amitriptyline   Click here for help

GtoPdb Ligand ID: 200

Synonyms: amitryptiline | Elavil® | Endep®
Approved drug PDB Ligand
amitriptyline is an approved drug (FDA (1961))
Compound class: Synthetic organic
Comment: Amitriptyline is a tricyclic antidepressant (TCA).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 3.24
Molecular weight 277.18
XLogP 4.93
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN(CCC=C1c2ccccc2CCc2c1cccc2)C
Isomeric SMILES CN(CCC=C1c2ccccc2CCc2c1cccc2)C
InChI InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3
InChI Key KRMDCWKBEZIMAB-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1961))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
dimethyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene]propyl})amine
International Nonproprietary Names Click here for help
INN number INN
976 amitriptyline
Synonyms Click here for help
amitryptiline | Elavil® | Endep®
Database Links Click here for help
BindingDB Ligand 50020712
CAS Registry No. 50-48-6
ChEBI CHEBI:2666
ChEMBL Ligand CHEMBL629
DrugBank Ligand DB00321
DrugCentral Ligand 180
GtoPdb PubChem SID 135649939
PubChem CID 2160
RCSB PDB Ligand TP0
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Wikipedia Amitriptyline