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Identification
- Summary
Pregabalin is an anticonvulsant drug used to treat neuropathic pain conditions and fibromyalgia, and for the treatment of partial onset seizures in combination with other anticonvulsants.
- Brand Names
- Lyrica
- Generic Name
- Pregabalin
- DrugBank Accession Number
- DB00230
- Background
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 characterized, there is evidence that pregabalin exerts its effects by binding to the α2δ subunit of voltage-dependent calcium channels.20,22 Pregabalin is marketed by Pfizer under the trade name Lyrica and Lyrica Cr (extended release).21,22 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
Structure for Pregabalin (DB00230)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Diabetic peripheral neuropathic pain •••••••••••• •••••••• ••••••••• ••••••• •••••••• ••••••• Used in combination to manage Epilepsies Combination Product in combination with: Mecobalamin (DB03614) •••••••••••• ••••••• ••• ••••••••••• •• •••••••••••••••• •••••••••• •••••••• ••••••• •••• •••••• Management of Fibromyalgia •••••••••••• •••••••• •••••••• Used in combination to manage Fibromyalgia Combination Product in combination with: Mecobalamin (DB03614) •••••••••••• •• •••••••••••••••• •••••••••• ••••••••• ••••••• ••• •••••••••• ••••••• •••• •••••• Used in combination for symptomatic treatment of Fibromyalgia Combination Product in combination with: Cyanocobalamin (DB00115) •••••••••••• ••••••• ••• •••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Although the structure of pregabalin is similar to gamma-aminobutyric acid (GABA), it does not bind to GABA receptors.6,20 Instead, it binds the alpha2-delta subunit of presynaptic voltage-gated calcium channels in the central nervous system.6,20 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
Target Actions Organism AVoltage-dependent calcium channel subunit alpha-2/delta-1 modulatorHumans - 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.8,22 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.22,16 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
- Metabolism
Less than 2% of pregabalin is metabolized and it is excreted virtually unchanged in the urine.8,22
Hover over products below to view reaction partners
- Route of elimination
Pregabalin is almost exclusively eliminated in the urine.17,18
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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The therapeutic efficacy of 1,2-Benzodiazepine can be increased when used in combination with Pregabalin. Abacavir Pregabalin may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose The risk or severity of hypoglycemia can be increased when Pregabalin is combined with Acarbose. Acebutolol Pregabalin may increase the bradycardic activities of Acebutolol. Aceclofenac Aceclofenac may decrease the excretion rate of Pregabalin which could result in a higher serum level. - 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Pregabalin Capsule 150 mg Oral Actavis Pharma Company 2013-03-06 2019-07-09 Canada 
Act Pregabalin Capsule 25 mg Oral Actavis Pharma Company 2013-03-06 2019-07-09 Canada Act Pregabalin Capsule 200 mg Oral Actavis Pharma Company Not applicable Not applicable Canada Act Pregabalin Capsule 300 mg Oral Actavis Pharma Company 2013-03-06 2019-07-09 Canada Act Pregabalin Capsule 75 mg Oral Actavis Pharma Company 2013-03-06 2019-07-09 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ach-pregabalin Capsule 225 mg Oral Accord Healthcare Inc 2021-05-27 Not applicable Canada Ach-pregabalin Capsule 100 mg Oral Accord Healthcare Inc Not applicable Not applicable Canada Ach-pregabalin Capsule 25 mg Oral Accord Healthcare Inc 2021-05-27 Not applicable Canada Ach-pregabalin Capsule 200 mg Oral Accord Healthcare Inc Not applicable Not applicable Canada Ach-pregabalin Capsule 75 mg Oral Accord Healthcare Inc 2021-05-27 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BAXANT PLUS B12 150/1 MG FILM TABLET,FILM TABLET, 60 ADET Pregabalin (150 mg) + Cyanocobalamin (1 mg) Tablet, film coated Oral SANTA FARMA İLAÇ SAN. A.Ş. 2020-08-14 Not applicable Turkey 
BAXANT PLUS B12 225/1 MG FILM TABLET,FILM TABLET, 60 ADET Pregabalin (225 mg) + Cyanocobalamin (1 mg) Tablet, film coated Oral SANTA FARMA İLAÇ SAN. A.Ş. 2020-08-14 Not applicable Turkey BAXANT PLUS B12 25/1 MG FILM TABLET ,TABLET, 60 ADET Pregabalin (25 mg) + Cyanocobalamin (1 mg) Tablet, film coated Oral SANTA FARMA İLAÇ SAN. A.Ş. 2020-08-14 Not applicable Turkey BAXANT PLUS B12 300/1 MG FILM TABLET,TABLET, 60 ADET Pregabalin (300 mg) + Cyanocobalamin (1 mg) Tablet, film coated Oral SANTA FARMA İLAÇ SAN. A.Ş. 2020-08-14 Not applicable Turkey BAXANT PLUS B12 75/1 MG FILM TABLET ,TABLET, 60 ADET Pregabalin (75 mg) + Cyanocobalamin (1 mg) Tablet, film coated Oral SANTA FARMA İLAÇ SAN. A.Ş. 2020-08-14 Not applicable Turkey
Categories
- ATC Codes
- N02BF02 — Pregabalin
- Drug Categories
- Acids, Acyclic
- Agents causing angioedema
- Amino Acids
- Amino Acids, Peptides, and Proteins
- Aminobutyrates
- Analgesics
- Anti-Anxiety Agents
- Anticonvulsants
- Bradycardia-Causing Agents
- Butyrates
- Central Nervous System Agents
- Central Nervous System Depressants
- Drugs that are Mainly Renally Excreted
- Gabapentinoids
- Hypoglycemia-Associated Agents
- Membrane Transport Modulators
- Miscellaneous Anticonvulsants
- Muscle Relaxants
- Muscle Relaxants, Centrally Acting Agents
- Nervous System
- Peripheral Nervous System Agents
- Potential QTc-Prolonging Agents
- Psychotropic Drugs
- QTc Prolonging Agents
- Sensory System Agents
- Tranquilizing Agents
- Vasodilating Agents
- 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)
- Affected organisms
- Humans and other mammals
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[C@H](CN)CC(O)=O
References
- Synthesis Reference
Mark Burk, "Asymmetric synthesis of pregabalin." U.S. Patent US20030212290, issued November 13, 2003.
US20030212290- General References
- Authors unspecified: Schedules of controlled substances: placement of pregabalin into schedule V. Final rule. Fed Regist. 2005 Jul 28;70(144):43633-5. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Ben-Menachem E: Pregabalin pharmacology and its relevance to clinical practice. Epilepsia. 2004;45 Suppl 6:13-8. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Stump P: [Pregabalin--profile of efficacy and tolerability in neuropathic pain]. Drugs Today (Barc). 2009 Oct;45 Suppl C:19-27. [Article]
- 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. [Article]
- 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. [Article]
- Cross AL, Sherman Al: Pregabalin . [Article]
- Pfizer [Link]
- FDA Label Pregabalin [Link]
- Pfizer Medical Information - Lyrica [Link]
- TITCK Product Information: Pagamax Plus (pregabalin/cyanocobalamin) for oral administration [Link]
- FDA Approved Drug Products: LYRICA (pregabalin) Capsule/solution, for oral use [Link]
- DailyMed Label: LYRICA CR (pregabalin) extended-release tablets, for oral use [Link]
- External Links
- Human Metabolome Database
- HMDB0014375
- KEGG Drug
- D02716
- PubChem Compound
- 5486971
- PubChem Substance
- 46504934
- ChemSpider
- 4589156
- BindingDB
- 50164279
- 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
- FDA label
- Download (3.46 MB)
- MSDS
- Download (106 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Available Not Available Acute and Chronic Pain Following Modified Radical Mastectomy 1 somestatus stop reason just information to hide Not Available Completed Not Available Achilles Tendon Surgery / Bunion of Unspecified Foot / Bunionette of Unspecified Foot / Fracture, Ankle / Hammertoe 1 somestatus stop reason just information to hide Not Available Completed Not Available Block 1 somestatus stop reason just information to hide Not Available Completed Not Available Chemotherapy Induced Peripheral Neuropathy (CIPN) 1 somestatus stop reason just information to hide Not Available Completed Not Available Epilepsy 2 somestatus stop reason just information to hide
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
Form Route Strength Capsule, coated Oral 50 mg Capsule, coated Oral 25 mg Tablet, film coated Oral Tablet, extended release Oral 165 mg Tablet, extended release Oral 330 mg Tablet, extended release Oral 82.5 mg Capsule Oral 150.000 MG Capsule Oral 25.000 MG Capsule Oral 50.000 MG Capsule Oral 300.000 mg Capsule Oral 75.0000 mg Tablet, film coated 150 mg Tablet, film coated 25 mg Tablet, film coated 300 mg Tablet, film coated 75 mg Solution Oral 2 g Tablet Oral Capsule Oral Capsule Oral 100 mg/1 Capsule Oral 150 mg/1 Capsule Oral 200 mg Capsule Oral 200 mg/1 Capsule Oral 225 mg/1 Capsule Oral 225 mg Capsule Oral 25 mg/1 Capsule Oral 300 mg/1 Capsule Oral 50 mg/1 Capsule Oral 75 mg/1 Solution Oral 2.000 g Capsule, coated Oral 5000000 mg Solution Oral 20 MG/ML Capsule, coated Oral 300 mg Capsule, coated Oral 75 mg Capsule Oral 100.00 mg Capsule Oral 200.00 mg Capsule Oral 300.00 mg Tablet, film coated, extended release Oral 165 mg/1 Tablet, film coated, extended release Oral 330 mg/1 Tablet, film coated, extended release Oral 82.5 mg/1 Capsule, coated Oral 150 mg Capsule, coated Oral 15000000 mg Capsule, coated Oral 2500000 mg Capsule, coated Oral 7500000 mg Capsule Oral 50.000 mg/Capsule Capsule Oral 75.000 mg Capsule Oral 25 mg Capsule Oral 300 mg Capsule Oral 75 mg Tablet, effervescent 100 mg Tablet, effervescent Tablet, effervescent 200 mg Tablet, effervescent 225 mg Capsule Oral 300.0 mg Capsule Oral 150 mg Capsule, gelatin coated Oral 150 mg Capsule, gelatin coated Oral 25 mg Capsule, gelatin coated Oral 300 mg Capsule, gelatin coated Oral 75 mg Capsule Oral Tablet, coated Oral 75 mg Capsule Oral 150 mg/1mg Capsule Oral 300 mg/1mg Capsule Oral 75 mg/1mg Solution Oral 20 mg/1mL Tablet, extended release Oral 165 mg/1 Tablet, extended release Oral 330 mg/1 Tablet, extended release Oral 82.5 mg/1 Capsule Oral 125 MG Capsule Oral 175 MG Capsule Oral 250 MG Capsule Oral 275 MG Capsule Oral 100 MG Capsule, coated Oral 30000000 mg Tablet Oral 100 MG Tablet Oral Tablet Oral 150 MG Tablet Oral 200 MG Tablet Oral 225 MG Tablet Oral 25 MG Tablet Oral 300 MG Tablet Oral 50 MG Tablet Oral 75 MG Capsule, gelatin coated Oral Tablet, effervescent Oral Tablet Oral 75.000 mg Capsule Oral 50.00 mg Capsule Oral 150.00 mg Capsule Oral 25.00 mg Capsule Oral 75.00 mg Powder Not applicable 1 kg/1kg Injection, solution 75 mg Capsule Oral 50 mg - Prices
Unit description Cost Unit Lyrica 100 mg capsule 2.88USD capsule Lyrica 150 mg capsule 2.88USD capsule Lyrica 50 mg capsule 2.88USD capsule Lyrica 75 mg capsule 2.88USD capsule Lyrica 200 mg capsule 2.75USD capsule Lyrica 225 mg capsule 2.75USD capsule Lyrica 25 mg capsule 2.75USD capsule Lyrica 300 mg capsule 2.75USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5563175 No 1996-10-08 2013-10-08 US 
CA2327285 No 2005-06-14 2019-05-10 Canada CA2297163 No 2001-11-20 2018-08-18 Canada US6001876 Yes 1999-12-14 2019-06-30 US USRE41920 Yes 2010-11-09 2019-06-30 US US6197819 Yes 2001-03-06 2019-06-30 US US9144559 Yes 2015-09-29 2027-05-02 US US8945620 Yes 2015-02-03 2027-05-02 US US10022447 Yes 2018-07-17 2027-05-02 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 176 - 178ºC https://www.who.int/medicines/access/controlled-substances/PreReviewPregabalin.pdf boiling point (°C) 144 - 147 ºC https://www.who.int/medicines/access/controlled-substances/PreReviewPregabalin.pdf water solubility Freely soluble https://www.who.int/medicines/access/controlled-substances/PreReviewPregabalin.pdf - Predicted Properties
Property Value Source Water Solubility 11.3 mg/mL ALOGPS logP -1.4 ALOGPS logP -1.3 Chemaxon logS -1.2 ALOGPS pKa (Strongest Acidic) 4.8 Chemaxon pKa (Strongest Basic) 10.23 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 63.32 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 43.68 m3·mol-1 Chemaxon Polarizability 18.08 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9727 Blood Brain Barrier + 0.9382 Caco-2 permeable - 0.6531 P-glycoprotein substrate Non-substrate 0.683 P-glycoprotein inhibitor I Non-inhibitor 0.965 P-glycoprotein inhibitor II Non-inhibitor 0.9424 Renal organic cation transporter Non-inhibitor 0.9245 CYP450 2C9 substrate Non-substrate 0.8758 CYP450 2D6 substrate Non-substrate 0.7926 CYP450 3A4 substrate Non-substrate 0.6914 CYP450 1A2 substrate Non-inhibitor 0.9385 CYP450 2C9 inhibitor Non-inhibitor 0.9425 CYP450 2D6 inhibitor Non-inhibitor 0.9539 CYP450 2C19 inhibitor Non-inhibitor 0.9629 CYP450 3A4 inhibitor Non-inhibitor 0.9352 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9784 Ames test Non AMES toxic 0.938 Carcinogenicity Non-carcinogens 0.5678 Biodegradation Ready biodegradable 0.8201 Rat acute toxicity 1.7046 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9868 hERG inhibition (predictor II) Non-inhibitor 0.8909
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 141.3918921 predictedDarkChem Lite v0.1.0 [M-H]- 141.1972921 predictedDarkChem Lite v0.1.0 [M-H]- 132.0922 predictedDeepCCS 1.0 (2019) [M+H]+ 141.9684921 predictedDarkChem Lite v0.1.0 [M+H]+ 141.8259921 predictedDarkChem Lite v0.1.0 [M+H]+ 135.92183 predictedDeepCCS 1.0 (2019) [M+Na]+ 141.3253921 predictedDarkChem Lite v0.1.0 [M+Na]+ 141.2861921 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.87373 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel (PubMed:35293990). Plays an important role in excitation-contraction coupling (By similarity)
- Specific Function
- Metal ion binding
- Gene Name
- CACNA2D1
- Uniprot ID
- P54289
- Uniprot Name
- Voltage-dependent calcium channel subunit alpha-2/delta-1
- Molecular Weight
- 124566.93 Da
References
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other
- General Function
- Sodium-dependent, high-affinity amino acid transporter that mediates the uptake of L-glutamate and also L-aspartate and D-aspartate (PubMed:21123949, PubMed:26690923, PubMed:33658209, PubMed:7521911, PubMed:7914198, PubMed:8857541). Can also transport L-cysteine (PubMed:21123949). Functions as a symporter that transports one amino acid molecule together with two or three Na(+) ions and one proton, in parallel with the counter-transport of one K(+) ion (PubMed:26690923, PubMed:33658209, PubMed:7521911, PubMed:8857541). Mediates Cl(-) flux that is not coupled to amino acid transport; this avoids the accumulation of negative charges due to aspartate and Na(+) symport (PubMed:26690923, PubMed:8857541). Plays an important role in L-glutamate and L-aspartate reabsorption in renal tubuli (PubMed:21123949). Plays a redundant role in the rapid removal of released glutamate from the synaptic cleft, which is essential for terminating the postsynaptic action of glutamate (By similarity). Contributes to glutathione biosynthesis and protection against oxidative stress via its role in L-glutamate and L-cysteine transport (By similarity). Negatively regulated by ARL6IP5 (By similarity)
- Specific Function
- Chloride transmembrane transporter activity
- Gene Name
- SLC1A1
- Uniprot ID
- P43005
- Uniprot Name
- Excitatory amino acid transporter 3
- Molecular Weight
- 57099.835 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- The heterodimer with SLC3A2 functions as a sodium-independent, high-affinity transporter that mediates uptake of large neutral amino acids such as phenylalanine, tyrosine, leucine, histidine, methionine, tryptophan, valine, isoleucine and alanine (PubMed:10049700, PubMed:10574970, PubMed:11557028, PubMed:11564694, PubMed:12117417, PubMed:12225859, PubMed:15769744, PubMed:18262359, PubMed:25998567, PubMed:30867591, PubMed:9751058). The heterodimer with SLC3A2 mediates the uptake of L-DOPA (By similarity). Functions as an amino acid exchanger (PubMed:11557028, PubMed:12117417, PubMed:12225859, PubMed:30867591). May play a role in the transport of L-DOPA across the blood-brain barrier (By similarity). May act as the major transporter of tyrosine in fibroblasts (Probable). May mediate blood-to-retina L-leucine transport across the inner blood-retinal barrier (By similarity). Can mediate the transport of thyroid hormones diiodothyronine (T2), triiodothyronine (T3) and thyroxine (T4) across the cell membrane (PubMed:11564694). When associated with LAPTM4B, the heterodimer formed by SLC3A2 and SLC7A5 is recruited to lysosomes to promote leucine uptake into these organelles, and thereby mediates mTORC1 activation (PubMed:25998567). Involved in the uptake of toxic methylmercury (MeHg) when administered as the L-cysteine or D,L-homocysteine complexes (PubMed:12117417). Involved in the cellular activity of small molecular weight nitrosothiols, via the stereoselective transport of L-nitrosocysteine (L-CNSO) across the membrane (PubMed:15769744)
- Specific Function
- Amino acid transmembrane transporter activity
- Gene Name
- SLC7A5
- Uniprot ID
- Q01650
- Uniprot Name
- Large neutral amino acids transporter small subunit 1
- Molecular Weight
- 55009.62 Da
References
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 16, 2024 01:02