Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL728

PROCHLORPERAZINE
💊 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
CN1CCN(CCCN2c3ccccc3Sc3ccc(Cl)cc32)CC1

Basic Information

ChEMBL ID CHEMBL728
Name PROCHLORPERAZINE
Phase Approved
Structure Type MOL
InChI Key WIKYUJGCLQQFNW-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Compazine Compro Prochlorperazine Prochlorperazine mesilate Prochlorperazine mesylate Proclorperazina Stemetil eff
39
Targets
80
Activities
3
Assay Types
10
PK Parameters
20
Publications
7
Known Names
11
Indications
1
Mechanisms

Molecular Properties

373.9
MW (Da)
4.58
ALogP
4
HBA
0
HBD
9.7
PSA (Ų)
0.78
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1956
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula C20H24ClN3S
MW 373.95
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -1.53

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dopamine D2 receptor antagonist ANTAGONIST D(2) dopamine receptor

Indications

Anxiety Postoperative Nausea and Vomiting Psychotic Disorders Schizophrenia Genital Neoplasms, Female Headache Migraine Disorders Nausea Nausea Cardiotoxicity Multiple Myeloma

ATC Classification

N05AB04
prochlorperazine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 46 meas. best 8.15
Ki 31 meas. best 8.7
EC50 3 meas. best 7.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 8.7 8.7 2.0 1
Histamine H1 receptor
CHEMBL231
Ki 8.55 8.55 2.8 1
D(2) dopamine receptor
CHEMBL217
Ki 8.44 8.44 3.6 1
D(3) dopamine receptor
CHEMBL234
Ki 8.35 8.35 4.5 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 8.32 8.32 4.7 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 8.15 8.15 7.1 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 8.0 8.0 10.0 1
D(2) dopamine receptor
CHEMBL217
IC50 7.96 7.96 11.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 7.92 7.92 12.0 1
D(3) dopamine receptor
CHEMBL234
IC50 7.89 7.89 13.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 7.89 7.89 13.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 7.8 7.8 16.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 7.64 7.64 23.0 1
Histamine H1 receptor
CHEMBL231
IC50 7.62 7.62 24.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 7.5 7.5 32.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 7.47 7.47 34.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 7.39 7.39 41.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 7.31 7.31 49.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 7.27 7.27 54.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 7.2 7.2 63.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.19 7.19 65.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 7.11 7.11 78.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 7.11 7.11 78.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 7.09 7.09 82.0 1
dengue virus type 2
CHEMBL613966
EC50 7.06 7.06 88.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 7.05 7.05 89.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.99 6.99 102.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 6.91 6.91 124.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 6.81 6.81 155.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 6.8 6.8 158.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 6.77 6.77 169.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 6.72 6.72 190.0 1
5-hydroxytryptamine receptor 4
CHEMBL5017
Ki 6.71 6.71 194.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 6.66 6.66 220.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 6.61 6.61 244.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 6.57 6.57 267.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 6.52 6.52 300.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 6.49 6.49 321.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 6.4 6.4 396.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 6.4 6.4 400.0 1
Unchecked
CHEMBL612545
Ki 6.38 6.0833 416.0 3
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 6.26 6.26 543.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.21 6.21 621.0 1
Unchecked
CHEMBL612545
IC50 6.17 4.9513 676.0 8
D(4) dopamine receptor
CHEMBL219
Ki 6.09 6.09 810.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 6.02 6.02 950.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 5.99 5.99 1013.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 5.96 5.96 1107.0 1
5-hydroxytryptamine receptor 4
CHEMBL5017
IC50 5.93 5.93 1164.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 5.93 5.93 1169.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 16.0 mL.min-1.kg-1 Homo sapiens
CL 29240.0 mL.min-1.kg-1 Homo sapiens
CL 51.7 uL.min-1.(10^6cells)-1 Homo sapiens
CL 144.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL 16.4 mL.min-1.kg-1 Homo sapiens
F 20.0 % Homo sapiens
Fu 0.003 - Not specified
Fu 0.553 - Homo sapiens
MRT 23.0 hr Homo sapiens
T1/2 9.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 2.018 nM 8.7 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Histamine H1 receptor Ki = 2.794 nM 8.55 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
D(2) dopamine receptor Ki = 3.608 nM 8.44 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
D(3) dopamine receptor Ki = 4.454 nM 8.35 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Alpha-2B adrenergic receptor Ki = 4.741 nM 8.32 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
5-hydroxytryptamine receptor 2A IC50 = 7.062 nM 8.15 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Alpha-2B adrenergic receptor IC50 = 10.0 nM 8.0 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
D(2) dopamine receptor IC50 = 11.0 nM 7.96 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
Alpha-2C adrenergic receptor Ki = 12.0 nM 7.92 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
D(3) dopamine receptor IC50 = 13.0 nM 7.89 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Alpha-1A adrenergic receptor Ki = 13.0 nM 7.89 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1D adrenergic receptor Ki = 16.0 nM 7.8 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
Sigma non-opioid intracellular receptor 1 Ki = 23.0 nM 7.64 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Histamine H1 receptor IC50 = 24.0 nM 7.62 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Alpha-1A adrenergic receptor IC50 = 32.0 nM 7.5 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1D adrenergic receptor IC50 = 34.0 nM 7.47 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 2C Ki = 41.0 nM 7.39 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Alpha-1B adrenergic receptor Ki = 49.0 nM 7.31 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
Sigma non-opioid intracellular receptor 1 IC50 = 54.0 nM 7.27 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Alpha-2A adrenergic receptor Ki = 63.0 nM 7.2 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 467
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
- 10.5281/zenodo.13943903 ADMET 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
6167716 10.1021/jm00135a006 ADMET 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
20014752 10.1021/tx900326k Hepatotoxicity 3
21998403 10.1124/dmd.111.042309 ADMET 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
18788725 10.1021/jm8003152 Solute carrier family 22 member 1 2
18027916 10.1021/jm070524a No relevant target 2
19188399 10.1128/aac.00956-08 Pleiotropic ABC efflux transporter of multiple drugs 2
10891117 10.1021/jm0000564 ADMET 2
10891117 10.1021/jm0000564 No relevant target 2

Data from ChEMBL 36 via Core Engine