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Compound Detail

CHEMBL753

PHENOXYBENZAMINE
💊 Approved Drug
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💊 Approved Drug
CC(COc1ccccc1)N(CCCl)Cc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL753
Name PHENOXYBENZAMINE
Phase Approved
Structure Type MOL
InChI Key QZVCTJOXCFMACW-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Bensylyt Benzylyt Dibenylin Fenoxibenzamina Phenoxybenzamine
6
Targets
7
Activities
2
Assay Types
1
PK Parameters
20
Publications
5
Known Names
4
Indications

Molecular Properties

303.8
MW (Da)
4.19
ALogP
2
HBA
0
HBD
12.5
PSA (Ų)
0.68
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1953
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula C18H22ClNO
MW 303.83
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.67

Indications

Cardiovascular Diseases Paraganglioma Pheochromocytoma Hernias, Diaphragmatic, Congenital

ATC Classification

C04AX02
phenoxybenzamine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: PERIPHERAL VASODILATORS

Activity Summary

IC50 5 meas. best 5.57
Ki 2 meas. best 8.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adrenergic receptor alpha-1
CHEMBL1907610
 Ki 8.74 8.74 1.8 1
Dopamine receptor
CHEMBL2093868
 Ki 6.92 6.92 120.0 1
Solute carrier family 22 member 1
CHEMBL5685
 IC50 5.57 5.195 2720.0 2
Solute carrier family 22 member 2
CHEMBL1743122
 IC50 5.31 5.31 4900.0 1
Solute carrier family 22 member 3
CHEMBL2073673
 IC50 5.21 5.21 6130.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
 IC50 4.35 4.35 45000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 197.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adrenergic receptor alpha-1 Ki = 1.8 nM 8.74 In vitro binding affinity was measured as the inhibition of [3H]WB-4101 binding ... 3016265
Dopamine receptor Ki = 120.0 nM 6.92 In vitro binding affinity to Dopamine receptors of rat striatal membranes by [3H... 3016265
Solute carrier family 22 member 1 IC50 = 2720.0 nM 5.57 TP_TRANSPORTER: inhibition of MPP+ uptake (MPP+: 0.25 uM) in OCT1-expressing HEK... 12110607
Solute carrier family 22 member 2 IC50 = 4900.0 nM 5.31 TP_TRANSPORTER: inhibition of MPP+ uptake (MPP+: 0.25 uM) in OCT2-expressing HEK... 12110607
Solute carrier family 22 member 3 IC50 = 6130.0 nM 5.21 TP_TRANSPORTER: inhibition of MPP+ uptake (MPP+: 0.25 uM) in OCT3-expressing HEK... 12110607
Solute carrier family 22 member 1 IC50 = 15100.0 nM 4.82 Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT... 18788725
Sodium channel alpha subunits; brain (Types I, II, III) IC50 = 45000.0 nM 4.35 Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on vol... 2579237

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
31477 10.1021/jm00209a007 Unchecked 5
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 2
24799086 10.1002/hep.27206 Homo sapiens 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
22931300 10.1021/tx300075j Liver microsomes 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
2579237 10.1021/jm00381a019 Sodium channel alpha subunits; brain (Types I, II, III) 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
18788725 10.1021/jm8003152 Solute carrier family 22 member 1 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2

Data from ChEMBL 36 via Core Engine