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Compound Detail

CHEMBL1201156

NORTRIPTYLINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
CNCCC=C1c2ccccc2CCc2ccccc21.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1201156
Name NORTRIPTYLINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key SHAYBENGXDALFF-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL445
Active Moiety CHEMBL445

Known Names

38489 Aventyl Aventyl hydrochloride Nortriptyline hcl Nortriptyline hydrochloride NSC-169453 Pamelor Psychostyl
3
Targets
11
Activities
2
Assay Types
0
PK Parameters
17
Publications
8
Known Names
5
Indications
2
Mechanisms

Molecular Properties

263.4
MW (Da)
3.83
ALogP
1
HBA
1
HBD
12.0
PSA (Ų)
0.83
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1964
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -triptyline
USAN Year 1963

Extended Properties

Molecular Formula C19H22ClN
MW 299.85
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.35

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

Depression Gastroparesis Psoriasis Carcinoma, Small Cell Dermatitis, Atopic

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 10 meas. best 7.4
EC50 1 meas. best 4.65

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 7.4 7.4 40.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.6 5.2 2511.9 7
Unchecked
CHEMBL612545
 EC50 4.65 4.65 22510.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent noradrenaline transporter IC50 = 40.0 nM 7.4 Inhibition of the Norepinephrine transporter (NET, SLC6A2) as assessed by GPCR-m... 34112854
Plasmodium falciparum IC50 = 2511.89 nM 5.6 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 2511.89 nM 5.6 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 5011.87 nM 5.3 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 3D7 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 HB3 after 72 hrs by SYBR g... 19734910
Unchecked EC50 = 22510.0 nM 4.65 PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP... -

Literature References

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

Data from ChEMBL 36 via Core Engine