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Compound Detail

CHEMBL564

PROMAZINE
💊 Approved Drug
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💊 Approved Drug
CN(C)CCCN1c2ccccc2Sc2ccccc21

Basic Information

ChEMBL ID CHEMBL564
Name PROMAZINE
Phase Approved
Structure Type MOL
InChI Key ZGUGWUXLJSTTMA-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Combelen NSC-31447 Promazina Promazine
40
Targets
78
Activities
3
Assay Types
11
PK Parameters
20
Publications
4
Known Names
1
Indications

Molecular Properties

284.4
MW (Da)
4.24
ALogP
3
HBA
0
HBD
6.5
PSA (Ų)
0.83
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1956
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Natural Product

Extended Properties

Molecular Formula C17H20N2S
MW 284.43
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -1.13

Indications

Psychotic Disorders

ATC Classification

N05AA03
promazine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Activity Summary

IC50 45 meas. best 8.46
Ki 30 meas. best 9.4
EC50 3 meas. best 5.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H1 receptor
CHEMBL231
Ki 9.4 9.4 0.4 1
Histamine H1 receptor
CHEMBL231
IC50 8.46 7.035 3.4 2
Alpha-1A adrenergic receptor
CHEMBL319
Ki 8.43 8.43 3.7 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 8.34 8.34 4.5 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 8.21 8.21 6.2 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 8.17 8.17 6.7 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 8.09 8.09 8.2 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 8.07 8.07 8.4 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 8.03 8.03 9.2 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 7.89 7.89 13.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 7.89 7.89 13.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 7.89 7.89 13.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 7.75 7.75 18.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 7.64 7.64 23.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 7.43 7.43 37.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 7.38 7.38 42.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 7.34 7.34 46.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 7.34 7.34 46.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 7.28 7.28 52.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 7.19 7.19 64.0 1
D(3) dopamine receptor
CHEMBL234
Ki 7.16 7.16 69.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 7.07 7.07 86.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 7.06 7.06 88.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 7.0 7.0 99.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 6.94 6.94 114.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 6.93 6.93 117.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 6.9 6.9 127.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.9 6.9 126.0 1
Dopamine receptor
CHEMBL2096970
IC50 6.89 6.89 130.0 1
D(2) dopamine receptor
CHEMBL217
Ki 6.78 6.78 168.0 1
D(3) dopamine receptor
CHEMBL234
IC50 6.69 6.69 205.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.66 6.66 221.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 6.6 6.6 253.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 6.57 6.57 271.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 6.56 6.56 274.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 6.52 6.52 300.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 6.52 6.52 299.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 6.47 6.47 337.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.46 6.46 347.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.41 6.41 387.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 6.38 6.38 416.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 6.31 6.31 487.0 1
Plasmodium falciparum
CHEMBL364
IC50 6.31 6.305 490.0 2
D(2) dopamine receptor
CHEMBL217
IC50 6.3 6.3 505.0 1
Unchecked
CHEMBL612545
Ki 6.13 5.81 732.0 5
Dopamine receptor
CHEMBL2093868
IC50 5.98 5.98 1040.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 5.96 5.96 1089.0 1
Unchecked
CHEMBL612545
IC50 5.96 5.6333 1098.0 6
D(1A) dopamine receptor
CHEMBL2056
Ki 5.91 5.91 1232.0 1
Histamine H1 receptor
CHEMBL4701
IC50 5.9 5.9 1258.9 1

Pharmacokinetic Data

Parameter Value Units Species
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 1595.0 mL.min-1.kg-1 Homo sapiens
CL 30.9 uL.min-1.(10^6cells)-1 Homo sapiens
CL 51.6 uL.min-1.(10^6cells)-1 Homo sapiens
CL 14.3 mL.min-1.kg-1 Homo sapiens
Fu 0.11 - Homo sapiens
Fu 0.11 - Homo sapiens
Fu 0.029 - Not specified
Fu 0.545 - Homo sapiens
MRT 9.6 hr Homo sapiens
T1/2 7.9 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H1 receptor Ki = 0.399 nM 9.4 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Histamine H1 receptor IC50 = 3.435 nM 8.46 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Alpha-1A adrenergic receptor Ki = 3.739 nM 8.43 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1B adrenergic receptor Ki = 4.532 nM 8.34 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1D adrenergic receptor Ki = 6.18 nM 8.21 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 2A Ki = 6.695 nM 8.17 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Alpha-1B adrenergic receptor IC50 = 8.187 nM 8.09 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-2B adrenergic receptor Ki = 8.418 nM 8.07 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Alpha-1A adrenergic receptor IC50 = 9.238 nM 8.03 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1D adrenergic receptor IC50 = 13.0 nM 7.89 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
Sodium-dependent noradrenaline transporter IC50 = 13.0 nM 7.89 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Sodium-dependent noradrenaline transporter Ki = 13.0 nM 7.89 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Alpha-2B adrenergic receptor IC50 = 18.0 nM 7.75 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
5-hydroxytryptamine receptor 2A IC50 = 23.0 nM 7.64 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Alpha-2C adrenergic receptor Ki = 37.0 nM 7.43 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Muscarinic acetylcholine receptor M4 Ki = 42.0 nM 7.38 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Sodium-dependent serotonin transporter Ki = 46.0 nM 7.34 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Muscarinic acetylcholine receptor M5 Ki = 46.0 nM 7.34 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
5-hydroxytryptamine receptor 2C Ki = 52.0 nM 7.28 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Muscarinic acetylcholine receptor M5 IC50 = 64.0 nM 7.19 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -

Literature References

Data from ChEMBL 36 via Core Engine