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SML2480

Sigma-Aldrich

Mirabegron

≥98% (HPLC)

Synonym(s):

2-(2-Amino-1,3-thiazol-4-yl)-N-[4-[2-[((2R)-2-hydroxy-2-phenylethyl)amino]ethyl]phenyl]acetamide, 2-Amino-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-4-thiazoleacetamide, YM 178, YM178(R)-Mirabegron

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About This Item

Empirical Formula (Hill Notation):
C21H24N4O2S
CAS Number:
223673-61-8
Molecular Weight:
396.51
MDL number:
MFCD11100356
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -16 to -22°, c = 0.5 in methanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O[C@@H](CNCCC1=CC=C(NC(CC2=CSC(N)=N2)=O)C=C1)C3=CC=CC=C3

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

InChI key

PBAPPPCECJKMCM-IBGZPJMESA-N

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Application

Mirabegron has been used as a β3-adrenergic receptor (β3-AR) agonist in an in vitro experiment to determine whether β3-AR stimulation specifically activates brown adipose tissue (BAT) thermogenesis in humans.

Biochem/physiol Actions

Mirabegron is a non-antimuscarinic orally active drug with the potential to treat patients with overactive bladder (OAB) symptoms. It aids in bladder relaxation by acting on neural control of the storage phase of micturition by targeting β3-AR. Mirabegron is also used to treat neurogenic detrusor overactivity (NDO) in pediatric patients.
Mirabegron is a potent and selective β3-adrenoceptor agonist that activates the β3 adrenergic receptor in the detrusor muscle in the bladder leading to muscle relaxation and an increase in bladder capacity.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rebecca Bragg et al.
The Consultant pharmacist : the journal of the American Society of Consultant Pharmacists, 29(12), 823-837 (2014-12-19)
To review the literature regarding the efficacy and safety of mirabegron for the treatment of overactive bladder (OAB). A literature search was performed using MEDLINE (PubMed) prior to December 31, 2013, using the terms "mirabegron" and "randomized-controlled trial." All published
Pradeep Tyagi et al.
Expert opinion on drug safety, 10(2), 287-294 (2010-12-15)
Mirabegron is being developed as a new treatment for the management of overactive bladder (OAB). It is an orally active drug that works by activating the β(3)-adrenoceptor with a better safety profile than antimuscarinic drugs. However, long-term adverse effects are
Toshiyuki Takasu et al.
The Journal of pharmacology and experimental therapeutics, 321(2), 642-647 (2007-02-13)
We evaluated the pharmacological characteristics of (R)-2-(2-aminothiazol-4-yl)-4'-{2-[(2-hydroxy-2-phenylethyl)amino]-ethyl} acetanilide (YM178). YM178 increased cyclic AMP accumulation in Chinese hamster ovary (CHO) cells expressing human beta3-adrenoceptor (AR). The half-maximal effective concentration (EC50) value was 22.4 nM. EC50 values of YM178 for human beta1-
Kentaro Konishi et al.
European journal of drug metabolism and pharmacokinetics, 43(3), 301-309 (2017-11-23)
Mirabegron is cleared by multiple mechanisms, including drug-metabolizing enzymes. One of the most important clearance pathways is direct glucuronidation. In humans, M11 (O-glucuronide), M13 (carbamoyl-glucuronide), and M14 (N-glucuronide) have been identified, of which M11 is one of the major metabolites
Susan J Keam
Paediatric drugs, 23(4), 411-415 (2021-06-01)
Mirabegron (MYRBETRIQ®), a beta-3 adrenergic agonist developed by Astellas Pharma Inc., is well established as a treatment for overactive bladder in adults and is available as extended-release (ER) tablets administered once daily. More recently, mirabegron has been investigated in pediatric
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