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Compound Detail

CHEMBL940

GABAPENTIN
💊 Approved Drug
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💊 Approved Drug
NCC1(CC(=O)O)CCCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL940
Name GABAPENTIN
Phase Approved
Structure Type MOL
InChI Key UGJMXCAKCUNAIE-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

CI-945 DM-1796 Gabapentin Gabapentina Gabapentine GOE 3450 GOE-3450 Gralise Neurontin NSC-742194 NSC-759254
5
Targets
22
Activities
2
Assay Types
26
PK Parameters
20
Publications
11
Known Names
20
Indications
1
Mechanisms

Molecular Properties

171.2
MW (Da)
1.37
ALogP
2
HBA
2
HBD
63.3
PSA (Ų)
0.67
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1993
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem gab-
USAN Year 1989

Extended Properties

Molecular Formula C9H17NO2
MW 171.24
Aromatic Rings 0
Heavy Atoms 12
NP-Likeness 0.69

Mechanism of Action

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

Indications

Epilepsy Neuralgia, Postherpetic Neuralgia, Postherpetic Restless Legs Syndrome Seizures Alcohol Drinking Alcoholism Anxiety Azoospermia Brain Injuries Carpal Tunnel Syndrome Chronic Pain Cystitis, Interstitial Delirium Dementia Depressive Disorder Diabetic Neuropathies Dyspepsia Epilepsies, Partial Fibromyalgia

ATC Classification

N02BF01
gabapentin
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Activity Summary

IC50 19 meas. best 7.57
Ki 3 meas. best 6.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Voltage-dependent calcium channel subunit alpha-2/delta-1
CHEMBL1919
 IC50 7.57 7.57 27.0 1
Voltage-dependent calcium channel alpha2delta subunit
CHEMBL3985
 IC50 7.16 7.005 70.0 2
Unchecked
CHEMBL612545
 IC50 7.16 6.446 70.0 15
Voltage-dependent calcium channel subunit alpha-2/delta-1
CHEMBL4676
 Ki 6.92 6.92 120.0 2
Voltage-dependent calcium channel subunit alpha-2/delta-1
CHEMBL3420
 IC50 5.05 5.05 8900.0 1
Unchecked
CHEMBL612545
 Ki 4.46 4.46 35000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 8600.0 ng.hr.mL-1 Rattus norvegicus
AUC 8600.0 ng.hr.mL-1 Rattus norvegicus
CL 6.0 mL.min-1.kg-1 Rattus norvegicus
CL 6.0 mL.min-1.kg-1 Rattus norvegicus
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL - mL.min-1.kg-1 Homo sapiens
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 1.8 mL.min-1.kg-1 Homo sapiens
CL 2.3 mL.min-1.kg-1 Canis lupus familiaris
CL 2.6 mL.min-1.kg-1 Macaca
CL 9.5 mL.min-1.kg-1 Rattus norvegicus
F 76.0 % Rattus norvegicus
F 60.0 % Homo sapiens
F 76.0 % Rattus norvegicus
F 25.0 % Macaca fascicularis
Fu 0.97 - Homo sapiens
Fu 0.97 - Homo sapiens
Fu 1.0 - Rattus norvegicus
Fu 1.06 - Rattus norvegicus
MRT 7.0 hr Homo sapiens
T1/2 1.5 hr Rattus norvegicus
T1/2 1.5 hr Rattus norvegicus
T1/2 5.3 hr Homo sapiens
T1/2 5.0 hr Homo sapiens
Vd 4.6 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Voltage-dependent calcium channel subunit alpha-2/delta-1 IC50 = 27.0 nM 7.57 Binding affinity towards alpha2-delta subunit of a voltage gated calcium channel... 15050626
Unchecked IC50 = 70.0 nM 7.16 Inhibition of [3H]gabapentin binding to pig brain membranes 15801823
Voltage-dependent calcium channel alpha2delta subunit IC50 = 70.0 nM 7.16 Displacement of [3H]gabapentin from alpha-2delta calcium channel in pig brain me... 15946842
Unchecked IC50 = 70.0 nM 7.16 Displacement of [3H]gabapentin from alpha2-delta subunit of voltage gated calciu... 19010672
Unchecked IC50 = 80.0 nM 7.1 In vitro inhibition of [3H]-gabapentin binding to partially purified rat neocort... -
Unchecked IC50 = 87.0 nM 7.06 Displacement of [3H]gabapentin from alpha2-delta calcium channel in pig brain 17489571
Voltage-dependent calcium channel subunit alpha-2/delta-1 Ki = 120.23 nM 6.92 Displacement of [3H]L-leucine from alpha-2delta containing calcium channel in mu... 16380257
Voltage-dependent calcium channel subunit alpha-2/delta-1 Ki = 120.0 nM 6.92 Displacement of [3H]L-leucine from alpha-2delta containing calcium channel in mu... 16380257
Unchecked IC50 = 140.0 nM 6.85 Displacement of [3H]gabapentin from voltage gated calcium channel alpha2delta fr... 21550803
Unchecked IC50 = 140.0 nM 6.85 Inhibition of voltage-dependent calcium channel subunit alpha-2/delta gabapentin... 23676307
Unchecked IC50 = 140.0 nM 6.85 Displacement of [3H]Gabapentin from alpha2delta calcium channel in pig brain tis... 21601457
Unchecked IC50 = 140.0 nM 6.85 Inhibition of Voltage-dependent calcium channel subunit alpha-2/delta 21550802
Unchecked IC50 = 140.0 nM 6.85 Displacement of [3H]gabapentin from Voltage-dependent calcium channel subunit al... 19910190
Voltage-dependent calcium channel alpha2delta subunit IC50 = 140.0 nM 6.85 Displacement of [3H]gabapentin from calcium channel alpha2delta in pig cerebral ... 19897364
Unchecked IC50 = 140.0 nM 6.85 Inhibition of specific binding of [3H]gabapentin to Gabapentin binding sites loc... 9599234
Unchecked IC50 = 140.0 nM 6.85 Displacement of [3H]gabapentin from alpha2-delta subunit of calcium channel 10476863
Unchecked IC50 = 140.0 nM 6.85 Binding affinity against alpha2-delta subunit of rat calcium channel -
Voltage-dependent calcium channel subunit alpha-2/delta-1 IC50 = 8900.0 nM 5.05 Inhibition of potassium-evoked [3H]norepinephrine release from rat neocortex 15946842
Unchecked IC50 = 30000.0 nM 4.52 Inhibition of [3H]leucine uptake into CHO cells by L-amino acid transporters 15801823
Unchecked IC50 = 30000.0 nM 4.52 Displacement of [3H]leucine from Large neutral amino acids transporter system L ... 19010672

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 467
17451232 10.1021/jm061431g Rattus norvegicus 40
23807113 10.1016/j.ejmech.2013.05.022 Rattus norvegicus 24
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
15920768 10.1002/jps.20373 ADMET 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.1016/S0960-894X(01)80855-6 Mus musculus 6
27517811 10.1016/j.ejmech.2016.07.032 NON-PROTEIN TARGET 6
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 5
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 5
15946842 10.1016/j.bmcl.2005.05.016 Rattus norvegicus 5
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 5
19010672 10.1016/j.bmcl.2008.10.101 Rattus norvegicus 5
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 5
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 5
34270254 10.1021/acs.jmedchem.1c00472 Rattus norvegicus 5

Data from ChEMBL 36 via Core Engine