Promazine

Summary

Promazine (CHEMBL564) is an approved small-molecule dopaminergic antagonist (ATC N05AA03) targeting DRD2 and DRD3; indicated across 1 condition including psychotic disorder.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: N05AA03
• Targets: 2 (DRD2, DRD3)
• Indications: 1 condition
• Chemistry: 284.4 Da · C17H20N2S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL564
Name	Promazine
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	4926
ChEBI	CHEBI:8459
ATC	N05AA03
Molecular formula	C17H20N2S
Molecular weight	284.4
InChIKey	ZGUGWUXLJSTTMA-UHFFFAOYSA-N

SMILES: CN(C)CCCN1C2=CC=CC=C2SC3=CC=CC=C31

IUPAC name: N,N-dimethyl-3-phenothiazin-10-ylpropan-1-amine

ChEBI definition: A phenothiazine deriative in which the phenothiazine tricycle has a 3-(dimethylaminopropyl) group at the N-10 position.

Pharmacological roles (ChEBI): dopaminergic antagonist, H1-receptor antagonist, muscarinic antagonist, serotonergic antagonist, phenothiazine antipsychotic drug, antiemetic, EC 3.4.21.26 (prolyl oligopeptidase) inhibitor.

Also known as: Combelen, NSC-31447, Promazina, Promazine, promazine, SID11111651, SID11111652, SID90341344, SID124881158, SID50100325, SID50104276, PROMAZINE

Parent form; salt/anhydrous children: CHEMBL1200469

Patent coverage: 3,302 distinct patent families (9,707 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 9,675 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
DRD2	D2 receptor	Antagonist	6.52	0%	P14416
DRD3	D3 receptor	Antagonist	6.8	0%	P35462

Broader ChEMBL bioactivity targets: 56 (assay-derived). Sample: Inositol monophosphatase 1, Thrombopoietin, Pleiotropic ABC efflux transporter of multiple drugs, Muscarinic acetylcholine receptor M4, 5-hydroxytryptamine receptor 2B, D(1B) dopamine receptor, Alpha-2A adrenergic receptor, Alpha-2C adrenergic receptor, Histamine H2 receptor, Alpha-2B adrenergic receptor, Thyrotropin receptor, Muscarinic acetylcholine receptor M5, D(1A) dopamine receptor, Dopamine receptor, Sodium channel alpha subunits; brain (Types I, II, III), Dopamine receptor, Beta-2 adrenergic receptor, Muscarinic acetylcholine receptor M2, 5-hydroxytryptamine receptor 1A, Muscarinic acetylcholine receptor M1.

Bioactivity

ChEMBL activities: 107 potent at pChembl ≥ 5 of 118 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
HRH1	9.4	Ki	0.4	nM	CHEMBL_ACT_7722269
HRH1	8.51	AC50	3.1	nM	CHEMBL_ACT_25211994
HRH1	8.46	IC50	3.44	nM	CHEMBL_ACT_7722268
P43140	8.43	Ki	3.74	nM	CHEMBL_ACT_7720174
P15823	8.34	Ki	4.53	nM	CHEMBL_ACT_7720176
ADRA1D	8.21	Ki	6.18	nM	CHEMBL_ACT_7720178
HTR2A	8.17	Ki	6.7	nM	CHEMBL_ACT_7724353
P15823	8.09	IC50	8.19	nM	CHEMBL_ACT_7720175
ADRA2B	8.07	Ki	8.42	nM	CHEMBL_ACT_7720182
P43140	8.03	IC50	9.24	nM	CHEMBL_ACT_7720173
ADRA1D	7.89	IC50	13	nM	CHEMBL_ACT_7720177
SLC6A2	7.89	IC50	13	nM	CHEMBL_ACT_7722178
SLC6A2	7.89	Ki	13	nM	CHEMBL_ACT_7722179
ADRA1A	7.86	AC50	13.8	nM	CHEMBL_ACT_25138329
ADRA1A	7.77	AC50	17.1	nM	CHEMBL_ACT_25137630
ADRA2B	7.75	IC50	18	nM	CHEMBL_ACT_7720181
HTR2A	7.64	IC50	23	nM	CHEMBL_ACT_7724352
ADRA2C	7.43	Ki	37	nM	CHEMBL_ACT_7720184
TSHR	7.4	Potency	39.8	nM	CHEMBL_ACT_3916977
CHRM4	7.38	Ki	42	nM	CHEMBL_ACT_7722303
HTR2A	7.36	AC50	43.9	nM	CHEMBL_ACT_25173440
CHRM5	7.34	Ki	46	nM	CHEMBL_ACT_7722305
SLC6A4	7.34	Ki	46	nM	CHEMBL_ACT_7724365
CYP2D6	7.3	Potency	50.1	nM	CHEMBL_ACT_5002342
CYP2D6	7.3	AC50	50.12	nM	CHEMBL_ACT_6010913
HTR2C	7.28	Ki	52	nM	CHEMBL_ACT_7724357
CHRM5	7.19	IC50	64	nM	CHEMBL_ACT_7722304
DRD3	7.16	Ki	69	nM	CHEMBL_ACT_7722239
DRD3	7.12	AC50	75	nM	CHEMBL_ACT_25193022
SLC6A4	7.07	IC50	86	nM	CHEMBL_ACT_7724364
SLC6A2	7.06	AC50	87	nM	CHEMBL_ACT_25144503
CHRM3	7.06	Ki	88	nM	CHEMBL_ACT_7722301
ADRA2B	7	AC50	100	nM	CHEMBL_ACT_25143196
HTR2C	7	IC50	99	nM	CHEMBL_ACT_7724356
HRH2	6.96	AC50	110.8	nM	CHEMBL_ACT_25114324
SIGMAR1	6.94	Ki	114	nM	CHEMBL_ACT_7724367
CHRM1	6.93	Ki	117	nM	CHEMBL_ACT_7722297
ADRA2A	6.9	Ki	126	nM	CHEMBL_ACT_7720180
HTR6	6.9	Ki	127	nM	CHEMBL_ACT_7724363
P20288	6.89	IC50	130	nM	CHEMBL_ACT_1034514
ADRA1A	6.85	AC50	140.7	nM	CHEMBL_ACT_25217716
HTR2C	6.82	AC50	150	nM	CHEMBL_ACT_25131304
DRD2	6.78	Ki	168	nM	CHEMBL_ACT_7722237
HTR2B	6.72	AC50	192.4	nM	CHEMBL_ACT_25163978
DRD3	6.69	IC50	205	nM	CHEMBL_ACT_7722238
HTR2B	6.66	Ki	221	nM	CHEMBL_ACT_7724355
HTR6	6.62	AC50	241.8	nM	CHEMBL_ACT_25118896
CYP2D6	6.6	Potency	251.2	nM	CHEMBL_ACT_5002409
CYP2D6	6.6	AC50	251.2	nM	CHEMBL_ACT_5988332
ADRA2C	6.6	IC50	253	nM	CHEMBL_ACT_7720183
SIGMAR1	6.57	IC50	271	nM	CHEMBL_ACT_7724366
HTR6	6.56	IC50	274	nM	CHEMBL_ACT_7724362
CYP2D6	6.52	IC50	300	nM	CHEMBL_ACT_7722228
CHRM4	6.52	IC50	299	nM	CHEMBL_ACT_7722302
ADRA2A	6.47	IC50	337	nM	CHEMBL_ACT_7720179
HTR2B	6.46	IC50	347	nM	CHEMBL_ACT_7724354
CHRM2	6.41	Ki	387	nM	CHEMBL_ACT_7722299
DRD2	6.4	AC50	400	nM	CHEMBL_ACT_25139819
CHRM3	6.38	IC50	416	nM	CHEMBL_ACT_7722300
CHRM1	6.31	IC50	487	nM	CHEMBL_ACT_7722296
DRD2	6.3	IC50	505	nM	CHEMBL_ACT_7722236
DRD4	6.26	AC50	551.3	nM	CHEMBL_ACT_25127287
CHRM5	6.23	AC50	589.3	nM	CHEMBL_ACT_25137382
ADRA2C	6.09	AC50	820	nM	CHEMBL_ACT_25147359
HTR5A	6.08	AC50	822.5	nM	CHEMBL_ACT_25163899
CHRM2	6	AC50	998.9	nM	CHEMBL_ACT_25195139
P18901	5.98	IC50	1040	nM	CHEMBL_ACT_1034513
DRD1	5.97	AC50	1077	nM	CHEMBL_ACT_25114607
CHRM2	5.96	IC50	1089	nM	CHEMBL_ACT_7722298
P08482	5.95	Potency	1122	nM	CHEMBL_ACT_4807536
CHRM1	5.92	AC50	1200	nM	CHEMBL_ACT_25134933
CHRM3	5.92	AC50	1200	nM	CHEMBL_ACT_25136199
DRD1	5.91	Ki	1232	nM	CHEMBL_ACT_7722235
P31390	5.9	IC50	1259	nM	CHEMBL_ACT_12085958
CYP1A2	5.9	AC50	1259	nM	CHEMBL_ACT_6051284
CHRM4	5.84	AC50	1436	nM	CHEMBL_ACT_25144401
OPRK1	5.7	AC50	1990	nM	CHEMBL_ACT_25128966
HTR7	5.67	AC50	2156	nM	CHEMBL_ACT_25119044
P08482	5.65	Potency	2239	nM	CHEMBL_ACT_4857839
HRH1	5.61	IC50	2455	nM	CHEMBL_ACT_12085949
DRD1	5.61	IC50	2464	nM	CHEMBL_ACT_7722234
HTR2A	5.6	AC50	2500	nM	CHEMBL_ACT_25224701
HRH2	5.55	Ki	2810	nM	CHEMBL_ACT_7722271
OPRM1	5.54	AC50	2900	nM	CHEMBL_ACT_25146640
HRH2	5.54	IC50	2858	nM	CHEMBL_ACT_7722270
P19327	5.53	Ki	2955	nM	CHEMBL_ACT_7724349
MALT1	5.42	IC50	3790	nM	CHEMBL_ACT_29290421
P97697	5.4	Potency	3981	nM	CHEMBL_ACT_4411536
HTR1A	5.36	AC50	4368	nM	CHEMBL_ACT_25164349
KDM1A	5.33	IC50	4707	nM	CHEMBL_ACT_25063936
ADRA2A	5.3	AC50	4996	nM	CHEMBL_ACT_25155809
HIF1A	5.3	Potency	5012	nM	CHEMBL_ACT_4126830
HIF1A	5.3	Potency	5012	nM	CHEMBL_ACT_4520241
PRNP	5.3	EC50	5000	nM	CHEMBL_ACT_847461
P19327	5.29	IC50	5172	nM	CHEMBL_ACT_7724348
SCN1A	5.27	IC50	5400	nM	CHEMBL_ACT_382328
DRD5	5.24	AC50	5778	nM	CHEMBL_ACT_25127517
HTR2B	5.24	AC50	5700	nM	CHEMBL_ACT_25227042
CYP1A2	5.2	AC50	6310	nM	CHEMBL_ACT_6046802
OPRM1	5.19	AC50	6500	nM	CHEMBL_ACT_25157111

Target pathways

Aggregated over 2 target gene(s): DRD2, DRD3.

Top Reactome pathways

2 total, by targets touching each:

Pathway	Targets	Genes
Dopamine receptors	2	DRD2, DRD3
G alpha (i) signalling events	1	DRD3

Dominant GO biological processes

GO term	Targets
G protein-coupled receptor internalization	2
intracellular calcium ion homeostasis	2
adenylate cyclase-inhibiting dopamine receptor signaling pathway	2
locomotory behavior	2
visual learning	2
response to xenobiotic stimulus	2
regulation of dopamine secretion	2
positive regulation of cytokinesis	2
circadian regulation of gene expression	2
response to histamine	2
response to cocaine	2
dopamine metabolic process	2
regulation of potassium ion transport	2
response to morphine	2
negative regulation of blood pressure	2

Indications & clinical

Indications

1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
psychotic disorder	4	MONDO:0005485	EFO:0005407

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

517 molecules share ≥1 primary target. Top 100 by shared-target count:

Molecule	Source	Status	Shared targets
DIHYDROERGOTAMINE	ChEMBL + PubChem	Phase 4 (approved)	DRD2, DRD3
GENTIAN VIOLET	ChEMBL + PubChem	Phase 4 (approved)	DRD2, DRD3
ACETOPHENAZINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
AMIODARONE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
AMISULPRIDE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
AMITRIPTYLINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
AMLODIPINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
AMOXAPINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
APOMORPHINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
ARMODAFINIL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
ASENAPINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
ASTEMIZOLE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
AZELASTINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
BAZEDOXIFENE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
BENPERIDOL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
BENZQUINAMIDE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
BENZTROPINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
BEPRIDIL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
BOSUTINIB	ChEMBL	Phase 4 (approved)	DRD2, DRD3
BREXPIPRAZOLE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
BROMOCRIPTINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
BROMPERIDOL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
BUSPIRONE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
BUTRIPTYLINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CABERGOLINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CARIPRAZINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CARVEDILOL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CHLORHEXIDINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CHLORPROMAZINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CHLORPROTHIXENE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CINACALCET	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CINNARIZINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CISAPRIDE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CLEMASTINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CLOMIPRAMINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CLOTRIMAZOLE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CLOZAPINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CYCLOBENZAPRINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
CYPROHEPTADINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DAUNORUBICIN	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DESIPRAMINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DESLORATADINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DIBENZEPIN	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DIETHYLSTILBESTROL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DIPHENIDOL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DISULFIRAM	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DOBUTAMINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DOMPERIDONE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DOPAMINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DOTHIEPIN	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DOXEPIN	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DROPERIDOL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
DULOXETINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
EBASTINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
ECONAZOLE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
EPALRESTAT	ChEMBL	Phase 4 (approved)	DRD2, DRD3
EPINEPHRINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
ERGOTAMINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
FENOLDOPAM	ChEMBL	Phase 4 (approved)	DRD2, DRD3
FENTANYL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
FEXOFENADINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
FLUPHENAZINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
FLUSPIRILENE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
FORMOTEROL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
HALOPERIDOL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
HALOPERIDOL DECANOATE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
HYDROXYZINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
IDARUBICIN	ChEMBL	Phase 4 (approved)	DRD2, DRD3
ILOPERIDONE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
IMIPRAMINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
INDOCYANINE GREEN ACID FORM	ChEMBL	Phase 4 (approved)	DRD2, DRD3
IPRINDOLE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
ISOPROTERENOL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
KETANSERIN	ChEMBL	Phase 4 (approved)	DRD2, DRD3
KETOTIFEN	ChEMBL	Phase 4 (approved)	DRD2, DRD3
LASOFOXIFENE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
LOFEPRAMINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
LOPERAMIDE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
LOXAPINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
LURASIDONE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
MAPROTILINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
MASOPROCOL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
MEBEVERINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
MECLIZINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
METHYLERGONOVINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
METHYSERGIDE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
METOCLOPRAMIDE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
MIANSERIN	ChEMBL	Phase 4 (approved)	DRD2, DRD3
MICONAZOLE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
MOLINDONE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
NAFTOPIDIL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
NEBIVOLOL	ChEMBL	Phase 4 (approved)	DRD2, DRD3
NEFAZODONE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
NITAZOXANIDE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
NITROXOLINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
NORTRIPTYLINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
OLANZAPINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
OLICERIDINE	ChEMBL	Phase 4 (approved)	DRD2, DRD3
OXAPROZIN	ChEMBL	Phase 4 (approved)	DRD2, DRD3