Compound Detail

CHEMBL445

NORTRIPTYLINE

💊 Approved Drug

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💊 Approved Drug

CNCCC=C1c2ccccc2CCc2ccccc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL445
Name	NORTRIPTYLINE
Phase	Approved
Structure Type	MOL
InChI Key	PHVGLTMQBUFIQQ-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Allegron Aventyl Desitriptilina Lumbeck Motipress Motival NCI-169453 Noramitriptyline Nortrilen Nortriptilina Nortriptyline NSC-757234 +1 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

263.4

MW (Da)

3.83

ALogP

HBA

HBD

12.0

PSA (Å²)

0.83

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1964
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	0.35

Indications

Depressive Disorder Depressive Disorder Anxiety Dementia Dyspepsia Gastroesophageal Reflux Gastroparesis Schizophrenia Irritable Bowel Syndrome Psoriasis Temporomandibular Joint Disorders Tobacco Use Disorder

ATC Classification

N06AA10

nortriptyline

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 64 meas. best 10.4

Ki 35 meas. best 8.5

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Alpha-1A adrenergic receptor CHEMBL319	IC50	10.4	8.46	0.0	2
Histamine H1 receptor CHEMBL4701	IC50	10.3	10.3	0.1	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	8.5	8.35	3.2	2
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	8.49	8.49	3.2	1
Histamine H1 receptor CHEMBL231	Ki	8.23	8.23	5.9	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	8.16	8.16	7.0	1
Rattus norvegicus CHEMBL376	IC50	8.15	6.925	7.0	2
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	8.09	8.09	8.2	1
Unchecked CHEMBL612545	IC50	8.05	5.6614	9.0	7
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	7.89	7.89	13.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	7.89	7.89	13.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.82	7.82	15.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	7.8	7.8	16.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	7.7	7.7	20.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	7.7	7.7	20.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	7.57	7.57	27.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	7.52	7.52	30.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	7.44	7.44	36.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	7.37	7.37	43.0	1
Histamine H1 receptor CHEMBL231	IC50	7.3	7.3	50.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	7.29	7.29	51.0	1
D(3) dopamine receptor CHEMBL234	Ki	7.21	7.21	61.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	7.09	7.09	82.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	7.07	7.07	86.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	7.03	7.03	94.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	7.02	7.02	95.0	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	6.94	6.94	114.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	6.91	6.91	123.0	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	6.91	6.91	123.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	6.87	6.87	136.0	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	6.87	6.87	134.0	1
Serotonin (5-HT) receptor CHEMBL2094123	IC50	6.77	6.77	170.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	6.77	6.77	171.0	1
D(3) dopamine receptor CHEMBL234	IC50	6.75	6.75	179.0	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	6.69	6.69	203.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	6.68	6.68	207.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.67	6.63	214.0	2
D(1A) dopamine receptor CHEMBL2056	Ki	6.57	6.57	269.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.56	6.56	275.0	1
Alpha-1D adrenergic receptor CHEMBL223	IC50	6.56	6.56	273.0	1
Unchecked CHEMBL612545	Ki	6.55	5.5788	280.0	8
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	6.46	6.46	347.0	1
Mus musculus CHEMBL375	IC50	6.3	5.735	500.0	2
Plasmodium falciparum CHEMBL364	IC50	6.3	6.27	500.0	2
D(1A) dopamine receptor CHEMBL2056	IC50	6.27	6.27	539.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	6.26	6.26	554.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	6.13	6.13	732.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	6.0	5.74	1000.0	3
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	5.97	5.97	1068.0	1
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	5.93	5.93	1170.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	10.0	mL.min-1.kg-1	Homo sapiens
CL	9.8	mL.min-1.kg-1	Homo sapiens
CL	10.0	mL.min-1.kg-1	Homo sapiens
CL	10.0	mL.min-1.kg-1	Homo sapiens
CL	144.0	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	3.0	mL.min-1.g-1	Homo sapiens
F	79.0	%	Homo sapiens
Fu	0.12	-	Homo sapiens
Fu	0.12	-	Homo sapiens
Fu	0.12	-	Homo sapiens
Fu	0.006	-	Homo sapiens
Fu	0.0046	-	Rattus norvegicus
Fu	0.004	-	Sus scrofa
Fu	0.009	-	Macaca fascicularis
Fu	0.007	-	Canis lupus familiaris
Fu	0.006	-	Cavia porcellus
Fu	0.008	-	Mus musculus
Fu	0.005	-	Rattus norvegicus
Fu	0.007	-	Rattus norvegicus
MRT	37.0	hr	Homo sapiens
T1/2	35.5	hr	-
T1/2	30.0	hr	Homo sapiens
Vd	35.0	L.kg-1	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Alpha-1A adrenergic receptor	IC50	=	0.04	nM	10.4	Compound was tested for its inhibitory activity against Alpha-1 adrenergic recep...	10447960
Histamine H1 receptor	IC50	=	0.05	nM	10.3	Compound tested for its inhibitory activity against Histamine H1 receptor	10447960
Sodium-dependent noradrenaline transporter	Ki	=	3.184	nM	8.5	DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5...	-
Sodium-dependent noradrenaline transporter	IC50	=	3.21	nM	8.49	DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5...	-
Histamine H1 receptor	Ki	=	5.862	nM	8.23	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
Sodium-dependent noradrenaline transporter	Ki	=	6.3	nM	8.2	Compound was evaluated for its binding affinity towards human NET (norepinephrin...	10715164
Sodium-dependent serotonin transporter	Ki	=	6.977	nM	8.16	DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind...	-
Rattus norvegicus	IC50	=	7.0	nM	8.15	In vitro inhibition of the accumulation of (-)-[3H]Norepinephrine in synaptosome...	2966246
5-hydroxytryptamine receptor 2C	Ki	=	8.169	nM	8.09	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
Unchecked	IC50	=	9.0	nM	8.05	Compound was tested for its inhibitory activity against Noradrenaline receptor	10447960
Muscarinic acetylcholine receptor M4	Ki	=	13.0	nM	7.89	DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Sodium-dependent serotonin transporter	IC50	=	13.0	nM	7.89	DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind...	-
5-hydroxytryptamine receptor 2A	Ki	=	15.0	nM	7.82	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2C	IC50	=	16.0	nM	7.8	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
Muscarinic acetylcholine receptor M1	Ki	=	20.0	nM	7.7	DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M5	Ki	=	20.0	nM	7.7	DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M5	IC50	=	27.0	nM	7.57	DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Alpha-2C adrenergic receptor	Ki	=	30.0	nM	7.52	DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912)	-
Muscarinic acetylcholine receptor M3	Ki	=	36.0	nM	7.44	DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Alpha-2B adrenergic receptor	Ki	=	43.0	nM	7.37	DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	467
19378992	10.1021/jm900143u	Mus musculus	23
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
20070106	10.1021/jm901371v	Homo sapiens	8
6167716	10.1021/jm00135a006	ADMET	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
10447960	10.1021/jm9910369	ADMET	5
21474681	10.1124/dmd.111.038778	Brain	5
18426954	10.1124/dmd.108.020479	ADMET	4
19256501	10.1021/jm801441s	No relevant target	4
-	10.6019/CHEMBL4651402	SARS-CoV-2	4
-	10.6019/CHEMBL3301361	ADMET	4
2966246	10.1021/jm00400a005	Mus musculus	4
6167716	10.1021/jm00135a006	No relevant target	4
20014752	10.1021/tx900326k	Hepatotoxicity	3
9240356	10.1021/jm9603781	Trypanothione reductase	3
3373495	10.1021/jm00401a031	Mus musculus	3
10447960	10.1021/jm9910369	Unchecked	3

Data from ChEMBL 36 via Core Engine