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Compound Detail

CHEMBL621

TRAZODONE
💊 Approved Drug
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💊 Approved Drug
O=c1n(CCCN2CCN(c3cccc(Cl)c3)CC2)nc2ccccn12

Basic Information

ChEMBL ID CHEMBL621
Name TRAZODONE
Phase Approved
Structure Type MOL
InChI Key PHLBKPHSAVXXEF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

J10.767K Trazodona Trazodone Trittico
23
Targets
46
Activities
4
Assay Types
25
PK Parameters
20
Publications
4
Known Names
12
Indications

Molecular Properties

371.9
MW (Da)
2.36
ALogP
6
HBA
0
HBD
45.8
PSA (Ų)
0.69
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1981
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1970

Extended Properties

Molecular Formula C19H22ClN5O
MW 371.87
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -2.50

Indications

Depressive Disorder Depressive Disorder Alzheimer Disease Anxiety Dementia Schizophrenia Sleep Initiation and Maintenance Disorders Sleep Wake Disorders Alcoholism Diabetic Neuropathies Depression, Postpartum Sleep Apnea, Obstructive

ATC Classification

N06AX05
trazodone
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 23 meas. best 7.77
Ki 20 meas. best 8.25
Kd 2 meas. best 5.26
EC50 1 meas. best 6.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 8.25 8.25 5.6 1
5-hydroxytryptamine receptor 2A
CHEMBL322
IC50 7.77 7.77 17.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 7.7 7.155 20.0 2
Histamine H1 receptor
CHEMBL231
Ki 7.38 7.38 42.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 7.33 7.33 47.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 7.33 7.33 47.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 7.21 7.21 61.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.17 7.15 68.0 2
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 7.04 7.04 91.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.99 6.99 102.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.97 6.97 107.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 6.96 6.96 111.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 6.93 6.93 117.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 6.93 6.93 118.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 6.89 6.89 130.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.75 6.75 178.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 6.75 6.7 178.0 2
Sodium-dependent serotonin transporter
CHEMBL228
IC50 6.72 6.72 192.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 6.58 6.58 265.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.55 6.55 282.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
IC50 6.55 6.55 281.0 2
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 6.51 6.51 311.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.47 6.47 341.0 1
Histamine H1 receptor
CHEMBL231
IC50 6.44 6.44 361.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 6.41 6.41 389.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
EC50 6.11 6.11 785.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 6.08 6.08 830.0 1
Unchecked
CHEMBL612545
Ki 6.08 5.895 826.0 2
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 6.04 6.04 909.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 6.03 6.03 926.0 1
D(3) dopamine receptor
CHEMBL234
Ki 5.9 5.9 1271.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
IC50 5.87 5.87 1356.0 1
Unchecked
CHEMBL612545
IC50 5.87 5.705 1342.0 2
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.71 5.71 1942.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 5.66 5.66 2203.0 1
D(3) dopamine receptor
CHEMBL234
IC50 5.43 5.43 3743.0 1
D(2) dopamine receptor
CHEMBL217
IC50 5.35 5.35 4485.0 1
ADMET
CHEMBL612558
Kd 5.26 5.26 5470.0 1
Albumin
CHEMBL4817
Kd 5.1 5.1 7950.0 1
Bile salt export pump
CHEMBL6020
IC50 4.05 4.05 90000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 32.5 mL.min-1.kg-1 Homo sapiens
CL 12.2 uL.min-1.(10^6cells)-1 Homo sapiens
CL 1.81 mL.min-1.kg-1 Homo sapiens
Cmax 5060.0 nM Homo sapiens
F 80.0 % Homo sapiens
Fu 0.07 - -
Fu 0.03 - -
Fu 0.07 - Homo sapiens
Fu 0.077 - Homo sapiens
Fu 0.055 - Rattus norvegicus
Fu 0.057 - Sus scrofa
Fu 0.082 - Macaca fascicularis
Fu 0.066 - Canis lupus familiaris
Fu 0.059 - Cavia porcellus
Fu 0.086 - Mus musculus
Fu 0.062 - Rattus norvegicus
Fu 0.0437 - Rattus norvegicus
Fu 0.085 - Rattus norvegicus
Fu 0.061 - Not specified
Fu 0.98 - Homo sapiens
MRT 6.2 hr Homo sapiens
T1/2 7.3 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 5.602 nM 8.25 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2A IC50 = 17.0 nM 7.77 Compound was tested for the inhibition of [3H]ketanserin binding to 5-hydroxytry... 9986703
5-hydroxytryptamine receptor 2A IC50 = 20.0 nM 7.7 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Histamine H1 receptor Ki = 42.0 nM 7.38 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Alpha-1A adrenergic receptor Ki = 47.0 nM 7.33 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 2C Ki = 47.0 nM 7.33 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Alpha-1B adrenergic receptor Ki = 61.0 nM 7.21 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 2B Ki = 68.0 nM 7.17 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B Ki = 74.0 nM 7.13 Displacement of [3H]-5HT from human 5-HT2B receptor expressed in african green m... 37584406
5-hydroxytryptamine receptor 2C IC50 = 91.0 nM 7.04 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Sodium-dependent serotonin transporter Ki = 102.0 nM 6.99 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
5-hydroxytryptamine receptor 2B IC50 = 107.0 nM 6.97 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Alpha-1B adrenergic receptor IC50 = 111.0 nM 6.96 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 1A Ki = 118.0 nM 6.93 Displacement of 8-OH-DPAT from human 5-HT1AR in human brain frontal cortex incub... 35367707
Alpha-1A adrenergic receptor IC50 = 117.0 nM 6.93 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1D adrenergic receptor Ki = 130.0 nM 6.89 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 1A Ki = 178.0 nM 6.75 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
Alpha-2B adrenergic receptor Ki = 178.0 nM 6.75 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Sodium-dependent serotonin transporter IC50 = 192.0 nM 6.72 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
5-hydroxytryptamine receptor 1A Ki = 223.87 nM 6.65 Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) r... 8568799

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 63
16472241 10.2174/1570163043334794 Hepatotoxicity 18
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
20070106 10.1021/jm901371v Homo sapiens 8
12061889 10.1021/jm0200409 ADMET 5
21474681 10.1124/dmd.111.038778 Brain 5
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
19256501 10.1021/jm801441s No relevant target 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
32122737 10.1016/j.bmcl.2020.127027 D(2) dopamine receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3

Data from ChEMBL 36 via Core Engine