Compound Detail

CHEMBL415

CLOMIPRAMINE

💊 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

CN(C)CCCN1c2ccccc2CCc2ccc(Cl)cc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL415
Name	CLOMIPRAMINE
Phase	Approved
Structure Type	MOL
InChI Key	GDLIGKIOYRNHDA-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

3-chloro-iminodibenzyl Anapramine Chlorimipramine Clomicalm Clomipramina Clomipramine NSC-169865

Targets

116

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

314.9

MW (Da)

4.53

ALogP

HBA

HBD

6.5

PSA (Å²)

0.82

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1989
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

USAN Stem	-pramine
USAN Year	1970

Extended Properties

Molecular Formula	C19H23ClN2
MW	314.86
Aromatic Rings	2
Heavy Atoms	22
NP-Likeness	-1.09

Indications

Depressive Disorder Depressive Disorder Anxiety Dementia Obsessive-Compulsive Disorder Premature Ejaculation Schizophrenia

ATC Classification

N06AA04

clomipramine

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 69 meas. best 10.4

Ki 44 meas. best 10.33

EC50 2 meas. best 5.3

Kd 1 meas.

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Alpha-1A adrenergic receptor CHEMBL319	IC50	10.4	8.7	0.0	2
Sodium-dependent serotonin transporter CHEMBL228	Ki	10.33	9.94	0.0	2
Sodium-dependent serotonin transporter CHEMBL228	IC50	10.06	8.61	0.1	2
Histamine H1 receptor CHEMBL4701	IC50	9.7	9.7	0.2	1
Serotonin (5-HT) receptor CHEMBL2094123	IC50	8.3	8.3	5.0	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	8.08	8.08	8.3	1
Histamine H1 receptor CHEMBL231	Ki	8.01	8.01	9.8	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	7.89	7.89	13.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	7.75	7.75	18.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.72	7.72	19.0	1
Sodium-dependent serotonin transporter CHEMBL313	IC50	7.7	7.375	20.0	2
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	7.66	7.66	22.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	7.47	7.47	34.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	7.44	7.44	36.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	7.42	7.42	38.0	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	7.4	7.4	40.0	1
Unchecked CHEMBL612545	Ki	7.37	5.8963	43.0	8
Alpha-2B adrenergic receptor CHEMBL1942	Ki	7.34	7.34	46.0	1
Unchecked CHEMBL612545	IC50	7.34	5.8133	46.0	9
D(3) dopamine receptor CHEMBL234	Ki	7.33	7.33	47.0	1
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	7.29	7.29	51.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	7.28	7.28	53.0	1
D(2) dopamine receptor CHEMBL339	Ki	7.25	7.25	56.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	7.19	7.17	64.6	2
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	7.17	7.17	67.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	7.16	7.16	70.0	1
Sodium-dependent serotonin transporter CHEMBL4642	IC50	7.16	7.16	70.0	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	7.14	7.14	73.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	7.12	7.12	75.0	1
Histamine H1 receptor CHEMBL231	IC50	7.07	7.07	85.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	7.07	7.07	86.0	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	7.06	7.06	88.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	7.04	7.04	91.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	7.04	7.04	91.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	7.0	7.0	101.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.95	6.945	112.0	2
Alpha-1B adrenergic receptor CHEMBL315	IC50	6.88	6.88	132.0	1
D(3) dopamine receptor CHEMBL234	IC50	6.86	6.86	139.0	1
D(2) dopamine receptor CHEMBL217	Ki	6.86	6.86	138.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.82	6.82	152.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	6.77	6.77	170.0	1
Alpha-1D adrenergic receptor CHEMBL223	IC50	6.75	6.75	180.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.69	6.69	205.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	6.62	6.62	239.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	6.62	6.62	241.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	6.61	6.61	245.0	1
D(2) dopamine receptor CHEMBL217	IC50	6.38	6.38	413.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.28	6.28	530.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	6.25	6.25	557.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.24	6.24	572.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	8.2	mL.min-1.kg-1	Homo sapiens
CL	1047.0	mL.min-1.kg-1	Homo sapiens
CL	134.0	uL.min-1.(10^6cells)-1	Homo sapiens
CL	122.5	uL.min-1.(10^6cells)-1	Homo sapiens
CL	10.9	mL.min-1.kg-1	Homo sapiens
F	79.0	%	Homo sapiens
Fu	0.04	-	Homo sapiens
Fu	0.029	-	Homo sapiens
Fu	0.19	-	Homo sapiens
Fu	0.004	-	Homo sapiens
Fu	0.006	-	Macaca fascicularis
Fu	0.004	-	Canis lupus familiaris
Fu	0.003	-	Cavia porcellus
Fu	0.004	-	Mus musculus
Fu	0.003	-	Rattus norvegicus
Fu	0.004	-	Rattus norvegicus
Fu	0.022	-	Not specified
Fu	0.186	-	Homo sapiens
MRT	26.0	hr	Homo sapiens
T1/2	35.0	hr	-
T1/2	26.0	hr	Homo sapiens
Vd	13.5	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
Sodium-dependent serotonin transporter	Ki	=	0.047	nM	10.33	DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind...	-
Sodium-dependent serotonin transporter	IC50	=	0.088	nM	10.06	DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind...	-
Histamine H1 receptor	IC50	=	0.2	nM	9.7	Compound tested for its inhibitory activity against Histamine H1 receptor	10447960
Sodium-dependent serotonin transporter	Ki	=	0.28	nM	9.55	Displacement of [3H]-imipramine from human serotonin transporter expressed in HE...	26372073
Serotonin (5-HT) receptor	IC50	=	5.0	nM	8.3	Compound was tested for its inhibitory activity against 5-hydroxytryptamine rece...	10447960
Serotonin 2 (5-HT2) receptor	Ki	=	8.3	nM	8.08	Binding affinity towards 5-hydroxytryptamine 2 receptor	3039136
Histamine H1 receptor	Ki	=	9.827	nM	8.01	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
Muscarinic acetylcholine receptor M4	Ki	=	13.0	nM	7.89	DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
5-hydroxytryptamine receptor 2C	Ki	=	18.0	nM	7.75	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2A	Ki	=	19.0	nM	7.72	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
Sodium-dependent serotonin transporter	IC50	=	20.0	nM	7.7	Inhibition of uptake of 5-HT in rat brain cortex	7452682
Muscarinic acetylcholine receptor M1	Ki	=	22.0	nM	7.66	DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
5-hydroxytryptamine receptor 2C	IC50	=	34.0	nM	7.47	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
Muscarinic acetylcholine receptor M3	Ki	=	36.0	nM	7.44	DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor M5	Ki	=	38.0	nM	7.42	DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Alpha-1A adrenergic receptor	Ki	=	40.0	nM	7.4	DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin)	-
Unchecked	Ki	=	43.0	nM	7.37	Compound was tested for its binding affinity towards brain (neocortex) Adenylate...	10447960
Alpha-2B adrenergic receptor	Ki	=	46.0	nM	7.34	DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin...	-
Unchecked	IC50	=	46.0	nM	7.34	Compound was tested for its inhibitory activity against Noradrenaline receptor	10447960

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1382
-	10.6019/CHEMBL3885881	Rattus norvegicus	270
16472241	10.2174/1570163043334794	Hepatotoxicity	18
17870537	10.1016/j.bmc.2007.08.055	Mus musculus	17
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
17687333	10.1038/nature06038	Unchecked	8
1246052	10.1021/jm00223a010	Mus musculus	7
22757	10.1021/jm00199a014	Mus musculus	7
10447960	10.1021/jm9910369	ADMET	6
3806614	10.1021/jm00385a013	Mus musculus	5
6167716	10.1021/jm00135a006	ADMET	5
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	5
-	10.1007/s00044-009-9176-x	Mus musculus	5
21474681	10.1124/dmd.111.038778	Brain	5
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	4
16168645	10.1016/j.bmcl.2005.08.040	Mus musculus	4
18426954	10.1124/dmd.108.020479	ADMET	4
-	10.6019/CHEMBL4651402	SARS-CoV-2	4

Data from ChEMBL 36 via Core Engine