of calcium channels in the brain compared to gabapentin. Pregabalin was granted FDA approval at the end of 2004 for the treatment of neuropathic pain and epilepsy. In 2008, it became the first medication approved for the management of fibromyalgia. Although pregabalin was approved for GAD treatment in the European Union in 2006, it has not yet received FDA approval for GAD in the United States as of the time of writing.

• Chemische Eigenschaften

  Off-White Solid

• Originator

  Warner-Lambert (US)

• Verwenden

  Pregabalin is an anticonvulsant drug used for neuropathic pain, as an adjunct therapy for partial seizures, and in generalized anxiety disorder. It was designed as a more potent successor to gabapentin. Pregabalin is marketed by Pfizer under the trade nam

• Verwenden

  S-Enantiomer of Pregabalin. A GABA analogue used as an anticonvulsant. Anxiolytic analgesic used to treat peripheral neuropathic pain and fibromyalgia.

• Definition

  ChEBI: Pregabalin is a gamma-amino acid that is gamma-aminobutyric acid (GABA) carrying an isobutyl substitutent at the beta-position (the S-enantiomer). Binds with high affinity to the alpha2-delta site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues. It has a role as an anticonvulsant and a calcium channel blocker. It is functionally related to a gamma-aminobutyric acid.

• Trademarks

  Lyrica (CP).

• Allgemeine Beschreibung

  Pregabalin, marketed as the anticonvulsant drug Lyrica, is used in the treatment of epilepsy and generalized anxiety disorder. Along with other anticonvulsants such as gabapentin and levetiracetam, pregabalin is also used to treat neuropathic pain. This certified reference standard is suitable for pregabalin GC/MS or LC/MS applications from forensic analysis, clinical toxicology and pain prescription monitoring to urine drug testing.

• Biochem/physiol Actions

  Pregabalin is a lipophilic GABA analog/ligand at α2δ subunit of voltage-dependent Ca2+ channels. Pregabalin is an anticonvulsant, anxiolytic analgesic used to treat peripheral neuropathic pain and fibromyalgia.

• Clinical Use

  Antiepileptic
  Neuropathic pain
  Generalised anxiety disorder

• Synthese

  Several syntheses of pregabalin (X) have been disclosed in the literature, including process scale-up comparison of several different routes. The most cost efficient route as described in the publication is shown in the Scheme. Condensation of diethyl malonate 69 in the presense of diisopropyl amine in acetic acid gave a,b-unsaturated diester 70 in high yield. Reaction of the enone diester with potassium cyanide gave cyano diester 71 in 95% yield. In a remarkable three step, one pot process, the nitrile in 71 was hydrolyzed followed by decarboxylation of one of the esters to provide 72 in 73% yield. Resolution of the two enantiomers was achieved using (S)-(+)-mandellic acid, one of the best acid found after many salt screening, to give, after two recrystallization, a 99:1 ratio of the desired diastereomer.Removal of the acid was done with wet THF instead of base separation, to avoid salt impurities, and one recrystallization in ethanol gave 100% ee diastereomer in 25 ¨C 29% overall yield.
  It?ˉs worth noting that the Pfizer group have come up with a new process of preparing pregabalin (X) via enantioselective reduction, that promises to further reduce cost and waste associated with the manufacture of this drug.

  

• target

  Estrogen receptor | Calcium Channel | GABA Receptor | Antifection | 5-HT Receptor | Progestogen receptor

• Arzneimittelwechselwirkung

  Potentially hazardous interactions with other drugs
  Antidepressants: anticonvulsant effect antagonised.
  Antimalarials: anticonvulsant effect antagonised by mefloquine.
  Antipsychotics: anticonvulsant effect antagonised.
  Orlistat: possible increased risk of convulsions.

• Stoffwechsel

  Pregabalin undergoes negligible metabolism, and about 98% of a dose is excreted in the urine as unchanged drug.

Pregabalin Upstream-Materialien And Downstream Produkte

Pregabalin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(870)Suppliers

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