OXYBUTYNIN

Search structure
Trade Names:
Synonyms:
Status: Approved (1975)
Entry Type: Small molecule
Molecule Category: Parent
ATC: G04BD04
UNII: K9P6MC7092

Structure
InChI Key XIQVNETUBQGFHX-UHFFFAOYSA-N
Smile CCN(CC)CC#CCOC(=O)C(O)(c1ccccc1)C1CCCCC1
InChI
InChI=1S/C22H31NO3/c1-3-23(4-2)17-11-12-18-26-21(24)22(25,19-13-7-5-8-14-19)20-15-9-6-10-16-20/h5,7-8,13-14,20,25H,3-4,6,9-10,15-18H2,1-2H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H31NO3
Molecular Weight 357.49
AlogP 3.34
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 49.77
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 26.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Muscarinic acetylcholine receptor M2 antagonist ISBN PubMed PubMed PubMed PubMed
Primary Target
M1 receptor
M3 receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 16100 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Acetylcholine receptor
- - 40 1-2 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 76
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 27400-27400 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Enuresis 3 D004775 ClinicalTrials
Polyneuropathies 3 D011115 ClinicalTrials
Hyperhidrosis 3 D006945 ClinicalTrials
Urinary Bladder, Neurogenic 3 D001750 ClinicalTrials
Sleep Apnea, Obstructive 2 D020181 ClinicalTrials
Sleep Apnea Syndromes 2 D012891 ClinicalTrials
Paget Disease, Extramammary 2 D010145 ClinicalTrials
Rhinitis, Allergic, Seasonal 2 D006255 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt
UNKNOWN

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Dry mouth 72.4
Gastrointestinal disorders Dry mouth 71.4
Gastrointestinal disorders Gastrointestinal disorder 71.4
Gastrointestinal disorders Dry mouth 41.6
Gastrointestinal disorders Dry mouth 34.9
General disorders and administration site conditions Application site pruritus 16.8
Cardiac disorders Dizziness 16.6
Nervous system disorders Nervous system disorder 16.6
Gastrointestinal disorders Constipation 15.1
Nervous system disorders Somnolence 14.1
General disorders and administration site conditions Application site pruritus 14.0
Nervous system disorders Somnolence 14.0
Gastrointestinal disorders Dry mouth 12.1
Gastrointestinal disorders Dry mouth 12.0
Gastrointestinal disorders Nausea 11.6
General disorders and administration site conditions Application site erythema 10.0
Gastrointestinal disorders Dry mouth 9.6
Eye disorders Eye disorder 9.6
Eye disorders Vision blurred 9.6
Gastrointestinal disorders Constipation 9.1
Gastrointestinal disorders Constipation 8.7
Gastrointestinal disorders Dry mouth 8.6
Renal and urinary disorders Urethral disorder 8.5
Renal and urinary disorders Urinary hesitation 8.5
Renal and urinary disorders Urinary tract disorder 8.5
General disorders and administration site conditions Application site erythema 8.3
Gastrointestinal disorders Dry mouth
Gastrointestinal disorders Dry mouth 8.3
Nervous system disorders Headache 8.0
Gastrointestinal disorders Diarrhoea 7.9
Nervous system disorders Headache 7.8
Nervous system disorders Headache 7.5
Gastrointestinal disorders Dry mouth 7.46
General disorders and administration site conditions Application site erythema 7.0
Infections and infestations Urinary tract infection 6.94
Gastrointestinal disorders Dry mouth 6.9
Gastrointestinal disorders Diarrhoea 6.8
Gastrointestinal disorders Diarrhoea 6.5
Infections and infestations Infection 6.5
Infections and infestations Infestation 6.5
Psychiatric disorders Nervousness 6.5
Psychiatric disorders Tension 6.5
Infections and infestations Urinary tract infection 6.5
General disorders and administration site conditions Application site pruritus 6.1
Gastrointestinal disorders Dyspepsia 6.0
Renal and urinary disorders Urinary retention 6.0
Nervous system disorders Somnolence 5.7
General disorders and administration site conditions Application site erythema 5.6
Nervous system disorders Somnolence 5.6
Nervous system disorders Insomnia 5.5
Psychiatric disorders Mental disorder 5.5
Infections and infestations Upper respiratory tract infection 5.4
Gastrointestinal disorders Nausea 5.2
Infections and infestations Urinary tract infection 5.2
Cardiac disorders Dizziness 5.0
Gastrointestinal disorders Dry mouth 5.0
Infections and infestations Upper respiratory tract infection
Gastrointestinal disorders Dry mouth
Cardiac disorders Dizziness 4.9
Gastrointestinal disorders Dyspepsia 4.7
Renal and urinary disorders Urinary retention 4.7
Gastrointestinal disorders Dyspepsia 4.5
Respiratory, thoracic and mediastinal disorders Nasal dryness 4.5
Gastrointestinal disorders Nausea 4.5
Cardiac disorders Palpitations 4.5
General disorders and administration site conditions Application site pruritus 4.3
Eye disorders Vision blurred 4.3
Infections and infestations Urinary tract infection
Eye disorders Dry eye 4.2
Eye disorders Vision blurred 4.2
Gastrointestinal disorders Dry mouth 4.1
General disorders and administration site conditions Application site rash 4.0
General disorders and administration site conditions Application site vesicles 4.0
Gastrointestinal disorders Constipation 4.0
Gastrointestinal disorders Diarrhoea 4.0
Cardiac disorders Oedema peripheral 4.0
Gastrointestinal disorders Constipation 3.9
General disorders and administration site conditions Application site erythema 3.74
Gastrointestinal disorders Diarrhoea 3.5
Investigations Residual urine volume 3.5
General disorders and administration site conditions Application site rash 3.3
Gastrointestinal disorders Constipation 3.3
General disorders and administration site conditions Application site rash 3.27
General disorders and administration site conditions Application site vesicles 3.2
Gastrointestinal disorders Diarrhoea 3.2
General disorders and administration site conditions Asthenia 3.1
Eye disorders Dry eye 3.1
General disorders and administration site conditions Fatigue 3.1
Gastrointestinal disorders Abdominal pain upper 3.0
General disorders and administration site conditions Asthenia 3.0
Respiratory, thoracic and mediastinal disorders Cough 3.0
Gastrointestinal disorders Diarrhoea 3.0
Skin and subcutaneous tissue disorders Dry skin 3.0
Renal and urinary disorders Dysuria 3.0
General disorders and administration site conditions Fatigue 3.0
Nervous system disorders Headache 3.0
Nervous system disorders Insomnia 3.0
Skin and subcutaneous tissue disorders Macule 3.0
Renal and urinary disorders Urinary retention 3.0
Eye disorders Visual impairment 3.0
Cardiac disorders Dizziness 2.83
Infections and infestations Nasopharyngitis 2.83
Nervous system disorders Insomnia 2.8
Respiratory, thoracic and mediastinal disorders Nasal dryness 2.8
Gastrointestinal disorders Dry mouth
General disorders and administration site conditions Asthenia 2.6
Skin and subcutaneous tissue disorders Dry skin 2.6
General disorders and administration site conditions Fatigue 2.6
Gastrointestinal disorders Abdominal pain 2.5
General disorders and administration site conditions Asthenia 2.5
Nervous system disorders Confusional state 2.5
Eye disorders Dry eye 2.5
Skin and subcutaneous tissue disorders Dry skin 2.5
Gastrointestinal disorders Dry throat 2.5
Renal and urinary disorders Dysuria 2.5
General disorders and administration site conditions Feeling abnormal 2.5
Gastrointestinal disorders Flatulence 2.5
Gastrointestinal disorders Gastrointestinal pain 2.5
Skin and subcutaneous tissue disorders Macule 2.5
Infections and infestations Nasopharyngitis 2.5
Cardiac disorders Oedema peripheral 2.5
Infections and infestations Upper respiratory tract infection 2.5
Eye disorders Visual impairment 2.5
Musculoskeletal and connective tissue disorders Back pain 2.4
Respiratory, thoracic and mediastinal disorders Cough 2.4
Renal and urinary disorders Dysuria 2.4
General disorders and administration site conditions Application site erythema
General disorders and administration site conditions Application site erythema 2.3
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 2.3
Cardiac disorders Dizziness 2.3
Investigations Residual urine volume 2.3
Renal and urinary disorders Urinary hesitation 2.3
Eye disorders Vision blurred 2.3
Infections and infestations Nasopharyngitis
Infections and infestations Upper respiratory tract infection 2.2
General disorders and administration site conditions Application site pruritus 2.1
General disorders and administration site conditions Asthenia 2.06
General disorders and administration site conditions Fatigue 2.06
Gastrointestinal disorders Viral diarrhoea 2.06
Gastrointestinal disorders Abdominal pain 2.0
Musculoskeletal and connective tissue disorders Arthralgia 2.0
Musculoskeletal and connective tissue disorders Back pain 2.0
Infections and infestations Bronchitis 2.0
Renal and urinary disorders Dysuria 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 2.0
Respiratory, thoracic and mediastinal disorders Sinus congestion 2.0
Nervous system disorders Sinus headache 2.0
Respiratory, thoracic and mediastinal disorders Cough 1.9
Gastrointestinal disorders Dry mouth 1.9
Renal and urinary disorders Dysuria 1.9
Respiratory, thoracic and mediastinal disorders Laryngeal pain 1.9
Gastrointestinal disorders Nausea 1.9
Gastrointestinal disorders Oropharyngeal pain 1.9
Renal and urinary disorders Urinary hesitation 1.9
General disorders and administration site conditions Application site rash 1.8
Skin and subcutaneous tissue disorders Dry skin 1.8
Gastrointestinal disorders Viral diarrhoea
General disorders and administration site conditions Application site erythema
General disorders and administration site conditions Application site erythema 1.7
General disorders and administration site conditions Asthenia 1.7
Psychiatric disorders Depression 1.7
Gastrointestinal disorders Dry mouth
Gastrointestinal disorders Dry mouth 1.7
Gastrointestinal disorders Dry throat 1.7
Renal and urinary disorders Dysuria 1.7
Respiratory, thoracic and mediastinal disorders Nasal dryness 1.7
Infections and infestations Sinusitis 1.7
Gastrointestinal disorders Abdominal pain 1.6
Gastrointestinal disorders Dry throat 1.6
Gastrointestinal disorders Dysgeusia 1.6
Gastrointestinal disorders Gastrointestinal pain 1.6
Gastrointestinal disorders Gastrooesophageal reflux disease 1.6
Gastrointestinal disorders Abdominal pain 1.5
Musculoskeletal and connective tissue disorders Arthralgia 1.5
Investigations Blood glucose increased 1.5
Investigations Blood pressure increased 1.5
Cardiac disorders Dizziness 1.5
Gastrointestinal disorders Dysgeusia 1.5
Gastrointestinal disorders Dysphagia 1.5
Gastrointestinal disorders Gastrointestinal pain 1.5
Nervous system disorders Headache 1.5
Respiratory, thoracic and mediastinal disorders Laryngeal pain 1.5
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.5
Infections and infestations Nasopharyngitis 1.5
Psychiatric disorders Nervousness 1.5
Gastrointestinal disorders Oropharyngeal pain 1.5
Cardiac disorders Palpitations 1.5
Skin and subcutaneous tissue disorders Pruritus 1.5
Psychiatric disorders Tension 1.5
Gastrointestinal disorders Vomiting 1.5
Gastrointestinal disorders Diarrhoea 1.4
Cardiac disorders Chest pain 1.3
Gastrointestinal disorders Constipation 1.3
Vascular disorders Hypertension 1.3
Musculoskeletal and connective tissue disorders Pain in extremity 1.3
Skin and subcutaneous tissue disorders Pruritus 1.3
Gastrointestinal disorders Vomiting 1.3
Infections and infestations Bronchitis 1.2
Gastrointestinal disorders Flatulence 1.2
Renal and urinary disorders Urinary retention 1.2
Gastrointestinal disorders Vomiting 1.2
Gastrointestinal disorders Dysgeusia 1.1
General disorders and administration site conditions Asthenia
Immune system disorders Asthma 1.0
Renal and urinary disorders Bladder pain 1.0
Investigations Blood pressure increased 1.0
Nervous system disorders Confusional state 1.0
Infections and infestations Cystitis 1.0
Renal and urinary disorders Cystitis noninfective 1.0
Cardiac disorders Dizziness
Gastrointestinal disorders Dry mouth 1.0
Nervous system disorders Dysphonia 1.0
Gastrointestinal disorders Eructation 1.0
Eye disorders Eye irritation 1.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Feeling abnormal 1.0
General disorders and administration site conditions Flank pain 1.0
Metabolism and nutrition disorders Fluid retention 1.0
General disorders and administration site conditions Flushing 1.0
Infections and infestations Fungal infection 1.0
Gastrointestinal disorders Gastrooesophageal reflux disease 1.0
Vascular disorders Hypotension 1.0
General disorders and administration site conditions Oedema 1.0
General disorders and administration site conditions Pain 1.0
Musculoskeletal and connective tissue disorders Pain in extremity 1.0
Renal and urinary disorders Pollakiuria 1.0
Cardiac disorders Sinus arrhythmia 1.0
General disorders and administration site conditions Thirst 1.0
Gastrointestinal disorders Tongue coated 1.0
General disorders and administration site conditions Application site erythema
General disorders and administration site conditions Application site rash
General disorders and administration site conditions Application site rash 0.9
Gastrointestinal disorders Dry mouth 0.7
Gastrointestinal disorders Gastrooesophageal reflux disease 0.5
General disorders and administration site conditions Application site rash

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
30.19
Skin and subcutaneous tissue disorders
22.25
Injury, poisoning and procedural complications
20.42
Product issues
7.08
Nervous system disorders
4.02
Gastrointestinal disorders
3.24
Renal and urinary disorders
2.24

Cross References

Resources Reference
CAS NUMBER 5633-20-5
ChEBI 7856
ChEMBL CHEMBL1231
DrugBank DB01062
DrugCentral 2028
EPA CompTox DTXSID0023406
FDA SRS K9P6MC7092
Human Metabolome Database HMDB0015195
Guide to Pharmacology 359
KEGG C07360
PharmGKB PA164746030
PubChem 4634
SureChEMBL SCHEMBL2992
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