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Pregabalin Produkt Beschreibung

Pregabalin Struktur
148553-50-8
CAS-Nr.
148553-50-8
Englisch Name:
Pregabalin
Synonyma:
Lyrica;Pregablin;Pregabali;PREGABAIN;PREGABALIN;Neugaba 75;Pregabilin;Prebagalin;Maxgalin 75;TOS-BB-0910
CBNumber:
CB2251105
Summenformel:
C8H17NO2
Molgewicht:
159.23
MOL-Datei:
148553-50-8.mol

Pregabalin Eigenschaften

Schmelzpunkt:
194-196°C
alpha 
D23 +10.52° (c = 1.06 in water)
Siedepunkt:
274.0±23.0 °C(Predicted)
Dichte
0.997±0.06 g/cm3(Predicted)
Flammpunkt:
9℃
storage temp. 
2-8°C
Löslichkeit
deionized water: ≥10mg/mL
pka
4.23±0.10(Predicted)
Aggregatzustand
white powder
InChIKey
AYXYPKUFHZROOJ-ZETCQYMHSA-N
CAS Datenbank
148553-50-8(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,T,F
R-Sätze: 63-48/22-39/23/24/25-23/24/25-11
S-Sätze: 22-36/37-45-16-7
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
HS Code  29224999
Giftige Stoffe Daten 148553-50-8(Hazardous Substances Data)
Bildanzeige (GHS)
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H225 Flüssigkeit und Dampf leicht entzündbar. Entzündbare Flüssigkeiten Kategorie 2 Achtung P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H318 Verursacht schwere Augenschäden. Schwere Augenschädigung Kategorie 1 Achtung P280, P305+P351+P338, P310
H361 Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Reproduktionstoxizität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
H370 Schädigt die Organe. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 1 Achtung P260, P264, P270, P307+P311, P321,P405, P501
Sicherheit
P210 Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P260 Dampf/Aerosol/Nebel nicht einatmen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P311 GIFTINFORMATIONSZENTRUM/Arzt anrufen.
P301+P310 BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Pregabalin Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

As a follow-up to its g-aminobutyric acid (GABA) agonist gabapentin, Pfizer has developed and launched pregabalin for the treatment of epilepsy and neuropathic pain. Although pregabalin is a structural analog of GABA, it does not interact with GABA-A or GABA-B receptors or influence GABA uptake. The exact mechanism of action is unclear, but pregabalin may reduce excitatory neurotransmitter release by binding to the α2-δ protein subunit of voltage-gated calcium channels. The resulting inhibition of excess neuronal activity is believed to be the basis for pregabalin’s efficacy in epilepsy and neuropathic pain alleviation. Since the activity is attributed to the (S′)-enantiomer alone, an efficient asymmetric synthesis is employed for commercial production. The key step is the asymmetric hydrogenation of 3-cyano-5-methyl-3-hexenoic acid using a chiral rhodium catalyst to afford an intermediate that is enriched in the (S′)-enantiomer. The cyano group is ultimately reduced by routine hydrogenation with a nickel catalyst. Further enrichment of the final product is realized by selective recrystallization with (S′)-mandelic acid or simply recrystallizing from water/isopropanol. Compared to gabapentin, pregabalin is 2- to 10-fold more potent in various animal models. For example, in preventing maximal electroshock seizures (MES) in mice, pregabalin has an ED50 of 20 mg/kg p.o. versus 87 mg/kg for gabapentin. A comparable increase in potency is also observed in the rat MES model (ED50=1.8mg=kg p.o. for pregabalin versus 10.3 mg/kg for gabapentin). In addition, pregabalin’s linear pharmacokinetics (Cmax relates to dose) translates to better predictability of pharmacological effects. It has 90% oral bioavailability, with an elimination half-life of approximately 6 h. The primary route of excretion is via the renal system with negligible metabolism. Furthermore, its lack of activity at the cytochrome P450 enzymes was reflected in an absence of pharmacokinetic drug-drug interactions in relevant studies. In a placebocontrolled, fixed dose (up to 600mg/day) trial with pregabalin as an adjunctive therapy for epilepsy, 14 to 51% of patients showed at least a 50% decrease in seizure frequency with a clear dose-response relationship. In a flexible dosing group, (150 mg/day to 600 mg/day), the seizure reduction rate was 35.4%compared to 40.3% for a fixed dose of 600mg/day and 10.6% for placebo. The most common side effects were dizziness (29%) and somnolence (21%). In addition, weight gain (equal to or more than 7% increase from baseline) occurred in 40% of patients in the 12-week study; however, there was no affect on male fertility or efficacy of oral contraceptives in women. Regarding the use of pregabalin in treating painful diabetic peripheral neuropathy, oral administration of 300 and 600 mg/day t.i.d. was superior to placebo (39–48% compared to 15–18% with placebo) in relieving pain and improving pain-related sleep interference. While pregabalin was originally developed as an anticonvulsant for epilepsy, its success in treating neuropathic pain has led to its exploration in treating other CNS disorders, such as, anxiety, social phobia, and fibromyalgia.

Beschreibung

Pregabalin (Item No. 13663) is an analytical reference standard categorized as an anticonvulsant and analgesic. Pregabalin has a potential for abuse and misuse. Pregabalin is regulated as a Schedule V compound in the United States. This product is intended for research and forensic applications.

Chemische Eigenschaften

Off-White Solid

Originator

Warner-Lambert (US)

Verwenden

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

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

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.

Chemical Synthesis

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 – 29% overall yield.
It’s 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.

Pregabalin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Pregabalin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 638)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
XI'AN TIANGUANGYUAN BIOTECH CO., LTD.
+8618829239519 +86-86-18829239519
188 2923 9519 sales06@tgybio.com China 1228 58
Hebei Ruiyao Biotechnology Co. Ltd
15532235888 15632182983
031188180881 admin@ruiyaobio.com CHINA 846 58
Xi'an Kono chem co., Ltd.,
13289246953 029-86107037
info@konochemical.com CHINA 3000 58
Jinan Jianfeng Chemical Co., Ltd
15562555968
0531-88113608 info@pharmachemm.com CHINA 200 58
Hebei shuoxi biotechnology co. LTD
+8613081092107
whatsapp:+8613081092107 julia@hbshuoxi.com CHINA 973 58
Shijiazhuang Suking Biotechnology Co .,Ltd.
19955145978
19955145978 sales2@sxbiology.com CHINA 297 58
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
15327141851 027-81302090
027-81302088 2851686515@qq.com CHINA 280 58
Wuhan Mulei New Material Technology Co. Ltd
+8619831953957
Telegram/wickr: jane8886 jane@whmulei.com;amy@whmulei.com China 993 58
Hong Kong Tiansheng New Material Trading Co., Ltd
+8617320695765
17320695765 zxx@hktiansheng.com China 1047 58
Shanxi Lianxu New Material Co., LTD
+8618903404542
Whatsapp: +8618903404542 Wickr me: vevian cathy@lianxu815.com China 528 58

148553-50-8()Verwandte Suche:


  • 3(S)-(AMINOMETHYL)-5-METHYLHEXANOIC ACID
  • (3S)-3-(AMINOMETHYL)-5-METHYLHEXANOIC ACID
  • PREGABALIN
  • Pregablin
  • 3-(Aminomethyl)-5-methyl-hexanoic acid
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  • (S)-3-(Ammoniomethyl)-5-methylhexanoate
  • Lyrica
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  • LYRICA (pregabalin)
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  • PREGABALINE (S)-(+)-3-AMinoMethyl-5-Methylhexanoic acid
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  • Pregabalin SynonyMs 3-(AMinoMethyl)-5-Methyl-hexanoic acid
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  • 148553-50-8
  • 201-483-2
  • Miscellaneous Biochemicals
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