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Compound Detail

CHEMBL420

GUANABENZ
💊 Approved Drug
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💊 Approved Drug
N=C(N)N/N=C/c1c(Cl)cccc1Cl

Basic Information

ChEMBL ID CHEMBL420
Name GUANABENZ
Phase Approved
Structure Type MOL
InChI Key WDZVGELJXXEGPV-YIXHJXPBSA-N
Therapeutic ✓ Yes

Known Names

Guanabenz Guanabenzo NSC-68982 WY-8678
17
Targets
36
Activities
3
Assay Types
0
PK Parameters
20
Publications
4
Known Names
2
Indications

Molecular Properties

231.1
MW (Da)
1.81
ALogP
2
HBA
3
HBD
74.3
PSA (Ų)
0.41
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem guan-; -nab-
USAN Year 1971

Extended Properties

Molecular Formula C8H8Cl2N4
MW 231.09
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness -1.54

Indications

Multiple Sclerosis Multiple Sclerosis, Relapsing-Remitting

Activity Summary

IC50 18 meas. best 8.77
Ki 15 meas. best 8.71
EC50 3 meas. best 7.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adrenergic receptor alpha-2
CHEMBL2093864
IC50 8.77 8.77 1.7 1
Unchecked
CHEMBL612545
Ki 8.71 7.3733 1.9 3
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 7.82 7.82 15.0 1
Unchecked
CHEMBL612545
IC50 7.75 6.6 18.0 2
Nischarin
CHEMBL3923
Ki 7.46 7.46 34.7 2
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 7.39 7.39 41.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.21 7.21 62.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 7.17 7.17 68.0 1
Trace amine-associated receptor 1
CHEMBL5857
EC50 7.05 7.05 90.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 7.01 7.01 97.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.97 6.97 107.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.95 6.95 112.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 6.83 6.83 149.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 6.8 6.8 158.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.79 6.79 161.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.69 6.69 204.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 6.63 6.63 232.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 6.41 6.41 392.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 6.41 6.41 391.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
IC50 6.35 6.35 450.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 6.33 6.33 472.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 6.12 6.12 755.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.96 5.96 1106.0 1
Trace amine-associated receptor 1
CHEMBL5857
IC50 5.93 5.93 1173.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 5.93 5.93 1181.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 5.87 5.87 1365.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
IC50 5.75 5.75 1787.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 5.68 5.68 2068.0 1
Solute carrier family 22 member 1
CHEMBL5685
IC50 5.31 5.31 4850.0 1
Unchecked
CHEMBL612545
EC50 4.58 4.58 26000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adrenergic receptor alpha-2 IC50 = 1.7 nM 8.77 50% inhibition of specific [3H]clonidine binding (0.4 nM) to Alpha-2 adrenergic ... 6142954
Unchecked Ki = 1.933 nM 8.71 Displacement of [125I]PIC from human alpha2 adrenoceptors expressed in CHO cells 18621536
Unchecked Ki = 12.0 nM 7.92 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
Alpha-2A adrenergic receptor Ki = 15.0 nM 7.82 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
Unchecked IC50 = 18.0 nM 7.75 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
Nischarin Ki = 34.67 nM 7.46 Displacement of [125I]PIC from human imidazoline receptor 1 in human platelets a... 18621536
Nischarin Ki = 34.7 nM 7.46 Displacement of [125I]PIC from human imidazoline receptor 1 in human platelets a... 18621536
Alpha-2A adrenergic receptor IC50 = 41.0 nM 7.39 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
5-hydroxytryptamine receptor 2B Ki = 62.0 nM 7.21 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Alpha-2B adrenergic receptor Ki = 68.0 nM 7.17 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Trace amine-associated receptor 1 EC50 = 90.0 nM 7.05 Agonist activity at human TAAR1 receptor expressed in HEK293T cells cotransfecte... -
5-hydroxytryptamine receptor 2B IC50 = 97.0 nM 7.01 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2C Ki = 107.0 nM 6.97 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2A Ki = 112.0 nM 6.95 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Alpha-2B adrenergic receptor IC50 = 149.0 nM 6.83 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Alpha-1A adrenergic receptor Ki = 158.0 nM 6.8 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-2C adrenergic receptor Ki = 161.0 nM 6.79 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
5-hydroxytryptamine receptor 2C IC50 = 204.0 nM 6.69 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Alpha-1D adrenergic receptor Ki = 232.0 nM 6.63 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 2A IC50 = 392.0 nM 6.41 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
11300874 10.1021/jm001020e ADMET 4
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
18621536 10.1016/j.bmc.2008.06.051 Nischarin 2
18621536 10.1016/j.bmc.2008.06.051 Unchecked 2
- 10.1039/C5MD00400D Trace amine-associated receptor 1 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
17201410 10.1021/jm061045z ScN2a 2
31436981 10.1021/acs.jnatprod.9b00551 Unchecked 2
11300874 10.1021/jm001020e No relevant target 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
33269586 10.1021/acs.jnatprod.0c01168 Unchecked 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
11300874 10.1021/jm001020e Homo sapiens 1
2891854 10.1021/jm00396a020 Rattus norvegicus 1
2891854 10.1021/jm00396a020 Oryctolagus cuniculus 1
9544199 10.1021/jm970530e No relevant target 1
9544199 10.1021/jm970530e Homo sapiens 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1

Data from ChEMBL 36 via Core Engine