PREGABALIN

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC N03AX16
UNII 55JG375S6M
EPA CompTox DTXSID1045950

Structure

InChI Key AYXYPKUFHZROOJ-ZETCQYMHSA-N
Smiles CC(C)C[C@H](CN)CC(=O)O
InChI
InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H17NO2
Molecular Weight 159.23
AlogP 1.08
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 63.32
Molecular species ZWITTERION
Aromatic Rings 0.0
Heavy Atoms 11.0

Bioactivity

Mechanism of Action Action Reference
Voltage-gated calcium channel modulator MODULATOR FDA PubMed
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
- 73-80 - 19 -
Ion channel Ligand-gated ion channel P2X receptor
- - - - 31
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 101
Assay Description Organism Bioactivity Reference
In vitro inhibition of [3H]-gabapentin binding to partially purified rat neocortex synaptic plasma membranes Rattus norvegicus 37.0 nM
In vitro percent inhibition of [3H]gabapentin binding at log molar concentration of -4.5 Rattus norvegicus 100.0 %
In vitro percent inhibition of [3H]gabapentin binding at log molar concentration of -5 Rattus norvegicus 98.0 %
In vitro percent inhibition of [3H]gabapentin binding at log molar concentration of -5.5 Rattus norvegicus 94.0 %
In vitro percent inhibition of [3H]gabapentin binding at log molar concentration of -6 Rattus norvegicus 90.0 %
In vitro percent inhibition of [3H]gabapentin binding at log molar concentration of -6.5 Rattus norvegicus 85.0 %
In vitro percent inhibition of [3H]gabapentin binding at log molar concentration of -7 Rattus norvegicus 75.0 %
In vitro percent inhibition of [3H]gabapentin binding at log molar concentration of -7.5 Rattus norvegicus 50.0 %
In vitro percent inhibition of [3H]gabapentin binding at log molar concentration of -8 Rattus norvegicus 25.0 %
Equilibrium dissociation constant for Voltage-gated calcium channel alpha2-delta subunit as inhibition of [3H]gabapentin binding to pig brain membranes Sus scrofa 19.0 nM
Inhibition of [3H]gabapentin binding to pig brain membranes Sus scrofa 80.0 nM
Displacement of [3H]gabapentin from alpha-2delta calcium channel in pig brain membrane Sus scrofa 73.0 nM
Binding affinity to alpha-2delta calcium channel None 19.0 nM
Displacement of [3H]gabapentin from alpha2-delta subunit of voltage gated calcium channel in pig brain membrane Sus scrofa 80.0 nM
Displacement of [3H]gabapentin from calcium channel alpha2delta in pig cerebral cortex membrane after 30 mins Sus scrofa 80.0 nM
Inhibition of [3H]gabapentin binding to voltage gated calcium channel alpha2delta from rat cerebral cortex at 10 uM by scintillation counting Rattus norvegicus 92.0 %
Displacement of [3H]gabapentin from Voltage-dependent calcium channel subunit alpha-2/delta in pig cerebral cortex by scintillation counting Sus scrofa 80.0 nM
Displacement of [3H]Gabapentin from alpha2delta calcium channel in pig brain tissue homogenates after 45 mins by scintillation counting Sus scrofa 80.0 nM
Inhibition of Voltage-dependent calcium channel subunit alpha-2/delta None 80.0 nM
Displacement of [3H]gabapentin from voltage gated calcium channel alpha2delta from pig cerebral cortex by scintillation counting Sus scrofa 80.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 120.58 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 101.4 %
Antinociceptive activity in rat spinal dorsal horn assessed as inhibition of electrically-stimulated long term potentiation at 20 uM by Di-4-ANEPPS dye-based assay relative to control Rattus norvegicus 31.0 %
Antagonist activity at P2X7 receptor in neuropathic rat dorsal horn assessed as inhibition of long term potentiation-induced neropathic pain at 20 uM relative to control Rattus norvegicus 31.0 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 5.38 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.13 %
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 0.04 % 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 0.04 %
Displacement of [3H]-gabapentin from human Cav alpha2delta1 expressed in CHO-K1 cell membranes incubated for 60 mins by scintillation counting method Homo sapiens 19.0 nM
Displacement of [3H]-gabapentin from human Cav alpha2delta2 expressed in HEK293 cell membranes incubated for 60 mins by scintillation counting method Homo sapiens 99.0 nM
Displacement of [3H]-gabapentin from human Cav alpha2delta1 expressed in CHO-K1 cell membranes incubated for 60 mins by scintillation counting method Homo sapiens 19.0 nM
Inhibition of recombinant CYP3A4 (unknown origin) using BFC as substrate at 1 uM measured after 30 mins in presence of NADPH generating system by fluorescence assay relative to control Homo sapiens 43.0 %

Related Entries

Cross References

Resources Reference
ChEBI 64356
ChEMBL CHEMBL1059
DrugBank DB00230
DrugCentral 2255
FDA SRS 55JG375S6M
Human Metabolome Database HMDB0014375
Guide to Pharmacology 5484
KEGG D02716
PharmGKB PA164754814
PubChem 5486971
SureChEMBL SCHEMBL17510367
ZINC ZINC000000005152
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