Compound Detail

CHEMBL844

BRIMONIDINE

💊 Approved Drug

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💊 Approved Drug

Brc1c(NC2=NCCN2)ccc2nccnc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL844
Name	BRIMONIDINE
Phase	Approved
Structure Type	MOL
InChI Key	XYLJNLCSTIOKRM-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

AGN-190342 FREE BASE Brimonidina Brimonidine NSC-318825 UK-14304 UK-1430418 FREE BASE

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

292.1

MW (Da)

1.76

ALogP

HBA

HBD

62.2

PSA (Å²)

0.84

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1996
Availability	OTC
Chirality	Achiral

Routes of Administration

Topical

Flags

Natural Product

USAN Year

1991

Extended Properties

Molecular Formula	C11H10BrN5
MW	292.14
Aromatic Rings	2
Heavy Atoms	17
NP-Likeness	-0.67

Indications

Eye Manifestations Glaucoma Ocular Hypertension Rosacea Diabetic Retinopathy Dry Eye Syndromes Glaucoma, Open-Angle Presbyopia

ATC Classification

D11AX21

brimonidine

Level 1: DERMATOLOGICALS

Level 2: OTHER DERMATOLOGICAL PREPARATIONS

S01EA05

brimonidine

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

S01GA07

brimonidine

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

Activity Summary

Ki 24 meas. best 8.85

EC50 13 meas. best 9.21

IC50 12 meas. best 8.52

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Alpha-2A adrenergic receptor CHEMBL1867	EC50	9.21	8.89	0.6	3
Unchecked CHEMBL612545	Ki	8.85	8.08	1.4	2
Adrenergic receptor alpha-2 CHEMBL2095158	Ki	8.85	8.6967	1.4	3
Alpha-2A adrenergic receptor CHEMBL1867	Ki	8.57	7.8967	2.7	3
Adrenergic receptor alpha-2 CHEMBL2095158	IC50	8.52	8.52	3.0	1
Alpha-2C adrenergic receptor CHEMBL1916	EC50	8.47	8.1967	3.4	3
Adrenergic receptor alpha-2 CHEMBL2093864	IC50	8.44	8.44	3.6	1
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	7.52	7.52	30.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	7.46	6.89	34.7	2
Alpha-2C adrenergic receptor CHEMBL1916	Ki	7.36	7.22	44.0	2
Alpha-2B adrenergic receptor CHEMBL266	Ki	7.28	7.28	52.0	1
Alpha-2B adrenergic receptor CHEMBL266	EC50	7.26	7.26	55.0	1
Unchecked CHEMBL612545	IC50	7.13	7.13	74.0	1
Alpha-2B adrenergic receptor CHEMBL1942	EC50	6.55	6.55	281.8	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	6.53	6.53	298.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	6.13	6.13	740.0	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	6.07	6.05	846.0	2
Alpha-1B adrenergic receptor CHEMBL3988626	EC50	6.03	6.03	943.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	5.98	5.98	1047.0	1
Alpha-1A adrenergic receptor CHEMBL4892	EC50	5.95	5.95	1132.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	5.84	5.84	1458.0	1
Alpha-1D adrenergic receptor CHEMBL223	IC50	5.76	5.76	1720.0	1
Adrenergic receptor alpha-1 CHEMBL2094251	Ki	5.75	5.73	1800.0	3
Adrenergic receptor alpha-1 CHEMBL1907610	IC50	5.62	5.62	2400.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	5.59	5.59	2551.0	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	5.59	5.59	2568.0	1
Alpha-1A adrenergic receptor CHEMBL229	Ki	5.55	5.55	2818.4	1
Alpha-1B adrenergic receptor CHEMBL232	Ki	5.27	5.27	5370.3	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	5.2	5.2	6344.0	1
Plasmodium falciparum CHEMBL364	IC50	5.1	5.0333	7943.3	3
Unchecked CHEMBL612545	EC50	4.94	4.94	11400.0	1
Adrenergic receptor alpha-2 CHEMBL2095158	EC50	4.94	4.94	11400.0	2

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Alpha-2A adrenergic receptor	EC50	=	0.6166	nM	9.21	Alpha-2A adrenergic receptor agonistic potency as inhibition of forskolin-stimul...	-
Alpha-2A adrenergic receptor	EC50	=	0.86	nM	9.07	Agonist activity at human recombinant alpha-2A receptor expressed in PC12 cells ...	-
Adrenergic receptor alpha-2	Ki	=	1.413	nM	8.85	Binding affinity to alpha2 adrenoceptor in human cortical membrane	19133776
Unchecked	Ki	=	1.413	nM	8.85	Displacement of [3H]RX821002 from alpha2 adrenergic receptor in human brain pref...	18459731
Adrenergic receptor alpha-2	Ki	=	2.4	nM	8.62	Binding affinity for Alpha-2 adrenergic receptor of CHO-C10 membrane preparation	-
Adrenergic receptor alpha-2	Ki	=	2.4	nM	8.62	Binding affinity towards Alpha-2 adrenergic receptor of HT-29 cells	-
Alpha-2A adrenergic receptor	Ki	=	2.7	nM	8.57	Displacement of rauwolscine from human Alpha-2A adrenergic receptor expressed in...	9016324
Adrenergic receptor alpha-2	IC50	=	3.0	nM	8.52	Inhibition of [3H]p-aminoclonidine (PAC) binding to alpha-2 adrenergic receptor ...	3037080
Alpha-2C adrenergic receptor	EC50	=	3.4	nM	8.47	Effective concentration at Alpha-2C adrenergic receptor from CHO-C4 cells	9016324
Adrenergic receptor alpha-2	IC50	=	3.6	nM	8.44	Binding affinity against Alpha-2 adrenergic receptor is the ability to inhibit t...	6142954
Alpha-2A adrenergic receptor	EC50	=	4.1	nM	8.39	Effective concentration at Alpha-2A adrenergic receptor from CHO-C10 cells	9016324
Alpha-2A adrenergic receptor	Ki	=	6.761	nM	8.17	Binding affinity for human Alpha-2A adrenergic receptor from cultured LM(tk-) ce...	-
Alpha-2C adrenergic receptor	EC50	=	8.0	nM	8.1	Agonist activity at human recombinant alpha-2C receptor expressed in PC12 cells ...	-
Alpha-2C adrenergic receptor	EC50	=	9.55	nM	8.02	Alpha-2C adrenergic receptor agonistic potency as inhibition of forskolin-stimul...	-
Adrenergic receptor alpha-2	Ki	=	30.0	nM	7.52	Binding affinity towards alpha-2 adrenergic receptor in rat using [3H]rauwolscin...	2864446
Alpha-2B adrenergic receptor	Ki	=	34.67	nM	7.46	Binding affinity for human Alpha-2B adrenergic receptor from cultured Y-1 cells ...	-
Alpha-2C adrenergic receptor	Ki	=	44.0	nM	7.36	Displacement of rauwolscine from human Alpha-2C adrenergic receptor expressed in...	9016324
Unchecked	Ki	=	49.0	nM	7.31	DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan)	-
Alpha-2B adrenergic receptor	Ki	=	52.0	nM	7.28	Displacement of rauwolscine from rat Alpha-2B adrenergic receptor expressed in C...	9016324
Alpha-2B adrenergic receptor	EC50	=	55.0	nM	7.26	Effective Concentration at Alpha-2B adrenergic receptor from CHO-RNG cells	9016324

Literature References

PubMed	DOI	Target Context	# Activities
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
2567783	10.1021/jm00127a037	Rattus norvegicus	4
-	10.1016/0960-894X(95)00391-6	Alpha-2A adrenergic receptor	3
9016324	10.1021/jm9605142	Alpha-2C adrenergic receptor	3
9016324	10.1021/jm9605142	Alpha-2B adrenergic receptor	3
9016324	10.1021/jm9605142	Alpha-2A adrenergic receptor	3
-	10.1016/0960-894X(95)00391-6	Alpha-2B adrenergic receptor	3
37468498	10.1038/s41467-023-40064-9	Nuclear receptor subfamily 1 group I member 2	3
-	10.1016/0960-894X(95)00391-6	Alpha-2C adrenergic receptor	3
19734910	10.1038/nchembio.215	Plasmodium falciparum	3
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
19133776	10.1021/jm800838r	Adrenergic receptor alpha-2	2
18459731	10.1021/jm800026x	Unchecked	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
37468498	10.1038/s41467-023-40064-9	Peroxisome proliferator-activated receptor gamma	2
6264080	10.1021/jm00137a006	Adrenergic receptor alpha	2
17691718	10.1021/jm070229q	Adrenergic receptor alpha-2	2

Data from ChEMBL 36 via Core Engine