Identification

Name
Pregabalin
Accession Number
DB00230  (APRD01198)
Type
Small Molecule
Groups
Approved, Illicit, Investigational
Description

Pregabalin is an anticonvulsant drug used for neuropathic pain, epilepsy and generalized anxiety disorder.[4] It presents antihyperalgesic actions by binding to the α2δ subunit of the voltage-dependent calcium channels without presenting antinociceptive actions.[5] Pregabalin is marketed by Pfizer under the trade name Lyrica and Lyrica Cr (extended release).[13] It is considered to have a dependence liability if misused, and is classified as a Schedule V drug in the U.S.[4]

Structure
Thumb
Synonyms
  • (S)-3-(aminomethyl)-5-methylhexanoic acid
  • (S)-3-Isobutyl gaba
  • 3-Isobutyl gaba
  • CI 1008
  • Pregabalina
  • S-(+)-3-isobutylgaba
External IDs
CI-1008
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act PregabalinCapsule100 mgOralActavis Pharma CompanyNot applicableNot applicableCanada
Act PregabalinCapsule300 mgOralActavis Pharma Company2013-03-06Not applicableCanada
Act PregabalinCapsule75 mgOralActavis Pharma Company2013-03-06Not applicableCanada
Act PregabalinCapsule225 mgOralActavis Pharma Company2013-03-06Not applicableCanada
Act PregabalinCapsule50 mgOralActavis Pharma Company2013-03-06Not applicableCanada
Act PregabalinCapsule200 mgOralActavis Pharma CompanyNot applicableNot applicableCanada
Act PregabalinCapsule150 mgOralActavis Pharma Company2013-03-06Not applicableCanada
Act PregabalinCapsule25 mgOralActavis Pharma Company2013-03-06Not applicableCanada
LyricaCapsule100 mgOralPfizerNot applicableNot applicableCanada
LyricaCapsule75 mg/1OralH.J. Harkins Company2004-12-30Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ach-pregabalinCapsule50 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Ach-pregabalinCapsule225 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Ach-pregabalinCapsule100 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Ach-pregabalinCapsule25 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Ach-pregabalinCapsule200 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Ach-pregabalinCapsule75 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Ach-pregabalinCapsule300 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Ach-pregabalinCapsule150 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Apo-pregabalinCapsule225 mgOralApotex Corporation2013-05-09Not applicableCanada
Apo-pregabalinCapsule50 mgOralApotex Corporation2013-06-06Not applicableCanada
International/Other Brands
Lyrica (Pfizer) / Lyrica Cr (Pfizer)
Categories
UNII
55JG375S6M
CAS number
148553-50-8
Weight
Average: 159.2261
Monoisotopic: 159.125928793
Chemical Formula
C8H17NO2
InChI Key
AYXYPKUFHZROOJ-ZETCQYMHSA-N
InChI
InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1
IUPAC Name
(3S)-3-(aminomethyl)-5-methylhexanoic acid
SMILES
CC(C)C[C@H](CN)CC(O)=O

Pharmacology

Indication

Pregabalin is used for the management of neuropathic pain associated with diabetic peripheral neuropathy or spinal cord injury, and postherpetic neuralgia. It is not approved for the management of fibromyalgia or as adjuntive therapy for adult partial onset seizures.[Label]

Associated Conditions
Pharmacodynamics

Pregabalin is a structural analog of the inhibitory neurotransmitter gamma-aminobutyric acid (GABA). It has been reported that its action presents the function of modulating the release of many excitatory neurotransmitters such as glutamate, norepinephrine, subtance-P and calcitonin gene related peptide.This modulation can cause an inhibitory modulation of overexcited neurons allowing them to get back to a normal state, including te decrease on the hyper excitability caused by tissue damage.[6] The neurotransmitter modulation allows pregabalin to present antiallodynic, anxiolytic and anticonvulsant activity.[7]

Mechanism of action

Pregabalin binds presynaptically to the alpha2-delta subunit of the voltage-gated calcium channels in central nervous system tissues located in the brain and spinal cord.[6] The mechanism of action has not been fully elucidated but studies suggest that pregabalin produces a disruption of calcium channel traficking or a reduction of calcium currents. The inhibition of subunits of voltage-gated calcium channels reduces calcium release which in order inhibits the release of several neurotransmitters [Label] Studies also suggest that the descending noradrenergic and serotonergic pathways originating from the brainstem may be involved with the mechanism of pregabalin. Interestingly, although pregabalin is a structural derivative of inhibitory neurotransmitter gamma-aminobutyric acid (GABA), it does not bind directly to GABA or benzodiazepine receptors.[8]

TargetActionsOrganism
AVoltage-dependent P/Q-type calcium channel subunit alpha-1A
inhibitor
Human
Absorption

Pregabalin has linear and dose-proportional absorption with a steady state achieved at 48-72 hours. Nowadays, there are two different formulations of pregabalin with different pharmacokinetic profiles, this is important due to the fact that the newest formulation has a propety of extended release. Pregabalin, in its both forms, presents a rapid absorption at fasting state. Pregabalin has a Cmax of 3.2mcg/ml, Tmax 0.7 hours and AUC 31.5mcg h/ml, while pregabalin CR (extended release) presents a Cmax 2.0mcg/ml, Tmax 8 hours and AUC 29.4mcg h/ml. Pregabalin is absorbed from the small intestine and proximal colon and its AUC values will depend on the type and quantity of meal calories ingested. [9]

Volume of distribution

Pregabalin does not bind to plasma proteins. The apparent volume of distribution after oral administration is 0.5 L/kg. Pregabalin passage across bloos brain barrier (BBB) is done through the system L. [10]

Protein binding

Pregabalin does not bind to plasma proteins.[Label]

Metabolism

Pregabalin undergoes negligible metabolism in humans.[11]

Route of elimination

Pregabalin presents mainly a renal excretion, it has been reported that 90% of the administered dose is recovered unchanged in the urine. Secondly, it is possible to find N-methylated pregabalin in urine, and this metabolite can account for 0.9% of the dose. Pregabalin (S-enantiomer) did not undergo racemization to the R-enantiomer in pre-clinical studies. [11]

Half life

Mean elimination half-life is 6.3 hours in subjects with normal renal function.[12]

Clearance

Mean renal clearance is estimated to be 67 to 80.9 ml/min in young healthy subjects. Due to its lack of plasma protein binding, it is indicated the presence of renal tubular reabsorption.[Label]

Toxicity

Most common adverse reactions presented in clinical trials are dizziness, somnolence, peripheral edema, nausea, blurred vision, dry mouth and weight gain.[Label]

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Pregabalin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Pregabalin.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Pregabalin is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of 2,5-Dimethoxy-4-ethylthioamphetamine can be increased when used in combination with Pregabalin.
3-isobutyl-1-methyl-7H-xanthinePregabalin may increase the excretion rate of 3-isobutyl-1-methyl-7H-xanthine which could result in a lower serum level and potentially a reduction in efficacy.
3,4-MethylenedioxyamphetamineThe therapeutic efficacy of 3,4-Methylenedioxyamphetamine can be increased when used in combination with Pregabalin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Pregabalin.
4-Bromo-2,5-dimethoxyamphetamineThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyamphetamine can be increased when used in combination with Pregabalin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Pregabalin.
4-MethoxyamphetamineThe therapeutic efficacy of 4-Methoxyamphetamine can be increased when used in combination with Pregabalin.
Food Interactions
  • Avoid alcohol (may increase CNS effects).
  • When taken with food, Cmax decreases, while Tmax is prolonged. Despite these observations, the total absorption of pregabalin is not effected to a clinically relevant degree. Pregabalin can be taken with or without food.

References

Synthesis Reference

Mark Burk, "Asymmetric synthesis of pregabalin." U.S. Patent US20030212290, issued November 13, 2003.

US20030212290
General References
  1. Authors unspecified: Schedules of controlled substances: placement of pregabalin into schedule V. Final rule. Fed Regist. 2005 Jul 28;70(144):43633-5. [PubMed:16050051]
  2. Su TZ, Feng MR, Weber ML: Mediation of highly concentrative uptake of pregabalin by L-type amino acid transport in Chinese hamster ovary and Caco-2 cells. J Pharmacol Exp Ther. 2005 Jun;313(3):1406-15. Epub 2005 Mar 15. [PubMed:15769862]
  3. Li Z, Taylor CP, Weber M, Piechan J, Prior F, Bian F, Cui M, Hoffman D, Donevan S: Pregabalin is a potent and selective ligand for alpha(2)delta-1 and alpha(2)delta-2 calcium channel subunits. Eur J Pharmacol. 2011 Sep 30;667(1-3):80-90. doi: 10.1016/j.ejphar.2011.05.054. Epub 2011 Jun 1. [PubMed:21651903]
  4. Bonnet U, Scherbaum N: How addictive are gabapentin and pregabalin? A systematic review. Eur Neuropsychopharmacol. 2017 Oct 5. pii: S0924-977X(17)30897-0. doi: 10.1016/j.euroneuro.2017.08.430. [PubMed:28988943]
  5. Field MJ, Oles RJ, Lewis AS, McCleary S, Hughes J, Singh L: Gabapentin (neurontin) and S-(+)-3-isobutylgaba represent a novel class of selective antihyperalgesic agents. Br J Pharmacol. 1997 Aug;121(8):1513-22. [PubMed:9283683]
  6. Rajappa GC, Vig S, Bevanaguddaiah Y, Anadaswamy TC: Efficacy of Pregabalin as Premedication for Post-Operative Analgesia in Vaginal Hysterectomy. Anesth Pain Med. 2016 May 14;6(3):e34591. doi: 10.5812/aapm.34591. eCollection 2016 Jun. [PubMed:27642577]
  7. Bender G, Florian JA Jr, Bramwell S, Field MJ, Tan KK, Marshall S, DeJongh J, Bies RR, Danhof M: Pharmacokinetic-pharmacodynamic analysis of the static allodynia response to pregabalin and sildenafil in a rat model of neuropathic pain. J Pharmacol Exp Ther. 2010 Aug;334(2):599-608. doi: 10.1124/jpet.110.166074. Epub 2010 May 5. [PubMed:20444880]
  8. Ben-Menachem E: Pregabalin pharmacology and its relevance to clinical practice. Epilepsia. 2004;45 Suppl 6:13-8. [PubMed:15315511]
  9. Prompila N, Eiamart W, Jumroen Y, Sayankuldilok N, Chariyavilaskul P, Ketchat W, Wittayalertpanya S: Pharmacokinetics and bioequivalence of a pregabalin 150-mg capsule in healthy Thai subjects. Int J Clin Pharmacol Ther. 2017 Oct;55(10):811-817. doi: 10.5414/CP202954. [PubMed:28513426]
  10. Hong T, Han S, Lee J, Jeon S, Yim DS: Comparison of oral absorption models for pregabalin: usefulness of transit compartment model. Drug Des Devel Ther. 2016 Dec 7;10:3995-4003. eCollection 2016. [PubMed:27994441]
  11. Rodriguez J, Castaneda G, Munoz L: Direct determination of pregabalin in human urine by nonaqueous CE-TOF-MS. Electrophoresis. 2013 May;34(9-10):1429-36. doi: 10.1002/elps.201200564. Epub 2013 Apr 16. [PubMed:23463484]
  12. Randinitis EJ, Posvar EL, Alvey CW, Sedman AJ, Cook JA, Bockbrader HN: Pharmacokinetics of pregabalin in subjects with various degrees of renal function. J Clin Pharmacol. 2003 Mar;43(3):277-83. [PubMed:12638396]
  13. Pfizer [Link]
External Links
Human Metabolome Database
HMDB0014375
KEGG Drug
D02716
PubChem Compound
5486971
PubChem Substance
46504934
ChemSpider
4589156
BindingDB
50164279
ChEBI
64356
ChEMBL
CHEMBL1059
Therapeutic Targets Database
DAP001264
PharmGKB
PA164754814
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pregabalin
ATC Codes
N03AX16 — Pregabalin
AHFS Codes
  • 28:12.92 — Miscellaneous Anticonvulsants
FDA label
Download (3.46 MB)
MSDS
Download (106 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentNicotine Dependence1
0CompletedTreatmentPost-Operative Pain1
0Not Yet RecruitingTreatmentFracture; Rib, Multiple1
0RecruitingTreatmentCannabis-use Disorders1
1CompletedNot AvailableHealthy Volunteers9
1CompletedNot AvailableNerve Pain1
1CompletedBasic ScienceHealthy Volunteers8
1CompletedOtherHealthy Volunteers1
1CompletedScreeningHealthy Volunteers1
1CompletedTreatmentDiabetic Neuropathies / Idiopathic Distal Sensory Polyneuropathy / Painful Small-Fiber Neuropathy / Postherpetic Neuralgia1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentPain, Acute1
1CompletedTreatmentPeripheral Neuropathy Pain1
1CompletedTreatmentPeripheral Nueropathy Pain1
1Not Yet RecruitingTreatmentHealthy Volunteers1
1RecruitingTreatmentPain, Neuropathic1
1Unknown StatusTreatmentRefractive Errors1
1, 2CompletedTreatmentEpilepsy, Localization Related1
1, 2CompletedTreatmentPrimary Total Knee Arthroplasty1
1, 2RecruitingTreatmentCoughing1
2Active Not RecruitingSupportive CarePostoperative pain1
2CompletedNot AvailableFeeling Anxious1
2CompletedSupportive CareBrain and Central Nervous System Tumors / Seizures1
2CompletedSupportive CarePain NOS / Peripheral Neuropathy1
2CompletedTreatmentAlcohol Dependence1
2CompletedTreatmentCRP1
2CompletedTreatmentDental Anxiety1
2CompletedTreatmentDiabetes Mellitus (DM) / Diabetic Neuropathies / Pain, Chronic1
2CompletedTreatmentDiabetic Neuropathic Pain1
2CompletedTreatmentDiabetic Neuropathies1
2CompletedTreatmentDiabetic Neuropathy, Painful2
2CompletedTreatmentDiabetic Neuropathy, Painful; Diabetic Neuropathies1
2CompletedTreatmentDiabetic Peripheral Neuropathic Pain (DPN)2
2CompletedTreatmentDiabetic Peripheral Neuropathy (DPN)1
2CompletedTreatmentDiabetic Peripheral Neuropathy (DPN) / Pain NOS1
2CompletedTreatmentElective Laparoscopic Cholecystectomy / Sevoflurane Anesthesia1
2CompletedTreatmentEpilepsy, Localization Related1
2CompletedTreatmentIdiopathic Small Fiber Neuropathy1
2CompletedTreatmentIrritable Bowel Syndrome (IBS)1
2CompletedTreatmentMalignancies / Pain NOS1
2CompletedTreatmentPain NOS1
2CompletedTreatmentPain NOS / Postherpetic Neuralgia1
2CompletedTreatmentPain, Neuropathic1
2CompletedTreatmentPostherpetic Neuralgia1
2CompletedTreatmentRestless Legs Syndrome (RLS)1
2CompletedTreatmentUrinary Bladder, Overactive1
2RecruitingTreatmentAlcohol Use Disorder (AUD)1
2RecruitingTreatmentEarache1
2RecruitingTreatmentGulf War Illness1
2TerminatedPreventionCancer, Breast / Malignant Lymphomas / Pain NOS1
2TerminatedTreatmentFibromyalgia1
2TerminatedTreatmentHerpes Zoster / Postherpetic Neuralgia1
2TerminatedTreatmentOrofacial Pain / Pain, Neuropathic1
2TerminatedTreatmentPain, Chronic1
2TerminatedTreatmentPainful Diabetic Peripheral Neuropathy (PDPN)1
2TerminatedTreatmentPostherpetic Neuralgia1
2TerminatedTreatmentVulvar Vestibulitis / Vulvodynia1
2TerminatedTreatmentNeurocostal neuralgia1
2Unknown StatusTreatmentCancer, Breast / Drug-Related Side Effects and Adverse Reactions / Pain NOS / Taxane1
2Unknown StatusTreatmentFibromyalgia / Pain, Chronic1
2WithdrawnTreatmentDiabetes Mellitus (DM) / Pain, Neuropathic1
2, 3Active Not RecruitingPreventionEye Dryness1
2, 3Active Not RecruitingPreventionPregabalin on Catheter Related Bladder Discomfort2
2, 3CompletedBasic ScienceFibromyalgia1
2, 3CompletedPreventionPostoperative pain1
2, 3CompletedTreatmentAcute Agitation / Dementias / Pain NOS1
2, 3CompletedTreatmentDiabetes Mellitus (DM) / Peripheral Neuropathy1
2, 3CompletedTreatmentPancreatitis, Chronic1
3CompletedHealth Services ResearchHysterectomy1
3CompletedPreventionChronic Post-surgical Pain / Post-mastectomy Pain Syndrome1
3CompletedPreventionDelirium / Pain NOS1
3CompletedPreventionPain NOS / Pain, Neuropathic / Polyneuropathies1
3CompletedPreventionPost-Operative Pain1
3CompletedSupportive CareCancer, Breast / Menopausal Hot Flushes1
3CompletedSupportive CareIntervertebral Disc Herniation1
3CompletedTreatmentBreast Cancer Surgery / Post Operative Pain1
3CompletedTreatmentDiabetic Neuropathies1
3CompletedTreatmentDiabetic Neuropathies / Neurocostal neuralgia1
3CompletedTreatmentDiabetic Neuropathy, Painful7
3CompletedTreatmentDiabetic Peripheral Neuropathy (DPN)1
3CompletedTreatmentDiabetic Peripheral Neuropathy (DPN) / Nerve Pain1
3CompletedTreatmentDisseminated Sclerosis / Pain, Neuropathic1
3CompletedTreatmentEpilepsies1
3CompletedTreatmentEpilepsy, Complex Partial / Epilepsy, Localization Related1
3CompletedTreatmentEpilepsy, Localization Related2
3CompletedTreatmentEpilepsy, Localization Related / Sleep Deprivation1
3CompletedTreatmentEpilepsy, Localization Related / Partial onset seizure Epilepsy1
3CompletedTreatmentFeeling Anxious1
3CompletedTreatmentFibromyalgia13
3CompletedTreatmentFibromyalgia / Sleep disorders and disturbances1
3CompletedTreatmentGeneralized Anxiety Disorder (GAD)2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Peripheral Neuropathy2
3CompletedTreatmentIdiopathic Restless Legs Syndrome1
3CompletedTreatmentInguinal Hernias / Postoperative pain1
3CompletedTreatmentLiver Cirrhosis / Muscle Cramps1
3CompletedTreatmentNeuroses, Anxiety1
3CompletedTreatmentOsteoarthritis (OA)1
3CompletedTreatmentOsteoarthritis (OA) / Postoperative pain1
3CompletedTreatmentPain Associated With Fibromyalgia3
3CompletedTreatmentPain NOS2
3CompletedTreatmentNeurocostal neuralgia / Pain NOS / Spinal Cord Diseases / Spinal Cord Injuries (SCI)1
3CompletedTreatmentPain, Chronic1
3CompletedTreatmentPain, Neuropathic4
3CompletedTreatmentPainful Diabetic Peripheral Neuropathy (PDPN)1
3CompletedTreatmentPost-Herpetic Neuralgia (PHN)1
3CompletedTreatmentPostherpetic Neuralgia2
3CompletedTreatmentPostoperative pain3
3CompletedTreatmentRadicular syndrome1
3CompletedTreatmentRestless Legs Syndrome (RLS)1
3CompletedTreatmentSeizure Disorder, Partial4
3CompletedTreatmentSeizures1
3CompletedTreatmentNeurocostal neuralgia / Spinal Cord Injuries (SCI)1
3CompletedTreatmentNeurocostal neuralgia2
3CompletedTreatmentPartial onset seizure Epilepsy2
3Not Yet RecruitingPreventionHerpetic Neuralgia1
3RecruitingPreventionPersistent Postoperative Pain1
3RecruitingPreventionPostoperative pain1
3RecruitingTreatmentAlcohol Use Disorder (AUD) / Post Traumatic Stress Disorder (PTSD)1
3RecruitingTreatmentEpilepsy, Partial Seizures / Epilepsy, Primary Generalized Tonic-Clonic Seizures1
3RecruitingTreatmentFibromyalgia1
3RecruitingTreatmentPain of Mononeuropathy1
3RecruitingTreatmentPeripheral Neuropathic Pain1
3RecruitingTreatmentPostherpetic Neuralgia1
3TerminatedPreventionPain NOS / Spinal Cord Trauma1
3TerminatedSupportive CarePerioperative Pain1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentEpilepsies1
3TerminatedTreatmentEpilepsy, Localization Related1
3TerminatedTreatmentFusion of Spine (Disease)1
3TerminatedTreatmentInfection, Human Immunodeficiency Virus I / Pain, Neuropathic1
3TerminatedTreatmentNeuropathy1
3Unknown StatusPreventionInguinal Hernias / Postoperative pain1
3Unknown StatusTreatmentChronic Prostatitis/Chronic Pelvic Pain Syndrome (CP/CPPS)1
3Unknown StatusTreatmentDiabetic Neuropathies1
3Unknown StatusTreatmentMalignancies / Neurocostal neuralgia1
3Unknown StatusTreatmentPostoperative pain1
3WithdrawnPreventionPain, Chronic1
3WithdrawnPreventionPhantom Pain1
3WithdrawnTreatmentMigraine Disorders1
3WithdrawnTreatmentRestless Legs Syndrome (RLS)1
4Active Not RecruitingTreatmentAlcohol Dependence1
4Active Not RecruitingTreatmentDiabetic Peripheral Neuropathy (DPN) / Fibromyalgia / Seizure Disorder, Partial1
4Active Not RecruitingTreatmentPost Operative Pain1
4CompletedNot AvailableHealthy Lactating Women1
4CompletedNot AvailableHealthy Volunteers2
4CompletedNot AvailableIrritable Bowel Syndrome (IBS)1
4CompletedNot AvailablePain, Neuropathic2
4CompletedNot AvailablePostoperative pain1
4CompletedDiagnosticAnxiety Disorders1
4CompletedOtherHealthy Volunteers1
4CompletedTreatmentAnxiety-comorbidity to Schizophrenia / Schizophrenic Disorders1
4CompletedTreatmentCentral Neuropathic Pain1
4CompletedTreatmentCervical Spondylosis / Cervical Spondylotic Myelopathy / Cervical Spondylotic Radiculopathy1
4CompletedTreatmentChemotherapy Induced Neuropathic Pain / Diabetic Peripheral Neuropathic Pain (DPN) / HIV-related Neuropathic Pain (HIV) / Postherpetic Neuralgia ( PHN )1
4CompletedTreatmentComplex Partial Seizure Disorder / Epilepsies / Epilepsy, Localization Related / Seizure Disorder, Partial1
4CompletedTreatmentCryptogenic Sensory Polyneuropathy1
4CompletedTreatmentDiabetic Neuropathies1
4CompletedTreatmentDiabetic Neuropathy, Painful3
4CompletedTreatmentDiabetic Peripheral Neuropathic Pain (DPN)2
4CompletedTreatmentDiabetic Peripheral Neuropathy (DPN)1
4CompletedTreatmentDisk Prolapse / Intervertebral Disk Displacement1
4CompletedTreatmentEffect of Laryngoscopy and Tracheal Intubation1
4CompletedTreatmentEpilepsies1
4CompletedTreatmentEpilepsy, Localization Related1
4CompletedTreatmentFailed Back Surgery Syndrome / Intervertebral Disc Herniation / Neuropathy; Radicular, Lumbar, Lumbosacral / Spinal Stenosis1
4CompletedTreatmentFibromyalgia4
4CompletedTreatmentGeneralized Anxiety Disorder (GAD)1
4CompletedTreatmentLaparoscopic Cholecystectomy / Postoperative pain1
4CompletedTreatmentLiving Donors1
4CompletedTreatmentLumbar Spinal Fusions1
4CompletedTreatmentNeurogenic Intermittent Claudication / Spinal Stenosis of Lumbar Region1
4CompletedTreatmentNeurologic Claudication in Patients With Lumbar Spinal Stenosis1
4CompletedTreatmentNon-diabetic Painful Peripheral Polyneuropathy / Peripheral Nerve Injury (PNI) / Postherpetic Neuralgia ( PHN )1
4CompletedTreatmentOpioids Use / Postoperative pain1
4CompletedTreatmentPain NOS1
4CompletedTreatmentPain NOS / Postoperative1
4CompletedTreatmentPain, Acute1
4CompletedTreatmentPain, Chronic1
4CompletedTreatmentPainful Diabetic Neuropathy and Post Herpetic Neuralgia1
4CompletedTreatmentPost-Herpetic Neuralgia (PHN)1
4CompletedTreatmentPost-Operative Pain1
4CompletedTreatmentPost-thoracotomy Pain1
4CompletedTreatmentPostherpetic Neuralgia ( PHN )1
4CompletedTreatmentPostoperative Pain Management1
4CompletedTreatmentPostoperative Pain Management / Total Knee Arthroplasty (TKA)1
4CompletedTreatmentPostoperative pain4
4CompletedTreatmentSeizures1
4CompletedTreatmentNeurocostal neuralgia / Spinal Cord Injuries (SCI)1
4CompletedTreatmentAdjunct to general anesthesia therapy / Surgery, Laparoscopic1
4CompletedTreatmentTremor, Essential2
4CompletedTreatmentNeurocostal neuralgia1
4Enrolling by InvitationTreatmentNonspecific Pain Post Traumatic Injury1
4Not Yet RecruitingPreventionKnee Osteoarthritis (Knee OA)1
4Not Yet RecruitingTreatmentHead and Neck Carcinoma / Postoperative pain1
4Not Yet RecruitingTreatmentPain, Neuropathic1
4RecruitingSupportive CareScoliosis / Spondylolisthesis1
4RecruitingTreatmentEpilepsy, Localization Related1
4RecruitingTreatmentHepatocellular Cancer1
4RecruitingTreatmentLumbar Disc Disease / Lumbar Radiculopathy / Prolapsed Lumbar Disc1
4RecruitingTreatmentObsessive Compulsive Disorder (OCD)1
4RecruitingTreatmentOpiate withdrawal symptoms1
4TerminatedBasic ScienceSubstance-Related Disorders1
4TerminatedTreatmentAbdominal Pain (AP) / Surgical Adhesions1
4TerminatedTreatmentArterial Occlusive Diseases / Critical Limb Ischemia (CLI) / Pain NOS / Transient ischemia attacks1
4TerminatedTreatmentBone Neoplasms / Malignancies / Pain, Intractable1
4TerminatedTreatmentChemotherapy-induced Peripheral Neuropathy (CIPN)1
4TerminatedTreatmentChronic Low Back Pain With a Neuropathic Component1
4TerminatedTreatmentEpilepsies / Feeling Anxious1
4TerminatedTreatmentEpilepsy, Complex Partial1
4TerminatedTreatmentMalignant Neoplasm of Pancreas / Visceral Pain1
4TerminatedTreatmentPostherpetic Neuralgia1
4TerminatedTreatmentPostoperative pain1
4TerminatedTreatmentUterine Artery Embolization / Uterine Leiomyomas1
4TerminatedTreatmentPartial onset seizure Epilepsy1
4Unknown StatusBasic ScienceDiabetes Mellitus (DM) / Painful Distal Symmetric Sensorimotor Polyneuropathy1
4Unknown StatusPreventionHyperalgesia / Illness, Chronic / Pain NOS / Pain, Neuropathic1
4Unknown StatusTreatmentFeeling Anxious1
4Unknown StatusTreatmentPain, Neuropathic / Spinal Cord Injuries (SCI)1
4Unknown StatusTreatmentPain, Neuropathic / Tactile Hyperalgesia1
4Unknown StatusTreatmentPolyneuropathies1
4Unknown StatusTreatmentUremic Pruritus2
4WithdrawnDiagnosticBack Pain Lower Back / Neurocostal neuralgia1
4WithdrawnTreatmentChronic Pain, Postoperative / Headaches1
4WithdrawnTreatmentDiabetic Polyneuropathy / Postherpetic Neuralgia1
4WithdrawnTreatmentFibromyalgia1
4WithdrawnTreatmentRestless Legs Syndrome (RLS)1
Not AvailableActive Not RecruitingPreventionPain, Cancer / Pain, Neuropathic / Persistent Post-surgical Pain1
Not AvailableActive Not RecruitingSupportive CarePain NOS / Peripheral Neuropathy1
Not AvailableAvailableNot AvailableAcute and Chronic Pain Following Modified Radical Mastectomy1
Not AvailableCompletedNot AvailableBlock1
Not AvailableCompletedNot AvailableEpilepsies1
Not AvailableCompletedNot AvailableEpilepsies / Fibromyalgia / Pain, Neuropathic / Post-market Surveillance1
Not AvailableCompletedNot AvailableEpilepsies / Neurocostal neuralgia1
Not AvailableCompletedNot AvailablePain Associated With Fibromyalgia1
Not AvailableCompletedNot AvailablePain, Neuropathic2
Not AvailableCompletedNot AvailableNeurocostal neuralgia1
Not AvailableCompletedOtherNeuropathy / Pain NOS1
Not AvailableCompletedOtherSedation, Conscious1
Not AvailableCompletedPreventionPain NOS2
Not AvailableCompletedPreventionPain, Neuropathic1
Not AvailableCompletedSupportive CarePain NOS1
Not AvailableCompletedSupportive CarePostoperative pain1
Not AvailableCompletedTreatmentHepatocellular,Carcinoma / Postoperative pain1
Not AvailableCompletedTreatmentPain NOS2
Not AvailableCompletedTreatmentPostoperative pain1
Not AvailableNot Yet RecruitingOtherPostoperative Pain After Knee Arthroscopy1
Not AvailableNot Yet RecruitingTreatmentFibromyalgia / Hyperbaric Oxygen1
Not AvailableNot Yet RecruitingTreatmentPain, Neuropathic1
Not AvailableNot Yet RecruitingTreatmentPeripheral Arterial Disease (PAD)1
Not AvailableRecruitingNot AvailablePain, Neuropathic / Postoperative pain1
Not AvailableRecruitingPreventionAnterior Cruciate Ligament (ACL) Reconstruction1
Not AvailableRecruitingSupportive CarePostoperative pain1
Not AvailableRecruitingSupportive CareSpine Surgery1
Not AvailableRecruitingTreatmentOropharyngeal Cancers / Squamous Cell Carcinoma to the Head and Neck1
Not AvailableRecruitingTreatmentLumbar epidural anesthesia therapy / Shivering1
Not AvailableSuspendedTreatmentSmall-Fiber Neuropathy1
Not AvailableTerminatedNot AvailableSpinal Cord Injuries (SCI)1
Not AvailableTerminatedTreatmentChronic Pain, Postoperative1
Not AvailableTerminatedTreatmentCocaine Abuse / Cocaine-Related Disorders1
Not AvailableTerminatedTreatmentComplex Regional Pain Syndromes (CRPS)1
Not AvailableTerminatedTreatmentPostoperative pain1
Not AvailableUnknown StatusSupportive CareNasal Septum Deviation1
Not AvailableUnknown StatusSupportive CarePain NOS1
Not AvailableUnknown StatusSupportive CarePostoperative pain1
Not AvailableUnknown StatusTreatmentFibromyalgia1
Not AvailableUnknown StatusTreatmentMultimodal Analgesia / Postoperative Pain Control1
Not AvailableUnknown StatusTreatmentTo Assess the Beneficial Preemptive and Preventive Effects of PGL on the Immediate and Late (1- and 3 Months) Postoperative Analgesia Requirements1
Not AvailableWithdrawnPreventionPain NOS1
Not AvailableWithdrawnTreatmentAnalgesia, Postoperative / CSOM - Chronic Suppurative Otitis Media1

Pharmacoeconomics

Manufacturers
  • Cp pharmaceuticals cv
  • Pfizer inc
Packagers
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • Cardinal Health
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Goedecke GmbH
  • Innoviant Pharmacy Inc.
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Shasun Chemicals & Drugs Ltd.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • US Pharmaceutical Group
Dosage forms
FormRouteStrength
CapsuleOral100 mg/1
CapsuleOral100 mg
CapsuleOral150 mg
CapsuleOral150 mg/1
CapsuleOral200 mg
CapsuleOral200 mg/1
CapsuleOral225 mg/1
CapsuleOral225 mg
CapsuleOral25 mg
CapsuleOral25 mg/1
CapsuleOral300 mg
CapsuleOral300 mg/1
CapsuleOral50 mg/1
CapsuleOral50 mg
CapsuleOral75 mg/1
CapsuleOral75 mg
SolutionOral20 mg/1mL
Tablet, film coated, extended releaseOral165 mg/1
Tablet, film coated, extended releaseOral330 mg/1
Tablet, film coated, extended releaseOral82.5 mg/1
Prices
Unit descriptionCostUnit
Lyrica 100 mg capsule2.88USD capsule
Lyrica 150 mg capsule2.88USD capsule
Lyrica 50 mg capsule2.88USD capsule
Lyrica 75 mg capsule2.88USD capsule
Lyrica 200 mg capsule2.75USD capsule
Lyrica 225 mg capsule2.75USD capsule
Lyrica 25 mg capsule2.75USD capsule
Lyrica 300 mg capsule2.75USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5563175No1996-10-082013-10-08Us
CA2327285No2005-06-142019-05-10Canada
CA2297163No2001-11-202018-08-18Canada
US6001876No1999-12-142018-12-30Us
USRE41920No2010-11-092018-12-30Us
US6197819No2001-03-062018-12-30Us
US9144559No2015-09-292026-11-02Us
US8945620No2015-02-032026-11-02Us
US10022447No2006-11-022026-11-02Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)186-188ºCNot Available
boiling point (°C)274ºC at 760 mm HgNot Available
water solubilityFreely soluble FDA label
logP-1.35FDA label
pKa4.2 and 10.6 FDA label
Predicted Properties
PropertyValueSource
Water Solubility11.3 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.8ChemAxon
pKa (Strongest Basic)10.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity43.68 m3·mol-1ChemAxon
Polarizability18.08 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9727
Blood Brain Barrier+0.9382
Caco-2 permeable-0.6531
P-glycoprotein substrateNon-substrate0.683
P-glycoprotein inhibitor INon-inhibitor0.965
P-glycoprotein inhibitor IINon-inhibitor0.9424
Renal organic cation transporterNon-inhibitor0.9245
CYP450 2C9 substrateNon-substrate0.8758
CYP450 2D6 substrateNon-substrate0.7926
CYP450 3A4 substrateNon-substrate0.6914
CYP450 1A2 substrateNon-inhibitor0.9385
CYP450 2C9 inhibitorNon-inhibitor0.9425
CYP450 2D6 inhibitorNon-inhibitor0.9539
CYP450 2C19 inhibitorNon-inhibitor0.9629
CYP450 3A4 inhibitorNon-inhibitor0.9352
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9784
Ames testNon AMES toxic0.938
CarcinogenicityNon-carcinogens0.5678
BiodegradationReady biodegradable0.8201
Rat acute toxicity1.7046 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9868
hERG inhibition (predictor II)Non-inhibitor0.8909
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0900000000-555454e7e8e11dab591d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0900000000-1a52554257d7f4b1c62e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0900000000-d48cd6eeef012787cc04
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0900000000-4b11df5208caa2e97dd2
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0900000000-605dc241ffd3a07a9220
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01ox-0900000000-fb081cde39dde2ce89f8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-3d95bb5278c7866658a0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-96cebf4a3610cbf02059
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-8900000000-385584fca9e88b90a95b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-9800000000-a1c6718b087b06101b8d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9200000000-5f291c943a1d1ae214ad
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9100000000-5283d02d98611a8c2c38
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9000000000-8797f8d2776fcdb4b6d5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9000000000-a9ddfcf2032ffc9f53ad

Taxonomy

Description
This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Gamma amino acids and derivatives
Alternative Parents
Medium-chain fatty acids / Branched fatty acids / Amino fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
show 1 more
Substituents
Gamma amino acid or derivatives / Medium-chain fatty acid / Amino fatty acid / Branched fatty acid / Fatty acyl / Fatty acid / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Amine
show 11 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
gamma-amino acid (CHEBI:64356)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity
Specific Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
Gene Name
CACNA1A
Uniprot ID
O00555
Uniprot Name
Voltage-dependent P/Q-type calcium channel subunit alpha-1A
Molecular Weight
282362.39 Da
References
  1. Gazulla J, Tintore M: The P/Q-type voltage-dependent calcium channel: a therapeutic target in spinocerebellar ataxia type 6. Acta Neurol Scand. 2007 May;115(5):356-63. [PubMed:17489948]
  2. Gazulla J, Tintore MA: The P/Q-type voltage-dependent calcium channel as pharmacological target in spinocerebellar ataxia type 6: gabapentin and pregabalin may be of therapeutic benefit. Med Hypotheses. 2007;68(1):131-6. Epub 2006 Aug 8. [PubMed:16899342]
  3. Jacquy J, Lossignol D, Sternon J: [Pregabalin (Lyrica) and neuropathic pain syndromes]. Rev Med Brux. 2006 Sep-Oct;27(5):445-50. [PubMed:17144644]
  4. Taylor CP, Angelotti T, Fauman E: Pharmacology and mechanism of action of pregabalin: the calcium channel alpha2-delta (alpha2-delta) subunit as a target for antiepileptic drug discovery. Epilepsy Res. 2007 Feb;73(2):137-50. Epub 2006 Nov 28. [PubMed:17126531]
  5. Field MJ, Cox PJ, Stott E, Melrose H, Offord J, Su TZ, Bramwell S, Corradini L, England S, Winks J, Kinloch RA, Hendrich J, Dolphin AC, Webb T, Williams D: Identification of the alpha2-delta-1 subunit of voltage-dependent calcium channels as a molecular target for pain mediating the analgesic actions of pregabalin. Proc Natl Acad Sci U S A. 2006 Nov 14;103(46):17537-42. Epub 2006 Nov 6. [PubMed:17088553]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [PubMed:22039822]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Other
General Function
Sodium:dicarboxylate symporter activity
Specific Function
Transports L-glutamate, L- and D-aspartate and L-cystein (PubMed:21123949). Essential for terminating the postsynaptic action of glutamate by rapidly removing released glutamate from the synaptic c...
Gene Name
SLC1A1
Uniprot ID
P43005
Uniprot Name
Excitatory amino acid transporter 3
Molecular Weight
57099.835 Da
References
  1. Ryu JH, Lee PB, Kim JH, Do SH, Kim CS: Effects of pregabalin on the activity of glutamate transporter type 3. Br J Anaesth. 2012 Aug;109(2):234-9. doi: 10.1093/bja/aes120. Epub 2012 Apr 16. [PubMed:22511482]

Drug created on June 13, 2005 07:24 / Updated on November 17, 2018 07:06