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Compound Detail

CHEMBL1231

OXYBUTYNIN
💊 Approved Drug
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💊 Approved Drug
CCN(CC)CC#CCOC(=O)C(O)(c1ccccc1)C1CCCCC1

Basic Information

ChEMBL ID CHEMBL1231
Name OXYBUTYNIN
Phase Approved
Structure Type MOL
InChI Key XIQVNETUBQGFHX-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Contimin 2.5 Contimin 5 Cystrin Kentera Kentera (previously oxybutynin nicobrand) Lyrinel xl Oxibutinina Oxybutynin Oxybutynine Oxytrol Oxytrol for women Promictuline +1 more
18
Targets
49
Activities
3
Assay Types
6
PK Parameters
20
Publications
13
Known Names
14
Indications
2
Mechanisms

Molecular Properties

357.5
MW (Da)
3.34
ALogP
4
HBA
1
HBD
49.8
PSA (Ų)
0.60
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1975
Availability OTC
Chirality Racemic

Routes of Administration

Oral Topical

Flags

Natural Product
USAN Year 1962

Extended Properties

Molecular Formula C22H31NO3
MW 357.49
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness -0.42

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Muscarinic acetylcholine receptor M3 antagonist ANTAGONIST Muscarinic acetylcholine receptor M3
Muscarinic acetylcholine receptor M2 antagonist ANTAGONIST Muscarinic acetylcholine receptor M2

Indications

Polyuria Urinary Bladder, Overactive Urinary Incontinence Urinary Incontinence, Urge Breast Neoplasms Enuresis Hyperhidrosis Polyneuropathies Urinary Bladder, Neurogenic Paget Disease, Extramammary Rhinitis, Allergic, Seasonal Sialorrhea Sleep Apnea Syndromes Sleep Apnea, Obstructive

ATC Classification

G04BD04
oxybutynin
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: UROLOGICALS

Activity Summary

Ki 29 meas. best 9.56
IC50 18 meas. best 8.7
Kd 2 meas. best 7.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 9.56 9.0 0.3 2
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 9.24 9.015 0.6 4
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 9.07 8.8967 0.8 3
Muscarinic acetylcholine receptor M3
CHEMBL320
Ki 9.02 8.65 0.9 2
Unchecked
CHEMBL612545
Ki 8.7 6.605 2.0 4
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 8.7 8.7 2.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 8.63 8.24 2.3 2
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 8.57 8.57 2.7 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 8.49 8.49 3.2 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 8.45 8.45 3.5 1
Muscarinic acetylcholine receptor M1
CHEMBL276
Ki 8.23 8.23 5.9 1
Muscarinic acetylcholine receptor M2
CHEMBL309
Ki 8.16 8.005 7.0 2
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 8.09 7.96 8.1 4
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 7.99 7.99 10.2 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 7.62 7.62 24.2 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 7.57 7.57 27.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Kd 7.4 7.4 39.8 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 7.17 7.17 67.9 1
Muscarinic acetylcholine receptor M3
CHEMBL5498
Kd 7.1 7.1 79.4 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 7.07 7.07 85.5 1
D(3) dopamine receptor
CHEMBL234
Ki 6.84 6.84 145.6 1
D(3) dopamine receptor
CHEMBL234
IC50 6.37 6.37 428.8 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.3 6.3 504.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 6.22 6.22 600.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.1 6.1 792.0 1
Unchecked
CHEMBL612545
IC50 5.95 5.82 1135.5 3
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.59 5.59 2573.7 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.59 5.59 2595.1 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL2366456
IC50 4.79 4.79 16100.0 1
Bile salt export pump
CHEMBL6020
IC50 4.56 4.56 27400.0 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 13.94 ng.hr.mL-1 Homo sapiens
CL 5.1 mL.min-1.kg-1 Homo sapiens
Cmax 22.0 nM Homo sapiens
Fu 0.0034 - Homo sapiens
MRT 2.7 hr Homo sapiens
T1/2 7.2 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Muscarinic acetylcholine receptor M4 Ki = 0.278 nM 9.56 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 Ki = 0.574 nM 9.24 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 Ki = 0.78 nM 9.11 Displacement of 1-[N-methyl- 3H]scopolamine from human muscarinic M3 receptor ex... 17188867
Muscarinic acetylcholine receptor M1 Ki = 0.847 nM 9.07 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 Ki = 0.95 nM 9.02 Affinity for rat Muscarinic acetylcholine receptor M3 15808475
Muscarinic acetylcholine receptor M1 Ki = 1.0 nM 9.0 Displacement of 1-[N-methyl- 3H]scopolamine from human muscarinic M1 receptor ex... 17188867
Muscarinic acetylcholine receptor M3 Ki = 1.3 nM 8.89 Binding affinity to human muscarinic M3 receptor 16275087
Muscarinic acetylcholine receptor M3 Ki = 1.514 nM 8.82 Displacement of [3H]N-methylscopolamine from human muscarinic M3 receptor expres... 22243489
Muscarinic acetylcholine receptor M4 IC50 = 1.994 nM 8.7 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Unchecked Ki = 2.0 nM 8.7 Inhibition of muscarinic acetylcholine receptor in rat cortex 23523385
Muscarinic acetylcholine receptor M5 Ki = 2.315 nM 8.63 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M1 Ki = 2.399 nM 8.62 Displacement of [3H]N-methylscopolamine from human muscarinic M1 receptor expres... 22243489
Muscarinic acetylcholine receptor M3 IC50 = 2.71 nM 8.57 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M5 IC50 = 3.222 nM 8.49 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M1 IC50 = 3.518 nM 8.45 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M4 Ki = 3.631 nM 8.44 Displacement of [3H]N-methylscopolamine from human muscarinic M4 receptor expres... 22243489
Muscarinic acetylcholine receptor M3 Ki = 5.3 nM 8.28 Binding affinity for rat salivary gland muscarinic acetylcholine receptor M3 usi... 16220976
Muscarinic acetylcholine receptor M1 Ki = 5.9 nM 8.23 Binding affinity for rat cortex muscarinic acetylcholine receptor M1 using [3H]p... 16220976
Muscarinic acetylcholine receptor M2 Ki = 6.97 nM 8.16 Affinity for rat Muscarinic acetylcholine receptor M2 15808475
Muscarinic acetylcholine receptor M2 Ki = 8.1 nM 8.09 Displacement of 1-[N-methyl- 3H]scopolamine from human muscarinic M2 receptor ex... 17188867

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 467
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 55
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
16220976 10.1021/jm050099q Rattus norvegicus 7
22243489 10.1021/jm2013216 Unchecked 5
22243489 10.1021/jm2013216 Rattus norvegicus 4
18426954 10.1124/dmd.108.020479 ADMET 4
17188867 10.1016/j.bmcl.2006.11.058 Rattus norvegicus 3
20931980 10.1021/jm1007374 Lethal(3)malignant brain tumor-like protein 1 2
- 10.6019/CHEMBL3301361 No relevant target 2
22931300 10.1021/tx300075j Liver microsomes 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
16275087 10.1016/j.bmcl.2005.09.079 Muscarinic acetylcholine receptor M2 2
16275087 10.1016/j.bmcl.2005.09.079 Muscarinic acetylcholine receptor M3 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
23956101 10.1093/toxsci/kft176 Homo sapiens 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
1447741 10.1021/jm00101a019 Muscarinic acetylcholine receptor 2

Data from ChEMBL 36 via Core Engine