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EBI Databases Small Molecules ChEMBL Database CHEMBL629

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL629
CHEMBL629
Compound Name AMITRIPTYLINE
ChEMBL Synonyms LENTIZOL | Elavil | Amitid | SAROTEN RETARD | DOMICAL | AMITID | AMITRIL | Limbitrol | Etrafon-Forte | AMITRIPTYLINE HYDROCHLORIDE | TRIPTAFEN-M | Etrafon-A | ENDEP | ELAVIL | Amitril | TRIPTAFEN | LIMBITROL 5 | Amitriptyline | Endep | TRYPTIZOL | CYTRIPTYLINE | TRYPTIZOL-75 | SAROTEN
Max Phase 4 (Approved)
Trade Names TRIPTAFEN-M | CYTRIPTYLINE | SAROTEN | TRYPTIZOL-75 | LENTIZOL | TRYPTIZOL | AMITID | DOMICAL | SAROTEN RETARD | AMITRIPTYLINE HYDROCHLORIDE | LIMBITROL 5 | TRIPTAFEN | AMITRIL | ELAVIL | ENDEP
Molecular Formula C20H23N

Additional synonyms for CHEMBL629 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN(C)CCC=C1c2ccccc2CCc3ccccc13
Standard InChI InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14- ...
Download InChI
Standard InChI Key KRMDCWKBEZIMAB-UHFFFAOYSA-N

Sources

  • BindingDB Database
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Drugs for Neglected Diseases Initiative (DNDi)
  • Open TG-GATEs
  • 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


CHEMBL629

Molecule Features

CHEMBL629 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

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

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Biliary DyskinesiaD001657EFO:0007169biliary dyskinesia2ClinicalTrials
Intervertebral Disc DisplacementD007405EFO:1001800Intervertebral Disc Displacement2ClinicalTrials
Nervous System DiseasesD009422EFO:0000618nervous system disease2ClinicalTrials
AnxietyD001007EFO:0005230anxiety3ClinicalTrials
Cystitis, InterstitialD018856EFO:1000869chronic interstitial cystitis3ClinicalTrials
Diabetes MellitusD003920EFO:0000400diabetes mellitus2ClinicalTrials
Digestive System DiseasesD004066EFO:0000405digestive system disease2ClinicalTrials
BursitisD002062EFO:1000941frozen shoulder2ClinicalTrials
DementiaD003704HP:0000726dementia3ClinicalTrials
Peripheral Nervous System DiseasesD010523EFO:0004149neuropathy2ClinicalTrials
PruritusD011537HP:0000989Pruritus2ClinicalTrials
FibromyalgiaD005356EFO:0005687fibromyalgia3ClinicalTrials
Migraine DisordersD008881EFO:0003821migraine disorder3ClinicalTrials
PainD010146EFO:0003843pain3ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression4ATC
ClinicalTrials
DailyMed
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FDA
HeadacheD006261HP:0002315Headache3ClinicalTrials
NeuralgiaD009437EFO:0005762neuropathic pain3ClinicalTrials
Paget Disease, ExtramammaryD010145EFO:0000512reproductive system disease2ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
Sleep Initiation and Maintenance DisordersD007319EFO:0004698insomnia3ClinicalTrials

Clinical Data

ClinicalTrials.gov AMITRIPTYLINE
The Cochrane Collaboration AMITRIPTYLINE

Metabolites for CHEMBL629

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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 CHEMBL629. 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
CHEMBL231 Histamine H1 receptor Homo sapiens 1.000
CHEMBL3943 Histamine H1 receptor Cavia porcellus 1.000
CHEMBL4701 Histamine H1 receptor Rattus norvegicus 1.000
CHEMBL1850 Dopamine D5 receptor Homo sapiens 1.000
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 0.997
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 0.995
CHEMBL1867 Alpha-2a adrenergic receptor Homo sapiens 0.994
CHEMBL2035 Muscarinic acetylcholine receptor M5 Homo sapiens 0.994
CHEMBL276 Muscarinic acetylcholine receptor M1 Rattus norvegicus 0.990
CHEMBL1821 Muscarinic acetylcholine receptor M4 Homo sapiens 0.981
CHEMBL1916 Alpha-2c adrenergic receptor Homo sapiens 0.975
CHEMBL2056 Dopamine D1 receptor Homo sapiens 0.949
CHEMBL216 Muscarinic acetylcholine receptor M1 Homo sapiens 0.844
CHEMBL309 Muscarinic acetylcholine receptor M2 Rattus norvegicus 0.826
CHEMBL1833 Serotonin 2b (5-HT2b) receptor Homo sapiens 0.816
CHEMBL319 Alpha-1a adrenergic receptor Rattus norvegicus 0.566
CHEMBL265 Dopamine D1 receptor Rattus norvegicus 0.537



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL231 Histamine H1 receptor Homo sapiens 1.000
CHEMBL3943 Histamine H1 receptor Cavia porcellus 1.000
CHEMBL4701 Histamine H1 receptor Rattus norvegicus 1.000
CHEMBL1850 Dopamine D5 receptor Homo sapiens 0.999
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 0.997
CHEMBL276 Muscarinic acetylcholine receptor M1 Rattus norvegicus 0.982
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 0.972
CHEMBL1867 Alpha-2a adrenergic receptor Homo sapiens 0.954
CHEMBL1916 Alpha-2c adrenergic receptor Homo sapiens 0.930
CHEMBL1821 Muscarinic acetylcholine receptor M4 Homo sapiens 0.893
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 0.873
CHEMBL2056 Dopamine D1 receptor Homo sapiens 0.858
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.847
CHEMBL2035 Muscarinic acetylcholine receptor M5 Homo sapiens 0.841
CHEMBL309 Muscarinic acetylcholine receptor M2 Rattus norvegicus 0.776
CHEMBL216 Muscarinic acetylcholine receptor M1 Homo sapiens 0.642
CHEMBL1833 Serotonin 2b (5-HT2b) receptor Homo sapiens 0.601
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.467
CHEMBL265 Dopamine D1 receptor Rattus norvegicus 0.458
CHEMBL1941 Histamine H2 receptor Homo sapiens 0.452

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
277.4 277.183 4.17 3 3.24 BASE


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


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 9.18 4.41 2.65 2 21 0.81

Structural Alerts

There are 1 structural alerts for CHEMBL629. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N06 - PSYCHOANALEPTICS
N06A - ANTIDEPRESSANTS
N06AA - Non-selective monoamine reuptake inhibitors
N06AA09 - amitriptyline
ChemSpider ChemSpider:KRMDCWKBEZIMAB-UHFFFAOYSA-N
DailyMed amitriptyline hydrochloride
PubChem SID: 11110782 SID: 11110783 SID: 124879280 SID: 90340850
Wikipedia Amitriptyline

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL629



ACToR 50-48-6
Atlas amitriptyline
BindingDB 50020712
Brenda 211300 24403 4978
ChEBI 2666
DrugBank DB00321
DrugCentral 180
eMolecules 739635
EPA CompTox Dashboard DTXSID7022594
FDA SRS 1806D8D52K
Guide to Pharmacology 200
Human Metabolome Database HMDB0014466
IBM Patent System B0D7EAA16AC69D8C1E4082455C097E29
KEGG Ligand C06824
LINCS LSM-3190
Mcule MCULE-3537115467
MolPort MolPort-001-662-651
Nikkaji J4.103C
PDBe TP0
PharmGKB PA448385
PubChem 2160
PubChem: Thomson Pharma 14775196
SureChEMBL SCHEMBL7824
ZINC ZINC000000968257

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