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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL668
CHEMBL668
Compound Name PROTRIPTYLINE
ChEMBL Synonyms VIVACTIL | PROTRIPTYLINE HYDROCHLORIDE | PROTRIPTYLINE | MK-240
Max Phase 4 (Approved)
Trade Names PROTRIPTYLINE HYDROCHLORIDE | VIVACTIL
Molecular Formula C19H21N

Additional synonyms for CHEMBL668 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CNCCCC1c2ccccc2C=Cc3ccccc13
Standard InChI InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16- ...
Download InChI
Standard InChI Key BWPIARFWQZKAIA-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL668

Molecule Features

CHEMBL668 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:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Norepinephrine transporter inhibitor Norepinephrine transporter PubMed
Serotonin transporter inhibitor Serotonin transporter PubMed

Clinical Data

ClinicalTrials.gov PROTRIPTYLINE
The Cochrane Collaboration PROTRIPTYLINE

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 CHEMBL668. 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
CHEMBL222 Norepinephrine transporter Homo sapiens 1.000
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 0.970
CHEMBL287 Sigma opioid receptor Homo sapiens 0.897
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 0.880
CHEMBL6184 Transporter Rattus norvegicus 0.847
CHEMBL228 Serotonin transporter Homo sapiens 0.721
CHEMBL1867 Alpha-2a adrenergic receptor Homo sapiens 0.697
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 0.683
CHEMBL1916 Alpha-2c adrenergic receptor Homo sapiens 0.660
CHEMBL223 Alpha-1d adrenergic receptor Homo sapiens 0.584
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.534
CHEMBL229 Alpha-1a adrenergic receptor Homo sapiens 0.440
CHEMBL232 Alpha-1b adrenergic receptor Homo sapiens 0.388
CHEMBL238 Dopamine transporter Homo sapiens 0.348
CHEMBL1945 Melatonin receptor 1A Homo sapiens 0.295



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL222 Norepinephrine transporter Homo sapiens 1.000
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.962
CHEMBL228 Serotonin transporter Homo sapiens 0.961
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 0.950
CHEMBL238 Dopamine transporter Homo sapiens 0.941
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 0.920
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 0.898
CHEMBL287 Sigma opioid receptor Homo sapiens 0.836
CHEMBL1867 Alpha-2a adrenergic receptor Homo sapiens 0.712
CHEMBL6184 Transporter Rattus norvegicus 0.710
CHEMBL1916 Alpha-2c adrenergic receptor Homo sapiens 0.404
CHEMBL223 Alpha-1d adrenergic receptor Homo sapiens 0.382
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.367
CHEMBL229 Alpha-1a adrenergic receptor Homo sapiens 0.299
CHEMBL224 Serotonin 2a (5-HT2a) receptor Homo sapiens 0.235
CHEMBL2370 Norepinephrine transporter Mus musculus 0.205

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
263.4 263.1674 4.04 4 12.03 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
1 1 0 1 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 10.61 4.36 1.51 2 20 0.82

Structural Alerts

There are 2 structural alerts for CHEMBL668. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N06 - PSYCHOANALEPTICS
N06A - ANTIDEPRESSANTS
N06AA - Non-selective monoamine reuptake inhibitors
N06AA11 - protriptyline

ChemSpider ChemSpider:BWPIARFWQZKAIA-UHFFFAOYSA-N
DailyMed protriptyline hydrochloride
PubChem SID: 11111679 SID: 11111680 SID: 50100330 SID: 50104299 SID: 90341254
Wikipedia Protriptyline

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL668



ACToR 438-60-8
BindingDB 50176062
Brenda 66192
ChEBI 8597
DrugBank DB00344
DrugCentral 2320
EPA CompTox Dashboard DTXSID0023535
FDA SRS 4NDU154T12
Guide to Pharmacology 7285
Human Metabolome Database HMDB0014488
IBM Patent System 8571F07D32A2F28912707BBDE7A4CD8B
KEGG Ligand C07408
LINCS LSM-2936
Mcule MCULE-6023848462
Nikkaji J5.739H
PharmGKB PA451168
PubChem 4976
PubChem: Thomson Pharma 15221639
SureChEMBL SCHEMBL34267
ZINC ZINC000001530764

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