General
Preferred name
PREGABALIN
Synonyms
Lyrica ()
pregabalin CR, Intellipharmaceutics ()
Alzain ()
Pregabalin mylan ()
Axalid ()
Vronogabic ()
CI-1008 ()
Pregabalin zentiva ()
NSC-759256 ()
Pregabalin sandoz ()
Lyrica cr ()
PD-144723 ()
Lecaent ()
YNP-1807 ()
Rewisca ()
Pregabalin sandoz gmbh ()
Pregabalin (CRM) ()
P&D ID
PD000713
CAS
1414928-41-8
148553-50-8
Tags
natural product
drug
available
Approved by
EMA
FDA
First approval
2004
Drug Status
investigational
approved
Drug indication
Anticonvulsant
Chronic obstructive pulmonary disease
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS Pregabalin is structurally analogous to the inhibitory neurotransmitter gamma-aminobutyric acid (GABA). The molecule exerts it's effect on voltage gated calcium channels by binding presynaptically to the alpha-2-delta subunit. Since voltage gated calcium channels are widely distributed throughout the central nervous system, pregabalin is able to modulate the release of several excitatory neurotransmitters such as glutamate, substance-P, norepinephrine and calcitonin gene related peptide. This results in inhibition of overexcited neurons, which ultimately returns them to a normal state of function [A31163]. As a result, Pregabalin has anticonvulsant, analgesic, anxiolytic and sleep modulating effects. [A173995]
ROE Pregabalin is mainly renally excreted with 98% of the drug eliminated unchanged in the urine, while less than 0.1% of the drug is eliminated through the fecal route. Further, based on preclinical studies, pregabalin does not appear to undergo racemization to the R enantiomer in the body [A31168].
INDICATION Pregabalin is used for the management of neuropathic pain associated with diabetic peripheral neuropathy, postherpetic neuralgia, and as adjunctive therapy for adult patients with partial onset seizures [FDA label].
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 [A175876].
METABOLISM In humans, less than 2% of pregabalin is metabolized and it is excreted virtually unchanged in the urine [A31165].
ABSORPTION Absorption of pregabalin is rapid and extensive reflecting it's relatively quick onset of efficacy. Maximal plasma concentration occurs ~1 hour after administration and steady state occurs within 24-48 hours. [A31165]
HALF-LIFE The elimination half life of pregabalin is roughly 6 hours [FDA Label].
MOA Although the mechanism of action has not been fully elucidated, studies involving structurally related drugs suggest that the presynaptic binding of pregabalin to voltage-gated calcium channels is key to the antiseizure and antinociceptive effects observed in animal models [FDA label]. 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 [A31163]. In addition, pregabalin prevents the alpha2-delta subunit from being trafficked from the dorsal root ganglia to the spinal dorsal horn which contributes to the blunting of excitatory neurotransmitter release [A36628]. Interestingly, although pregabalin is a structural derivative of inhibitory neurotransmitter gamma-aminobutyric acid (GABA), it does not bind directly to GABA or benzodiazepine receptors [A31165].
DESCRIPTION Pregabalin is a gabapentinoid class anti-seizure medication. Chemically, it is a 3-isobutyl derivative of the inhibitory neurotransmitter γ-aminobutyric acid (GABA), but it appears to function as a modulator of voltage-gated calcium channels, rather than a GABA receptor agonist. (GtoPdb)
Compound Sets
18
Axon Medchem Screening Library
1823
Cayman Chemical Bioactives
37861
13663
ChEMBL Approved Drugs
CHEMBL1059
ChEMBL Drugs
CHEMBL1059
DrugBank
DB00230
DrugBank Approved Drugs
DB00230
DrugCentral
2255
DrugCentral Approved Drugs
2255
DrugMAP
DMDVP3B
DrugMAP Approved Drugs
DMDVP3B
Guide to Pharmacology
5484
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
55JG375S6M
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
The Spectrum Collection
External IDs
37
Properties
(calculated by RDKit )
Molecular Weight
159.13
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
2
Rotatable Bonds
5
Ring Count
0
Aromatic Ring Count
0
cLogP
1.08
TPSA
63.32
Fraction CSP3
0.88
Chiral centers
1.0
Largest ring
0.0
QED
0.63
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Member status
virtual
MOA
L-Type Calcium Channel Blockers
Calcium Channels (Voltage-Gated) alpha2/delta-1 Subunit Ligands
Target
Ca Channel modulator
Biosynthetic Origin
Alkaloid
Therapeutic Indication
Antiepileptic
Therapeutic Class
CNS & PNS
Source data