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Gabapentin

Description Generic formulation Indications Dose titration Cautions Interactions Special populations Behavioural and cognitive effects in patients with epilepsy Psychiatric use
Gabapentin
Gabapentin structure
CAS No.
60142-96-3
Chemical Name:
Gabapentin
Synonyms
ci945;go3450;goe2450;GOE-3450;Aclonium;NEURONTIN;AKOS 92109;GABAPENTIN;Gababentin;GABAPENTINE
CBNumber:
CB3263316
Molecular Formula:
C9H17NO2
Formula Weight:
171.24
MOL File:
60142-96-3.mol

Gabapentin Properties

Melting point:
162°C
Boiling point:
314.4±15.0 °C(Predicted)
Density 
1.058±0.06 g/cm3(Predicted)
Flash point:
9℃
storage temp. 
Desiccate at +4°C
solubility 
H2O: 10 mg/mL
pka
pKa1 (25°) 3.68; pKa2 10.70
form 
solid
color 
off-white
Merck 
14,4319
BRN 
2359739
InChIKey
UGJMXCAKCUNAIE-UHFFFAOYSA-N
CAS DataBase Reference
60142-96-3(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
6CW7F3G59X
NCI Dictionary of Cancer Terms
gabapentin
EPA Substance Registry System
Cyclohexaneacetic acid, 1-(aminomethyl)- (60142-96-3)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07,GHS08,GHS02,GHS06
Signal word  Danger
Hazard statements  H225-H301+H311+H331-H370-H315-H319-H335-H360
Precautionary statements  P210-P260-P280-P301+P310-P311-P302+P352+P312-P304+P340+P312-P370+P378-P403+P235-P201-P305+P351+P338-P308+P313-P261
Hazard Codes  T,Xi,F
Risk Statements  61-36/37/38-39/23/24/25-23/24/25-11
Safety Statements  53-26-36/37/39-45-36-36/37-16
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
RTECS  GU6496000
HazardClass  IRRITANT
HS Code  29224999

Gabapentin price More Price(16)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich G-007 Gabapentin solution 1.0mg/mL in methanol, ampule of 1mL, certified reference material 60142-96-3 007-1ml $55 2020-08-18 Buy
Sigma-Aldrich 1287303 Gabapentin United States Pharmacopeia (USP) Reference Standard 60142-96-3 250mg $366 2020-08-18 Buy
TCI Chemical G0318 Gabapentin >98.0%(GC)(T) 60142-96-3 5g $62 2020-06-24 Buy
TCI Chemical G0318 Gabapentin >98.0%(GC)(T) 60142-96-3 25g $190 2020-06-24 Buy
Cayman Chemical 10008346 Gabapentin ≥98% 60142-96-3 25mg $71 2020-06-24 Buy

Gabapentin Chemical Properties,Uses,Production

Description

Gabapentin is a second- generation antiepileptic drug (AED) known under the proprietary brand name of Neurontin® (Pfizer, New York, NY) in the UK and USA.

Generic formulation

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

Indications

Epilepsy: monotherapy or adjunctive therapy of focal seizures with or without secondary generalization. Recommendations summarized from NICE (2012)

Dose titration

Monotherapy or adjunctive therapy
300 mg od for day 1300 mg bd for day 2300 mg td for day 3 (or 300 mg td for day 1), then increased by 300 mg every 2– 3 days, divided into three doses; usual maintenance 900– 3600 mg daily, divided into three doses (max. 4800 mg daily) If gabapentin has to be discontinued, it is recommended this should be done gradually over a minimum of 1 week, independent of the indication.

Cautions

Interactions

With AEDs
Nil.

With other drugs
With alcohol/food
There are no known specific interactions between alcohol and gabapentin and there are no specific foods that must be excluded from diet when taking gabapentin.

Special populations

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

Pregnancy

Behavioural and cognitive effects in patients with epilepsy

Gabapentin has a relatively favourable behavioural profile, although paradoxical hyperactivity, irritability and aggression have been occasionally reported, especially in patients with severe intellectual disabilities. The cognitive profile of gabapentin is equally favourable, as this AED has been associated with only minor cognitive difficulties (mainly in the attention domain).

Psychiatric use

Although gabapentin has no approved indications in psychiatry, it has shown efficacy in the treatment of anxiety disorders, especially social phobia. Other offlabel uses include other anxiety disorders (panic disorder, post- traumatic stress disorder), alcohol dependence and withdrawal, behavioural and psychological symptoms of dementia, and aggression. Gabapentin has also been proposed to be useful in the maintenance treatment of bipolar disorder as adjunctive therapy.

Description

Gabapentin was introduced in 1993 in the UK and early 1994 in the USA as an adjunctive therapy in the treatment of refractory partial seizures and secondarily generalized tonic-clonic seizures. Although being a lipophilic analog of the neurotransmitter GABA, gabapentin appears to exert its anticonvulsive function by a GABA receptor independent mechanism, possibly involving the L-system amino acid transporter protein. Gabapentin easily crosses the blood brain barrier and exhibits a favorable pharmacokinetic profile with high tolerability. It does not interfere with the metabolism of other concomitant administered antiepileptic drugs, thus having a low potential for drug interactions. Studies are currently underway for the use of gabapentin as mono-therapy for the treatment of various seizures.

Chemical Properties

White Crystalline Solid

Originator

Warner-Lambert (U.S.A.)

Uses

Amino acid structurally related to γ-Aminobutyric Acid (GABA), designed to cross the blood brain barrier. Used as an anticonvulsant.

Uses

antipsychotic, 5HT2A antagonist

Uses

selective H1-receptor antagonist

Uses

For the treatment of adult Restless Legs Syndrome (RLS) and postherpetic neuralgia (PHN).

Definition

ChEBI: A gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.

Indications

Gabapentin (Neurontin) significantly decreases pain scores and sleep interference associated with PHN. An initial dose of 300 mg/day is increased over 4 weeks (900, 1,800, 2,400, 3,600 mg/day divided t.i.d.) until efficacy is obtained or side effects become intolerable.

Manufacturing Process

32.8 g 1,1-cyclohexane-diacetic anhydride are mixed with 7 g anhydrous methanol and heated under reflux for 1 hour. After evaporation of the reaction mixture in a vacuum, was obtained 37.5 g monomethyl 1,1-cyclohexanediacetate in the form of a yellowish oil.
5.6 ml triethylamine in 16 ml anhydrous acetone are added dropwise at 0°C to a solution of 7.28 g monomethyl 1,1-cyclohexane-diacetate, then a solution of 3.6 ml ethyl chloroformate in 16 ml anhydrous acetone is added thereto. The reaction mixture is further stirred for 30 min at 0°C and and then a solution of 3.4 g sodium azide in 12 ml water added dropwise thereto. The reaction mixture is stirred for 1 hour at 0°C, then poured into ice water and extracted three times with 50 ml amounts of ice-cold toluene. The combined extracts are dried over anhydrous sodium sulphate at 0°C and subsequently introduced drop-wise into a flask pre-heated to 100°C. The mixture is then heated for a further hour under reflux and thereafter evaporated in a vacuum. The crude methyl 1-isocyanatomethyl-1-cyclohexane-acetate which remains behind is heated under reflux for 3 hours with 50 ml 20% hydrochloric acid. After cooling the solution, it is extracted three times with 100 ml amounts of chloroform to remove the 1-amino-methyl-1-cyclohexane-acetic acid lactam formed as a by-product product and the aqueous hydrochloric acid solution evaporated in a vacuum, whereby 1-aminomethyl-1-cyclohexane-acetic acid crystallises as the hydrochloride; m.p. 117-118°C, after recrystallisation from acetone/methanol/ether. After recrystallization from methanol/ether the melting point of the product is 129-133°C.
By treatment with a basic ion exchanger and crystallisation from ethanol/ether, there is obtained pure 1-amino-methyl-1-cyclohexane-acetic acid; melting point 162-166°C.

brand name

Neurontin (ParkeDavis); Neurontin (Pfizer).

Therapeutic Function

Anticonvulsant

Biological Functions

Gabapentin (Neurotonin) was initially designed to be a rigid analogue of GABA. When it was discovered to have antiepileptic properties, it was assumed that this activity was related to a GABAergic mechanism. However, subsequent studies have failed to show any GABAergic activity of gabapentin. Although it has not yet been possible to ascribe any definite mechanism to its antiepileptic activity, there is recent evidence that it may function as an agonist at GABAB receptors in the brain.
Gabapentin is recommended as adjunctive therapy in the treatment of partial seizures in adults.When used with other drugs, it appears to be an effective AED; it is usually not effective when employed alone for patients with severe seizures.
Gabapentin is generally well tolerated, with somnolence, dizziness, and ataxia the most commonly reported adverse effects. A low incidence of potentially serious side effects and no significant allergic reactions have been reported.

General Description

Gabapentin and its closely related analog pregabalin,(S)-3-isobutyl-GABA, are broad-spectrum anticonvulsantswith multiple mechanisms of action.24,51 Inaddition to modulating calcium influx and stimulateGABA biosynthesis as discussed earlier, they also competefor the biosynthesis of L-glutamic acid because oftheir structural similarity to L-leucine.51 Gabapentin andpregabalin have very little liability for causing metabolicbaseddrug–drug interactions, particularly when used incombination with other AEDs because they are not metabolizedin humans. More than 95% of the drug is excretedunchanged through the kidneys. However, there are somedifferences in their bioavailability. Unlike gabapentin,which exhibits 60% bioavailability when given in lowdoses because of intestinal uptake by a saturable smallneutral L-amino acid transporter, the absorption of pregabalinis almost complete (98%) and exhibits an ideal linear pharmacokinetic profile.24 This high bioavailability of pregabalincan be attributed to its closer structure similarity tothe essential amino acid, L-leucine.

Biological Activity

Anticonvulsant with several possible mechanisms of action. Increases GABA in the brain and binds to a novel site associated with voltage-sensitive Ca 2+ channels. Prevents neuronal death and is antinociceptive and anxiolytic.

Side effects

Dose-limiting adverse effects include somnolence, dizziness, ataxia, peripheral edema, and infection (22).

Veterinary Drugs and Treatments

Gabapentin may be useful as adjunctive therapy for refractory or complex partial seizures, or in the treatment of chronic pain in dogs or cats.

Gabapentin Preparation Products And Raw materials

Raw materials

Preparation Products


Gabapentin Suppliers

Global( 389)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Beijing Yibai Biotechnology Co., Ltd
0086-182-6772-3597
sales04@yibaibiotech.com CHINA 420 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22622 55
Hangzhou FandaChem Co.,Ltd.
0086 158 5814 5714 (Mobile
+86-571-56059825 fandachem@gmail.com CHINA 8290 55
PI & PI BIOTECH INC.
18371201331
020-81716319 Sales@pipitech.com CHINA 3048 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 25016 60
Anhui Royal Chemical Co., Ltd.
+86-025-86655873
marketing@royal-chem.com CHINA 537 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 2799 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 30023 58
Shenzhen Nexconn Pharmatechs Ltd
15013857715
admin@nexconn.com CHINA 3004 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28230 58

Related articles


View Lastest Price from Gabapentin manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2020-11-27 Gabapentin
60142-96-3
US $20.00 / KG 1KG 99% 20 tons Hebei Dongdu Import and Export Co. LTD
2020-11-12 Gabapentin hydrochloride
60142-96-3
US $100.00 / KG 1KG 99% 20 Tons Longyan Tianhua Biological Technology Co., Ltd
2020-07-17 Gabapentin
60142-96-3
US $120.00 / Kg/Drum 1KG 99% 100tons/month Hebei Yanxi Chemical Co., Ltd.

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