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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1027
CHEMBL1027
Compound Name TIAGABINE
ChEMBL Synonyms TIAGABINE | Abbott-70569 | TIAGABINE HYDROCHLORIDE | ABBOTT-70569.HCL | ABT-569 | ABBOTT-70569-1 | ABBOTT-70569.1 | NO-05-0328 | A-70569-1 | NNC-05-0328 | GABITRIL | ABBOTT-70569
Max Phase 4 (Approved)
Trade Names GABITRIL | TIAGABINE HYDROCHLORIDE
Molecular Formula C20H25NO2S2

Additional synonyms for CHEMBL1027 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cc1ccsc1C(=CCCN2CCC[C@H](C2)C(=O)O)c3sccc3C
Standard InChI InChI=1S/C20H25NO2S2/c1-14-7-11-24-18(14)17(19-15(2)8-12-25- ...
Download InChI
Standard InChI Key PBJUNZJWGZTSKL-MRXNPFEDSA-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


CHEMBL1027

Molecule Features

CHEMBL1027 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N 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
GABA transporter 1 inhibitor GABA transporter 1 DailyMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
AlcoholismD000437EFO:0003829alcohol dependence1ClinicalTrials
Cocaine-Related DisordersD019970EFO:0002610cocaine dependence2ClinicalTrials
AnxietyD001007EFO:0005230anxiety3ClinicalTrials
ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
EpilepsyD004827EFO:0000474epilepsy4ATC
Sleep Apnea, ObstructiveD020181EFO:0003918obstructive sleep apnea2ClinicalTrials

Clinical Data

ClinicalTrials.gov TIAGABINE
The Cochrane Collaboration TIAGABINE

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 CHEMBL1027. 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
CHEMBL4054 GABA transporter 1 Rattus norvegicus 1.000

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4054 GABA transporter 1 Rattus norvegicus 1.000

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
375.6 375.1327 5.04 6 40.54 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 1 1 3 1 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
3.86 9.62 4.03 1.53 2 25 0.77

Structural Alerts

There are no structural alerts for CHEMBL1027

Compound Cross References

ATC N - NERVOUS SYSTEM
N03 - ANTIEPILEPTICS
N03A - ANTIEPILEPTICS
N03AG - Fatty acid derivatives
N03AG06 - tiagabine

ChemSpider ChemSpider:PBJUNZJWGZTSKL-MRXNPFEDSA-N
DailyMed tiagabine hydrochloride
PubChem SID: 26758048
Wikipedia Tiagabine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1027



ACToR 115103-54-3
BindingDB 50368628 50039251
ChEBI 9586
DrugBank DB00906
DrugCentral 2648
eMolecules 902575
EPA CompTox Dashboard DTXSID5023663
FDA SRS Z80I64HMNP
Guide to Pharmacology 4685 4818
Human Metabolome Database HMDB0015042
IBM Patent System 2A54FF11305812382853DF43B8557A9F
KEGG Ligand C07503
LINCS LSM-5700
MolPort MolPort-006-167-658
Nikkaji J390.632I
PharmGKB PA451682
PubChem 60648 40467242
PubChem: Thomson Pharma 14804309 14926800
SureChEMBL SCHEMBL34653
ZINC ZINC000003831531

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