Phentolamine

Summary

Phentolamine (CHEMBL597) is an approved small-molecule α-adrenergic antagonist (ATC C04AB01) targeting ADRA1A, ADRA1B, and ADRA1D; indicated across 6 conditions including cardiovascular disorder and presbyopia.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: C04AB01 (+1 more)
• Targets: 6 (ADRA1A, ADRA1B, ADRA1D…)
• Indications: 6 conditions
• Clinical trials: 12
• Chemistry: 281.35 Da · C17H19N3O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL597
Name	Phentolamine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	5775
ChEBI	CHEBI:8081
ATC	C04AB01, V03AB36
Molecular formula	C17H19N3O
Molecular weight	281.35
InChIKey	MRBDMNSDAVCSSF-UHFFFAOYSA-N

SMILES: CC1=CC=C(C=C1)N(CC2=NCCN2)C3=CC(=CC=C3)O

IUPAC name: 3-[N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-4-methylanilino]phenol

ChEBI definition: A substituted aniline that is 3-aminophenol in which the hydrogens of the amino group are replaced by 4-methylphenyl and 4,5-dihydro-1H-imidazol-2-ylmethyl groups respectively. An α-adrenergic antagonist, it is used for the treatment of hypertension.

Pharmacological roles (ChEBI): α-adrenergic antagonist, vasodilator agent.

Also known as: Fentolamina, Phentolamin, Phentolamine, phentolamine, SID11112200, SID26751466, SID860967, SID50085867, SID90341742, SID104171285, SID26751465, SID26751467

Parent form; salt/anhydrous children: CHEMBL1200873, CHEMBL1204146

Patent coverage: 4,322 distinct patent families (14,731 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 14,636 (99%) 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
ADRA1A	α1A-adrenoceptor	Antagonist	8.3		P35348
ADRA1B	α1B-adrenoceptor	Antagonist	7.6	0%	P35368
ADRA1D	α1D-adrenoceptor	Inverse agonist	7.8	0.2%	P25100
ADRA2A	α2A-adrenoceptor	Agonist	7.1	0.1%	P08913
ADRA2B	α2B-adrenoceptor	Antagonist	8.2	0.2%	P18089
ADRA2C	α2C-adrenoceptor	Antagonist	7.9	0%	P18825

Broader ChEMBL bioactivity targets: 37 (assay-derived). Sample: Prelamin-A/C, 4’-phosphopantetheinyl transferase ffp, 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, Adrenergic receptor alpha-1, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Adrenergic receptor alpha-2, Adrenergic receptor alpha, Adrenergic receptor alpha-1, Adrenergic receptor alpha-2, Adrenergic receptor alpha, Sodium channel alpha subunits; brain (Types I, II, III), 5-hydroxytryptamine receptor 1A, Alpha-1D adrenergic receptor, 5-hydroxytryptamine receptor 2A, 5-hydroxytryptamine receptor 2C, Sodium-dependent serotonin transporter, Alpha-1A adrenergic receptor, Histamine H1 receptor.

Bioactivity

ChEMBL activities: 119 potent at pChembl ≥ 5 of 129 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
ADRA1A	9.22	Ki	0.6	nM	CHEMBL_ACT_15614540
P18130	9.1	Ki	0.79	nM	CHEMBL_ACT_1186204
ADRA1A	9.1	AC50	0.8	nM	CHEMBL_ACT_25230027
Q28838	9.03	Ki	0.93	nM	CHEMBL_ACT_519744
ADRA1A	8.96	IC50	1.1	nM	CHEMBL_ACT_15614505
P19328	8.85	Ki	1.4	nM	CHEMBL_ACT_346636
P19328	8.82	Kd	1.51	nM	CHEMBL_ACT_307153
ADRA2A	8.77	Ki	1.7	nM	CHEMBL_ACT_2439757
Q28838	8.68	Ki	2.1	nM	CHEMBL_ACT_519745
ADRA2A	8.65	Ki	2.25	nM	CHEMBL_ACT_7734413
ADRA2A	8.59	Ki	2.6	nM	CHEMBL_ACT_316764
P15823	8.57	IC50	2.7	nM	CHEMBL_ACT_563760
P15823	8.5	Kd	3.16	nM	CHEMBL_ACT_131624
ADRA2A	8.5	Kd	3.16	nM	CHEMBL_ACT_131625
ADRA2A	8.43	Kd	3.71	nM	CHEMBL_ACT_131622
ADRA1A	8.38	Ki	4.12	nM	CHEMBL_ACT_1614724
P15823	8.38	Kd	4.17	nM	CHEMBL_ACT_319804
P22909	8.33	Ki	4.7	nM	CHEMBL_ACT_316765
P43140	8.33	Ki	4.66	nM	CHEMBL_ACT_7734407
P15823	8.32	Kd	4.79	nM	CHEMBL_ACT_131621
ADRA1B	8.32	Ki	4.8	nM	CHEMBL_ACT_15614544
ADRA2A	8.3	Ki	5	nM	CHEMBL_ACT_1246154
P15823	8.28	IC50	5.2	nM	CHEMBL_ACT_1117435
P15823	8.22	Kd	6.03	nM	CHEMBL_ACT_131620
ADRA2A	8.22	IC50	6	nM	CHEMBL_ACT_7734412
O02824	8.2	Kd	6.31	nM	CHEMBL_ACT_1186205
P18130	8.17	Ki	6.8	nM	CHEMBL_ACT_1196282
ADRA1D	8.12	Ki	7.6	nM	CHEMBL_ACT_15614548
ADRA2B	8.12	Ki	7.6	nM	CHEMBL_ACT_316766
P15823	8.1	Kd	7.94	nM	CHEMBL_ACT_519748
ADRA2B	8.09	Ki	8.23	nM	CHEMBL_ACT_7734415
ADRA2C	8.08	Ki	8.4	nM	CHEMBL_ACT_316767
P15823	8.05	IC50	9	nM	CHEMBL_ACT_913436
P19328	8.03	Ki	9.3	nM	CHEMBL_ACT_1095131
P19328	8.03	Kd	9.33	nM	CHEMBL_ACT_927509
P15823	8.02	Kd	9.55	nM	CHEMBL_ACT_307151
P15823	8.01	Ki	9.8	nM	CHEMBL_ACT_1095132
P15823	8.01	Kd	9.77	nM	CHEMBL_ACT_981893
P19328	8	Kd	10	nM	CHEMBL_ACT_64352
P19328	8	IC50	10	nM	CHEMBL_ACT_981891
P15823	8	IC50	10	nM	CHEMBL_ACT_981892
P15823	7.99	Ki	10.2	nM	CHEMBL_ACT_10943658
P15823	7.99	Ki	10.3	nM	CHEMBL_ACT_14570458
ADRA1B	7.97	IC50	10.8	nM	CHEMBL_ACT_15614499
P43140	7.96	IC50	11	nM	CHEMBL_ACT_7734406
ADRA1D	7.96	Ki	11	nM	CHEMBL_ACT_7734411
NISCH	7.94	Ki	11.4	nM	CHEMBL_ACT_2564078
NISCH	7.94	Ki	11.4	nM	CHEMBL_ACT_2564079
P15823	7.94	Kd	11.48	nM	CHEMBL_ACT_927510
ADRA1A	7.92	Ki	12	nM	CHEMBL_ACT_18530193
P15823	7.92	IC50	12	nM	CHEMBL_ACT_562222
ADRA1D	7.9	IC50	12.5	nM	CHEMBL_ACT_15614493
P15823	7.9	Kd	12.59	nM	CHEMBL_ACT_50303
P15823	7.9	Kd	12.59	nM	CHEMBL_ACT_64351
ADRA1D	7.82	Kd	15.14	nM	CHEMBL_ACT_307154
ADRA2A	7.81	Kd	15.49	nM	CHEMBL_ACT_307152
P15823	7.8	Ki	16	nM	CHEMBL_ACT_12090727
P15823	7.8	Ki	16	nM	CHEMBL_ACT_18393145
ADRA1D	7.8	Kd	15.85	nM	CHEMBL_ACT_282497
ADRA2C	7.8	Ki	16	nM	CHEMBL_ACT_7734417
P19328	7.78	Kd	16.6	nM	CHEMBL_ACT_307150
P15823	7.75	Ki	18	nM	CHEMBL_ACT_1031479
P15823	7.75	Ki	18	nM	CHEMBL_ACT_13375466
P15823	7.75	Ki	18	nM	CHEMBL_ACT_16758663
ADRA2B	7.75	IC50	18	nM	CHEMBL_ACT_7734414
P15823	7.75	Ki	18	nM	CHEMBL_ACT_946242
ADRA1D	7.71	Ki	19.4	nM	CHEMBL_ACT_1614726
P19328	7.7	IC50	20	nM	CHEMBL_ACT_164146
P15823	7.7	Kd	19.95	nM	CHEMBL_ACT_319805
P15823	7.7	Kd	19.95	nM	CHEMBL_ACT_50304
P19328	7.66	Ki	22	nM	CHEMBL_ACT_535658
ADRA1D	7.66	IC50	22	nM	CHEMBL_ACT_7734410
P15823	7.63	Ki	23.44	nM	CHEMBL_ACT_15186161
ADRA1A	7.49	Kd	32.36	nM	CHEMBL_ACT_164143
P15823	7.44	IC50	36	nM	CHEMBL_ACT_276106
P19328	7.43	IC50	37.5	nM	CHEMBL_ACT_67056
P15823	7.41	IC50	39	nM	CHEMBL_ACT_164145
ADRA1A	7.38	AC50	41.3	nM	CHEMBL_ACT_25138094
P23944	7.35	Ki	45	nM	CHEMBL_ACT_1196284
P15823	7.35	Ki	45	nM	CHEMBL_ACT_7734409
ADRA2A	7.34	AC50	46	nM	CHEMBL_ACT_25157086
ADRA1B	7.32	Ki	47.4	nM	CHEMBL_ACT_1614725
ADRA2B	7.32	Ki	48	nM	CHEMBL_ACT_1614728
ADRA2A	7.25	Ki	55.9	nM	CHEMBL_ACT_1614727
ADRA2C	7.09	Ki	80.3	nM	CHEMBL_ACT_1614729
P15823	7.09	IC50	82	nM	CHEMBL_ACT_7734408
P15823	7.05	IC50	90	nM	CHEMBL_ACT_1005588
P15823	7.05	Ki	90	nM	CHEMBL_ACT_1196281
ADRA2B	7	AC50	101	nM	CHEMBL_ACT_25143978
HTR2A	6.99	Ki	103	nM	CHEMBL_ACT_7738652
ADRA2C	6.96	IC50	110	nM	CHEMBL_ACT_7734416
P15823	6.95	Kd	112.2	nM	CHEMBL_ACT_164141
P15823	6.86	Kd	138	nM	CHEMBL_ACT_654199
HTR2C	6.68	Ki	207	nM	CHEMBL_ACT_7738656
P18841	6.66	Ki	220	nM	CHEMBL_ACT_1196283
ADRA1A	6.66	AC50	220	nM	CHEMBL_ACT_25218269
ADRA1A	6.54	AC50	290	nM	CHEMBL_ACT_25219129
P19328	6.47	Kd	338.8	nM	CHEMBL_ACT_164142
HTR2A	6.45	IC50	359	nM	CHEMBL_ACT_7738651
HTR2C	6.4	IC50	396	nM	CHEMBL_ACT_7738655

Target pathways

Aggregated over 6 target gene(s): ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C.

Top Reactome pathways

21 total, by targets touching each:

Pathway	Targets	Genes
Signal Transduction	6	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
Signaling by GPCR	6	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
Class A/1 (Rhodopsin-like receptors)	6	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
Amine ligand-binding receptors	6	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
GPCR downstream signalling	6	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
Adrenoceptors	6	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
GPCR ligand binding	6	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
Hemostasis	3	ADRA2A, ADRA2B, ADRA2C
Adrenaline signalling through Alpha-2 adrenergic receptor	3	ADRA2A, ADRA2B, ADRA2C
G alpha (q) signalling events	3	ADRA1A, ADRA1B, ADRA1D
G alpha (12/13) signalling events	3	ADRA1A, ADRA1B, ADRA1D
G alpha (i) signalling events	3	ADRA2A, ADRA2B, ADRA2C
G alpha (z) signalling events	3	ADRA2A, ADRA2B, ADRA2C
Platelet activation, signaling and aggregation	3	ADRA2A, ADRA2B, ADRA2C
Platelet Aggregation (Plug Formation)	3	ADRA2A, ADRA2B, ADRA2C
Metabolism	2	ADRA2A, ADRA2C
Integration of energy metabolism	2	ADRA2A, ADRA2C
Metabolism of proteins	2	ADRA2A, ADRA2C
Adrenaline,noradrenaline inhibits insulin secretion	2	ADRA2A, ADRA2C
Regulation of insulin secretion	2	ADRA2A, ADRA2C
Surfactant metabolism	2	ADRA2A, ADRA2C

Dominant GO biological processes

GO term	Targets
signal transduction	6
G protein-coupled receptor signaling pathway	6
positive regulation of MAPK cascade	6
adrenergic receptor signaling pathway	6
cell-cell signaling	5
regulation of vasoconstriction	5
adenylate cyclase-activating adrenergic receptor signaling pathway	4
phospholipase C-activating G protein-coupled receptor signaling pathway	3
positive regulation of cytosolic calcium ion concentration	3
neuron-glial cell signaling	3
epidermal growth factor receptor signaling pathway	3
negative regulation of norepinephrine secretion	3
platelet activation	3
negative regulation of epinephrine secretion	3
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction	3

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
cardiovascular disorder	4	MONDO:0004995	EFO:0000319

1 disease in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
presbyopia	3	MONDO:0001330	MONDO:0001330

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 12.

Phase distribution

Phase	Trials
Not specified	5
EARLY_PHASE1	4
PHASE1	2
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT06286059	PHASE2/PHASE3	UNKNOWN	Efficacy of Phentolamine in Prevention of Contrast-Associated Acute Kidney Injury After Complex PCI
NCT02966665	PHASE1	RECRUITING	: Vascular Function in Health and Disease
NCT03318094	PHASE1	ACTIVE_NOT_RECRUITING	Role of Sympathetic Vasoconstriction on Insulin-Mediated Microvascular Recruitment and Glucose Uptake in Obesity
NCT04436731	EARLY_PHASE1	ACTIVE_NOT_RECRUITING	Sex Disparities in Hypoxic Sympatholysis and Impact of Obesity
NCT06787066	EARLY_PHASE1	RECRUITING	Sympathetic Vascular Transduction Across the Menopause Transition: Contributing Mechanisms
NCT03079921	EARLY_PHASE1	COMPLETED	Adrenergic System in Islet Transplantation
NCT06172998	EARLY_PHASE1	UNKNOWN	New Perspective on Exploring the Post-apneic BP Surge in Patients With OSA
NCT06422494	Not specified	ACTIVE_NOT_RECRUITING	The Role of the Adrenergic System in Hypoglycaemia Induced Inflammatory Response in People With Type 1 Diabetes and People Without Type 1 Diabetes-RAID-II
NCT06620991	Not specified	NOT_YET_RECRUITING	Pre-operative Phentolamine Vs Intraoperative Esmolol Efficacy for Hypotensive Anesthesia in Functional Endoscopic Sinus Surgery
NCT07012512	Not specified	NOT_YET_RECRUITING	Adjusted Study Protocol: Within-Subject Paired-Eye Design Comparing Pilocarpine 0.1%, Phentolamine 0.75%, and Combination Therapy for Cyclopentolate Reversal in Children
NCT00132106	Not specified	UNKNOWN	The Effect of Alfa-Adrenergic Receptor Blockade on Insulin-Stimulated Forearm Glucose Uptake and Metabolism in Chronic Heart Failure
NCT06385600	Not specified	UNKNOWN	Intravenous Labetalol vs Phentolamine for the Management of Severe Preeclampsia.

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.

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

Molecule	Source	Status	Shared targets
CLOZAPINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
DIHYDROERGOTAMINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
OLANZAPINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
TAMSULOSIN	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
TEGASEROD	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
ALFUZOSIN	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
APRACLONIDINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
ASENAPINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
AZELASTINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
BREXPIPRAZOLE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
BRIMONIDINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
CARIPRAZINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
CISAPRIDE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
CLONIDINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
DEXMEDETOMIDINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
DOXAZOSIN	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
EBASTINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
EPINEPHRINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
HALOPERIDOL	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
INDORAMIN	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
LABETALOL	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
MOXISYLYTE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
NAFTOPIDIL	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
NEFAZODONE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
NOREPINEPHRINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
OXYMETAZOLINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
PRAZOSIN	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
QUETIAPINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
RISPERIDONE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
SERTINDOLE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
SILODOSIN	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
TERAZOSIN	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
TOLAZOLINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
VERAPAMIL	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
VILAZODONE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
XYLOMETAZOLINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
ZIPRASIDONE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
BUNAZOSIN	ChEMBL	Phase 3	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
IDAZOXAN	ChEMBL	Phase 3	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
LATREPIRDINE	ChEMBL	Phase 3	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
MEDETOMIDINE	ChEMBL	Phase 3	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
YOHIMBINE	ChEMBL	Phase 3	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
CIRAZOLINE	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
DEXNIGULDIPINE	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
IPSAPIRONE	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
NIGULDIPINE	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
PIPEROXAN	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
PIZOTYLINE	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
SPIRAMIDE	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
SPIROXATRINE	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
ZOTEPINE	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2B, ADRA2C
GENTIAN VIOLET	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
PRAMIPEXOLE	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
AMITRIPTYLINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
AMLODIPINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2C
AMOXAPINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
APOMORPHINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
ASTEMIZOLE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
BENZTROPINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
BROMOCRIPTINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
CARVEDILOL	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
CHLORPROMAZINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
CINNARIZINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
CLEMASTINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
CLOMIPRAMINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
CYPROHEPTADINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
DIETHYLSTILBESTROL	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
DOBUTAMINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
DOMPERIDONE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
DOXEPIN	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
ERGOTAMINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
FLUPHENAZINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
GUANABENZ	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
GUANFACINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
KETOTIFEN	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
MAPROTILINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
MIANSERIN	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
NORTRIPTYLINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
PERGOLIDE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
PHENYLEPHRINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA2A, ADRA2B, ADRA2C
PROCHLORPERAZINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
PROMAZINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
PROMETHAZINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
RALOXIFENE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
TERCONAZOLE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
TERFENADINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1B, ADRA1D, ADRA2A, ADRA2C
THIORIDAZINE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
TRAZODONE	ChEMBL	Phase 4 (approved)	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
LISURIDE	ChEMBL	Phase 3	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
FANANSERIN	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA2A, ADRA2B, ADRA2C
FLUNARIZINE	ChEMBL	Phase 2	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
METERGOLINE	ChEMBL	Phase 2	ADRA1A, ADRA1D, ADRA2A, ADRA2B, ADRA2C
RITANSERIN	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA2A, ADRA2B, ADRA2C
SPIPERONE	ChEMBL	Phase 2	ADRA1A, ADRA1B, ADRA2A, ADRA2B, ADRA2C
ACLIDINIUM BROMIDE	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA2A, ADRA2B, ADRA2C
Afatinib	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA2A, ADRA2B, ADRA2C
CHENODIOL	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA2A, ADRA2B, ADRA2C
CLOFARABINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA2A, ADRA2B, ADRA2C
CRIZOTINIB	ChEMBL + PubChem	Phase 4 (approved)	ADRA1A, ADRA2A, ADRA2B, ADRA2C