Compound Detail

CHEMBL597

PHENTOLAMINE

💊 Approved Drug

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💊 Approved Drug

Cc1ccc(N(CC2=NCCN2)c2cccc(O)c2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL597
Name	PHENTOLAMINE
Phase	Approved
Structure Type	MOL
InChI Key	MRBDMNSDAVCSSF-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Fentolamina Phentolamin Phentolamine

Targets

110

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

281.4

MW (Da)

2.84

ALogP

HBA

HBD

47.9

PSA (Å²)

0.91

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1952
Availability	Prescription
Chirality	Achiral

Routes of Administration

Parenteral Topical

Flags

Natural Product

Extended Properties

Molecular Formula	C17H19N3O
MW	281.36
Aromatic Rings	2
Heavy Atoms	21
NP-Likeness	-0.24

Indications

Cardiovascular Diseases Mydriasis Presbyopia Hypoglycemia Obesity Sleep Apnea, Obstructive

ATC Classification

C04AB01

phentolamine

Level 1: CARDIOVASCULAR SYSTEM

Level 2: PERIPHERAL VASODILATORS

V03AB36

phentolamine

Level 1: VARIOUS

Level 2: ALL OTHER THERAPEUTIC PRODUCTS

Activity Summary

Ki 52 meas. best 9.22

IC50 31 meas. best 8.96

Kd 27 meas. best 8.82

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Alpha-1A adrenergic receptor CHEMBL229	Ki	9.22	8.5067	0.6	3
Alpha-1A adrenergic receptor CHEMBL4892	Ki	9.1	8.635	0.8	2
Alpha-2A adrenergic receptor CHEMBL4744	Ki	9.03	8.855	0.9	2
Alpha-1A adrenergic receptor CHEMBL229	IC50	8.96	8.96	1.1	1
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	8.85	8.18	1.4	3
Adrenergic receptor alpha-2 CHEMBL2093864	Kd	8.82	7.82	1.5	5
Alpha-2A adrenergic receptor CHEMBL1867	Ki	8.77	8.315	1.7	4
Adrenergic receptor alpha-1 CHEMBL1907610	IC50	8.57	7.9529	2.7	7
Adrenergic receptor alpha-2 CHEMBL2095158	Kd	8.5	8.155	3.2	2
Adrenergic receptor alpha CHEMBL2094111	Kd	8.5	8.128	3.2	5
Adrenergic receptor alpha CHEMBL2095203	Kd	8.43	8.43	3.7	1
Adrenergic receptor alpha-1 CHEMBL1907610	Kd	8.38	7.7622	4.2	9
Alpha-2A adrenergic receptor CHEMBL327	Ki	8.33	8.33	4.7	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	8.33	8.33	4.7	1
Alpha-1B adrenergic receptor CHEMBL232	Ki	8.32	7.82	4.8	2
Adrenergic receptor alpha-2 CHEMBL2095158	Ki	8.3	8.3	5.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	8.22	8.22	6.0	1
Alpha-1A adrenergic receptor CHEMBL3637	Kd	8.2	8.2	6.3	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	8.12	7.8433	7.6	3
Alpha-1D adrenergic receptor CHEMBL223	Ki	8.12	7.93	7.6	3
Alpha-2C adrenergic receptor CHEMBL1916	Ki	8.08	7.6567	8.4	3
Rattus norvegicus CHEMBL376	Kd	8.07	8.07	8.5	1
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	8.01	7.7518	9.8	11
Adrenergic receptor alpha-2 CHEMBL2093864	IC50	8.0	7.71	10.0	3
Alpha-1B adrenergic receptor CHEMBL232	IC50	7.97	7.97	10.8	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	7.96	7.96	11.0	1
Nischarin CHEMBL3923	Ki	7.94	7.94	11.4	2
Alpha-1D adrenergic receptor CHEMBL223	IC50	7.9	7.78	12.5	2
Unchecked CHEMBL612545	Ki	7.89	7.17	13.0	4
Adrenergic receptor alpha-1 CHEMBL2094251	Kd	7.82	7.81	15.1	2
Alpha-2B adrenergic receptor CHEMBL1942	IC50	7.75	7.75	18.0	1
Alpha-1A adrenergic receptor CHEMBL229	Kd	7.49	7.49	32.4	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	7.35	7.35	45.0	1
Alpha-1D adrenergic receptor CHEMBL326	Ki	7.35	7.35	45.0	1
Unchecked CHEMBL612545	IC50	7.24	6.685	58.0	2
Alpha-1B adrenergic receptor CHEMBL315	IC50	7.09	7.09	82.0	1
Adrenergic receptor alpha CHEMBL2094111	IC50	7.05	7.05	90.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.99	6.99	103.0	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	6.96	6.96	110.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.68	6.68	207.0	1
Alpha-1B adrenergic receptor CHEMBL3122	Ki	6.66	6.66	220.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	6.45	6.45	359.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	6.4	6.4	396.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	6.26	6.26	549.5	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	5.62	5.62	2422.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	5.42	5.42	3807.0	1
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682	IC50	5.08	5.08	8400.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	5.0	5.0	10000.0	1
Histamine H1 receptor CHEMBL4701	IC50	4.9	4.9	12589.2	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	4.78	4.78	16448.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Cmax	86.0	nM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Alpha-1A adrenergic receptor	Ki	=	0.6	nM	9.22	Displacement of [3H]-Prazosin from human alpha-1A adrenergic receptor transfecte...	26005522
Alpha-1A adrenergic receptor	Ki	=	0.7943	nM	9.1	In vitro for the displacement of [3H]prazosin binding to bovine Alpha-1A adrener...	9276013
Alpha-2A adrenergic receptor	Ki	=	0.93	nM	9.03	Binding affinity against alpha-2 adrenergic receptor from calf cerebral cortex, ...	6139481
Alpha-1A adrenergic receptor	IC50	=	1.1	nM	8.96	Displacement of [3H]-Prazosin from human alpha-1A adrenergic receptor transfecte...	26005522
Adrenergic receptor alpha-2	Ki	=	1.4	nM	8.85	Binding affinity towards Alpha-2 adrenergic receptor, using [3H]- atipamezole as...	1827843
Adrenergic receptor alpha-2	Kd	=	1.514	nM	8.82	Antagonistic activity against adrenergic alpha-2 receptor in longitudinal muscle...	2886664
Alpha-2A adrenergic receptor	Ki	=	1.7	nM	8.77	Displacement of [3H]RX781094 from alpha2 adrenergic receptor	8496700
Alpha-2A adrenergic receptor	Ki	=	2.1	nM	8.68	Binding affinity against alpha-2 adrenergic receptor from calf cerebral cortex, ...	6139481
Alpha-2A adrenergic receptor	Ki	=	2.25	nM	8.65	DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912)	-
Alpha-2A adrenergic receptor	Ki	=	2.6	nM	8.59	The compound was tested for binding affinity against Alpha-2A adrenergic recepto...	7658428
Adrenergic receptor alpha-1	IC50	=	2.7	nM	8.57	The compound was tested for the concentration to inhibit 50% of Alpha-1 adrenerg...	9572886
Adrenergic receptor alpha-2	Kd	=	3.162	nM	8.5	In vitro for relative blocking action (pA2) of Presynaptic Alpha-2 adrenergic re...	6124636
Adrenergic receptor alpha	Kd	=	3.162	nM	8.5	In vitro relative blocking action (pA2) of the post-synaptic alpha-1-adrenocepto...	6124636
Adrenergic receptor alpha	Kd	=	3.715	nM	8.43	Evaluated for norepinephrine as agonist.	6124636
Alpha-1A adrenergic receptor	Ki	=	4.12	nM	8.38	Binding affinity towards alpha-1A adrenergic receptor expressed in human embryon...	16153828
Adrenergic receptor alpha-1	Kd	=	4.169	nM	8.38	Alpha-2 adrenergic receptor pA2 value against clonidine in vitro experiment in r...	6133953
Alpha-2A adrenergic receptor	Ki	=	4.7	nM	8.33	The compound was tested for binding affinity against alpha-2D adrenergic recepto...	7658428
Alpha-1A adrenergic receptor	Ki	=	4.655	nM	8.33	DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin)	-
Adrenergic receptor alpha	Kd	=	4.786	nM	8.32	Evaluated for norepinephrine as agonist.	6124636
Alpha-1B adrenergic receptor	Ki	=	4.8	nM	8.32	Displacement of [3H]-Prazosin from human alpha-1B adrenergic receptor transfecte...	26005522

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	467
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
6125596	10.1021/jm00349a010	Rattus norvegicus	12
7310808	10.1021/jm00143a012	Canis familiaris	12
6124636	10.1021/jm00348a013	Adrenergic receptor alpha	5
7310808	10.1021/jm00143a012	Rattus norvegicus	4
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	4
9544563	10.1021/np9703712	Rattus norvegicus	4
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	4
6827559	10.1021/jm00357a017	Rattus norvegicus	4
2886664	10.1021/jm00391a015	Adrenergic receptor alpha-2	3
2886664	10.1021/jm00391a015	Adrenergic receptor alpha-1	3
6142954	10.1021/jm00370a011	Adrenergic receptor alpha-2	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
6124636	10.1021/jm00348a013	No relevant target	3
16153828	10.1016/j.bmcl.2005.07.083	Alpha-1D adrenergic receptor	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2A	3
16033273	10.1021/jm0408969	Unchecked	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 1A	3

Data from ChEMBL 36 via Core Engine