Identification

Name
Pregabalin
Accession Number
DB00230
Description

Pregabalin is structurally similar to gamma-aminobutyric acid (GABA) - an inhibitory neurotransmitter.13 It may be used to manage neuropathic pain, postherpetic neuralgia, and fibromyalgia among other conditions.20 Although as per the FDA Label the mechanism of action has not been definitively defined, there is evidence that pregabalin exerts its effects by binding to the α2δ subunit of voltage-dependent calcium channels.2022 Pregabalin is marketed by Pfizer under the trade name Lyrica and Lyrica Cr (extended release).2122 It may have dependence liability if misused but the risk appears to be highest in patients with current or past substance use disorders.4

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 159.2261
Monoisotopic: 159.125928793
Chemical Formula
C8H17NO2
Synonyms
  • (S)-3-Isobutyl GABA
  • 3-Isobutyl GABA
  • Pregabalin
  • Pregabalina
External IDs
  • CI 1008
  • CI-1008
  • PD-144723
  • YNP-1807

Pharmacology

Indication

Pregabalin is indicated for the management of neuropathic pain associated with diabetic peripheral neuropathy, postherpetic neuralgia, fibromyalgia, neuropathic pain associated with spinal cord injury, and as adjunctive therapy for the treatment of partial-onset seizures in patients 1 month of age and older.22

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Although the structure of pregabalin is similar to gamma-aminobutyric acid (GABA), it does not bind to GABA receptors.620 Instead, it binds the alpha2-delta subunit of presynaptic voltage-gated calcium channels in the central nervous system.620 Pregabalin does not modulate dopamine receptors, serotonin receptors, opiate receptors, sodium channels or cyclooxygenase activity.20

Mechanism of action

Although the mechanism of action has not been fully elucidated, studies involving structurally related drugs suggest that presynaptic binding of pregabalin to voltage-gated calcium channels is key to the antiseizure and antinociceptive effects observed in animal models.22

By binding presynaptically to the alpha2-delta subunit of voltage-gated calcium channels in the central nervous system, pregabalin modulates the release of several excitatory neurotransmitters including glutamate, substance-P, norepinephrine, and calcitonin gene related peptide.6 In addition, pregabalin prevents the alpha2-delta subunit from being trafficked from the dorsal root ganglia to the spinal dorsal horn, which may also contribute to the mechanism of action.15

Although pregabalin is a structural derivative of the inhibitory neurotransmitter gamma-aminobutyric acid (GABA), it does not bind directly to GABA or benzodiazepine receptors.8

TargetActionsOrganism
AVoltage-dependent calcium channel subunit alpha-2/delta-1Not AvailableHumans
Absorption

After oral dosing administered in the fasted state, pregabalin absorption is rapid, and extensive.8 Pregabalin oral bioavailability is reported to be ≥90% regardless of the dose.8 Cmax is attained within 1.5 hours after single or multiple doses, and steady state is attained within 24-48 hours with repeated administration.822 Both Cmax and AUC appear to be dose proportional.8

Food decreases the rate of pregabalin absorption and as a result, lowers the Cmax by an estimated 25-30% and increases the Tmax to approximately 3 hours.22 However, the effect of food does not appear to impact the total absorption of pregabalin in a way that is clinically relevant. As a result, pregabalin can be administered with or without food.22

Volume of distribution

After oral administration of pregabalin, the reported apparent volume of distribution is roughly 0.5 L/kg.22

Although pregabalin is not very lipophilic, it is able to cross the blood brain barrier(BBB).16 System L transporters facilitate the transport of large amino acids across the BBB and it has been confirmed that pregabalin is a substrate.2216 This information suggests that system L transporters are responsible for pregabalin uptake into the BBB.16

In rat models, pregabalin has been shown to cross the placenta.22

Protein binding

Pregabalin is not plasma protein bound.822

Metabolism

Less than 2% of pregabalin is metabolized and it is excreted virtually unchanged in the urine.822

Hover over products below to view reaction partners

Route of elimination

Pregabalin is almost exclusively eliminated in the urine.1718

Further, based on preclinical studies, pregabalin does not appear to undergo racemization to the R enantiomer in the body.11

Half-life

The elimination half life of pregabalin is 6.3 hours.22

Clearance

In young healthy subjects the mean renal clearance is estimated to be 67.0 to 80.9 mL mL/min.22 Given pregabalin's lack of plasma protein binding, this clearance rate suggests that renal tubular reabsorption is involved.22

Adverse Effects
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Toxicity

In a systematic review that included 38 randomized controlled trials, there were 20 identified adverse effects that were significantly associated with pregabalin, most of which involve the central nervous system and cognition. The identified adverse effects include vertigo, dizziness, balance disorder, incoordination, ataxia, blurred vision, diplopia, amblyopia, somnolence, confusional state, tremor, disturbance in attention, abnormal thinking, asthenia, fatigue, euphoria, edema, peripheral edema, dry mouth, and constipation 14.

The most common symptoms of pregabalin toxicity (dose range includes 800 mg/day and single doses up to 11,500 mg) include somnolence, confusion, restlessness, agitation, depression, affective disorder and seizures.23

Since there is no antidote for pregabalin overdose, patients should receive general supportive care. If appropriate, gastric lavage or emesis may help eliminate unabsorbed pregabalin (healthcare providers should take standard precautions to maintain the airway).23

Pregabalin pharmacokinetic properties suggest that extra-corporeal elimination methods including haemodialysis, may be useful in situations of severe toxicity.19 However, there are cases where patients have presented with very high serum levels of pregabalin and have been successfully managed with supportive care alone.19

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

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirPregabalin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseThe risk or severity of hypoglycemia can be increased when Pregabalin is combined with Acarbose.
AcebutololPregabalin may increase the arrhythmogenic activities of Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Pregabalin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Pregabalin which could result in a higher serum level.
AcetaminophenPregabalin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideThe therapeutic efficacy of Acetazolamide can be increased when used in combination with Pregabalin.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Pregabalin is combined with Acetohexamide.
AcetophenazineThe therapeutic efficacy of Acetophenazine can be increased when used in combination with Pregabalin.
AcetyldigitoxinPregabalin may increase the arrhythmogenic activities of Acetyldigitoxin.
Additional Data Available
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  • Severity
    Severity
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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
  • Avoid alcohol. Alcohol may increase CNS effects.
  • Take with or without food. Food alters drug absorption, but not to a clinically significant extent.

Products

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Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act PregabalinCapsuleOralActavis Pharma CompanyNot applicableNot applicableCanada flag
Act PregabalinCapsuleOralActavis Pharma Company2013-03-062019-07-09Canada flag
Act PregabalinCapsuleOralActavis Pharma Company2013-03-062019-07-09Canada flag
Act PregabalinCapsuleOralActavis Pharma CompanyNot applicableNot applicableCanada flag
Act PregabalinCapsuleOralActavis Pharma Company2013-03-062019-07-09Canada flag
Act PregabalinCapsuleOralActavis Pharma Company2013-03-062019-07-09Canada flag
Act PregabalinCapsuleOralActavis Pharma Company2013-03-062019-07-09Canada flag
Act PregabalinCapsuleOralActavis Pharma Company2013-03-062019-07-09Canada flag
LyricaCapsule225 mg/1OralRebel Distributors2004-12-30Not applicableUS flag
LyricaCapsule50 mg/1OralPD-Rx Pharmaceuticals, Inc.2004-12-30Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
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  • Product Code
    Product Code
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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ach-pregabalinCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-pregabalinCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-pregabalinCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-pregabalinCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-pregabalinCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-pregabalinCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-pregabalinCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-pregabalinCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ag-pregabalinCapsuleOralAngita Pharma Inc.2018-09-28Not applicableCanada flag
Ag-pregabalinCapsuleOralAngita Pharma Inc.2018-09-28Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
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  • Product Code
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Categories

ATC Codes
N03AX16 — Pregabalin
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Amine / Amino acid / Amino fatty acid / Branched fatty acid / Carbonyl group / Carboxylic acid / Fatty acid / Fatty acyl / Gamma amino acid or derivatives
show 11 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
gamma-amino acid (CHEBI:64356)

Chemical Identifiers

UNII
55JG375S6M
CAS number
148553-50-8
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[[email protected]](CN)CC(O)=O

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. Gajraj NM: Pregabalin: its pharmacology and use in pain management. Anesth Analg. 2007 Dec;105(6):1805-15. doi: 10.1213/01.ane.0000287643.13410.5e. [PubMed:18042886]
  14. Zaccara G, Gangemi P, Perucca P, Specchio L: The adverse event profile of pregabalin: a systematic review and meta-analysis of randomized controlled trials. Epilepsia. 2011 Apr;52(4):826-36. doi: 10.1111/j.1528-1167.2010.02966.x. Epub 2011 Feb 14. [PubMed:21320112]
  15. Toth C: Pregabalin: latest safety evidence and clinical implications for the management of neuropathic pain. Ther Adv Drug Saf. 2014 Feb;5(1):38-56. doi: 10.1177/2042098613505614. [PubMed:25083261]
  16. Takahashi Y, Nishimura T, Higuchi K, Noguchi S, Tega Y, Kurosawa T, Deguchi Y, Tomi M: Transport of Pregabalin Via L-Type Amino Acid Transporter 1 (SLC7A5) in Human Brain Capillary Endothelial Cell Line. Pharm Res. 2018 Oct 29;35(12):246. doi: 10.1007/s11095-018-2532-0. [PubMed:30374619]
  17. Stump P: [Pregabalin--profile of efficacy and tolerability in neuropathic pain]. Drugs Today (Barc). 2009 Oct;45 Suppl C:19-27. [PubMed:20087482]
  18. Lee DW, Lee HJ, Kim HJ, Chang SH, Park DJ: Two cases of pregabalin neurotoxicity in chronic kidney disease patients. NDT Plus. 2011 Apr;4(2):138. doi: 10.1093/ndtplus/sfq219. [PubMed:25984138]
  19. Wood DM, Berry DJ, Glover G, Eastwood J, Dargan PI: Significant pregabalin toxicity managed with supportive care alone. J Med Toxicol. 2010 Dec;6(4):435-7. doi: 10.1007/s13181-010-0052-3. [PubMed:20373065]
  20. Cross AL, Sherman Al: Pregabalin . [PubMed:29261857]
  21. Pfizer [Link]
  22. FDA Label Pregabalin [Link]
  23. Pfizer Medical Information - Lyrica [Link]
  24. TITCK Product Information: Pagamax Plus (pregabalin/cyanocobalamin) for oral administration [Link]
Human Metabolome Database
HMDB0014375
KEGG Drug
D02716
PubChem Compound
5486971
PubChem Substance
46504934
ChemSpider
4589156
BindingDB
50164279
RxNav
187832
ChEBI
64356
ChEMBL
CHEMBL1059
ZINC
ZINC000000005152
Therapeutic Targets Database
DAP001264
PharmGKB
PA164754814
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pregabalin
AHFS Codes
  • 28:12.92 — Miscellaneous Anticonvulsants
FDA label
Download (3.46 MB)
MSDS
Download (106 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentLumbar Disc Disease / Lumbar Radiculopathy / Prolapsed Lumbar Disc1
4CompletedNot AvailableHealthy Lactating Women1
4CompletedNot AvailableHealthy Volunteers2
4CompletedNot AvailableIrritable Bowel Syndrome (IBS)1
4CompletedNot AvailablePostoperative pain1
4CompletedBasic ScienceChronic Migraine / Fibromyalgia / Pain, Chronic1
4CompletedDiagnosticAnxiety Disorders1
4CompletedOtherHealthy Volunteers1
4CompletedPreventionOsteoarthritis of the Knee1
4CompletedSupportive CareScoliosis / Spondylolisthesis1

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
Tablet, film coatedOral150 mg
Tablet, film coatedOral225 mg
Tablet, film coatedOral25 mg
Tablet, film coatedOral300 mg
Tablet, film coatedOral75 mg
Tablet, coated150 mg
Tablet, coated25 mg
Tablet, coated300 mg
Tablet, coated75 mg
CapsuleOral100 mg/1
CapsuleOral150 mg/1
CapsuleOral200 mg/1
CapsuleOral225 mg/1
CapsuleOral25 mg/1
CapsuleOral300 mg/1
CapsuleOral50 mg/1
CapsuleOral75 mg/1
Capsule, coatedOral50 mg
CapsuleOral
SolutionOral20 MG/ML
SolutionOral
Tablet, film coated, extended releaseOral165 mg/1
Tablet, film coated, extended releaseOral330 mg/1
Tablet, film coated, extended releaseOral82.5 mg/1
SolutionOral2 g
Capsule, coatedOral25 mg
Tablet, effervescent100 mg
Tablet, effervescent150 mg
Tablet, effervescent200 mg
Tablet, effervescent225 mg
Tablet, effervescent25 mg
Tablet, effervescent300 mg
Tablet, effervescent75 mg
Capsule, gelatin coatedOral150 mg
Capsule, gelatin coatedOral25 mg
Capsule, gelatin coatedOral300 mg
Capsule, gelatin coatedOral75 mg
Capsule, gelatin coatedOral50 mg
CapsuleOral150 mg/1mg
CapsuleOral300 mg/1mg
CapsuleOral75 mg/1mg
SolutionOral20 mg/1mL
CapsuleOral100 mg
CapsuleOral150 mg
CapsuleOral200 mg
CapsuleOral225 mg
CapsuleOral25 mg
CapsuleOral300 mg
CapsuleOral50 mg
CapsuleOral75 mg
CapsuleOral125 MG
CapsuleOral175 MG
CapsuleOral250 MG
CapsuleOral275 MG
Capsule, coatedOral300 mg
Capsule, coatedOral150 mg
Capsule, coatedOral75 mg
TabletOral100 MG
TabletOral150 MG
TabletOral200 MG
TabletOral225 MG
TabletOral25 MG
TabletOral300 MG
TabletOral50 MG
TabletOral75 MG
Tablet, effervescentOral150 mg
Tablet, effervescentOral25 mg
Tablet, effervescentOral300 mg
Tablet, effervescentOral75 mg
PowderNot applicable1 kg/1kg
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)Region
US5563175No1996-10-082013-10-08US flag
CA2327285No2005-06-142019-05-10Canada flag
CA2297163No2001-11-202018-08-18Canada flag
US6001876Yes1999-12-142019-06-30US flag
USRE41920Yes2010-11-092019-06-30US flag
US6197819Yes2001-03-062019-06-30US flag
US9144559Yes2015-09-292027-05-02US flag
US8945620Yes2015-02-032027-05-02US flag
US10022447Yes2018-07-172027-05-02US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)176 - 178ºChttps://www.who.int/medicines/access/controlled-substances/PreReviewPregabalin.pdf
boiling point (°C)144 - 147 ºChttps://www.who.int/medicines/access/controlled-substances/PreReviewPregabalin.pdf
water solubilityFreely soluble https://www.who.int/medicines/access/controlled-substances/PreReviewPregabalin.pdf
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

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Voltage-gated calcium channel activity
Specific Function
The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Plays an important role in excitation-...
Gene Name
CACNA2D1
Uniprot ID
P54289
Uniprot Name
Voltage-dependent calcium channel subunit alpha-2/delta-1
Molecular Weight
124566.93 Da
References
  1. Verma V, Singh N, Singh Jaggi A: Pregabalin in neuropathic pain: evidences and possible mechanisms. Curr Neuropharmacol. 2014 Jan;12(1):44-56. doi: 10.2174/1570159X1201140117162802. [PubMed:24533015]

Transporters

Kind
Protein
Organism
Humans
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]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Peptide antigen binding
Specific Function
Sodium-independent, high-affinity transport of large neutral amino acids such as phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Involved in cellular a...
Gene Name
SLC7A5
Uniprot ID
Q01650
Uniprot Name
Large neutral amino acids transporter small subunit 1
Molecular Weight
55009.62 Da
References
  1. Takahashi Y, Nishimura T, Higuchi K, Noguchi S, Tega Y, Kurosawa T, Deguchi Y, Tomi M: Transport of Pregabalin Via L-Type Amino Acid Transporter 1 (SLC7A5) in Human Brain Capillary Endothelial Cell Line. Pharm Res. 2018 Oct 29;35(12):246. doi: 10.1007/s11095-018-2532-0. [PubMed:30374619]

Drug created on June 13, 2005 07:24 / Updated on November 30, 2020 13:38

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