Pregabalin

HCID 5486971

Basic information

CAS
148553-50-8
Standard SMILES
CC(C)C[C@H](CN)CC(=O)O
InChIKey
AYXYPKUFHZROOJ-ZETCQYMHSA-N
Molecular formula
C8H17NO2
Average molar mass
159.23 g/mol
Monoisotopic mass
159.12592878

Overview

Pregabalin is a gamma-amino acid that is gamma-aminobutyric acid (GABA) carrying an isobutyl substitutent at the beta-position (the S-enantiomer). Binds with high affinity to the alpha2-delta site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues. It has a role as an anticonvulsant and a calcium channel blocker. It is functionally related to a gamma-aminobutyric acid.

Names & identifiers

Preferred name
Pregabalin
IUPAC
(3S)-3-(aminomethyl)-5-methylhexanoic acid

Names & synonyms

Pregabalin148553-50-8Lyrica(S)-3-(Aminomethyl)-5-methylhexanoic acid3-isobutyl GABA(3S)-3-(aminomethyl)-5-methylhexanoic acidCI-1008PregabalinePregabalinaVronogabicPregabalin mylanPregabalin sandoz
Show more names
Pregabalin zentiva(R-)-3-isobutyl GABAPD-144723Pregabalin sandoz gmbhCI 1008DTXSID1045950(S)-3-Isobutyl GABAPD 144723

Database identifiers

CAS
148553-50-8
PubChem CID
5486971
DTXSID
DTXSID1045950
ChEMBL
CHEMBL1059
ChEBI
CHEBI:64356
UNII
55JG375S6M
EC Number
604-639-1
Nikkaji
J702.547E

Properties

Computed structural properties

XLogP
-1.6
Topological polar surface area
63.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
5
Heavy atoms
11

Experimental & physicochemical properties

Drugs · 6 items

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

DEA Schedule V Controlled Substance -> Depressants

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Antiepileptic

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

LogP1.3
Color/FormWhite to off-white crystalline solid
Solubility · 3 items

Freely soluble

Freely soluble in water and both basic and acidic solutions

1.13e+01 g/L

Human Drugs · 6 items

Breast Feeding; Lactation; Milk, Human; Analgesics; Anticonvulsants

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

Animal Drugs · 3 items

EMA approved medicines: Veterinary medicine

Active Ingredients (Pregabalin) -> FDA Greenbook

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 0.5% (1 of 199) of reports.

Danger

H318 (72.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P203, P260, P264+P265, P280, P305+P354+P338, P317, P318, P319, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 199 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationDEA schedule V controlled substance
FDA Requirements · 2 items

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl pregabalin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule V includes pregabalin, DEA Code #2782; Drug class: Depressants.

Hazard Classes and CategoriesEye Dam. 1 (72.9%)

Safety & protection

Storage ConditionsStore at 25 °C (77 °F); excursions permitted to 15 to 30 °C (59 to 86 °F).
Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxicology

Interactions · 5 items

Patients who require concomitant treatment with central nervous system depressants such as opiates or benzodiazepines should be informed that they may experience additive CNS side effects, such as somnolence.

The pharmacokinetic interactions of pregabalin and gabapentin were investigated in 12 healthy subjects following concomitant single-dose administration of 100-mg pregabalin and 300-mg gabapentin and in 18 healthy subjects following concomitant multiple-dose administration... Gabapentin pharmacokinetics following single- and multiple-dose administration were unaltered by pregabalin coadministration. The extent of pregabalin absorption was unaffected by gabapentin coadministration, although there was a small reduction in rate of absorption.

Pregabalin coadministration had no effect on the steady-state pharmacokinetics of norethindrone and ethinyl estradiol (1 mg/35 mug, respectively) in healthy subjects.

Multiple-dose administration of pregabalin in healthy subjects had no effect on the rate and extent of lorazepam single-dose pharmacokinetics and single-dose administration of lorazepam had no effect on the steady-state pharmacokinetics of pregabalin.

For more Interactions (Complete) data for PREGABALIN (8 total), please visit the HSDB record page.

Hepatotoxicity · 1 item

Limited data is available on the hepatotoxicity of pregabalin. In prelicensure clinical trials in diabetic neuropathy and epilepsy, therapy with pregabalin was not associated with an increased frequency of serum aminotransferase elevations or liver toxicity. Since its approval and more wide scale use, however, pregabalin has been linked to rare instances of clinically apparent liver injury. Most cases were mild and frequently without jaundice. The latency to onset of injury was short, symptoms of liver injury arising within 3 to 14 days. Both cholestatic and hepatocellular patterns of injury have been reported. Signs of hypersensitivity (fever, rash, eosinophilia) and autoimmunity were not present. Some cases have been severe and associated with marked jaundice and prolongation of the prothrombin time, but all cases ultimately resolved after the medication was stopped without evidence of residual injury.

Adverse EffectsMost reported adverse effects caused by pregabalin were mild to moderate intensity, dose-dependent, and occurred within the first 2 weeks of initiating treatment.
Toxicity SummarySigns and Symptoms of Overdose
Human Toxicity Excerpts · 5 items

/HUMAN EXPOSURE STUDIES/ In a double-blind, placebo-controlled clinical trial to assess the effect of pregabalin on sperm motility, 30 healthy male subjects were exposed to pregabalin at a dose of 600 mg/day. After 3 months of treatment (one complete sperm cycle), the difference between placebo- and pregabalin-treated subjects in mean percent sperm with normal motility was <4% and neither group had a mean change from baseline of more than 2%. Effects on other male reproductive parameters in humans have not been adequately studied.

/CASE REPORTS/ /Investigators/ present a patient who, after unintended rapid up-titration of pregabalin, experienced psychotic symptoms associated with rhythmic EEG-changes resolving completely after discontinuation of pregabalin and benzodiazepine administration.

/CASE REPORTS/ /Investigators/ report two patients with refractory epilepsy who developed unilateral painful gynecomastia and lower extremity pain (one of them localized and the other one diffuse), shortly after receiving Pregabalin (PGB). Neither of them had previous endocrinologic problems or complaints about pain on their medical history. PGB was stopped in one patient and reduced in the other one, with complete disparition of the symptoms in the following weeks in both patients.

/CASE REPORTS/ /Investigators/ present the cases of 5 men who reported mild to moderate erectile dysfunction or impotence for the first time when treated with the new antiepileptic drug pregabalin as add-on therapy.

For more Human Toxicity Excerpts (Complete) data for PREGABALIN (7 total), please visit the HSDB record page.

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Pregabalin

vLess-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Regulatory information

FDA Requirements · 2 items

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl pregabalin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule V includes pregabalin, DEA Code #2782; Drug class: Depressants.

Chemistry & industry

Pharmacology

ATC Code · 3 items

N03AX16

N - Nervous system

QN - Nervous system

Protein BindingPregabalin is not plasma protein bound.
Pharmacodynamics · 1 item

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

Mechanism of Action · 6 items

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

Pregabalin is an anticonvulsant that is structurally related to the inhibitory CNS neurotransmitter gamma-aminobutyric acid (GABA). Pregabalin also has demonstrated analgesic activity. Although pregabalin was developed as a structural analog of GABA, the drug does not bind directly to GABA-A, GABA-B, or benzodiazepine receptors; does not augment GABA-A responses in cultured neurons; and does not alter brain concentrations of GABA in rats or affect GABA uptake or degradation. However, in cultured neurons, prolonged application of pregabalin increases the density of GABA transporter protein and increases the rate of functional GABA transport.

Pregabalin binds with high affinity to the alpha2-delta site (an auxiliary subunit of voltage-gated calcium channels) in CNS tissues. ... In vitro, pregabalin reduces the calcium-dependent release of several neurotransmitters, including glutamate, norepinephrine, and substance P, possibly by modulation of calcium channel function.

Pregabalin does not block sodium channels, is not active at opiate receptors, and does not alter cyclooxygenase enzyme activity. It is inactive at serotonin and dopamine receptors and does not inhibit dopamine, serotonin, or noradrenaline reuptake.

Pregabalin is a potent ligand for the alpha-2-delta subunit of voltage-gated calcium channels in the central nervous system that exhibits potent anticonvulsant, analgesic, and anxiolytic activity in a range of animal models. ... Potent binding to the alpha-2-delta site reduces depolarization-induced calcium influx with a consequential modulation in excitatory neurotransmitter release. Pregabalin has no demonstrated effects on GABAergic mechanisms. ...

For more Mechanism of Action (Complete) data for PREGABALIN (6 total), please visit the HSDB record page.

Biological Half-Life · 2 items

The elimination half life of pregabalin is 6.3 hours.

Pregabalin is eliminated from the systemic circulation primarily by renal excretion as unchanged drug with a mean elimination half-life of 6.3 hours in subjects with normal renal function.

Metabolism/Metabolites · 2 items

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

Pregabalin undergoes negligible metabolism in humans. Following a dose of radiolabeled pregabalin, approximately 90% of the administered dose was recovered in the urine as unchanged pregabalin. The N-methylated derivative of pregabalin, the major metabolite of pregabalin found in urine, accounted for 0.9% of the dose. In preclinical studies, pregabalin (S-enantiomer) did not undergo racemization to the R-enantiomer in mice, rats, rabbits, or monkeys.

Uses & manufacturing

Uses · 3 items

MEDICATION

THERAP CAT: Anticonvulsant

Use (kg) in Switzerland (2009): >1000

Formulations/PreparationsLyrica
Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Related reactions

74 records

Compound notes

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