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Compound Detail

CHEMBL1200964

AMITRIPTYLINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
CN(C)CCC=C1c2ccccc2CCc2ccccc21.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1200964
Name AMITRIPTYLINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key KFYRPLNVJVHZGT-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL629
Active Moiety CHEMBL629

Known Names

Amitid Amitril Amitriptyline hcl Amitriptyline hydrochloride Amitriptyline hydrochloride component of etrafon-a Amitriptyline hydrochloride component of limbitrol Amitriptyline hydrochloride component of limbitrol ds Amitriptylini hydrochloridum Cytriptyline Domical Elavil Endep +13 more
3
Targets
9
Activities
1
Assay Types
0
PK Parameters
20
Publications
25
Known Names
4
Indications
2
Mechanisms

Molecular Properties

277.4
MW (Da)
4.17
ALogP
1
HBA
0
HBD
3.2
PSA (Ų)
0.81
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1961
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning
USAN Stem -triptyline

Extended Properties

Molecular Formula C20H24ClN
MW 313.87
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.11

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serotonin transporter inhibitor INHIBITOR Sodium-dependent serotonin transporter ✓ ✓
Norepinephrine transporter inhibitor INHIBITOR Sodium-dependent noradrenaline transporter ✓ ✓

Indications

Depressive Disorder Erythromelalgia Peripheral Nervous System Diseases Pruritus

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 9 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 6.7 6.7 200.0 1
Unchecked
CHEMBL612545
 IC50 5.52 5.365 2999.1 2
Plasmodium falciparum
CHEMBL364
 IC50 5.0 4.9333 10000.0 6

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent noradrenaline transporter IC50 = 200.0 nM 6.7 Inhibition of the Norepinephrine transporter (NET, SLC6A2) as assessed by GPCR-m... 34112854
Unchecked IC50 = 2999.14 nM 5.52 PubChem BioAssay. insulin secretion from INS-1E cells in the presence of 5 mM gl... -
Unchecked IC50 = 6243.37 nM 5.21 PubChem BioAssay. tonic K+ channel activity under 0.1 mM glucose conditions in I... -
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
423198 10.1021/jm00188a012 Mus musculus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
17417631 10.1038/nchembio873 Unchecked 1
- 10.6019/CHEMBL4513141 Candida albicans 1
- 10.6019/CHEMBL4513141 Cryptococcus neoformans 1
- 10.6019/CHEMBL4513141 Escherichia coli 1
- 10.6019/CHEMBL4513141 Klebsiella pneumoniae 1
- 10.6019/CHEMBL4513141 Pseudomonas aeruginosa 1
- 10.6019/CHEMBL4513141 Acinetobacter baumannii 1
- 10.6019/CHEMBL4513141 Staphylococcus aureus 1
20553011 10.1021/tx1000865 Hepatotoxicity 1
34112854 10.1038/s41598-021-91700-7 Sodium-dependent noradrenaline transporter 1

Data from ChEMBL 36 via Core Engine