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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL661
CHEMBL661
Compound Name ALPRAZOLAM
ChEMBL Synonyms XANAX XR | NIRAVAM | U-31,889 | XANAX | ALPRAZOLAM
Max Phase 4 (Approved)
Trade Names ALPRAZOLAM | XANAX | XANAX XR | NIRAVAM
Molecular Formula C17H13ClN4

Additional synonyms for CHEMBL661 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cc1nnc2CN=C(c3ccccc3)c4cc(Cl)ccc4n12
Standard InChI InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12) ...
Download InChI
Standard InChI Key VREFGVBLTWBCJP-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • Curated Drug Pharmacokinetic Data
  • DrugMatrix
  • 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


CHEMBL661

Molecule Features

CHEMBL661 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule 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-A receptor; anion channel positive allosteric modulator GABA-A receptor; anion channel PubMed PubMed

Clinical Data

ClinicalTrials.gov ALPRAZOLAM
The Cochrane Collaboration ALPRAZOLAM

Metabolites for CHEMBL661

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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 CHEMBL661. 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
CHEMBL250 Platelet activating factor receptor Homo sapiens 1.000
CHEMBL1962 GABA receptor alpha-1 subunit Homo sapiens 1.000
CHEMBL1889 Vasopressin V1a receptor Homo sapiens 1.000
CHEMBL4552 Peripheral-type benzodiazepine receptor Rattus norvegicus 0.286

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL250 Platelet activating factor receptor Homo sapiens 1.000
CHEMBL1962 GABA receptor alpha-1 subunit Homo sapiens 1.000
CHEMBL1889 Vasopressin V1a receptor Homo sapiens 1.000
CHEMBL1790 Vasopressin V2 receptor Homo sapiens 0.923
CHEMBL4552 Peripheral-type benzodiazepine receptor Rattus norvegicus 0.498

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
308.8 308.0829 3.58 1 43.07 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 0 0 4 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 2.37 1.92 1.92 3 22 0.69

Structural Alerts

There are no structural alerts for CHEMBL661

Compound Cross References

ATC N - NERVOUS SYSTEM
N05 - PSYCHOLEPTICS
N05B - ANXIOLYTICS
N05BA - Benzodiazepine derivatives
N05BA12 - alprazolam

ChemSpider ChemSpider:VREFGVBLTWBCJP-UHFFFAOYSA-N
DailyMed alprazolam
PubChem SID: 144205245 SID: 26719699 SID: 29215419
Wikipedia Alprazolam

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL661



ACToR 28981-97-7
BindingDB 50001728
Brenda 88187
ChEBI 2611
DrugBank DB00404
DrugCentral 136
eMolecules 524672
EPA CompTox Dashboard DTXSID4022577
FDA SRS YU55MQ3IZY
Guide to Pharmacology 7111
Human Metabolome Database HMDB0014548
IBM Patent System 724D67DC468B1CF0CB782666CB1707BE
KEGG Ligand C06817
LINCS LSM-5460
Mcule MCULE-1215564244
NIH Clinical Collection SAM001246696
Nikkaji J9.279G
PDBe 08H
PharmGKB PA448333
PubChem 2118
PubChem: Drugs of the Future 12013413
PubChem: Thomson Pharma 14800856
SureChEMBL SCHEMBL8398
ZINC ZINC000000000903

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