MIRABEGRON

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Trade Names:
Synonyms:
Status: Approved (2012)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: G04BD12
UNII: MVR3JL3B2V

Structure
InChI Key PBAPPPCECJKMCM-IBGZPJMESA-N
Smile Nc1nc(CC(=O)Nc2ccc(CCNC[C@H](O)c3ccccc3)cc2)cs1
InChI
InChI=1S/C21H24N4O2S/c22-21-25-18(14-28-21)12-20(27)24-17-8-6-15(7-9-17)10-11-23-13-19(26)16-4-2-1-3-5-16/h1-9,14,19,23,26H,10-13H2,(H2,22,25)(H,24,27)/t19-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H24N4O2S
Molecular Weight 396.52
AlogP 2.77
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 9.0
Polar Surface Area 100.27
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 28.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Beta-3 adrenergic receptor agonist Expert
Primary Target
β3-adrenoceptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- - - - 87

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Urinary Bladder, Overactive 4 D053201 ClinicalTrials
Cystitis, Interstitial 3 D018856 ClinicalTrials
Kidney Calculi 3 D007669 ClinicalTrials
Heart Failure 2 D006333 ClinicalTrials
Hypertrophy, Left Ventricular 2 D017379 ClinicalTrials
Urinary Bladder, Neurogenic 2 D001750 ClinicalTrials
Prediabetic State 2 D011236 ClinicalTrials
Pain 2 D010146 ClinicalTrials
Kidney Diseases 1 D007674 ClinicalTrials
Polycystic Ovary Syndrome 1 D011085 ClinicalTrials
Liver Diseases 1 D008107 ClinicalTrials
Esophageal Achalasia 0 D004931 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Vascular disorders Hypertension 11.3
Vascular disorders Hypertension 9.6
Vascular disorders Hypertension 9.2
Gastrointestinal disorders Dry mouth 8.6
Vascular disorders Hypertension
Vascular disorders Hypertension 7.5
Infections and infestations Urinary tract infection 6.4
Infections and infestations Urinary tract infection 5.9
Infections and infestations Urinary tract infection 4.2
Nervous system disorders Headache 4.1
Infections and infestations Nasopharyngitis 3.9
Infections and infestations Nasopharyngitis 3.5
Infections and infestations Influenza 3.4
Nervous system disorders Headache 3.2
Infections and infestations Nasopharyngitis 3.1
Nervous system disorders Headache
Infections and infestations Urinary tract infection 2.9
Musculoskeletal and connective tissue disorders Back pain 2.8
Gastrointestinal disorders Constipation 2.8
Gastrointestinal disorders Dry mouth 2.8
Gastrointestinal disorders Constipation 2.7
Cardiac disorders Dizziness 2.7
Infections and infestations Sinusitis 2.7
Cardiac disorders Dizziness 2.6
Infections and infestations Influenza 2.6
Nervous system disorders Headache 2.5
Infections and infestations Nasopharyngitis
Renal and urinary disorders Bladder pain 2.3
Infections and infestations Cystitis 2.3
Renal and urinary disorders Cystitis noninfective 2.3
Musculoskeletal and connective tissue disorders Arthralgia 2.1
Renal and urinary disorders Bladder pain 2.1
Infections and infestations Cystitis 2.1
Renal and urinary disorders Cystitis noninfective 2.1
Nervous system disorders Headache 2.1
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.1
Infections and infestations Upper respiratory tract infection 2.1
Musculoskeletal and connective tissue disorders Arthralgia 2.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Infections and infestations Urinary tract infection
Infections and infestations Upper respiratory tract infection
Musculoskeletal and connective tissue disorders Arthralgia 1.6
Musculoskeletal and connective tissue disorders Back pain 1.6
Gastrointestinal disorders Constipation 1.6
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.6
Cardiac disorders Tachycardia 1.6
Gastrointestinal disorders Diarrhoea 1.5
Infections and infestations Sinusitis 1.5
Infections and infestations Upper respiratory tract infection 1.5
Gastrointestinal disorders Abdominal pain 1.4
General disorders and administration site conditions Asthenia 1.4
Gastrointestinal disorders Constipation
General disorders and administration site conditions Fatigue 1.4
Gastrointestinal disorders Gastrointestinal pain 1.4
Musculoskeletal and connective tissue disorders Arthralgia 1.3
Gastrointestinal disorders Diarrhoea
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.3
General disorders and administration site conditions Asthenia 1.2
Gastrointestinal disorders Diarrhoea 1.2
General disorders and administration site conditions Fatigue 1.2
Cardiac disorders Tachycardia 1.2
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Constipation 0.9
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Abdominal pain 0.6
Gastrointestinal disorders Gastrointestinal pain 0.6
Nervous system disorders Headache 0.6
Cardiac disorders Tachycardia
Cardiac disorders Dizziness 0.5
Vascular disorders Hypertension 0.5
Nervous system disorders Cerebrovascular accident 0.4
Eye disorders Dry eye 0.4
Gastrointestinal disorders Nausea 0.4
Infections and infestations Urinary tract infection 0.4
Eye disorders Vision blurred 0.4
Cardiac disorders Atrial fibrillation 0.2
Musculoskeletal and connective tissue disorders Osteoarthritis 0.2
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Prostate cancer 0.1

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
16.45
Injury, poisoning and procedural complications
11.34
Nervous system disorders
10.79
Renal and urinary disorders
9.29
Gastrointestinal disorders
8.16
Cardiac disorders
5.56
Vascular disorders
5.15
Respiratory, thoracic and mediastinal disorders
4.69
Investigations
4.63
Skin and subcutaneous tissue disorders
4.18
Psychiatric disorders
4.07
Musculoskeletal and connective tissue disorders
3.74
Infections and infestations
2.94

Cross References

Resources Reference
CAS NUMBER 223673-61-8
ChEBI 65349
ChEMBL CHEMBL2095212
DrugBank DB08893
DrugCentral 4382
FDA SRS MVR3JL3B2V
Guide to Pharmacology 7445
PDB H6U
PubChem 9865528
SureChEMBL SCHEMBL904788
ZINC ZINC000001996784
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