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Compound Detail

CHEMBL9967

PIRENZEPINE
🧪 Phase II
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🧪 Phase II
CN1CCN(CC(=O)N2c3ccccc3C(=O)Nc3cccnc32)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL9967
Name PIRENZEPINE
Phase Phase II
Structure Type MOL
InChI Key RMHMFHUVIITRHF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

350320 9110700 ACI-91 Gastri p Gastrozepin Pirenzepina Pirenzepine Wst-057
18
Targets
168
Activities
3
Assay Types
4
PK Parameters
20
Publications
8
Known Names
5
Indications
1
Mechanisms

Molecular Properties

351.4
MW (Da)
1.56
ALogP
5
HBA
1
HBD
68.8
PSA (Ų)
0.89
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -pine
USAN Year 1986

Extended Properties

Molecular Formula C19H21N5O2
MW 351.41
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -1.04

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Muscarinic acetylcholine receptor M1 antagonist ANTAGONIST Muscarinic acetylcholine receptor M1 ✓ ✓

Indications

Gastroesophageal Reflux Peptic Ulcer Diabetic Neuropathies Peripheral Nervous System Diseases Stomach Ulcer

ATC Classification

A02BX03
pirenzepine
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR ACID RELATED DISORDERS

Activity Summary

IC50 96 meas. best 8.94
Ki 66 meas. best 8.55
Kd 6 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Muscarinic acetylcholine receptor M4
CHEMBL1821
 IC50 8.94 6.8775 1.1 4
Muscarinic acetylcholine receptor M1
CHEMBL216
 IC50 8.83 7.6773 1.5 15
Muscarinic acetylcholine receptor M1
CHEMBL216
 Ki 8.55 7.8527 2.8 15
Muscarinic acetylcholine receptor M1
CHEMBL2672
 Ki 8.44 7.605 3.6 2
Muscarinic acetylcholine receptor M1
CHEMBL276
 IC50 8.42 7.67 3.8 2
Muscarinic acetylcholine receptor M1
CHEMBL276
 Ki 8.28 8.1425 5.2 8
Rattus norvegicus
CHEMBL376
 Ki 8.09 8.09 8.1 1
Unchecked
CHEMBL612545
 Ki 8.08 7.6967 8.4 3
Unchecked
CHEMBL612545
 Kd 8.05 7.1333 8.9 3
Muscarinic acetylcholine receptor M4
CHEMBL1821
 Ki 7.86 7.4333 13.8 3
Muscarinic acetylcholine receptor M1
CHEMBL216
 Kd 7.7 7.7 20.0 1
Muscarinic acetylcholine receptor M3
CHEMBL320
 Ki 7.55 6.8683 28.0 6
Muscarinic acetylcholine receptor M4
CHEMBL317
 Ki 7.46 7.1333 34.7 3
Muscarinic acetylcholine receptor M5
CHEMBL2035
 Ki 7.45 7.175 35.5 2
Muscarinic acetylcholine receptor M3
CHEMBL245
 Ki 7.32 7.06 47.9 2
Unchecked
CHEMBL612545
 IC50 7.3 7.3 50.0 1
Muscarinic acetylcholine receptor
CHEMBL1907609
 Ki 7.22 7.22 60.0 1
Muscarinic acetylcholine receptor M3
CHEMBL5498
 Ki 6.96 6.96 110.0 1
Muscarinic acetylcholine receptor M2
CHEMBL309
 Ki 6.92 6.2182 120.0 11
Muscarinic acetylcholine receptor
CHEMBL1907609
 IC50 6.77 6.2283 170.0 64
Muscarinic acetylcholine receptor M2
CHEMBL211
 Ki 6.76 6.5525 173.8 4
Muscarinic acetylcholine receptor M3
CHEMBL320
 IC50 6.52 6.37 300.0 2
Muscarinic acetylcholine receptor M5
CHEMBL2035
 IC50 6.47 6.47 340.6 1
Muscarinic acetylcholine receptor DM1
CHEMBL2366467
 Ki 6.41 6.39 390.0 2
Muscarinic acetylcholine receptor
CHEMBL2094109
 Ki 6.28 6.28 530.0 1
Muscarinic acetylcholine receptor M2
CHEMBL309
 IC50 6.16 6.06 690.0 3
Muscarinic acetylcholine receptor
CHEMBL2097162
 IC50 6.12 6.12 750.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
 IC50 6.02 6.02 955.6 1
Muscarinic acetylcholine receptor M2
CHEMBL211
 IC50 6.01 6.01 968.2 1
Rattus norvegicus
CHEMBL376
 IC50 5.55 5.55 2800.0 1
Cavia porcellus
CHEMBL369
 Kd 4.3 4.3 50118.7 1
Muscarinic acetylcholine receptor M2
CHEMBL211
 Kd 4.3 4.3 50118.7 1

Pharmacokinetic Data

Parameter Value Units Species
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 6.76 uL.min-1.(10^6cells)-1 Rattus norvegicus
F 49.0 % Homo sapiens
KA 0.011 uM Oryctolagus cuniculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Muscarinic acetylcholine receptor M4 IC50 = 1.148 nM 8.94 Antagonist activity at human M4 receptor expressed in HEK293T cells assessed as ... 25275964
Muscarinic acetylcholine receptor M1 IC50 = 1.479 nM 8.83 Antagonist activity at human M1 receptor expressed in HEK293T cells assessed as ... 25275964
Muscarinic acetylcholine receptor M1 Ki = 2.818 nM 8.55 Displacement of [3H]N-methylscopolamine chloride from human cloned muscarinic M1... 18595721
Muscarinic acetylcholine receptor M1 Ki = 3.6 nM 8.44 Binding affinity against Muscarinic acetylcholine receptor M1 by displacement of... 3385735
Muscarinic acetylcholine receptor M1 IC50 = 3.8 nM 8.42 Displacement of [3H]pirenzepine binding to muscarinic M1 receptor in brain corte... 10571170
Muscarinic acetylcholine receptor M1 Ki = 4.6 nM 8.34 Compound was evaluated for displacement of [3H]QNB from human Muscarinic m1 rece... -
Muscarinic acetylcholine receptor M1 Ki = 5.2 nM 8.28 Displacement of [3H]pirenzepine from muscarinic M1 receptor of rat cortex homoge... -
Muscarinic acetylcholine receptor M1 Ki = 5.21 nM 8.28 Ability to displace [3H]pirenzepine (PZ) from M1 receptor in rat cortex homogena... 8464039
Muscarinic acetylcholine receptor M1 Ki = 5.21 nM 8.28 Displacement of [3H]pirenzepine from muscarinic acetylcholine receptor M1 in rat... 1920350
Muscarinic acetylcholine receptor M1 Ki = 6.457 nM 8.19 Compound was tested for inhibiting [3H]pirenzepine Binding to Muscarinic recepto... -
Muscarinic acetylcholine receptor M1 Ki = 6.457 nM 8.19 Inhibition of binding of [3H]pirenzepine to muscarinic receptor (M1) in rat cort... -
Muscarinic acetylcholine receptor M1 Ki = 6.457 nM 8.19 Tested for affinity constant against M1 muscarinic receptor in rat cortex using ... 7932564
Muscarinic acetylcholine receptor M1 Ki = 6.457 nM 8.19 Affinity constant measured against M1 muscarinic receptor in rat cortex 8246244
Rattus norvegicus Ki = 8.1 nM 8.09 Evaluated for the phosphatidyl inositol turnover at Muscarinic acetylcholine rec... 3385735
Unchecked Ki = 8.4 nM 8.08 Displacement of [3H]-QNB from Wistar rat brain membrane mAChR assessed as inhibi... 34160229
Unchecked Kd = 8.913 nM 8.05 Antagonist activity at peripheral muscarinic M4 receptor in rabbit vas deferens ... 18595721
Muscarinic acetylcholine receptor M1 Ki = 9.1 nM 8.04 Binding affinity to human M1 muscarinic receptor 23379472
Muscarinic acetylcholine receptor M1 Ki = 10.0 nM 8.0 Binding affinity to human muscarinic M1 receptor by radioligand displacement ass... 23466604
Muscarinic acetylcholine receptor M1 IC50 = 12.0 nM 7.92 Inhibition of human muscarinic M1 receptor 18588282
Muscarinic acetylcholine receptor M1 IC50 = 12.0 nM 7.92 Binding affinity to human muscarinic M1 receptor by radioligand displacement ass... 23466604

Literature References

PubMed DOI Target Context # Activities
2724292 10.1021/jm00126a004 Muscarinic acetylcholine receptor 60
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
17319687 10.1021/jf0631934 Musca domestica 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
25275964 10.1021/jm501173q Muscarinic acetylcholine receptor M4 6
25275964 10.1021/jm501173q Muscarinic acetylcholine receptor M1 6
20202841 10.1016/j.bmcl.2010.02.041 Unchecked 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 4
20879794 10.1021/jf102525e No relevant target 4
2738887 10.1021/jm00127a020 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
1560440 10.1021/jm00085a016 Muscarinic acetylcholine receptor 3
15294002 10.1021/jm040800a Muscarinic acetylcholine receptor M1 3
17418579 10.1016/j.bmc.2007.03.040 ADMET 3
1619616 10.1021/jm00091a007 Muscarinic acetylcholine receptor 3
25765911 10.1016/j.bmcl.2015.02.012 Muscarinic acetylcholine receptor M1 3
18595721 10.1016/j.bmc.2008.06.025 Unchecked 3
- 10.6019/CHEMBL3301361 No relevant target 3
18178088 10.1016/j.bmcl.2007.12.051 Unchecked 3
- 10.6019/CHEMBL3301361 ADMET 3

Data from ChEMBL 36 via Core Engine