Phenoxybenzamine
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Also known as BensylytBenzylytDibenylinFenoxibenzaminaSID26752309SID26752310SID90341231SID104171113SID144203638SID124879342SID124879343SID174007411SID170465147PHENOXYBENZAMINE HYDROCHLORIDEPhenoxybenzamine (hydrochloride)
Summary
Phenoxybenzamine (CHEMBL753) is an approved small molecule (ATC C04AX02) targeting ADRA1D and ADRA2B; indicated across 4 conditions including cardiovascular disorder and adrenal gland pheochromocytoma.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: C04AX02
- Targets: 2 (ADRA1D, ADRA2B)
- Indications: 4 conditions
- Clinical trials: 6
- Chemistry: 303.8 Da · C18H22ClNO
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL753 |
| Name | Phenoxybenzamine |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 4768 |
| ATC | C04AX02 |
| Molecular formula | C18H22ClNO |
| Molecular weight | 303.8 |
| InChIKey | QZVCTJOXCFMACW-UHFFFAOYSA-N |
SMILES: CC(COC1=CC=CC=C1)N(CCCl)CC2=CC=CC=C2
IUPAC name: N-benzyl-N-(2-chloroethyl)-1-phenoxypropan-2-amine
Also known as: Bensylyt, Benzylyt, Dibenylin, Fenoxibenzamina, Phenoxybenzamine, phenoxybenzamine, SID26752309, SID26752310, SID90341231, SID104171113, SID144203638, SID124879342
Parent form; salt/anhydrous children: CHEMBL1200787
Patent coverage: 2,800 distinct patent families (9,814 SureChEMBL compound mentions), from 1 matched compound structure(s). 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 |
|---|---|---|---|---|---|
| ADRA1D | α1D-adrenoceptor | Antagonist | 8.4 | 0.2% | P25100 |
| ADRA2B | α2B-adrenoceptor | Antagonist | 6.4 | 0.2% | P18089 |
Broader ChEMBL bioactivity targets: 31 (assay-derived). Sample: Survival motor neuron protein, Solute carrier family 22 member 2, 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, Adrenergic receptor alpha-1, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, D(1A) dopamine receptor, Estrogen receptor, Solute carrier family 22 member 3.
Bioactivity
ChEMBL activities: 19 potent at pChembl ≥ 5 of 33 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P15823 | 8.74 | Ki | 1.8 | nM | CHEMBL_ACT_555847 |
| P18901 | 6.92 | Ki | 120 | nM | CHEMBL_ACT_555846 |
| ADRA1A | 6.47 | AC50 | 340 | nM | CHEMBL_ACT_25218204 |
| ADRA2B | 5.77 | AC50 | 1700 | nM | CHEMBL_ACT_25143895 |
| ADRA2C | 5.68 | AC50 | 2100 | nM | CHEMBL_ACT_25148072 |
| DRD1 | 5.66 | AC50 | 2200 | nM | CHEMBL_ACT_25180709 |
| HTR2A | 5.64 | AC50 | 2300 | nM | CHEMBL_ACT_25225351 |
| SLC22A1 | 5.57 | IC50 | 2720 | nM | CHEMBL_ACT_11001323 |
| HRH1 | 5.52 | AC50 | 3000 | nM | CHEMBL_ACT_25212706 |
| ADRA2A | 5.5 | AC50 | 3200 | nM | CHEMBL_ACT_25220078 |
| SLC22A2 | 5.31 | IC50 | 4900 | nM | CHEMBL_ACT_11001724 |
| DRD2 | 5.3 | AC50 | 5000 | nM | CHEMBL_ACT_25140528 |
| SLC6A3 | 5.29 | AC50 | 5100 | nM | CHEMBL_ACT_25124142 |
| DRD3 | 5.24 | AC50 | 5800 | nM | CHEMBL_ACT_25193721 |
| HTR2B | 5.22 | AC50 | 6000 | nM | CHEMBL_ACT_25227709 |
| SLC22A3 | 5.21 | IC50 | 6130 | nM | CHEMBL_ACT_11001798 |
| CHRM1 | 5.16 | AC50 | 7000 | nM | CHEMBL_ACT_25135650 |
| OPRM1 | 5.05 | AC50 | 8900 | nM | CHEMBL_ACT_25157582 |
| CHRM2 | 5 | AC50 | 10000 | nM | CHEMBL_ACT_25213921 |
Target pathways
Aggregated over 2 target gene(s): ADRA1D, ADRA2B.
Top Reactome pathways
15 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 2 | ADRA1D, ADRA2B |
| Signaling by GPCR | 2 | ADRA1D, ADRA2B |
| Class A/1 (Rhodopsin-like receptors) | 2 | ADRA1D, ADRA2B |
| Amine ligand-binding receptors | 2 | ADRA1D, ADRA2B |
| GPCR downstream signalling | 2 | ADRA1D, ADRA2B |
| Adrenoceptors | 2 | ADRA1D, ADRA2B |
| GPCR ligand binding | 2 | ADRA1D, ADRA2B |
| Hemostasis | 1 | ADRA2B |
| Adrenaline signalling through Alpha-2 adrenergic receptor | 1 | ADRA2B |
| G alpha (q) signalling events | 1 | ADRA1D |
| G alpha (12/13) signalling events | 1 | ADRA1D |
| G alpha (i) signalling events | 1 | ADRA2B |
| G alpha (z) signalling events | 1 | ADRA2B |
| Platelet activation, signaling and aggregation | 1 | ADRA2B |
| Platelet Aggregation (Plug Formation) | 1 | ADRA2B |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| G protein-coupled receptor signaling pathway | 2 |
| cell-cell signaling | 2 |
| positive regulation of MAPK cascade | 2 |
| signal transduction | 2 |
| adrenergic receptor signaling pathway | 2 |
| adenylate cyclase-modulating G protein-coupled receptor signaling pathway | 1 |
| phospholipase C-activating G protein-coupled receptor signaling pathway | 1 |
| positive regulation of cytosolic calcium ion concentration | 1 |
| positive regulation of cell population proliferation | 1 |
| positive regulation of vasoconstriction | 1 |
| adenylate cyclase-activating adrenergic receptor signaling pathway | 1 |
| neuron-glial cell signaling | 1 |
| regulation of vascular associated smooth muscle contraction | 1 |
| epidermal growth factor receptor signaling pathway | 1 |
| adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway | 1 |
Indications & clinical
Indications
4 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| cardiovascular disorder | 4 | MONDO:0004995 | EFO:0000319 |
| adrenal gland pheochromocytoma | 3 | MONDO:0004974 | EFO:0000239 |
| paraganglioma | 3 | MONDO:0000448 | EFO:1000453 |
| congenital heart disease | 2 | MONDO:0005453 | EFO:0005207 |
Clinical trials
Total trials: 6.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE4 | 2 |
| PHASE2 | 2 |
| PHASE3 | 1 |
| Not specified | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT05702944 | PHASE4 | RECRUITING | The Effect and Safety of Omitting Preoperative Alpha-adrenergic Blockade for Normotensive Pheochromocytoma |
| NCT01379898 | PHASE4 | COMPLETED | Phenoxybenzamine Versus Doxazosin in PCC Patients |
| NCT03176693 | PHASE3 | COMPLETED | Preoperative Alpha Blockade for Pheochromocytoma |
| NCT00569855 | PHASE2 | COMPLETED | Intravenous Phenoxybenzamine Use in Pediatric Patients Undergoing Open-Heart Surgery |
| NCT00770705 | PHASE2 | WITHDRAWN | Parenteral Phenoxybenzamine During Congenital Heart Disease Surgery |
| NCT00620945 | Not specified | TERMINATED | Use of Phenoxybenzamine [PBZ] IV to Assist High Flow Low Pressure Perfusion [HFLPP] on Cardio-pulmonary Bypass |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 4 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
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.
374 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| CLOZAPINE | ChEMBL + PubChem | Phase 4 (approved) | ADRA1D, ADRA2B |
| DIHYDROERGOTAMINE | ChEMBL + PubChem | Phase 4 (approved) | ADRA1D, ADRA2B |
| OLANZAPINE | ChEMBL + PubChem | Phase 4 (approved) | ADRA1D, ADRA2B |
| Pramipexole | ChEMBL + PubChem | Phase 4 (approved) | ADRA1D, ADRA2B |
| TAMSULOSIN | ChEMBL + PubChem | Phase 4 (approved) | ADRA1D, ADRA2B |
| TEGASEROD | ChEMBL + PubChem | Phase 4 (approved) | ADRA1D, ADRA2B |
| ALFUZOSIN | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| APOMORPHINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| APRACLONIDINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| ASENAPINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| AZELASTINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| BENZTROPINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| BREXPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| BRIMONIDINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| BROMOCRIPTINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| CARIPRAZINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| CARVEDILOL | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| CHLORPROMAZINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| CINNARIZINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| CISAPRIDE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| CLOMIPRAMINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| CLONIDINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| CYPROHEPTADINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| DAPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| DEXCHLORPHENIRAMINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| DEXMEDETOMIDINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| DIMENHYDRINATE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| DOBUTAMINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| DOMPERIDONE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| DOXAZOSIN | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| DOXEPIN | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| DROPERIDOL | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| EBASTINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| ECONAZOLE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| EPINEPHRINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| ERGOTAMINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| FLUPHENAZINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| GENTIAN VIOLET | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| GUANABENZ | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| GUANFACINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| HALOPERIDOL | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| HYDROXYCHLOROQUINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| INDORAMIN | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| KETOTIFEN | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| LABETALOL | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| MAPROTILINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| MEPAZINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| MIANSERIN | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| MICONAZOLE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| MOXISYLYTE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| NAFTOPIDIL | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| NEFAZODONE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
| NOREPINEPHRINE | ChEMBL | Phase 4 (approved) | ADRA1D, ADRA2B |
Related Atlas pages
- Genes: ADRA1D, ADRA2B
- Diseases: cardiovascular disorder, adrenal gland pheochromocytoma, paraganglioma
- Drugs: Clozapine, Dihydroergotamine, Olanzapine, Pramipexole, Tamsulosin, Tegaserod, Alfuzosin, Amitriptyline, Amoxapine, Apomorphine, Apraclonidine, Aripiprazole, Asenapine, Astemizole, Azelastine, Benztropine, Brexpiprazole, Brimonidine, Bromocriptine, Cariprazine, Carvedilol, Chlorpromazine, Cinnarizine, Cisapride, Clemastine, Clomipramine, Clonidine, Clotrimazole, Cyproheptadine, Dapiprazole, Dexchlorpheniramine, Dexmedetomidine, Diethylstilbestrol, Dimenhydrinate, Dobutamine, Domperidone, Doxazosin, Doxepin, Droperidol, Ebastine, Econazole, Epinephrine, Ergotamine, Fluphenazine, Guanabenz, Guanfacine, Haloperidol, Hydroxychloroquine, Indoramin, Ketotifen, Labetalol, Maprotiline, Mepazine, Mianserin, Miconazole, Moxisylyte, Naftopidil, Nefazodone, Norepinephrine