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Compound Detail

CHEMBL862

GUANFACINE
💊 Approved Drug
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💊 Approved Drug
N=C(N)NC(=O)Cc1c(Cl)cccc1Cl

Basic Information

ChEMBL ID CHEMBL862
Name GUANFACINE
Phase Approved
Structure Type MOL
InChI Key INJOMKTZOLKMBF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Guanfacina Guanfacine Intuniv NSC-759121
11
Targets
23
Activities
3
Assay Types
9
PK Parameters
20
Publications
4
Known Names
17
Indications

Molecular Properties

246.1
MW (Da)
1.55
ALogP
2
HBA
3
HBD
79.0
PSA (Ų)
0.55
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1986
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem guan-
USAN Year 1979

Extended Properties

Molecular Formula C9H9Cl2N3O
MW 246.10
Aromatic Rings 1
Heavy Atoms 15
NP-Likeness -1.12

Indications

Hypertension Alzheimer Disease Delirium Tourette Syndrome Alcohol Drinking Alcoholism Attention Deficit Disorder with Hyperactivity Cocaine-Related Disorders Depressive Disorder Marijuana Abuse Schizotypal Personality Disorder Smoking Cessation Stroke Substance-Related Disorders Tobacco Use Disorder Trigeminal Neuralgia Stress Disorders, Post-Traumatic

ATC Classification

C02AC02
guanfacine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: ANTIHYPERTENSIVES

Activity Summary

Ki 12 meas. best 7.72
IC50 8 meas. best 7.35
EC50 3 meas. best 7.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Nischarin
CHEMBL3923
Ki 7.72 7.72 19.0 1
Unchecked
CHEMBL612545
Ki 7.52 7.52 30.0 1
Unchecked
CHEMBL612545
IC50 7.35 7.35 45.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 7.3 7.3 50.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
EC50 7.28 7.28 52.5 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.94 6.94 114.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 6.87 6.87 134.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 6.6 6.6 249.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
EC50 6.54 6.54 288.4 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 6.26 6.26 546.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
EC50 6.22 6.22 602.6 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.12 6.12 761.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.07 6.07 861.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.03 6.03 937.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 5.88 5.88 1335.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 5.87 5.87 1348.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 5.84 5.84 1453.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 5.68 5.68 2098.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 5.52 5.52 3014.0 1
Alpha-1A adrenergic receptor
CHEMBL229
Ki 5.33 5.33 4677.4 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.19 5.19 6447.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 4.93 4.93 11749.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 5.9 mL.min-1.kg-1 Homo sapiens
CL 2.9 mL.min-1.kg-1 Homo sapiens
CL 5.9 mL.min-1.kg-1 Homo sapiens
CL 4.5 mL.min-1.kg-1 Homo sapiens
CL 137.6 mL.min-1.g-1 Homo sapiens
Fu 0.28 - Homo sapiens
Fu 0.28 - Homo sapiens
MRT 22.0 hr Homo sapiens
T1/2 15.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Nischarin Ki = 19.01 nM 7.72 Displacement of [125I]PIC from human imidazoline receptor 1 in human platelets a... 18621536
Unchecked Ki = 30.0 nM 7.52 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
Unchecked IC50 = 45.0 nM 7.35 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
Alpha-2A adrenergic receptor Ki = 50.0 nM 7.3 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
Alpha-2A adrenergic receptor EC50 = 52.48 nM 7.28 Agonist activity at human alpha2A-adrenoceptor expressed in HEK293 cells assesse... 38889119
Alpha-2B adrenergic receptor Ki = 114.0 nM 6.94 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Alpha-2A adrenergic receptor IC50 = 134.0 nM 6.87 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
Alpha-2B adrenergic receptor IC50 = 249.0 nM 6.6 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Alpha-2B adrenergic receptor EC50 = 288.4 nM 6.54 Agonist activity at human alpha2B-adrenoceptor expressed in HEK293 cells assesse... 38889119
Alpha-1A adrenergic receptor Ki = 546.0 nM 6.26 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-2C adrenergic receptor EC50 = 602.56 nM 6.22 Agonist activity at human alpha2C-adrenoceptor expressed in HEK293 cells assesse... 38889119
5-hydroxytryptamine receptor 2C Ki = 761.0 nM 6.12 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2A Ki = 861.0 nM 6.07 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Alpha-2C adrenergic receptor Ki = 937.0 nM 6.03 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
5-hydroxytryptamine receptor 2B Ki = 1335.0 nM 5.88 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Alpha-1A adrenergic receptor IC50 = 1348.0 nM 5.87 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 2C IC50 = 1453.0 nM 5.84 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B IC50 = 2098.0 nM 5.68 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2A IC50 = 3014.0 nM 5.52 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Alpha-1A adrenergic receptor Ki = 4677.35 nM 5.33 Binding affinity to human alpha1A-adrenoceptor 38889119

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 88
31158845 10.1038/s41586-019-1291-3 ADMET 60
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20070106 10.1021/jm901371v Homo sapiens 8
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
33606526 10.1021/acs.jmedchem.0c02047 POU domain, class 2, transcription factor 1 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
19445515 10.1021/jm900403j Homo sapiens 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine