Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL668

PROTRIPTYLINE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
CNCCCC1c2ccccc2C=Cc2ccccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL668
Name PROTRIPTYLINE
Phase Approved
Structure Type MOL
InChI Key BWPIARFWQZKAIA-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Protriptilina Protriptyline
3
Targets
21
Activities
4
Assay Types
2
PK Parameters
20
Publications
2
Known Names
1
Indications

Molecular Properties

263.4
MW (Da)
4.30
ALogP
1
HBA
1
HBD
12.0
PSA (Ų)
0.81
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1967
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -triptyline
USAN Year 1963

Extended Properties

Molecular Formula C19H21N
MW 263.38
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.44

Indications

Depressive Disorder

ATC Classification

N06AA11
protriptyline
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 13 meas. best 8.96
Ki 6 meas. best 8.8
EC50 1 meas. best 5.11
Kd 1 meas. best 8.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 8.96 8.4709 1.1 11
Sodium-dependent noradrenaline transporter
CHEMBL222
 Kd 8.85 8.85 1.4 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 8.8 8.615 1.6 6
T47D
CHEMBL614361
 EC50 5.11 5.11 7700.0 1
Voltage-dependent N-type calcium channel subunit alpha-1B
CHEMBL4478
 IC50 4.85 4.85 14000.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 80.0 % Homo sapiens
F 85.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent noradrenaline transporter IC50 = 1.1 nM 8.96 Percent inhibition against Norepinephrine transporter at 1 uM nonselective 16250647
Sodium-dependent noradrenaline transporter Kd = 1.4 nM 8.85 Inhibition of human NET 20945906
Sodium-dependent noradrenaline transporter Ki = 1.6 nM 8.8 Binding affinity to human norepinephrine transporter by radioligand displacement... 23466604
Sodium-dependent noradrenaline transporter IC50 = 1.7 nM 8.77 Displacement of [3H]nisoxetine from human NET expressed in CHO cells after 120 m... 22420844
Sodium-dependent noradrenaline transporter Ki = 2.0 nM 8.7 Binding affinity to norepinephrine transporter (unknown origin) assessed as inhi... 28849908
Sodium-dependent noradrenaline transporter Ki = 2.0 nM 8.7 Displacement of [3H]nisoxetine from human NET expressed in CHO cells after 120 m... 22420844
Sodium-dependent noradrenaline transporter IC50 = 2.1 nM 8.68 Binding affinity to human norepinephrine transporter by radioligand displacement... 23466604
Sodium-dependent noradrenaline transporter Ki = 2.1 nM 8.68 Displacement of [3H]nisoxetine from human recombinant norepinephrine transporter... 27997171
Sodium-dependent noradrenaline transporter Ki = 2.3 nM 8.64 Displacement of [3H]nisoxetine from human NE transporter 21726069
Sodium-dependent noradrenaline transporter IC50 = 2.5 nM 8.6 Binding affinity to human nonepinephrine transporter by radioligand displacement... 23582449
Sodium-dependent noradrenaline transporter IC50 = 2.7 nM 8.57 Inhibition of norepinephrine transporter (unknown origin) 28849908
Sodium-dependent noradrenaline transporter IC50 = 2.8 nM 8.55 Displacement of [3H]nisoxentine from human recombinant norepinephrine transporte... 26988801
Sodium-dependent noradrenaline transporter IC50 = 2.8 nM 8.55 Displacement of [3H]nisoxetine from human recombinant norepinephrine transporter... 27876250
Sodium-dependent noradrenaline transporter IC50 = 2.9 nM 8.54 Displacement of [3H]nisoxetine from human recombinant norepinephrine transporter... 27997171
Sodium-dependent noradrenaline transporter Ki = 6.8 nM 8.17 Displacement of radiolabeled protriptyline from human NET 18983139
Sodium-dependent noradrenaline transporter IC50 = 7.1 nM 8.15 Inhibition of human NET 18588282
Sodium-dependent noradrenaline transporter IC50 = 9.1 nM 8.04 Displacement of radiolabeled protriptyline from human NET 18983139
Sodium-dependent noradrenaline transporter IC50 = 17.0 nM 7.77 Inhibition of human aorepinephrine transporter 20875743
T47D EC50 = 7700.0 nM 5.11 Induction of morphological changes in human T47D cells assessed as number of nuc... 31757681
Voltage-dependent N-type calcium channel subunit alpha-1B IC50 = 14000.0 nM 4.85 Inhibition of endogenous human CaV2.2 in human SH-SY5Y cells in presence of nife... 35308021

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
31757681 10.1016/j.bmc.2019.115209 T47D 5
31757681 10.1016/j.bmc.2019.115209 HCC1954 5
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
3373495 10.1021/jm00401a031 Mus musculus 3
28849908 10.1021/acschembio.7b00481 Sodium-dependent noradrenaline transporter 2
23466604 10.1016/j.ejmech.2013.01.044 Sodium-dependent noradrenaline transporter 2
22420844 10.1021/jm300138g Sodium-dependent noradrenaline transporter 2
27997171 10.1021/acs.jmedchem.6b01422 Sodium-dependent noradrenaline transporter 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
18983139 10.1021/jm8007618 Sodium-dependent noradrenaline transporter 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4651402 Vero C1008 2
10891117 10.1021/jm0000564 ADMET 2
10891117 10.1021/jm0000564 No relevant target 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2

Data from ChEMBL 36 via Core Engine