Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H24N4O2S |
Molecular Weight | 396.506 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(CC(=O)NC2=CC=C(CCNC[C@H](O)C3=CC=CC=C3)C=C2)=CS1
InChI
InChIKey=PBAPPPCECJKMCM-IBGZPJMESA-N
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
Molecular Formula | C21H24N4O2S |
Molecular Weight | 396.506 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=20878594
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=20878594
Mirabegron (trade name Myrbetriq in the US and Betmiga in Europe) is a drug for the treatment of overactive bladder (OAB). It was developed by Astellas Pharma and was approved in the United States in July 2012. Originally developed as a treatment for diabetes, the development of mirabegron was later refocused to OAB. Mirabegron is an orally bioavailable agonist of the human beta-3 adrenergic receptor (ADRB3), with muscle relaxing, neuroprotective and potential antineoplastic activities. Upon oral administration, mirabegron binds to and activates ADRB3, which leads to smooth muscle relaxation. Mirabegron also restores sympathetic stimulation in mesenchymal stem cell (MSC) niches, inhibits JAK2-mutated hematopoietic stem cell (HSC) expansion and blocks the progression of myeloproliferative neoplasms (MPNs). Lack of sympathetic stimulation of the MSC and HSC niche is associated with the development of MPNs.
CNS Activity
Sources: http://onlinelibrary.wiley.com/doi/10.1111/ijcp.12433/fullhttp://onlinelibrary.wiley.com/doi/10.1111/ijcp.12433/full
Curator's Comment: Mirabegron has a low propensity to cross the blood–brain barrier
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL246 |
22.4 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | MYRBETRIQ Approved UseIndicated for the treatment of overactive bladder (OAB) with symptoms of urge urinary incontinence, urgency, and urinary frequency. Launch Date2012 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.8 ng/mL |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRABEGRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
29.4 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25791612 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRABEGRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
177 ng × h/mL |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRABEGRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
46.82 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25791612 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRABEGRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
41.5 h |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRABEGRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
28.1 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25791612 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRABEGRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
29% |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
MIRABEGRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
200 mg 1 times / day multiple, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
healthy, 23.6 years (range: 20–27 years) Health Status: healthy Age Group: 23.6 years (range: 20–27 years) Sex: M Sources: |
Other AEs: Pulse rate increased... Other AEs: Pulse rate increased (2%) Sources: |
400 mg single, oral Highest studied dose |
healthy, 23.8 years (range: 20–27 years) Health Status: healthy Age Group: 23.8 years (range: 20–27 years) Sex: M Sources: |
|
200 mg 1 times / day multiple, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 58.0±13.7 years Health Status: unhealthy Age Group: 58.0±13.7 years Sex: M+F Sources: |
Other AEs: Cardiac disorders, Eye disorders... Other AEs: Cardiac disorders (3%) Sources: Eye disorders (3.6%) Constipation (1.8%) Dyspepsia (2.4%) |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
Disc. AE: Constipation, Hypertension... AEs leading to discontinuation/dose reduction: Constipation (0.2%) Sources: Hypertension (0.2%) Tachycardia (0.1%) Atrial fibrillation (0.5%) Palpitations (0.5%) Edema peripheral (0.5%) Pyrexia (0.5%) ALT increased (0.4%) AST increased (0.4%) Bilirubin increased (0.4%) Liver enzyme abnormal (0.4%) Hypertensive crisis (0.3%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Pulse rate increased | 2% | 200 mg 1 times / day multiple, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
healthy, 23.6 years (range: 20–27 years) Health Status: healthy Age Group: 23.6 years (range: 20–27 years) Sex: M Sources: |
Constipation | 1.8% | 200 mg 1 times / day multiple, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 58.0±13.7 years Health Status: unhealthy Age Group: 58.0±13.7 years Sex: M+F Sources: |
Dyspepsia | 2.4% | 200 mg 1 times / day multiple, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 58.0±13.7 years Health Status: unhealthy Age Group: 58.0±13.7 years Sex: M+F Sources: |
Cardiac disorders | 3% | 200 mg 1 times / day multiple, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 58.0±13.7 years Health Status: unhealthy Age Group: 58.0±13.7 years Sex: M+F Sources: |
Eye disorders | 3.6% | 200 mg 1 times / day multiple, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, 58.0±13.7 years Health Status: unhealthy Age Group: 58.0±13.7 years Sex: M+F Sources: |
Tachycardia | 0.1% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
Constipation | 0.2% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
Hypertension | 0.2% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
Hypertensive crisis | 0.3% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
ALT increased | 0.4% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
AST increased | 0.4% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
Bilirubin increased | 0.4% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
Liver enzyme abnormal | 0.4% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
Atrial fibrillation | 0.5% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
Edema peripheral | 0.5% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
Palpitations | 0.5% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
Pyrexia | 0.5% Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202611Orig1s000ClinPharmR.pdf#page=27 Page: 27.0 |
moderate | yes (co-administration study) Comment: Cmax and AUC of metoprolol increased by 90% and 229% and of desipramine by 79% and 241%, respectively; The Cmax and AUC of tamsulosin was increased by 60% when co-administered with mirabegron Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202611Orig1s000ClinPharmR.pdf#page=27 Page: 27.0 |
||
Page: 13.0 |
no | |||
Page: 13.0 |
no | |||
Page: 13.0 |
unlikely | |||
Page: 13.0 |
unlikely | |||
Page: 13.0 |
unlikely | |||
Page: 13.0 |
unlikely | |||
Page: 13.0 |
unlikely | |||
Page: 13.0 |
unlikely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202611Orig1s000ClinPharmR.pdf#page=30 Page: 30.0 |
weak | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202611Orig1s000ClinPharmR.pdf#page=30 Page: 30.0 |
weak | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202611Orig1s000ClinPharmR.pdf#page=30 Page: 30.0 |
weak | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202611Orig1s000ClinPharmR.pdf#page=30 Page: 30.0 |
weak | yes (co-administration study) Comment: The Cmax and AUC of tamsulosin (a CYP2D6 and CYP3A4 substrate) was increased by 60% when co-administered with mirabegron Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202611Orig1s000ClinPharmR.pdf#page=30 Page: 30.0 |
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202611Orig1s000PharmR.pdf#page=46 Page: 46.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of pre-contraction on β-adrenoceptor-mediated relaxation of rat urinary bladder. | 2009 Dec |
|
Pharmacotherapy of the overactive bladder. | 2009 Oct |
|
Mirabegron, a β₃-adrenoceptor agonist for the potential treatment of urinary frequency, urinary incontinence or urgency associated with overactive bladder. | 2010 Oct |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Patents
Sample Use Guides
25 mg once daily, with or without food. 25 mg is effective within 8 weeks. Based on individual efficacy and
tolerability, may increase dose to 50 mg once daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/23239087
Mirabegron increased cAMP accumulation with EC(50) value = 19 nmol/L in CHO cells expressing rat β(3)-adrenoceptors.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:22:06 GMT 2025
by
admin
on
Mon Mar 31 18:22:06 GMT 2025
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Record UNII |
MVR3JL3B2V
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C48149
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LIVERTOX |
NBK547887
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NDF-RT |
N0000185008
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WHO-VATC |
QG04BD12
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WHO-ATC |
G04BD12
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EMA ASSESSMENT REPORTS |
BETMIGA (AUTHORIZED: URINARY BLADDER, OVERACTIVE)
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DB08893
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9865528
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Mirabegron
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Mirabegron
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CHEMBL2095212
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100000126336
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N0000185007
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PRIMARY | Adrenergic beta3-Agonists [MoA] | ||
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DTXSID101021648
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m11690
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MVR3JL3B2V
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BETANIS
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PRIMARY | APPROVED JUNE 2011 | ||
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223673-61-8
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WW-31
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MVR3JL3B2V
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N0000182137
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PRIMARY | Cytochrome P450 2D6 Inhibitors [MoA] | ||
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SUB32690
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65349
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C90633
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1300786
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PRIMARY | RxNorm | ||
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4382
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
CYP
3A4 is the primary responsible isoenzyme for in vitro hepatic oxidative
metabolism of mirabegron, with a minor role of CYP2D6
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
In vitro studies suggest a role for CYP2D6 and CYP3A4 in the oxidative metabolism of mirabegron
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE INACTIVE -> PARENT |
In vitro and ex vivo studies have shown the involvement of uridine diphospho-glucuronosyltransferases (UGT)
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
URINE
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METABOLITE INACTIVE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE INACTIVE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT |
PLASMA; URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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PARENT -> IMPURITY |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Elimination PHARMACOKINETIC |
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