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Compound Detail

CHEMBL279229

URAPIDIL
🧪 Phase III
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🧪 Phase III
COc1ccccc1N1CCN(CCCNc2cc(=O)n(C)c(=O)n2C)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL279229
Name URAPIDIL
Phase Phase III
Structure Type MOL
InChI Key ICMGLRUYEQNHPF-UHFFFAOYSA-N

Known Names

Ebrantil NSC-310405 Urapidil
3
Targets
3
Activities
2
Assay Types
6
PK Parameters
20
Publications
3
Known Names
4
Indications

Molecular Properties

387.5
MW (Da)
0.72
ALogP
8
HBA
1
HBD
71.7
PSA (Ų)
0.71
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -dil

Extended Properties

Molecular Formula C20H29N5O3
MW 387.48
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -1.38

Indications

Cerebrovascular Disorders Hypertension Pre-Eclampsia Stroke

ATC Classification

C02CA06
urapidil
Level 1: CARDIOVASCULAR SYSTEM
Level 2: ANTIHYPERTENSIVES

Activity Summary

Ki 2 meas. best 6.89
Kd 1 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 7.1 7.1 79.4 1
Adrenergic receptor alpha-1
CHEMBL1907610
 Ki 6.89 6.89 127.9 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 6.67 6.67 213.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2.6 mL.min-1.kg-1 Homo sapiens
CL 3.1 mL.min-1.kg-1 Homo sapiens
CL 3.1 mL.min-1.kg-1 Homo sapiens
F 79.0 % Homo sapiens
MRT 4.0 hr Homo sapiens
T1/2 3.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 79.43 nM 7.1 Antagonistic Alpha-1 adrenergic receptor activity against phenylephrine-induced ... 10386934
Adrenergic receptor alpha-1 Ki = 127.9 nM 6.89 Displacement of [3H]prazosin from rat cerebral cortex adrenergic receptor alpha1... 29730027
5-hydroxytryptamine receptor 1A Ki = 213.0 nM 6.67 Binding affinity to 5-HT1A receptor (unknown origin) 29730027

Literature References

PubMed DOI Target Context # Activities
20070106 10.1021/jm901371v Homo sapiens 8
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
10891117 10.1021/jm0000564 ADMET 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Androgen receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 2
10891117 10.1021/jm0000564 No relevant target 2
23956101 10.1093/toxsci/kft176 Bile salt export pump 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 2 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
22961681 10.1124/dmd.112.047068 Bile salt export pump 1

Data from ChEMBL 36 via Core Engine