ChemicalBook
Chinese Japanese Germany Korea

Pregabalin

Description Generic formulation Indications Dose titration Plasma levels monitoring Antiepileptic drus and therapeutic drugs for neuropathic pain Cautions Adverse effects Interactions Special populations Behavioural and cognitive effects in patients with epilepsy Psychiatric use
Pregabalin
Pregabalin structure
CAS No.
148553-50-8
Chemical Name:
Pregabalin
Synonyms
Lyrica;Pregablin;Pregabali;PREGABAIN;PREGABALIN;Neugaba 75;Pregabilin;Prebagalin;Maxgalin 75;TOS-BB-0910
CBNumber:
CB2251105
Molecular Formula:
C8H17NO2
Formula Weight:
159.23
MOL File:
148553-50-8.mol

Pregabalin Properties

Melting point:
194-196°C
alpha 
D23 +10.52° (c = 1.06 in water)
Boiling point:
274.0±23.0 °C(Predicted)
Density 
0.997±0.06 g/cm3(Predicted)
Flash point:
9℃
storage temp. 
2-8°C
solubility 
deionized water: ≥10mg/mL
pka
4.23±0.10(Predicted)
form 
white powder
InChIKey
AYXYPKUFHZROOJ-ZETCQYMHSA-N
CAS DataBase Reference
148553-50-8(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
55JG375S6M
NCI Dictionary of Cancer Terms
Lyrica; pregabalin
NCI Drug Dictionary
Lyrica
ATC code
N03AX16
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS02,GHS06,GHS08,GHS05
Signal word  Danger
Hazard statements  H318-H361-H225-H301+H311+H331-H370
Precautionary statements  P210-P260-P280-P301+P310-P311-P305+P351+P338+P310-P305+P351+P338
Hazard Codes  Xn,T,F
Risk Statements  63-48/22-39/23/24/25-23/24/25-11
Safety Statements  22-36/37-45-16-7
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
HS Code  29224999

Pregabalin price More Price(10)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich P-066 Pregabalin solution 1.0mg/mL in methanol, ampule of 1mL, certified reference material 148553-50-8 066-1ml $158 2020-08-18 Buy
Sigma-Aldrich P-066 Pregabalin solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 148553-50-8 1 mL $163 2021-03-22 Buy
Sigma-Aldrich Y0001805 Pregabalin European Pharmacopoeia (EP) Reference Standard 148553-50-8 $190 2021-03-22 Buy
Sigma-Aldrich P-120 Pregabalin solution 10.0mg/mL in water, ampule of 1mL, certified reference material 148553-50-8 120-1ml $469 2020-08-18 Buy
Sigma-Aldrich P-120 Pregabalin solution 10.0?mg/mL in water, ampule of 1?mL, certified reference material, Cerilliant? 148553-50-8 1 mL $484 2021-03-22 Buy

Pregabalin Chemical Properties,Uses,Production

Description

Pregabalin is a second- generation antiepileptic drug (AED) known with the proprietary brand name of Lyrica® (Pfizer, Tadworth) in the UK and USA (Pfizer, New York, NY).

Generic formulation

MHRA/ CHM advice to minimize risk when switching patients with epilepsy between different manufacturers’ products (including generic products):

Indications

Epilepsy
Adjunctive therapy of focal seizures with and without secondary generalization.

Recommendations summarized from NICE (2012)
Psychiatry
Generalized anxiety disorder.

Neurology
Peripheral and central neuropathic pain.

Dose titration

If stopping pregabalin, it is recommended to taper over at least 1 week to avoid abrupt withdrawal.

Plasma levels monitoring

Pregabalin pharmacokinetics are linear over the recommended daily dose range; inter- subject pharmacokinetic variability for pregabalin is low (<20%) and multiple dose pharmacokinetics are predictable from single- dose data. Therefore, there is no need for routine monitoring of plasma concentrations of pregabalin.

Antiepileptic drus and therapeutic drugs for neuropathic pain

Pregabalin is a new antiepileptic drug, having a γ-amino butyric acid structure on its molecular structure, which has anticonvulsant effects, and is successfully developed by the company Pfizer for the treatment of peripheral neuropathic pain, or adjuvant treatment of partial seizures.
In December 2008, the US Food and Drug Administration (FDA) approved pregabalin (trade name "Lyrica") for the treatment of diabetic peripheral neuropathic pain (DPN) and postherpetic neuralgia (PHN)which are Both the most common neuropathic pains.
Neuropathic pain is one of the most difficult chronic pain syndromes to treat , dull pain, burning, tingling as the main feature, there are a lot of incentives of neuralgia, diabetes, infections (such as herpes zoster), cancer and AIDS, etc. can cause neurological pain, in Europe about 3% of the population suffer from neuralgia torture.
The above information is edited by the chemicalbook of Tian Ye.

Cautions

  1. Patients with conditions that may precipitate encephalopathy.
  2. Patients with severe congestive heart failure.

Adverse effects

Pregabalin can be associated with adverse effects at the level of the nervous system and other systems.

Interactions

With alcohol/food

Special populations

Hepatic impairment
No dose adjustment is required for patients with hepatic impairment.

Renal impairment
Reduce maintenance dose according to degree of reduction in creatinine clearance.

Pregnancy

Behavioural and cognitive effects in patients with epilepsy

Pregalin is characterized by a good behavioural profile. This AED does not appear to have significant negative effects on mood or behaviour in patients with epilepsy, although depression has been reported in some patients (dose- dependent effects of mild- to- moderate intensity). A potential abuse or misuse of pregabalin has also been reported, with implications in terms of dependence and withdrawal. pregabalin is also associated with limited negative cognitive effects, mainly related to sedation, decreased arousal, decreased attention and concentration (dose- dependent effects of mild- to- moderate intensity).

Psychiatric use

Pregabalin has an approved indication and is widely used for the treatment of generalized anxiety disorder. Several randomized, double- blind, placebocontrolled trials found that pregabalin is an effective treatment for patients with generalized anxiety disorder and social anxiety disorder. Possible implications in the treatment of mood disorders and benzodiazepines dependence are emerging. Moreover, pregabalin may be a therapeutic agent for the treatment of alcohol abuse, in both withdrawal phase and relapse prevention.

Description

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.

Chemical Properties

Off-White Solid

Originator

Warner-Lambert (US)

Uses

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

Uses

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

brand name

Lyrica (CP).

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 Preparation Products And Raw materials

Raw materials

Preparation Products


Pregabalin Suppliers

Global( 627)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
XI'AN TIANGUANGYUAN BIOTECH CO., LTD.
18802962783
rebecca@tgybio.com CHINA 1217 58
HEBEI YINGONG NEW MATERIAL TECHNOLOGY CO.,LTD
+8619933070948
claire@hbyingong.com China 443 58
Hebei Ruiyao Biotechnology Co. Ltd
15532235888 15632182983
031188180881 admin@ruiyaobio.com CHINA 846 58
Cangzhou Wanyou New Material Technology Co.,Ltd
18631714998
sales@czwytech.com CHINA 914 58
Xi'an Kono chem co., Ltd.,
13289246953 029-86107037
info@konochemical.com CHINA 3000 58
Hebei Xibaijie Biotechnology Co., Ltd.
0086 15232103582
aiana@hbxibaijie.com CHINA 636 58
Casorganics US Corp
+17326109938
sales@casorganics.com CHINA 175 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 300 58

View Lastest Price from Pregabalin manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-29 Pregabalin
148553-50-8
US $30.00 / KG 1KG 99% 1000kg/month Shanxi Lianxu New Material Co., LTD
2021-11-29 Pregabalin
148553-50-8
US $30.00 / KG 1KG 99% 1000kg/month Shanxi Lianxu New Material Co., LTD
2021-11-29 Pregabalin
148553-50-8
US $10.00 / g 1g 99% 20 tons Jinan Jianfeng Chemical Co., Ltd

148553-50-8(Pregabalin)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved