Mirabegron

Structural formula
General
Non-proprietary name	Mirabegron
other names	2- (2-Amino-1,3-thiazol-4-yl) -N- [4- [2 - [((2R) -2-hydroxy-2-phenylethyl) amino] ethyl] phenyl] acetamide ( IUPAC ); Betmiga ® ; Myr Betriq ™; Betanis ® ; YM 178; YM178 (R) -Mirabegron;
Molecular formula	C 21 H 24 N 4 O 2 S
Brief description	White dust
External identifiers / databases
EC number	800-126-3
ECHA InfoCard	100.226.392
PubChem	9865528
ChemSpider	8041219
DrugBank	DB08893
Wikidata	Q3702534
Drug information
ATC code	G04 BD12
Drug class	β 3 sympathomimetics
Mechanism of action	selective β 3 - agonist , relaxation of the smooth bladder muscle
properties
Molar mass	396.51 g · mol -1
Melting point	138-140 ° C
solubility	sparingly soluble in DMF , DMSO and ethanol , insoluble in water
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 302-317-319-361-373-410
	P: 201-202-260-264-272-273-280-301 + 312-302 + 352-305 + 351 + 338-308 + 313-314-330-333 + 313-337 + 313-362 + 364-391
Toxicological data	980 mg • kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mirabegron ( INN ) is a prescription drug from the group of β ₃ - sympathomimetics . It has been approved in the EU for the treatment of overactive bladder since 2012 . It is used in the symptomatic therapy of imperative urination , increased micturition frequency and urge incontinence . It is the first active ingredient from the group of β ₃ sympathomimetics.

Mechanism of action

Mirabegron acts as a β ₃ - adrenoceptor agonist . A sympathetic innervation of the urinary bladder leads to an increase in the bladder capacity and a decrease in the contractility of the bladder muscles. Animal studies and experiments on isolated bladder muscle cells showed relaxation of the bladder smooth muscles. An increase in micturition volume was found in vivo .

trade

Mirabegron is sold under the trade names Betmiga ^® (EU), Myr Betriq ™ (USA) and Betanis ^® (Japan).

It is approved in the USA, Europe and Japan, among others. In Germany, the drug was sold for one year from June 2014. However, compared to the cheaper anticholinergics , Mirabegron showed no additional benefit, which is why it was initially withdrawn from the market.

It has been on the market again since August 15, 2017. However, it is only used as an alternative therapeutic agent for side effects of anticholinergic drugs, especially for dry mouth .

Application and dosage

Mirabegron is administered orally as a prolonged-release tablet at a dose of 25 or 50 mg once a day.

Side effects

Common side effects (≥ 1/100 to <1/10) are urinary tract infections and tachycardia . Headaches, dizziness, nausea, constipation and diarrhea are less common .

Contraindication

Mirabegron is contraindicated in severe hypertension . There have been cases of hypertensive crises which can clearly be traced back to the medication with Betmiga ^® .

literature

E. Mutschler: drug effects. 11th edition. WVG, Stuttgart 2020, ISBN 978-3-8047-3663-4 .
ED Deeks: Mirabegron: A Review in Overactive Bladder Syndrome. In: Drugs. Volume 78, 2018, pp. 833-844. DOI: 10.1007 / s40265-018-0924-4
M. Sanford: Mirabegron: A Review of Its Use in Patients with Overactive Bladder Syndrome. In: Drugs. Volume 73, 2013, pp. 1213-1225. DOI: 10.1007 / s40265-013-0086-3

Individual evidence

↑ ^a ^b Mirabegron data sheet at ACS , accessed on May 15, 2020.

↑ ^a ^b ^c Mirabegron data sheet from Cayman Chemical , PDF, 27 kB, accessed on May 15, 2020.

↑ Mirabegron data sheet at DrugBank , accessed on May 15, 2020.

↑ Safety data sheet ClearSynth , accessed on May 16, 2020.

↑ ^a ^b Dossier on benefit assessment, Federal Joint Committee , PDF, 265 KB, accessed on May 16, 2020.

^ S. Aditya, SK Mathur: Mirabegron: A first-in-class beta-3 agonist for overactive bladder. In: J Mahatma Gandhi Inst Med Sci. Volume 20, 2015, pp. 128-133.

↑ T. Hatanaka, M. Ukai, M. Watanabe et al .: In vitro and in vivo pharmacological profile of the selective β3-adrenoceptor agonist mirabegron in rats. In: Naunyn-Schmiedeberg's Arch Pharmacol. Volume 386, 2013, pp. 247-253. DOI: 10.1007 / s00210-012-0821-4

↑ ^a ^b ^c Active ingredient NEWS Mirabegron , edition 05/2017, accessed on May 15, 2020.

↑ Mirabegron re-marketed , accessed on May 14, 2020.

↑ Betmiga Instructions for Use Astellas , accessed on May 16, 2020.

↑ Information sheet Mirabegron Astellas , Sep 2015, PDF, 96 kB, accessed on May 15, 2020.

↑ Rote-Hand-Brief Astellas , Sep 2015, PDF, 377 KB, accessed on May 16, 2020.

[ACS-1] Mirabegron data sheet at ACS , accessed on May 15, 2020.

[Cayman-2] Mirabegron data sheet from Cayman Chemical , PDF, 27 kB, accessed on May 15, 2020.

[3] Mirabegron data sheet at DrugBank , accessed on May 15, 2020.

[4] Safety data sheet ClearSynth , accessed on May 16, 2020.

[gba-5] Dossier on benefit assessment, Federal Joint Committee , PDF, 265 KB, accessed on May 16, 2020.

[6] S. Aditya, SK Mathur: Mirabegron: A first-in-class beta-3 agonist for overactive bladder. In: J Mahatma Gandhi Inst Med Sci. Volume 20, 2015, pp. 128-133.

[7] T. Hatanaka, M. Ukai, M. Watanabe et al .: In vitro and in vivo pharmacological profile of the selective β3-adrenoceptor agonist mirabegron in rats. In: Naunyn-Schmiedeberg's Arch Pharmacol. Volume 386, 2013, pp. 247-253. DOI: 10.1007 / s00210-012-0821-4

[KBV-8] Active ingredient NEWS Mirabegron , edition 05/2017, accessed on May 15, 2020.

[9] Mirabegron re-marketed , accessed on May 14, 2020.

[10] Betmiga Instructions for Use Astellas , accessed on May 16, 2020.

[11] Information sheet Mirabegron Astellas , Sep 2015, PDF, 96 kB, accessed on May 15, 2020.

[12] Rote-Hand-Brief Astellas , Sep 2015, PDF, 377 KB, accessed on May 16, 2020.