U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H16NO2.Na
Molecular Weight 181.2079
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PREGABALIN SODIUM

SMILES

[Na+].CC(C)C[C@H](CN)CC([O-])=O

InChI

InChIKey=RDOYGLCZFATQEB-FJXQXJEOSA-M
InChI=1S/C8H17NO2.Na/c1-6(2)3-7(5-9)4-8(10)11;/h6-7H,3-5,9H2,1-2H3,(H,10,11);/q;+1/p-1/t7-;/m0./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C8H16NO2
Molecular Weight 158.2181
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17126531

Pregabalin, marketed under the brand name Lyrica among others. LYRICA is indicated for: Neuropathic pain associated with diabetic peripheral neuropathy (DPN) Postherpetic neuralgia (PHN); Adjunctive therapy for adult patients with partial onset seizures; Fibromyalgia; Neuropathic pain associated with spinal cord injury. It has been shown the clinical effects of pregabalin are likely due to direct and selective interactions with α(2)δ-1 and α(2)δ-2 subunits of voltage-gated calcium channels. While pregabalin is a structural derivative of the inhibitory neurotransmitter gamma aminobutyric acid (GABA), it does not bind directly to GABAA, GABAB, or benzodiazepine receptors, does not augment GABAA responses in cultured neurons, does not alter rat brain GABA concentration or have acute effects on GABA uptake or degradation. However, in cultured neurons prolonged application of pregabalin increases the density of GABA transporter protein and increases the rate of functional GABA transport. Pregabalin does not block sodium channels, is not active at opiate receptors, and does not alter cyclooxygenase enzyme activity. It is inactive at serotonin and dopamine receptors and does not inhibit dopamine, serotonin, or noradrenaline reuptake.

CNS Activity

Curator's Comment: Known to be CNS penetrant in mouse, rat, monkey. Human data not available

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
LYRICA

Approved Use

LYRICA is indicated for: Management of neuropathic pain associated with diabetic peripheral neuropathy Management of postherpetic neuralgia Adjunctive therapy for adult patients with partial onset seizures Management of fibromyalgia Management of neuropathic pain associated with spinal cord injury LYRICA is indicated for: Neuropathic pain associated with diabetic peripheral neuropathy (DPN) (1) Postherpetic neuralgia (PHN) (1) Adjunctive therapy for adult patients with partial onset seizures (1) Fibromyalgia (1) Neuropathic pain associated with spinal cord injury (1)

Launch Date

2004
Palliative
LYRICA

Approved Use

LYRICA is indicated for: Management of neuropathic pain associated with diabetic peripheral neuropathy Management of postherpetic neuralgia Adjunctive therapy for adult patients with partial onset seizures Management of fibromyalgia Management of neuropathic pain associated with spinal cord injury LYRICA is indicated for: Neuropathic pain associated with diabetic peripheral neuropathy (DPN) (1) Postherpetic neuralgia (PHN) (1) Adjunctive therapy for adult patients with partial onset seizures (1) Fibromyalgia (1) Neuropathic pain associated with spinal cord injury (1)

Launch Date

2004
Palliative
LYRICA

Approved Use

LYRICA is indicated for: Management of neuropathic pain associated with diabetic peripheral neuropathy Management of postherpetic neuralgia Adjunctive therapy for adult patients with partial onset seizures Management of fibromyalgia Management of neuropathic pain associated with spinal cord injury LYRICA is indicated for: Neuropathic pain associated with diabetic peripheral neuropathy (DPN) (1) Postherpetic neuralgia (PHN) (1) Adjunctive therapy for adult patients with partial onset seizures (1) Fibromyalgia (1) Neuropathic pain associated with spinal cord injury (1)

Launch Date

2004
Palliative
LYRICA

Approved Use

LYRICA is indicated for: Management of neuropathic pain associated with diabetic peripheral neuropathy Management of postherpetic neuralgia Adjunctive therapy for adult patients with partial onset seizures Management of fibromyalgia Management of neuropathic pain associated with spinal cord injury LYRICA is indicated for: Neuropathic pain associated with diabetic peripheral neuropathy (DPN) (1) Postherpetic neuralgia (PHN) (1) Adjunctive therapy for adult patients with partial onset seizures (1) Fibromyalgia (1) Neuropathic pain associated with spinal cord injury (1)

Launch Date

2004
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4568.68 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PREGABALIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
29831.454 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PREGABALIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.3 h
unknown, oral
PREGABALIN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
healthy, 24.8 years
n = 10
Health Status: healthy
Age Group: 24.8 years
Sex: M
Population Size: 10
Sources:
Other AEs: Vision blurred, Nausea...
Other AEs:
Vision blurred (moderate, 1 patient)
Nausea (moderate, 1 patient)
Dizziness (mild, 4 patients)
Dysarthria (moderate, 1 patient)
Headache (mild, 2 patients)
Sources:
600 mg 1 times / day multiple, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, 53.91 years
n = 22
Health Status: unhealthy
Condition: Essential Tremor
Age Group: 53.91 years
Sex: M+F
Population Size: 22
Sources:
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Disc. AE: Dizziness, Somnolence...
AEs leading to
discontinuation/dose reduction:
Dizziness (3.47%)
Somnolence (2.76%)
Asthenia (0.82%)
Confusion (0.72%)
Peripheral edema (0.61%)
Headache (1.12%)
Amblyopia (0.82%)
Dry mouth (0.72%)
Nausea (0.72%)
Infection (0.41%)
Ataxia (0.41%)
Neuropathy (0.41%)
Tremor (0.41%)
Constipation (0.31%)
Diarrhea (0.31%)
Incoordination (0.31%)
Abnormal thinking (0.31%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Headache mild, 2 patients
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
healthy, 24.8 years
n = 10
Health Status: healthy
Age Group: 24.8 years
Sex: M
Population Size: 10
Sources:
Dizziness mild, 4 patients
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
healthy, 24.8 years
n = 10
Health Status: healthy
Age Group: 24.8 years
Sex: M
Population Size: 10
Sources:
Dysarthria moderate, 1 patient
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
healthy, 24.8 years
n = 10
Health Status: healthy
Age Group: 24.8 years
Sex: M
Population Size: 10
Sources:
Nausea moderate, 1 patient
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
healthy, 24.8 years
n = 10
Health Status: healthy
Age Group: 24.8 years
Sex: M
Population Size: 10
Sources:
Vision blurred moderate, 1 patient
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
healthy, 24.8 years
n = 10
Health Status: healthy
Age Group: 24.8 years
Sex: M
Population Size: 10
Sources:
Abnormal thinking 0.31%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Constipation 0.31%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Diarrhea 0.31%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Incoordination 0.31%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Ataxia 0.41%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Infection 0.41%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Neuropathy 0.41%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Tremor 0.41%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Peripheral edema 0.61%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Confusion 0.72%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Dry mouth 0.72%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Nausea 0.72%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Amblyopia 0.82%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Asthenia 0.82%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Headache 1.12%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Somnolence 2.76%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Dizziness 3.47%
Disc. AE
150 mg 1 times / day steady, oral
unhealthy, adult
n = 979
Overview

OverviewOther

Drug as perpetrator​Drug as victimTox targets
PubMed

PubMed

TitleDatePubMed
New single-isomer compounds on the horizon.
2002 Apr
The role of GABA in the pathophysiology and treatment of anxiety disorders.
2003
Gateways to clinical trials.
2003 Dec
Genotype-dependence of gabapentin and pregabalin sensitivity: the pharmacogenetic mediation of analgesia is specific to the type of pain being inhibited.
2003 Dec
Evaluation of mixture modeling with count data using NONMEM.
2003 Jun
Future Pain Drugs - Europe 2003. 15-16 September 2003, London, UK.
2003 Nov
The use of clinical trial simulation to support dose selection: application to development of a new treatment for chronic neuropathic pain.
2003 Nov
Gateways to clinical trials.
2003 Oct
Gateways to clinical trials.
2003 Sep
Pregabalin and gabapentin reduce release of substance P and CGRP from rat spinal tissues only after inflammation or activation of protein kinase C.
2003 Sep
Pregabalin: in the treatment of painful diabetic peripheral neuropathy.
2004
[New molecular targets in pharmacological treatment of anxiety disorders].
2004
Antiepileptic drugs in the treatment of anxiety disorders: role in therapy.
2004
Selecting pharmacotherapy for generalized anxiety disorder.
2004
Pregabalin as adjunctive therapy for partial seizures.
2004
Pregabalin pharmacology and its relevance to clinical practice.
2004
Newer anticonvulsants in the treatment of bipolar disorder.
2004
Efficacy of the novel anxiolytic pregabalin in social anxiety disorder: a placebo-controlled, multicenter study.
2004 Apr
Gateways to clinical trials.
2004 Apr
Anticonvulsants as anxiolytics, part 2: Pregabalin and gabapentin as alpha(2)delta ligands at voltage-gated calcium channels.
2004 Apr
Mechanism of action of alpha2delta ligands: voltage sensitive calcium channel (VSCC) modulators.
2004 Aug
Pregabalin for the treatment of painful diabetic peripheral neuropathy: a double-blind, placebo-controlled trial.
2004 Aug
Pharmaceutical treatment options for fibromyalgia.
2004 Aug
A study comparing the actions of gabapentin and pregabalin on the electrophysiological properties of cultured DRG neurones from neonatal rats.
2004 Aug 4
Pregabalin relieves symptoms of painful diabetic neuropathy: a randomized controlled trial.
2004 Dec 14
High dose pregabalin is effective for the treatment of generalised anxiety disorder.
2004 Feb
Pregabalin (Pfizer).
2004 Jan
Pregabalin add-on treatment: a randomized, double-blind, placebo-controlled, dose-response study in adults with partial seizures.
2004 Jan
Gateways to clinical trials.
2004 Jan-Feb
Gateways to clinical trials.
2004 Jul-Aug
Neuromodulating drugs for the symptomatic treatment of neuropathic pain.
2004 Jun
Gateways to clinical trials.
2004 Mar
Pharmacologic management part 1: better-studied neuropathic pain diseases.
2004 Mar
Anticonvulsants and the relief of chronic pain: pregabalin and gabapentin as alpha(2)delta ligands at voltage-gated calcium channels.
2004 May
American Chemical Society--227th annual meeting. Neuroprotection. 28 March - 1 April 2004, Anaheim, CA, USA.
2004 May
Pregabalin reduces pain and improves sleep and mood disturbances in patients with post-herpetic neuralgia: results of a randomised, placebo-controlled clinical trial.
2004 May
[How neuropathic is sciatica? The mixed pain concept].
2004 May
Effect of gabapentin derivates on mechanical allodynia-like behaviour in a rat model of chronic sciatic constriction injury.
2004 May 17
Highly selective asymmetric hydrogenation using a three hindered quadrant bisphosphine rhodium catalyst.
2004 May 19
[New options in the treatment of various forms of diabetic neuropathy].
2004 May 20
Gateways to clinical trials.
2004 Nov
Gateways to clinical trials.
2004 Oct
Efficacy and tolerability of the new antiepileptic drugs: comparison of two recent guidelines.
2004 Oct
'Protective premedication': an option with gabapentin and related drugs? A review of gabapentin and pregabalin in in the treatment of post-operative pain.
2004 Oct
Simultaneous high-performance liquid chromatographic analysis of pregabalin, gabapentin and vigabatrin in human serum by precolumn derivatization with o-phtaldialdehyde and fluorescence detection.
2004 Oct 25
Dual effects of gabapentin and pregabalin on glutamate release at rat entorhinal synapses in vitro.
2004 Sep
Practice parameter: treatment of postherpetic neuralgia: an evidence-based report of the Quality Standards Subcommittee of the American Academy of Neurology.
2004 Sep 28
Progress report on new antiepileptic drugs: a summary of the Seventh Eilat Conference (EILAT VII).
2004 Sep-Oct
The biology and pharmacology of calcium channel alpha2-delta proteins Pfizer Satellite Symposium to the 2003 Society for Neuroscience Meeting. Sheraton New Orleans Hotel, New Orleans, LA November 10, 2003.
2004 Summer
Pregabalin: in the treatment of postherpetic neuralgia.
2005
Patents

Sample Use Guides

Neuropathic Pain Associated with Diabetic Peripheral Neuropathy: The maximum recommended dose is 100 mg three times a day (300 mg/day) in patients with creatinine clearance of at least 60 mL/min. Postherpetic Neuralgia: The recommended dose is 75 to 150 mg two times a day, or 50 to 100 mg three times a day (150 to 300 mg/day) in patients with creatinine clearance of at least 60 mL/min. Begin dosing at 75 mg two times a day, or 50 mg three times a day (150 mg/day). The dose may be increased to 300 mg/day within 1 week based on efficacy and tolerability. Adjunctive Therapy for Adult Patients with Partial Onset Seizures: LYRICA at doses of 150 to 600 mg/day has been shown to be effective as adjunctive therapy in the treatment of partial onset seizures in adults. Both the efficacy and adverse event profiles of In general, it is recommended that patients be started on a total daily dose no greater than 150 mg/day (75 mg two times a day, or 50 mg three times a day). Management of Fibromyalgia: The recommended dose is 300 to 450 mg/day. Begin dosing at 75 mg two times a day (150 mg/day). The dose may be increased to 150 mg two times a day (300 mg/day) within 1 week based on efficacy and tolerability. Neuropathic Pain Associated with Spinal Cord Injury: The recommended dose range is 150 to 600 mg/day. The recommended starting dose is 75 mg two times a day (150 mg/day). The dose may be increased to 150 mg two times a day (300 mg/day) within 1 week based on efficacy and tolerability.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Pregabalin antagonizes the neurotoxic effects of copper
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:24:48 GMT 2023
Edited
by admin
on Sat Dec 16 18:24:48 GMT 2023
Record UNII
3DA4H8E58A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PREGABALIN SODIUM
Common Name English
HEXANOIC ACID, 3-(AMINOMETHYL)-5-METHYL-, MONOSODIUM SALT, (3S)-
Systematic Name English
HEXANOIC ACID, 3-(AMINOMETHYL)-5-METHYL-, SODIUM SALT (1:1), (3S)-
Systematic Name English
Code System Code Type Description
CAS
914254-22-1
Created by admin on Sat Dec 16 18:24:48 GMT 2023 , Edited by admin on Sat Dec 16 18:24:48 GMT 2023
PRIMARY
PUBCHEM
23669189
Created by admin on Sat Dec 16 18:24:48 GMT 2023 , Edited by admin on Sat Dec 16 18:24:48 GMT 2023
PRIMARY
FDA UNII
3DA4H8E58A
Created by admin on Sat Dec 16 18:24:48 GMT 2023 , Edited by admin on Sat Dec 16 18:24:48 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY