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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1059
CHEMBL1059
Compound Name PREGABALIN
ChEMBL Synonyms REWISCA | PD-144723 | LECAENT | LYRICA | AXALID | PREGABALIN | LYRICA CR | ALZAIN | CI-1008
Max Phase 4 (Approved)
Trade Names AXALID | LECAENT | REWISCA | LYRICA CR | PREGABALIN | ALZAIN | LYRICA
Molecular Formula C8H17NO2

Additional synonyms for CHEMBL1059 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC(C)C[C@H](CN)CC(=O)O
Standard InChI InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2 ...
Download InChI
Standard InChI Key AYXYPKUFHZROOJ-ZETCQYMHSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1059

Molecule Features

CHEMBL1059 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Voltage-gated calcium channel modulator Voltage-gated calcium channel FDA PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma1ClinicalTrials
CoughD003371HP:0012735Cough1ClinicalTrials
Migraine DisordersD008881EFO:0003821migraine disorder3ClinicalTrials
Oropharyngeal NeoplasmsD009959EFO:1001931oropharynx cancer1ClinicalTrials
Peripheral Nervous System DiseasesD010523EFO:0004149neuropathy3ClinicalTrials
Dry Eye SyndromesD015352EFO:1000906dry eye syndrome2ClinicalTrials
Irritable Bowel SyndromeD043183EFO:0000555irritable bowel syndrome2ClinicalTrials
OsteoarthritisD010003EFO:0002506osteoarthritis3ClinicalTrials
Restless Legs SyndromeD012148EFO:0004270restless legs syndrome3ClinicalTrials
Urinary Bladder, OveractiveD053201EFO:1000781overactive bladder2ClinicalTrials
DementiaD003704HP:0000726dementia3ClinicalTrials
Intervertebral Disc DisplacementD007405EFO:0004994lumbar disc degeneration3ClinicalTrials
Liver CirrhosisD008103EFO:0001422cirrhosis of liver3ClinicalTrials
Neurotic DisordersD009497EFO:0004257neurotic disorder3ClinicalTrials
Refractive ErrorsD012030HP:0000539Abnormality of refraction1ClinicalTrials
AnxietyD001007EFO:0005230anxiety3ClinicalTrials
FibromyalgiaD005356EFO:0005687fibromyalgia3ClinicalTrials
Pancreatitis, ChronicD050500EFO:0000342chronic pancreatitis2ClinicalTrials
PregnancyD011247EFO:0002950pregnancy1ClinicalTrials
Fractures, BoneD050723EFO:0003931bone fracture3ClinicalTrials
PainD010146EFO:0003843pain3ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
SeizuresD012640HP:0001250Seizures3ClinicalTrials
Diabetic NeuropathiesD003929EFO:1000783diabetic neuropathy3ClinicalTrials
Epilepsies, PartialD004828EFO:0004263partial epilepsy3ClinicalTrials
EpilepsyD004827EFO:0000474epilepsy4ATC
ClinicalTrials
Marijuana AbuseD002189EFO:0004218marijuana dependence0ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression3ClinicalTrials
Diabetes MellitusD003920EFO:0000400diabetes mellitus2ClinicalTrials
Epilepsy, Tonic-ClonicD0048303ClinicalTrials
Herpes Zoster OticusD016697EFO:0007281geniculate herpes zoster3ClinicalTrials
NeuralgiaD009437EFO:0005762neuropathic pain3ClinicalTrials
Tobacco Use DisorderD014029EFO:0003768nicotine dependence0ClinicalTrials
AlcoholismD000437EFO:0003829alcohol dependence2ClinicalTrials
Epilepsy, Complex PartialD017029EFO:1000877complex partial epilepsy3ClinicalTrials

Clinical Data

ClinicalTrials.gov PREGABALIN
The Cochrane Collaboration PREGABALIN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1059. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL3247 HMG-CoA reductase Rattus norvegicus 0.998
CHEMBL2714 Pepsin A Sus scrofa 0.994
CHEMBL402 HMG-CoA reductase Homo sapiens 0.994
CHEMBL2590 Aminopeptidase N Sus scrofa 0.993
CHEMBL3419 Carboxypeptidase B2 isoform A Homo sapiens 0.977
CHEMBL1907 Aminopeptidase N Homo sapiens 0.924
CHEMBL4106 Cathepsin D Bos taurus 0.915
CHEMBL3768 Neprilysin Oryctolagus cuniculus 0.903
CHEMBL2676 Endothelin-converting enzyme 1 Rattus norvegicus 0.893
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 0.883
CHEMBL3369 Neprilysin Rattus norvegicus 0.849
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.840
CHEMBL4588 Matrix metalloproteinase 8 Homo sapiens 0.795
CHEMBL3392 Thermolysin Bacillus thermoproteolyticus 0.737
CHEMBL3308 Caspase-6 Homo sapiens 0.712
CHEMBL2552 Carboxypeptidase B Homo sapiens 0.647
CHEMBL3439 Aminopeptidase A Homo sapiens 0.624
CHEMBL321 Matrix metalloproteinase 9 Homo sapiens 0.615
CHEMBL286 Renin Homo sapiens 0.608
CHEMBL3776 Caspase-8 Homo sapiens 0.576



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3985 Voltage-dependent calcium channel alpha2delta subunit Sus scrofa 1.000
CHEMBL3419 Carboxypeptidase B2 isoform A Homo sapiens 0.997
CHEMBL3247 HMG-CoA reductase Rattus norvegicus 0.994
CHEMBL2714 Pepsin A Sus scrofa 0.993
CHEMBL402 HMG-CoA reductase Homo sapiens 0.992
CHEMBL3965 Leucine aminopeptidase Homo sapiens 0.992
CHEMBL2552 Carboxypeptidase B Homo sapiens 0.988
CHEMBL1907 Aminopeptidase N Homo sapiens 0.978
CHEMBL2590 Aminopeptidase N Sus scrofa 0.977
CHEMBL4106 Cathepsin D Bos taurus 0.975
CHEMBL3439 Aminopeptidase A Homo sapiens 0.964
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.956
CHEMBL3768 Neprilysin Oryctolagus cuniculus 0.913
CHEMBL3392 Thermolysin Bacillus thermoproteolyticus 0.904
CHEMBL3369 Neprilysin Rattus norvegicus 0.867
CHEMBL3308 Caspase-6 Homo sapiens 0.835
CHEMBL2334 Caspase-3 Homo sapiens 0.791
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 0.783
CHEMBL2676 Endothelin-converting enzyme 1 Rattus norvegicus 0.760
CHEMBL4588 Matrix metalloproteinase 8 Homo sapiens 0.742

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
159.2 159.1259 1.08 5 63.32 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 2 0 3 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.23 11.31 1.09 -1.41 0 11 0.63

Structural Alerts

There are 1 structural alerts for CHEMBL1059. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N03 - ANTIEPILEPTICS
N03A - ANTIEPILEPTICS
N03AX - Other antiepileptics
N03AX16 - pregabalin

ChemSpider ChemSpider:AYXYPKUFHZROOJ-ZETCQYMHSA-N
DailyMed pregabalin
PubChem SID: 144205028
Wikipedia Pregabalin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1059



ACToR 148553-50-8
BindingDB 50164279
ChEBI 64356
ChemicalBook CB2251105
DrugBank DB00230
DrugCentral 2255
eMolecules 8324194
EPA CompTox Dashboard DTXSID1045950
FDA SRS 55JG375S6M
Guide to Pharmacology 5484
Human Metabolome Database HMDB0014375
IBM Patent System 434C2888E53C4CF52B80C96B3E137330
Mcule MCULE-4620415947
Nikkaji J702.547E
PharmGKB PA164754814
PubChem 5486971 25271887
PubChem: Drugs of the Future 12014780
PubChem: Thomson Pharma 15219358 15171006
SureChEMBL SCHEMBL8227 SCHEMBL17510367
ZINC ZINC000000005152

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/AYXYPKUFHZROOJ-ZETCQYMHSA-N spacer
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