Compound Detail

CHEMBL1200492

NEFAZODONE HYDROCHLORIDE

💊 Approved Drug

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💊 Approved Drug

CCc1nn(CCCN2CCN(c3cccc(Cl)c3)CC2)c(=O)n1CCOc1ccccc1.Cl

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1200492
Name	NEFAZODONE HYDROCHLORIDE
Phase	Approved
Structure Type	MOL
InChI Key	DYCKFEBIOUQECE-UHFFFAOYSA-N
Therapeutic	✓ Yes
Parent Compound	CHEMBL623
Active Moiety	CHEMBL623

Known Names

BMY 13754 BMY-13754 Dutonin MJ 13,754-1 MJ-13754-1 Nefazodone hcl Nefazodone hydrochloride NSC-760344 Serzone

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

470.0

MW (Da)

3.55

ALogP

HBA

HBD

55.5

PSA (Å²)

0.45

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1994
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning Withdrawn

USAN Year

1984

Extended Properties

Molecular Formula	C25H33Cl2N5O2
MW	506.48
Aromatic Rings	3
Heavy Atoms	33
NP-Likeness	-1.96

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Serotonin transporter inhibitor	INHIBITOR	Sodium-dependent serotonin transporter	✓	✓
Serotonin 2a (5-HT2a) receptor antagonist	ANTAGONIST	5-hydroxytryptamine receptor 2A	✓	✓
Serotonin 2c (5-HT2c) receptor antagonist	ANTAGONIST	5-hydroxytryptamine receptor 2C	✓	✓
Norepinephrine transporter inhibitor	INHIBITOR	Sodium-dependent noradrenaline transporter	✓	✓

Indications

Depression Depressive Disorder, Major

Drug Warnings

Withdrawn

hepatotoxicity

Adverse hepatic events

Country: Canada; Spain; Turkey Year: 2003

Withdrawn

hepatotoxicity

Adverse hepatic events

Country: Canada; Spain; Turkey Year: 2003

Withdrawn

hepatotoxicity

Adverse hepatic events

Country: Canada; Spain; Turkey Year: 2003

Black Box Warning

psychiatric toxicity

Country: United States

Black Box Warning

hepatotoxicity

Country: United States

Activity Summary

Ki 23 meas. best 7.81

IC50 4 meas. best 5.47

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.81	7.81	15.6	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	7.15	7.15	70.2	1
5-hydroxytryptamine receptor 1D CHEMBL1983	Ki	6.92	6.92	121.7	1
Histamine H1 receptor CHEMBL231	Ki	6.9	6.9	124.9	1
Alpha-1A adrenergic receptor CHEMBL229	Ki	6.86	6.86	137.3	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	6.76	6.76	175.3	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	6.72	6.72	192.4	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	6.67	6.67	215.7	1
Sigma intracellular receptor 2 CHEMBL4105907	Ki	6.65	6.65	221.9	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.6	6.6	253.1	1
5-hydroxytryptamine receptor 1B CHEMBL1898	Ki	6.58	6.58	262.1	1
D(4) dopamine receptor CHEMBL219	Ki	6.49	6.49	326.3	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.45	6.45	358.9	1
D(3) dopamine receptor CHEMBL234	Ki	6.42	6.42	380.2	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	6.35	6.35	445.2	1
Alpha-1B adrenergic receptor CHEMBL232	Ki	6.24	6.24	572.4	1
D(1A) dopamine receptor CHEMBL2056	Ki	6.15	6.15	711.6	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	6.14	6.14	730.5	1
D(2) dopamine receptor CHEMBL217	Ki	6.13	6.13	735.5	1
5-hydroxytryptamine receptor 5A CHEMBL3426	Ki	5.96	5.96	1092.1	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	5.95	5.95	1114.7	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	5.86	5.86	1370.9	1
Translocator protein CHEMBL5742	Ki	5.7	5.7	1986.3	1
Psychosine receptor CHEMBL3714081	IC50	5.47	5.47	3388.6	1
G-protein coupled receptor 35 CHEMBL1293267	IC50	5.46	5.46	3479.2	1
N-formyl peptide receptor 3 CHEMBL5646	IC50	5.43	5.43	3674.4	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	5.18	5.18	6596.5	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2A	Ki	=	15.62	nM	7.81	PDSP Secondary Binding target: HTR2A - Compounds are tested at 10 uM concentrati...	-
5-hydroxytryptamine receptor 7	Ki	=	70.25	nM	7.15	PDSP Secondary Binding target: HTR7 - Compounds are tested at 10 uM concentratio...	-
5-hydroxytryptamine receptor 1D	Ki	=	121.68	nM	6.92	PDSP Secondary Binding target: HTR1D - Compounds are tested at 10 uM concentrati...	-
Histamine H1 receptor	Ki	=	124.91	nM	6.9	PDSP Secondary Binding target: HRH1 - Compounds are tested at 10 uM concentratio...	-
Alpha-1A adrenergic receptor	Ki	=	137.29	nM	6.86	PDSP Secondary Binding target: ADRA1A - Compounds are tested at 10 uM concentrat...	-
Sodium-dependent serotonin transporter	Ki	=	175.27	nM	6.76	PDSP Secondary Binding target: SLC6A4 - Compounds are tested at 10 uM concentrat...	-
Alpha-2B adrenergic receptor	Ki	=	192.4	nM	6.72	PDSP Secondary Binding target: ADRA2B - Compounds are tested at 10 uM concentrat...	-
Sodium-dependent dopamine transporter	Ki	=	215.65	nM	6.67	PDSP Secondary Binding target: SLC6A3 - Compounds are tested at 10 uM concentrat...	-
Sigma intracellular receptor 2	Ki	=	221.95	nM	6.65	PDSP Secondary Binding target: TMEM97 - Compounds are tested at 10 uM concentrat...	-
5-hydroxytryptamine receptor 2C	Ki	=	253.05	nM	6.6	PDSP Secondary Binding target: HTR2C - Compounds are tested at 10 uM concentrati...	-
5-hydroxytryptamine receptor 1B	Ki	=	262.12	nM	6.58	PDSP Secondary Binding target: HTR1B - Compounds are tested at 10 uM concentrati...	-
D(4) dopamine receptor	Ki	=	326.32	nM	6.49	PDSP Secondary Binding target: DRD4 - Compounds are tested at 10 uM concentratio...	-
Alpha-2C adrenergic receptor	Ki	=	358.92	nM	6.45	PDSP Secondary Binding target: ADRA2C - Compounds are tested at 10 uM concentrat...	-
D(3) dopamine receptor	Ki	=	380.19	nM	6.42	PDSP Secondary Binding target: DRD3 - Compounds are tested at 10 uM concentratio...	-
Alpha-1D adrenergic receptor	Ki	=	445.25	nM	6.35	PDSP Secondary Binding target: ADRA1D - Compounds are tested at 10 uM concentrat...	-
Alpha-1B adrenergic receptor	Ki	=	572.4	nM	6.24	PDSP Secondary Binding target: ADRA1B - Compounds are tested at 10 uM concentrat...	-
D(1A) dopamine receptor	Ki	=	711.62	nM	6.15	PDSP Secondary Binding target: DRD1 - Compounds are tested at 10 uM concentratio...	-
Sodium-dependent noradrenaline transporter	Ki	=	730.55	nM	6.14	PDSP Secondary Binding target: SLC6A2 - Compounds are tested at 10 uM concentrat...	-
D(2) dopamine receptor	Ki	=	735.53	nM	6.13	PDSP Secondary Binding target: DRD2 - Compounds are tested at 10 uM concentratio...	-
5-hydroxytryptamine receptor 5A	Ki	=	1092.07	nM	5.96	PDSP Secondary Binding target: HTR5A - Compounds are tested at 10 uM concentrati...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL4689842	Fibroblast	345
-	10.6019/CHEMBL4689842	HEK-293T	345
-	10.6019/CHEMBL4689842	U2OS	344
-	10.6019/CHEMBL5209801	Free fatty acid receptor 4	5
-	10.6019/CHEMBL5209801	Beta-2 adrenergic receptor	5
-	10.6019/CHEMBL5209801	Type-1 angiotensin II receptor	5
-	10.6019/CHEMBL5209801	Sphingosine 1-phosphate receptor 1	5
-	10.6019/CHEMBL5209801	Glucagon-like peptide 1 receptor	5
-	10.6019/CHEMBL5209801	Adhesion G-protein coupled receptor F1	5
-	10.6019/CHEMBL5209801	CX3C chemokine receptor 1	5
-	10.6019/CHEMBL5209801	Apelin receptor	5
-	10.6019/CHEMBL5209801	C5a anaphylatoxin chemotactic receptor 1	5
-	10.6019/CHEMBL5209801	N-formyl peptide receptor 2	5
-	10.6019/CHEMBL5209801	Glucose-dependent insulinotropic receptor	5
-	10.6019/CHEMBL5209801	Alpha-2A adrenergic receptor	5
-	10.6019/CHEMBL5209801	G-protein coupled receptor 35	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
-	10.6019/CHEMBL5665443	Uracil-DNA glycosylase	1
-	10.6019/CHEMBL4513141	Candida albicans	1

Data from ChEMBL 36 via Core Engine