GABAPENTIN

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC N03AX12
UNII 6CW7F3G59X
EPA CompTox DTXSID0020074

Structure

InChI Key UGJMXCAKCUNAIE-UHFFFAOYSA-N
Smiles NCC1(CC(=O)O)CCCCC1
InChI
InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H17NO2
Molecular Weight 171.24
AlogP 1.37
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 3.0
Polar Surface Area 63.32
Molecular species ZWITTERION
Aromatic Rings 0.0
Heavy Atoms 12.0

Bioactivity

Mechanism of Action Action Reference
Voltage-gated calcium channel modulator MODULATOR FDA ISBN PubMed Wikipedia
Protein: Voltage-gated calcium channel
Description: Voltage-dependent L-type calcium channel subunit beta-4
Organism : Homo sapiens
O00305 ENSG00000182389
Protein: Voltage-gated calcium channel
Description: Voltage-dependent P/Q-type calcium channel subunit alpha-1A
Organism : Homo sapiens
O00555 ENSG00000141837
Protein: Voltage-gated calcium channel
Description: Voltage-dependent T-type calcium channel subunit alpha-1G
Organism : Homo sapiens
O43497 ENSG00000006283
Protein: Voltage-gated calcium channel
Description: Voltage-dependent calcium channel gamma-3 subunit
Organism : Homo sapiens
O60359 ENSG00000006116
Protein: Voltage-gated calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1F
Organism : Homo sapiens
O60840 ENSG00000102001
Protein: Voltage-gated calcium channel
Description: Voltage-dependent T-type calcium channel subunit alpha-1H
Organism : Homo sapiens
O95180 ENSG00000196557
Protein: Voltage-gated calcium channel
Description: Voltage-dependent calcium channel gamma-7 subunit
Organism : Homo sapiens
P62955 ENSG00000105605
Protein: Voltage-gated calcium channel
Description: Voltage-dependent N-type calcium channel subunit alpha-1B
Organism : Homo sapiens
Q00975 ENSG00000148408
Protein: Voltage-gated calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1D
Organism : Homo sapiens
Q01668 ENSG00000157388
Protein: Voltage-gated calcium channel
Description: Voltage-dependent L-type calcium channel subunit beta-1
Organism : Homo sapiens
Q02641 ENSG00000067191
Protein: Voltage-gated calcium channel
Description: Voltage-dependent L-type calcium channel subunit beta-2
Organism : Homo sapiens
Q08289 ENSG00000165995
Protein: Voltage-gated calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1S
Organism : Homo sapiens
Q13698 ENSG00000081248
Protein: Voltage-gated calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1C
Organism : Homo sapiens
Q13936 ENSG00000151067
Protein: Voltage-gated calcium channel
Description: Voltage-dependent R-type calcium channel subunit alpha-1E
Organism : Homo sapiens
Q15878 ENSG00000198216
Protein: Voltage-gated calcium channel
Description: Voltage-dependent calcium channel subunit alpha-2/delta-4
Organism : Homo sapiens
Q7Z3S7 ENSG00000151062
Protein: Voltage-gated calcium channel
Description: Voltage-dependent calcium channel subunit alpha-2/delta-3
Organism : Homo sapiens
Q8IZS8 ENSG00000157445
Protein: Voltage-gated calcium channel
Description: Voltage-dependent calcium channel gamma-8 subunit
Organism : Homo sapiens
Q8WXS5 ENSG00000142408
Protein: Voltage-gated calcium channel
Description: Voltage-dependent calcium channel gamma-6 subunit
Organism : Homo sapiens
Q9BXT2 ENSG00000130433
Protein: Voltage-gated calcium channel
Description: Voltage-dependent calcium channel subunit alpha-2/delta-2
Organism : Homo sapiens
Q9NY47 ENSG00000007402
Protein: Voltage-gated calcium channel
Description: Voltage-dependent T-type calcium channel subunit alpha-1I
Organism : Homo sapiens
Q9P0X4 ENSG00000100346
Protein: Voltage-gated calcium channel
Description: Voltage-dependent calcium channel gamma-4 subunit
Organism : Homo sapiens
Q9UBN1 ENSG00000075461
Protein: Voltage-gated calcium channel
Description: Voltage-dependent calcium channel gamma-5 subunit
Organism : Homo sapiens
Q9UF02 ENSG00000075429
Protein: Voltage-gated calcium channel
Description: Voltage-dependent calcium channel gamma-2 subunit
Organism : Homo sapiens
Q9Y698 ENSG00000166862
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Calcium channel auxiliary subunit alpha2delta family
- 70-140 - 120-120 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 15
Assay Description Organism Bioactivity Reference
Binding affinity towards alpha2-delta subunit of a voltage gated calcium channel using [3H]gabapentin in human brain membrane (A710 membrane) Homo sapiens 27.0 nM
Binding affinity against alpha2-delta subunit of rat calcium channel Rattus norvegicus 140.0 nM
Displacement of [3H]gabapentin from alpha2-delta subunit of calcium channel None 140.0 nM
In vitro inhibition of [3H]-gabapentin binding to partially purified rat neocortex synaptic plasma membranes Rattus norvegicus 80.0 nM
Inhibition of [3H]gabapentin binding to pig brain membranes Sus scrofa 70.0 nM
Displacement of [3H]L-leucine from alpha-2delta containing calcium channel in murine brain Mus musculus 120.0 nM Displacement of [3H]L-leucine from alpha-2delta containing calcium channel in murine brain Mus musculus 120.23 nM
Displacement of [3H]gabapentin from alpha-2delta calcium channel in pig brain membrane Sus scrofa 70.0 nM
Displacement of [3H]gabapentin from alpha2-delta calcium channel in pig brain Sus scrofa 87.0 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 15.1 %
Displacement of [3H]gabapentin from alpha2-delta subunit of voltage gated calcium channel in pig brain membrane Sus scrofa 70.0 nM
Displacement of [3H]gabapentin from calcium channel alpha2delta in pig cerebral cortex membrane after 30 mins Sus scrofa 140.0 nM
Displacement of [3H]gabapentin from Voltage-dependent calcium channel subunit alpha-2/delta in pig cerebral cortex by scintillation counting Sus scrofa 140.0 nM
Displacement of [3H]Gabapentin from alpha2delta calcium channel in pig brain tissue homogenates after 45 mins by scintillation counting Sus scrofa 140.0 nM
Inhibition of Voltage-dependent calcium channel subunit alpha-2/delta None 140.0 nM
Displacement of [3H]gabapentin from voltage gated calcium channel alpha2delta from pig cerebral cortex by scintillation counting Sus scrofa 140.0 nM
Analgesic activity in Sprague-Dawley rat assessed as inhibition of formalin-induced pain at 100 mg/kg, po Rattus norvegicus 33.0 %
Inhibition of voltage-dependent calcium channel subunit alpha-2/delta gabapentin binding site (unknown origin) Homo sapiens 140.0 nM
Analgesic activity in rat model of chronic constriction injury-induced neuropathic pain assessed as reversal of mechanical allodynia at 30 mg/kg dosed twice daily for 8 days relative to untreated control Rattus norvegicus 100.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 71.84 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.12 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.12 %

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
Czech Republic
Germany
Romania
Slovenia

Cross References

Resources Reference
ChEBI 42797
ChEMBL CHEMBL940
DrugBank DB00996
DrugCentral 1264
FDA SRS 6CW7F3G59X
Human Metabolome Database HMDB0005015
Guide to Pharmacology 5483
KEGG D00332
PDB GBN
PharmGKB PA449720
PubChem 3446
SureChEMBL SCHEMBL8343
ZINC ZINC000000004949
CONTENTS