Compound Detail

CHEMBL72

DESIPRAMINE

💊 Approved Drug

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💊 Approved Drug

CNCCCN1c2ccccc2CCc2ccccc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL72
Name	DESIPRAMINE
Phase	Approved
Structure Type	MOL
InChI Key	HCYAFALTSJYZDH-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Desipramina Desipramine Imipramine, demethyl- Monodemethylimipramine N-desmethylimipramine Norimipramine

Targets

122

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

266.4

MW (Da)

3.53

ALogP

HBA

HBD

15.3

PSA (Å²)

0.85

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	-pramine
USAN Year	1962

Extended Properties

Molecular Formula	C18H22N2
MW	266.39
Aromatic Rings	2
Heavy Atoms	20
NP-Likeness	-0.44

Indications

Depressive Disorder Depressive Disorder Depressive Disorder, Major Alcoholism Gastroesophageal Reflux Stress Disorders, Post-Traumatic Cocaine-Related Disorders Rett Syndrome Sciatica Sleep Apnea, Obstructive Erectile Dysfunction Neoplasms

ATC Classification

N06AA01

desipramine

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 82 meas. best 9.6

Ki 36 meas. best 9.31

EC50 2 meas. best 7.16

Kd 2 meas. best 9.08

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Alpha-1A adrenergic receptor CHEMBL319	IC50	9.6	8.245	0.2	2
Sodium-dependent dopamine transporter CHEMBL238	Ki	9.31	6.7233	0.5	3
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	9.22	8.5827	0.6	15
Norepinephrine transporter CHEMBL304	Ki	9.19	8.4833	0.7	3
Unchecked CHEMBL612545	IC50	9.13	6.402	0.7	5
Transporter CHEMBL6184	Ki	9.11	9.11	0.8	1
Histamine H1 receptor CHEMBL4701	IC50	9.1	9.1	0.8	1
Sodium-dependent noradrenaline transporter CHEMBL222	Kd	9.08	9.08	0.8	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	9.03	8.5494	0.9	16
Sus scrofa CHEMBL613488	IC50	8.49	6.6933	3.2	3
Rattus norvegicus CHEMBL376	IC50	7.96	6.2817	11.0	6
Sodium-dependent serotonin transporter CHEMBL228	Ki	7.72	7.71	19.1	2
Sodium-dependent serotonin transporter CHEMBL228	IC50	7.28	6.9225	52.4	4
Norepinephrine transporter CHEMBL304	IC50	7.16	6.155	70.0	4
Mus musculus CHEMBL375	EC50	7.16	6.04	70.0	2
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.8	6.8	160.0	1
Sodium-dependent serotonin transporter CHEMBL313	Ki	6.79	6.7733	163.0	3
Unchecked CHEMBL612545	Ki	6.5	6.48	320.0	2
Serotonin (5-HT) receptor CHEMBL2094123	IC50	6.46	6.46	350.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.86	5.6022	1380.4	9
Sodium channel protein type 5 subunit alpha CHEMBL1980	IC50	5.82	5.82	1520.0	1
Sodium-dependent noradrenaline transporter CHEMBL2370	IC50	5.8	5.8	1600.0	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL2366456	IC50	5.77	5.77	1709.0	2
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682	IC50	5.62	5.62	2400.0	1
Solute carrier family 22 member 1 CHEMBL2073670	Ki	5.55	5.55	2800.0	1
Sodium-dependent serotonin transporter CHEMBL313	IC50	5.52	5.22	3000.0	2
Histamine H2 receptor CHEMBL2882	IC50	5.42	5.42	3800.0	1
Solute carrier family 22 member 1 CHEMBL5685	Ki	5.27	5.27	5360.0	1
Sodium-dependent dopamine transporter CHEMBL338	Ki	5.18	5.18	6530.0	1
Sodium-dependent dopamine transporter CHEMBL338	IC50	5.11	5.11	7800.0	1
Solute carrier family 22 member 1 CHEMBL5685	IC50	5.04	4.645	9180.0	2
Sodium-dependent serotonin transporter CHEMBL4642	IC50	5.03	5.03	9300.0	1
Solute carrier family 22 member 2 CHEMBL1770032	IC50	5.0	5.0	10000.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	5.0	4.492	9900.0	5
Voltage-dependent N-type calcium channel subunit alpha-1B CHEMBL4478	IC50	4.96	4.96	11000.0	1
Plasmodium falciparum CHEMBL364	IC50	4.94	4.88	11400.0	3
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	IC50	4.93	4.93	11700.0	1
Solute carrier family 22 member 3 CHEMBL2073673	Ki	4.85	4.85	14000.0	1
Solute carrier family 22 member 2 CHEMBL1743122	Ki	4.8	4.8	16000.0	1
Solute carrier family 22 member 1 CHEMBL2073670	IC50	4.76	4.76	17500.0	1
HeLa CHEMBL399	IC50	4.75	4.75	17780.0	1
ADMET CHEMBL612558	IC50	4.64	4.64	22900.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	4.64	4.64	22816.6	1
DG-75 CHEMBL2366199	IC50	4.4	4.4	39810.0	1
Solute carrier family 22 member 3 CHEMBL1770033	IC50	4.17	4.17	68000.0	1
Solute carrier family 22 member 4 CHEMBL2073667	IC50	4.1	4.1	80000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	10.3	mL.min-1.kg-1	Homo sapiens
CL	11.0	mL.min-1.kg-1	Homo sapiens
CL	10.8	mL.min-1.kg-1	Homo sapiens
CL	11.0	mL.min-1.kg-1	Homo sapiens
CL	11.0	mL.min-1.kg-1	Homo sapiens
CL	6.92	uL.min-1.(10^6cells)-1	Homo sapiens
CL	10.47	mL.min-1.g-1	Homo sapiens
CL	150.0	uL.min-1.(10^6cells)-1	Rattus norvegicus
F	49.0	%	Homo sapiens
F	70.0	%	Homo sapiens
Fu	0.18	-	-
Fu	0.003	-	-
Fu	0.15	-	Homo sapiens
Fu	0.16	-	Homo sapiens
Fu	0.16	-	Homo sapiens
Fu	0.011	-	Homo sapiens
Fu	0.012	-	Macaca fascicularis
Fu	0.017	-	Canis lupus familiaris
Fu	0.007	-	Cavia porcellus
Fu	0.011	-	Mus musculus
Fu	0.008	-	Rattus norvegicus
Fu	0.013	-	Rattus norvegicus
MRT	23.0	hr	Homo sapiens
T1/2	37.5	hr	-
T1/2	22.0	hr	Homo sapiens
Vd	22.0	L.kg-1	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Alpha-1A adrenergic receptor	IC50	=	0.25	nM	9.6	Compound was tested for its inhibitory activity against Alpha-1 adrenergic recep...	10447960
Sodium-dependent dopamine transporter	Ki	=	0.49	nM	9.31	In vitro competitive binding versus [N-methyl-3H]WIN-35428 in murine kidney cell...	12620070
Sodium-dependent noradrenaline transporter	Ki	=	0.6	nM	9.22	Inhibition of norepinephrine reuptake at NET	19836247
Norepinephrine transporter	Ki	=	0.65	nM	9.19	Inhibition of uptake of tritiated norepinephrine (NE) in rat synaptosomes	3039136
Unchecked	IC50	=	0.7413	nM	9.13	Inhibition of [3H]NE uptake at human NET EL2 chimera mutant expressed in african...	17428804
Transporter	Ki	=	0.78	nM	9.11	Displacement of [3H]nisoxetine from rat NET in rat cerebral cortex	20945906
Histamine H1 receptor	IC50	=	0.8	nM	9.1	Compound tested for its inhibitory activity against Histamine H1 receptor	10447960
Sodium-dependent noradrenaline transporter	Kd	=	0.83	nM	9.08	Inhibition of human NET	20945906
Sodium-dependent noradrenaline transporter	Ki	=	0.92	nM	9.04	Displacement of [125I]RTI55 from human recombinant norepinephrine transporter ex...	23403082
Sodium-dependent noradrenaline transporter	IC50	=	0.93	nM	9.03	Displacement of [125I]RTI-55 from human NET expressed in MDCK cell membrane	16989524
Sodium-dependent noradrenaline transporter	IC50	=	0.93	nM	9.03	Displacement of [125I]RTI55 from human recombinant norepinephrine transporter ex...	23403082
Sodium-dependent noradrenaline transporter	Ki	=	1.0	nM	9.0	Binding affinity at NET	17123820
Sodium-dependent noradrenaline transporter	Ki	=	1.1	nM	8.96	Displacement of [3H]Nisoxetine from norepinephrine transporter (unknown origin)	24365159
Sodium-dependent noradrenaline transporter	Ki	=	1.148	nM	8.94	Displacement of [3H]Nisoxetine from norepinephrine transporter (unknown origin)	24365159
Sodium-dependent noradrenaline transporter	IC50	=	1.5	nM	8.82	Displacement of [3H]Nisoxetine from human recombinant NET over-expressed in dog ...	24012181
Sodium-dependent noradrenaline transporter	Ki	=	1.8	nM	8.74	Uptake Assay Protocol: NET: This protocol was designed to measure inhibition of ...	-
Unchecked	IC50	=	2.0	nM	8.7	Compound was tested for its inhibitory activity against Noradrenaline receptor	10447960
Sodium-dependent noradrenaline transporter	Ki	=	2.1	nM	8.68	Displacement of [3H]nisoxetine from human NET expressed in MDCK-Net6 cells	20462211
Sodium-dependent noradrenaline transporter	Ki	=	2.1	nM	8.68	Displacement of [3H]nisoxetine from human NET expressed in MDCK-Net6 cells	21916421
Sodium-dependent noradrenaline transporter	Ki	=	2.1	nM	8.68	Inhibition of [3H]nisoxetine binding to human NET expressed in MDCK-Net6 cells b...	19722525

Literature References

PubMed	DOI	Target Context	# Activities
17428804	10.1074/jbc.m610813200	Sodium-dependent noradrenaline transporter	30
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
17418579	10.1016/j.bmc.2007.03.040	ADMET	8
20070106	10.1021/jm901371v	Homo sapiens	8
22757	10.1021/jm00199a014	Mus musculus	8
-	10.6019/CHEMBL3301361	ADMET	6
10447960	10.1021/jm9910369	ADMET	6
3373495	10.1021/jm00401a031	Rattus norvegicus	5
3806614	10.1021/jm00385a013	Mus musculus	5
3806599	10.1021/jm00384a040	Mus musculus	5
21474681	10.1124/dmd.111.038778	Brain	5
12061889	10.1021/jm0200409	ADMET	5
6167716	10.1021/jm00135a006	No relevant target	4
4009610	10.1021/jm00145a005	Mus musculus	4
20879794	10.1021/jf102525e	No relevant target	4
18557608	10.1021/jm8002262	Mus musculus	4
11300874	10.1021/jm001020e	ADMET	4
17846138	10.1128/aac.00669-07	Plasmodium falciparum	4

Data from ChEMBL 36 via Core Engine