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Compound Detail

CHEMBL1059

PREGABALIN
💊 Approved Drug
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💊 Approved Drug
CC(C)C[C@H](CN)CC(=O)O

Basic Information

ChEMBL ID CHEMBL1059
Name PREGABALIN
Phase Approved
Structure Type MOL
InChI Key AYXYPKUFHZROOJ-ZETCQYMHSA-N
Therapeutic ✓ Yes

Known Names

Alzain Axalid Bonqat CI-1008 Lecaent Lyrica Lyrica cr NSC-759256 PD-144723 Pregabalin Pregabalin accord Pregabalin mylan +11 more
4
Targets
19
Activities
2
Assay Types
13
PK Parameters
20
Publications
23
Known Names
20
Indications
1
Mechanisms

Molecular Properties

159.2
MW (Da)
1.08
ALogP
2
HBA
2
HBD
63.3
PSA (Ų)
0.63
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2004
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -gab-
USAN Year 1997

Extended Properties

Molecular Formula C8H17NO2
MW 159.23
Aromatic Rings 0
Heavy Atoms 11
NP-Likeness 1.19

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Voltage-gated calcium channel modulator MODULATOR Voltage-gated calcium channel

Indications

Anxiety Disorders Anxiety Disorders Epilepsy Epilepsy Fibromyalgia Neuralgia Neuralgia Seizures Seizures Spinal Cord Injuries Anxiety Breast Neoplasms Burning Mouth Syndrome Chronic Pain Dementia Depressive Disorder Diabetic Neuropathies Epilepsies, Partial Epilepsy, Complex Partial Epilepsy, Tonic-Clonic

ATC Classification

N02BF02
pregabalin
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Activity Summary

IC50 14 meas. best 7.43
Ki 5 meas. best 7.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Voltage-dependent calcium channel subunit alpha-2/delta-1
CHEMBL1919
Ki 7.72 7.72 19.0 2
Unchecked
CHEMBL612545
Ki 7.72 7.72 19.0 2
Unchecked
CHEMBL612545
IC50 7.43 7.1471 37.0 7
Voltage-dependent calcium channel alpha2delta subunit
CHEMBL3985
IC50 7.14 7.12 73.0 2
Voltage-dependent calcium channel subunit alpha-2/delta-2
CHEMBL3896
Ki 7.0 7.0 99.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 14800.0 ng.hr.mL-1 Rattus norvegicus
AUC 18940000.0 ng.hr.mL-1 Mus musculus
AUC 5.8 g.hr Rattus norvegicus
AUC 18.0 g.hr Rattus norvegicus
CL 2.9 mL.min-1.kg-1 Rattus norvegicus
CL 7.77 mL.min-1.kg-1 Mus musculus
Cmax 8415.5 nM Mus musculus
F 83.0 % Rattus norvegicus
F 88.0 % Mus musculus
T1/2 2.7 hr Rattus norvegicus
T1/2 2.54 hr Mus musculus
T1/2 1.5 hr Homo sapiens
T1/2 1.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 19.0 nM 7.72 Equilibrium dissociation constant for Voltage-gated calcium channel alpha2-delta... 15828841
Unchecked Ki = 19.0 nM 7.72 Binding affinity to alpha-2delta calcium channel 16621528
Voltage-dependent calcium channel subunit alpha-2/delta-1 Ki = 19.0 nM 7.72 Displacement of [3H]-gabapentin from human Cav alpha2delta1 expressed in CHO-K1 ... 33591743
Voltage-dependent calcium channel subunit alpha-2/delta-1 Ki = 19.0 nM 7.72 Displacement of [3H]-gabapentin from human Cav alpha2delta1 expressed in CHO-K1 ... 34795870
Unchecked IC50 = 37.0 nM 7.43 In vitro inhibition of [3H]-gabapentin binding to partially purified rat neocort... -
Voltage-dependent calcium channel alpha2delta subunit IC50 = 73.0 nM 7.14 Displacement of [3H]gabapentin from alpha-2delta calcium channel in pig brain me... 16099652
Unchecked IC50 = 80.0 nM 7.1 Inhibition of [3H]gabapentin binding to pig brain membranes 15801823
Unchecked IC50 = 80.0 nM 7.1 Displacement of [3H]gabapentin from alpha2-delta subunit of voltage gated calciu... 19010672
Voltage-dependent calcium channel alpha2delta subunit IC50 = 80.0 nM 7.1 Displacement of [3H]gabapentin from calcium channel alpha2delta in pig cerebral ... 19897364
Unchecked IC50 = 80.0 nM 7.1 Displacement of [3H]gabapentin from Voltage-dependent calcium channel subunit al... 19910190
Unchecked IC50 = 80.0 nM 7.1 Displacement of [3H]gabapentin from voltage gated calcium channel alpha2delta fr... 21550803
Unchecked IC50 = 80.0 nM 7.1 Inhibition of Voltage-dependent calcium channel subunit alpha-2/delta 21550802
Unchecked IC50 = 80.0 nM 7.1 Displacement of [3H]Gabapentin from alpha2delta calcium channel in pig brain tis... 21601457
Voltage-dependent calcium channel subunit alpha-2/delta-2 Ki = 99.0 nM 7.0 Displacement of [3H]-gabapentin from human Cav alpha2delta2 expressed in HEK293 ... 33591743

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
- 10.1016/S0960-894X(01)80855-6 Unchecked 9
29752183 10.1016/j.bmcl.2018.05.006 Mus musculus 8
21381762 10.1021/jm101376k Rattus norvegicus 8
27956036 10.1016/j.bmc.2016.11.052 Unchecked 6
19010672 10.1016/j.bmcl.2008.10.101 Rattus norvegicus 6
23103098 10.1016/j.bmcl.2012.10.001 Rattus norvegicus 4
30108836 10.1039/C7MD00131B Rattus norvegicus 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
24055075 10.1016/j.bmc.2013.08.031 Mus musculus 3
22784008 10.1021/jm3007323 Mus musculus 3
26138193 10.1016/j.bmc.2015.06.038 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 3
23103098 10.1016/j.bmcl.2012.10.001 Mus musculus 3
15828841 10.1021/jm0491086 Rattus norvegicus 3
15828841 10.1021/jm0491086 Unchecked 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3

Data from ChEMBL 36 via Core Engine