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Compound Detail

CHEMBL1201203

BENZTROPINE
💊 Approved Drug
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💊 Approved Drug
CN1[C@@H]2CC[C@H]1C[C@@H](OC(c1ccccc1)c1ccccc1)C2

Basic Information

ChEMBL ID CHEMBL1201203
Name BENZTROPINE
Phase Approved
Structure Type MOL
InChI Key GIJXKZJWITVLHI-PMOLBWCYSA-N
Therapeutic ✓ Yes

Known Names

Benzatropina Benzatropine Benztropine Cobrentin NK-02
31
Targets
87
Activities
3
Assay Types
0
PK Parameters
20
Publications
5
Known Names
4
Indications

Molecular Properties

307.4
MW (Da)
4.42
ALogP
2
HBA
0
HBD
12.5
PSA (Ų)
0.83
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1954
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem -trop-

Extended Properties

Molecular Formula C21H25NO
MW 307.44
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.20

Indications

Parkinson Disease Cocaine-Related Disorders Sciatica Temporomandibular Joint Disorders

ATC Classification

N04AC01
benzatropine
Level 1: NERVOUS SYSTEM
Level 2: ANTI-PARKINSON DRUGS

Activity Summary

IC50 44 meas. best 9.26
Ki 41 meas. best 9.88
EC50 2 meas. best 4.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 9.88 9.88 0.1 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 9.56 9.56 0.3 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 9.48 9.48 0.3 1
Histamine H1 receptor
CHEMBL231
Ki 9.43 9.43 0.4 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 9.26 9.26 0.5 1
Muscarinic acetylcholine receptor M1
CHEMBL276
Ki 9.23 9.16 0.6 3
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 8.89 8.295 1.3 2
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 8.84 8.84 1.5 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 8.7 8.7 2.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 8.62 8.46 2.4 2
Muscarinic acetylcholine receptor M2
CHEMBL309
Ki 8.59 8.59 2.6 1
Histamine H1 receptor
CHEMBL231
IC50 8.5 8.5 3.2 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 8.44 8.44 3.7 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 8.16 8.16 7.0 1
Sodium-dependent dopamine transporter
CHEMBL338
Ki 8.1 7.0529 7.9 7
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 8.0 7.6 10.0 2
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 7.62 7.62 24.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 7.58 7.58 26.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 7.52 7.52 30.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 7.5 7.5 32.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 7.39 7.39 41.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 7.28 7.28 52.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 7.24 7.24 57.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 7.24 7.24 57.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 7.23 7.23 59.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 7.21 7.21 61.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 7.19 7.19 65.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 7.13 7.13 74.0 1
Unchecked
CHEMBL612545
Ki 6.95 6.014 112.0 5
Sodium-dependent dopamine transporter
CHEMBL338
IC50 6.93 6.57 118.0 6
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.9 6.9 127.0 1
Rattus norvegicus
CHEMBL376
Ki 6.89 5.81 130.0 2
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 6.86 6.86 139.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 6.85 6.85 142.0 1
Unchecked
CHEMBL612545
IC50 6.74 5.7817 183.0 6
Sodium-dependent dopamine transporter
CHEMBL238
Ki 6.71 6.71 193.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.7 6.7 200.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.69 6.69 204.0 1
D(3) dopamine receptor
CHEMBL234
Ki 6.65 6.65 222.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 6.61 6.5433 243.0 3
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 6.4 6.4 395.0 1
Rattus norvegicus
CHEMBL376
IC50 6.39 6.39 403.0 2
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 6.26 6.26 544.0 1
D(3) dopamine receptor
CHEMBL234
IC50 6.18 6.18 654.0 1
Histamine H2 receptor
CHEMBL1941
Ki 5.93 5.93 1185.0 1
Histamine H2 receptor
CHEMBL1941
IC50 5.92 5.92 1206.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 5.89 5.89 1294.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.86 5.86 1379.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.86 5.86 1391.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 5.55 5.55 2788.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Muscarinic acetylcholine receptor M1 Ki = 0.131 nM 9.88 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 Ki = 0.272 nM 9.56 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M4 Ki = 0.333 nM 9.48 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Histamine H1 receptor Ki = 0.37 nM 9.43 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Muscarinic acetylcholine receptor M1 IC50 = 0.544 nM 9.26 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M1 Ki = 0.59 nM 9.23 Displacement of [3H]pirenzepine binding at Muscarinic acetylcholine receptor M1 ... 9083473
Muscarinic acetylcholine receptor M1 Ki = 0.59 nM 9.23 Binding affinity against Muscarinic receptor from rat brain membranes using [3H]... 11689080
Muscarinic acetylcholine receptor M1 Ki = 0.95 nM 9.02 Affinity for rat M1 acetylcholine receptor using [3H]pirenzepine displacement. 7562926
Muscarinic acetylcholine receptor M3 IC50 = 1.285 nM 8.89 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M5 Ki = 1.451 nM 8.84 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M5 IC50 = 2.019 nM 8.7 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M4 IC50 = 2.385 nM 8.62 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M2 Ki = 2.6 nM 8.59 Affinity for rat M1 acetylcholine receptor using [3H]-AF DX 384 displacement. 7562926
Histamine H1 receptor IC50 = 3.183 nM 8.5 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Muscarinic acetylcholine receptor M2 Ki = 3.668 nM 8.44 DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M4 IC50 = 5.012 nM 8.3 Antagonist activity at human recombinant muscarinic receptor M4 expressed in CHO... 33488977
5-hydroxytryptamine receptor 2A Ki = 6.968 nM 8.16 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Sodium-dependent dopamine transporter Ki = 7.943 nM 8.1 Binding affinity to dopamine transporter (DAT) using [3H]WIN-35428 as a radiolig... 11063611
Muscarinic acetylcholine receptor M2 IC50 = 10.0 nM 8.0 DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 IC50 = 19.95 nM 7.7 Antagonist activity at human recombinant muscarinic receptor M3 expressed in CHO... 33488977

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 3
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 3
9083473 10.1021/jm950782k Sodium-dependent dopamine transporter 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
11689080 10.1021/jm0101592 Rattus norvegicus 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
7562926 10.1021/jm00020a006 Sodium-dependent dopamine transporter 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
15857139 10.1021/jm0490235 Sodium-dependent dopamine transporter 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2

Data from ChEMBL 36 via Core Engine