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MedKoo Cat#: 314233 | Name: Mirabegron
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mirabegron (formerly YM-178, trade name Myrbetriq) is a drug for the treatment of overactive bladder. It was developed by Astellas Pharma and was approved in the United States in July 2012. Mirabegron activates the β3 adrenergic receptor in the detrusor muscle in the bladder, which leads to muscle relaxation and an increase in bladder capacity. (Source: http://en.wikipedia.org/wiki/Mirabegron)

Chemical Structure

Mirabegron
Mirabegron
CAS#223673-61-8

Theoretical Analysis

MedKoo Cat#: 314233

Name: Mirabegron

CAS#: 223673-61-8

Chemical Formula: C21H24N4O2S

Exact Mass: 396.1620

Molecular Weight: 396.51

Elemental Analysis: C, 63.61; H, 6.10; N, 14.13; O, 8.07; S, 8.09

Price and Availability

Size Price Availability Quantity
1g USD 350.00 2 weeks
2g USD 600.00 2 weeks
5g USD 1,250.00 2 weeks
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Related CAS #
No Data
Synonym
YM-178; YM178; YM 178; Mirabegron; Myrbetriq; Betanis; Betmiga
IUPAC/Chemical Name
2-(2-Amino-1,3-thiazol-4-yl)-N-[4-(2-{[(2R)-2-hydroxy-2-phenylethyl]amino}ethyl)phenyl]acetamide
InChi Key
PBAPPPCECJKMCM-IBGZPJMESA-N
InChi Code
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
SMILES Code
O=C(NC1=CC=C(CCNC[C@H](O)C2=CC=CC=C2)C=C1)CC3=CSC(N)=N3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Mirabegron is a selective β3-adrenoceptor agonist with EC50 of 22.4 nM.
In vitro activity:
Mirabegron was shown to be a time-dependent inhibitor of CYP2D6 in the presence of NADPH as the IC(50) value in human liver microsomes decreased from 13 to 4.3 μM after 30-min pre-incubation. Further evaluation indicated that mirabegron may act partly as an irreversible or quasi-irreversible metabolism-dependent inhibitor of CYP2D6. Reference: Xenobiotica. 2012 Dec;42(12):1187-96. https://pubmed.ncbi.nlm.nih.gov/22834478/
In vivo activity:
In apolipoprotein E-/- (ApoE-/-) and low-density lipoprotein (LDL) receptor-/- (Ldlr-/-) mice, oral administration of clinically relevant doses of mirabegron markedly accelerates atherosclerotic plaque growth and instability by a mechanism of increasing plasma levels of both LDL-cholesterol and very LDL-cholesterol remnants. Stimulation of atherosclerotic plaque development by mirabegron is dependent on thermogenesis-triggered lipolysis. Reference: Proc Natl Acad Sci U S A. 2019 May 28;116(22):10937-10942. https://pubmed.ncbi.nlm.nih.gov/31085638/
Solvent mg/mL mM
Solubility
DMF 5.0 12.61
DMSO 55.9 141.01
DMSO:PBS (pH 7.2) (1:6) 0.1 0.25
Ethanol 6.3 15.91
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 396.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Takusagawa S, Miyashita A, Iwatsubo T, Usui T. In vitro inhibition and induction of human cytochrome P450 enzymes by mirabegron, a potent and selective β3-adrenoceptor agonist. Xenobiotica. 2012 Dec;42(12):1187-96. doi: 10.3109/00498254.2012.700140. Epub 2012 Jul 27. PMID: 22834478. 2. Aizawa N, Homma Y, Igawa Y. Effects of mirabegron, a novel β3-adrenoceptor agonist, on primary bladder afferent activity and bladder microcontractions in rats compared with the effects of oxybutynin. Eur Urol. 2012 Dec;62(6):1165-73. doi: 10.1016/j.eururo.2012.08.056. Epub 2012 Sep 5. PMID: 22981677. 3. Sui W, Li H, Yang Y, Jing X, Xue F, Cheng J, Dong M, Zhang M, Pan H, Chen Y, Zhang Y, Zhou Q, Shi W, Wang X, Zhang H, Zhang C, Zhang Y, Cao Y. Bladder drug mirabegron exacerbates atherosclerosis through activation of brown fat-mediated lipolysis. Proc Natl Acad Sci U S A. 2019 May 28;116(22):10937-10942. doi: 10.1073/pnas.1901655116. Epub 2019 May 13. PMID: 31085638; PMCID: PMC6561204. 4. Hatanaka T, Ukai M, Watanabe M, Someya A, Ohtake A, Suzuki M, Ueshima K, Sato S, Kaku S. Effect of mirabegron, a novel β3-adrenoceptor agonist, on bladder function during storage phase in rats. Naunyn Schmiedebergs Arch Pharmacol. 2013 Jan;386(1):71-8. doi: 10.1007/s00210-012-0814-3. Epub 2012 Dec 9. PMID: 23224420.
In vitro protocol:
1. Takusagawa S, Miyashita A, Iwatsubo T, Usui T. In vitro inhibition and induction of human cytochrome P450 enzymes by mirabegron, a potent and selective β3-adrenoceptor agonist. Xenobiotica. 2012 Dec;42(12):1187-96. doi: 10.3109/00498254.2012.700140. Epub 2012 Jul 27. PMID: 22834478. 2. Aizawa N, Homma Y, Igawa Y. Effects of mirabegron, a novel β3-adrenoceptor agonist, on primary bladder afferent activity and bladder microcontractions in rats compared with the effects of oxybutynin. Eur Urol. 2012 Dec;62(6):1165-73. doi: 10.1016/j.eururo.2012.08.056. Epub 2012 Sep 5. PMID: 22981677.
In vivo protocol:
1. Sui W, Li H, Yang Y, Jing X, Xue F, Cheng J, Dong M, Zhang M, Pan H, Chen Y, Zhang Y, Zhou Q, Shi W, Wang X, Zhang H, Zhang C, Zhang Y, Cao Y. Bladder drug mirabegron exacerbates atherosclerosis through activation of brown fat-mediated lipolysis. Proc Natl Acad Sci U S A. 2019 May 28;116(22):10937-10942. doi: 10.1073/pnas.1901655116. Epub 2019 May 13. PMID: 31085638; PMCID: PMC6561204. 2. Hatanaka T, Ukai M, Watanabe M, Someya A, Ohtake A, Suzuki M, Ueshima K, Sato S, Kaku S. Effect of mirabegron, a novel β3-adrenoceptor agonist, on bladder function during storage phase in rats. Naunyn Schmiedebergs Arch Pharmacol. 2013 Jan;386(1):71-8. doi: 10.1007/s00210-012-0814-3. Epub 2012 Dec 9. PMID: 23224420.
1: Rechberger T, Kulik-Rechberger B, Miotła P, Wróbel A. [The new era in the pharmacological treatment of overactive bladder (OAB): mirabegron--a new selective beta3agonist]. Ginekol Pol. 2014 Mar;85(3):214-9. Review. Polish. PubMed PMID: 24783434. 2: Imran M, Najmi AK, Tabrez S. Mirabegron for overactive bladder: a novel, first-in-class β3-agonist therapy. Urol J. 2013 Sep 26;10(3):935-40. Review. PubMed PMID: 24078498. 3: Sanford M. Mirabegron: a review of its use in patients with overactive bladder syndrome. Drugs. 2013 Jul;73(11):1213-25. doi: 10.1007/s40265-013-0086-3. Review. PubMed PMID: 23818156. 4: Bridgeman MB, Friia NJ, Taft C, Shah M. Mirabegron: β3-adrenergic receptor agonist for the treatment of overactive bladder. Ann Pharmacother. 2013 Jul-Aug;47(7-8):1029-38. doi: 10.1345/aph.1S054. Epub 2013 Jun 11. Review. PubMed PMID: 23757386. 5: Kashyap M, Tyagi P. The pharmacokinetic evaluation of mirabegron as an overactive bladder therapy option. Expert Opin Drug Metab Toxicol. 2013 May;9(5):617-27. doi: 10.1517/17425255.2013.786700. Epub 2013 Apr 4. Review. PubMed PMID: 23550899. 6: Suzuki M, Ukai M, Sasamata M, Seki N. [Pharmacological and clinical profile of mirabegron (Betanis(®)): a new therapeutic agent for overactive bladder]. Nihon Yakurigaku Zasshi. 2012 May;139(5):219-25. Review. Japanese. PubMed PMID: 22687876. 7: Bhide AA, Digesu GA, Fernando R, Khullar V. Use of mirabegron in treating overactive bladder. Int Urogynecol J. 2012 Oct;23(10):1345-8. Epub 2012 Mar 13. Review. PubMed PMID: 22411211. 8: Bhide AA, Digesu GA, Fernando R, Khullar V. Mirabegron - a selective β3-adrenoreceptor agonist for the treatment of overactive bladder. Res Rep Urol. 2012 Jul 16;4:41-5. doi: 10.2147/RRU.S28930. eCollection 2012. Review. PubMed PMID: 24199179; PubMed Central PMCID: PMC3806442. 9: Tyagi P, Tyagi V, Chancellor M. Mirabegron: a safety review. Expert Opin Drug Saf. 2011 Mar;10(2):287-94. doi: 10.1517/14740338.2011.542146. Epub 2010 Dec 9. Review. PubMed PMID: 21142693.