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Chemistry

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Also known as: 223673-61-8, Myrbetriq, Betanis, Betmiga, Ym178, Mirabegron (ym178)
Molecular Formula
C21H24N4O2S
Molecular Weight
396.5  g/mol
InChI Key
PBAPPPCECJKMCM-IBGZPJMESA-N
FDA UNII
MVR3JL3B2V

Mirabegron
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.
Mirabegron is a beta3-Adrenergic Agonist. The mechanism of action of mirabegron is as an Adrenergic beta3-Agonist, and Cytochrome P450 2D6 Inhibitor, and Cytochrome P450 3A Inhibitor, and P-Glycoprotein Inhibitor.
1 2D Structure

Mirabegron

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(2-amino-1,3-thiazol-4-yl)-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]acetamide
2.1.2 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
2.1.3 InChI Key
PBAPPPCECJKMCM-IBGZPJMESA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)C(CNCCC2=CC=C(C=C2)NC(=O)CC3=CSC(=N3)N)O
2.1.5 Isomeric SMILES
C1=CC=C(C=C1)[C@H](CNCCC2=CC=C(C=C2)NC(=O)CC3=CSC(=N3)N)O
2.2 Other Identifiers
2.2.1 UNII
MVR3JL3B2V
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(2-aminothiazol-4-yl)-4'-(2-((2-hydroxy-2-phenylethyl)amino)ethyl)acetanilide

2. Betanis

3. Betmiga

4. Ym 178

5. Ym-178

2.3.2 Depositor-Supplied Synonyms

1. 223673-61-8

2. Myrbetriq

3. Betanis

4. Betmiga

5. Ym178

6. Mirabegron (ym178)

7. Ym-178

8. Ym 178

9. 2-(2-amino-1,3-thiazol-4-yl)-n-[4-(2-{[(2r)-2-hydroxy-2-phenylethyl]amino}ethyl)phenyl]acetamide

10. Mvr3jl3b2v

11. Chebi:65349

12. 2-amino-n-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-4-thiazoleacetamide

13. (r)-2-(2-aminothiazol-4-yl)-n-(4-(2-((2-hydroxy-2-phenylethyl)amino)ethyl)phenyl)acetamide

14. 4-thiazoleacetamide, 2-amino-n-(4-(2-(((2r)-2-hydroxy-2-phenylethyl)amino)ethyl)phenyl)-

15. Myrbetriq (tn)

16. 2-(2-amino-1,3-thiazol-4-yl)-n-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]acetamide

17. 2-(2-azanyl-1,3-thiazol-4-yl)-n-[4-[2-[[(2r)-2-oxidanyl-2-phenyl-ethyl]amino]ethyl]phenyl]ethanamide

18. Mirabegron [usan:inn]

19. Unii-mvr3jl3b2v

20. 2-(2-amino-1,3-thiazol-4-yl)-n-(4-(2-(((2r)-2-hydroxy-2-phenylethyl)amino)ethyl)phenyl)acetamide

21. Mirabegron [mi]

22. Mirabegron [inn]

23. Mirabegron [jan]

24. Mirabegron (usan/jan)

25. Mirabegron [usan]

26. Mirabegron [vandf]

27. Mirabegron [mart.]

28. Mirabegron [who-dd]

29. N-(4-(2-(2-hydroxy-2-phenylethylamino)ethyl)phenyl)-2-(2-aminothiazol-4-yl)acetamide

30. Schembl904788

31. Gtpl7445

32. Chembl2095212

33. Mirabegron [orange Book]

34. Amy1800

35. Dtxsid101021648

36. Hms3714i09

37. Hms3885m16

38. 2-(2-amino-1,3-thiazol-4-yl)-n-(4-{2-[(2-hydroxy-2-phenylethyl)amino]ethyl}phenyl)acetamide

39. Ex-a1050

40. Zinc1996784

41. Mfcd11100356

42. S4009

43. Akos016340341

44. Ccg-268611

45. Cs-0915

46. Db08893

47. Ks-1398

48. 2-(2-aminothiazol-4-yl)-4'-(2-((2-hydroxy-2-phenylethyl)amino)ethyl)acetanilide

49. Ncgc00386239-01

50. Hy-14773

51. Sw220301-1

52. D09535

53. Ab01565808_02

54. A816162

55. Ar-270/43507997

56. Q3702534

57. (r)-2-(2-aminothiazol-4-yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetanilide

58. (r)-2-(2-aminothiazol-4-yl)-4-{2-[(2-hydroxy-2-phenylethyl)amino]ethyl}acetanilide

59. (r)-2-(2-aminothiazol-4-yl)-n-(4-(2-(2-hydroxy-2-phenylethylamino)ethyl)phenyl)acetamide

60. 2-(2-aminothiazol-4-yl)-n-(4-(2-(((2r)-2-hydroxy-2-phenylethyl)amino)ethyl)phenyl)acetamide

61. H6u

62. Ym 178;2-(2-aminothiazol-4-yl)-n-[4-[2-[[(2r)-2-hydroxy-2-phenyl-ethyl]amino]ethyl]phenyl]acetamide

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 396.5 g/mol
Molecular Formula C21H24N4O2S
XLogP32.1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Exact Mass396.16199719 g/mol
Monoisotopic Mass396.16199719 g/mol
Topological Polar Surface Area129 Ų
Heavy Atom Count28
Formal Charge0
Complexity467
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameMyrbetriq
PubMed HealthMirabegron (Oral route)
Drug LabelMirabegron is a beta-3 adrenergic agonist. The chemical name is 2-(2-aminothiazol-4-yl)-N-[4-(2-{[(2R)-2-hydroxy-2-phenylethyl]amino}ethyl)phenyl]acetamide having an empirical formula of C21H24N4O2S and a molecular weight of 396.51. The structural fo...
Active IngredientMirabegron
Dosage FormTablet, extended release
RouteOral
Strength25mg; 50mg
Market StatusPrescription
CompanyApgdi

2 of 2  
Drug NameMyrbetriq
PubMed HealthMirabegron (Oral route)
Drug LabelMirabegron is a beta-3 adrenergic agonist. The chemical name is 2-(2-aminothiazol-4-yl)-N-[4-(2-{[(2R)-2-hydroxy-2-phenylethyl]amino}ethyl)phenyl]acetamide having an empirical formula of C21H24N4O2S and a molecular weight of 396.51. The structural fo...
Active IngredientMirabegron
Dosage FormTablet, extended release
RouteOral
Strength25mg; 50mg
Market StatusPrescription
CompanyApgdi

4.2 Drug Indication

Mirabegron is indicated for the treatment of overactive bladder (OAB) - with symptoms of urge urinary incontinence, urgency, and urinary frequency - either alone or in combination with [solifenacin]. It is also indicated for the treatment of neurogenic detrusor overactivity (NDO) in pediatric patients 3 years of age and older and weighing 35kg or more.


Symptomatic treatment of urgency.

Increased micturition frequency and / or urgency incontinence as may occur in adult patients with overactive-bladder syndrome.


Treatment of idiopathic overactive bladder


Treatment of neurogenic detrusor overactivity


5 Pharmacology and Biochemistry
5.1 Pharmacology

Mirabegron exerts its pharmacologic effects by forcing bladder smooth muscle to relax, thereby expanding its capacity and relieving urgency. Mirabegron does not appear to adversely affect the mean maximum flow rate or mean detrusor pressure at maximum flow rate in patients with lower urinary tract symptoms and bladder outlet obstruction (BOO), but should be used with in patients with BOO due to reports of significant urinary retention. Furthermore, mirabegron increases both blood pressure and heart rate in a dose-dependent manner and should therefore be used with caution in patients with severely uncontrolled hypertension or others for whom these increases may prove dangerous.


5.2 MeSH Pharmacological Classification

Adrenergic beta-3 Receptor Agonists

Compounds that bind to and activate ADRENERGIC BETA-3 RECEPTORS. (See all compounds classified as Adrenergic beta-3 Receptor Agonists.)


Urological Agents

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS. (See all compounds classified as Urological Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
MIRABEGRON
5.3.2 FDA UNII
MVR3JL3B2V
5.3.3 Pharmacological Classes
Cytochrome P450 2D6 Inhibitors [MoA]; Cytochrome P450 3A Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]; beta3-Adrenergic Agonist [EPC]; Adrenergic beta3-Agonists [MoA]
5.4 ATC Code

G04BD12


G - Genito urinary system and sex hormones

G04 - Urologicals

G04B - Urologicals

G04BD - Drugs for urinary frequency and incontinence

G04BD12 - Mirabegron


5.5 Absorption, Distribution and Excretion

Absorption

The absolute bioavailability of orally administered mirabegron ranges from 29% at a dose of 25 mg to 35% at a dose of 50 mg. The Tmax for the extended-release tablet and suspension formulations are approximately 3.5 hours, while the Tmax for the granule formulation is 4-5 hours. Both Cmax and AUC increase more than dose proportionally - an increase in dose from 50mg to 100mg results in a 2.9- and 2.6-fold increase in Cmax and AUC, respectively, whereas an increase from 50mg to 200mg results in a 8.4- and 6.5-fold increase in Cmax and AUC, respectively. Steady-state concentrations of mirabegron are achieved after approximately 7 days of once-daily administration.


Route of Elimination

Of a 160mg radiolabeled dose administered to healthy volunteers, approximately 55% of the radioactivity was recovered in the urine and 34% in the feces. Approximately 25% of unchanged mirabegron was recovered in the urine while 0% was recovered in the feces. Renal elimination is achieved primarily via active tubular secretion with some contribution by glomerular filtration.


Volume of Distribution

Following intravenous administration, mirabegron has an apparent steady-state volume of distribution (Vd) of 1670 L indicating extensive distribution.


Clearance

Total plasma clearance following intravenous administration is approximately 57 L/h, with renal clearance accounting for roughly 25% at approximately 13 L/h.


5.6 Metabolism/Metabolites

Mirabegron is extensively metabolized via a number of mechanisms, although unchanged parent drug is still the major circulating component following oral administration. Presumed metabolic pathways and their resultant metabolites include amide hydrolysis (M5, M16, M17), glucuronidation (mirabegron O-glucuronide, N-glucuronide, N-carbamoylglucuronide, M12), and secondary amine oxidation or dealkylation (M8, M9, M15), amongst others. The enzymes responsible for the oxidative metabolism of mirabegron are thought to be CYP3A4 and CYP2D6, while the UDP-glucuronosyltransferases responsible for conjugation reactions have been identified as UGT2B7, UGT1A3, and UGT1A8. Other enzymes that may be involved in the metabolism of mirabegron include butylcholinesterase and possibly alcohol dehydrogenase.


5.7 Biological Half-Life

The mean terminal elimination half-life of mirabegron in adults being treated for overactive bladder is approximately 50 hours. In pediatric patients receiving the granule formulation for the treatment of neurogenic detrusor overactivity, the mean terminal elimination half-life is approximately 26-31 hours.


5.8 Mechanism of Action

Mirabegron is a potent and selective agonist of beta-3 adrenergic receptors. The activation of beta-3 receptors relaxes detrusor smooth muscle during the storage phase of the urinary bladder fill-void cycle, which increases the bladder's storage capacity thereby alleviating feelings of urgency and frequency.


API Reference Price

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27-Jan-2022
24-Apr-2025
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Looking for 223673-61-8 / Mirabegron API manufacturers, exporters & distributors?

Mirabegron manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Mirabegron API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Mirabegron manufacturer or Mirabegron supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Mirabegron manufacturer or Mirabegron supplier.

PharmaCompass also assists you with knowing the Mirabegron API Price utilized in the formulation of products. Mirabegron API Price is not always fixed or binding as the Mirabegron Price is obtained through a variety of data sources. The Mirabegron Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Mirabegron

Synonyms

223673-61-8, Myrbetriq, Betanis, Betmiga, Ym178, Mirabegron (ym178)

Cas Number

223673-61-8

Unique Ingredient Identifier (UNII)

MVR3JL3B2V

About Mirabegron

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.

Myrbetriq Manufacturers

A Myrbetriq manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Myrbetriq, including repackagers and relabelers. The FDA regulates Myrbetriq manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Myrbetriq API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Myrbetriq manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Myrbetriq Suppliers

A Myrbetriq supplier is an individual or a company that provides Myrbetriq active pharmaceutical ingredient (API) or Myrbetriq finished formulations upon request. The Myrbetriq suppliers may include Myrbetriq API manufacturers, exporters, distributors and traders.

click here to find a list of Myrbetriq suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Myrbetriq USDMF

A Myrbetriq DMF (Drug Master File) is a document detailing the whole manufacturing process of Myrbetriq active pharmaceutical ingredient (API) in detail. Different forms of Myrbetriq DMFs exist exist since differing nations have different regulations, such as Myrbetriq USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Myrbetriq DMF submitted to regulatory agencies in the US is known as a USDMF. Myrbetriq USDMF includes data on Myrbetriq's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Myrbetriq USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Myrbetriq suppliers with USDMF on PharmaCompass.

Myrbetriq KDMF

In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

Pharmaceutical companies submit a Myrbetriq Drug Master File in Korea (Myrbetriq KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of Myrbetriq. The MFDS reviews the Myrbetriq KDMF as part of the drug registration process and uses the information provided in the Myrbetriq KDMF to evaluate the safety and efficacy of the drug.

After submitting a Myrbetriq KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their Myrbetriq API can apply through the Korea Drug Master File (KDMF).

click here to find a list of Myrbetriq suppliers with KDMF on PharmaCompass.

Myrbetriq CEP

A Myrbetriq CEP of the European Pharmacopoeia monograph is often referred to as a Myrbetriq Certificate of Suitability (COS). The purpose of a Myrbetriq CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Myrbetriq EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Myrbetriq to their clients by showing that a Myrbetriq CEP has been issued for it. The manufacturer submits a Myrbetriq CEP (COS) as part of the market authorization procedure, and it takes on the role of a Myrbetriq CEP holder for the record. Additionally, the data presented in the Myrbetriq CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Myrbetriq DMF.

A Myrbetriq CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Myrbetriq CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Myrbetriq suppliers with CEP (COS) on PharmaCompass.

Myrbetriq WC

A Myrbetriq written confirmation (Myrbetriq WC) is an official document issued by a regulatory agency to a Myrbetriq manufacturer, verifying that the manufacturing facility of a Myrbetriq active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Myrbetriq APIs or Myrbetriq finished pharmaceutical products to another nation, regulatory agencies frequently require a Myrbetriq WC (written confirmation) as part of the regulatory process.

click here to find a list of Myrbetriq suppliers with Written Confirmation (WC) on PharmaCompass.

Myrbetriq NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Myrbetriq as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Myrbetriq API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Myrbetriq as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Myrbetriq and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Myrbetriq NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Myrbetriq suppliers with NDC on PharmaCompass.

Myrbetriq GMP

Myrbetriq Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Myrbetriq GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Myrbetriq GMP manufacturer or Myrbetriq GMP API supplier for your needs.

Myrbetriq CoA

A Myrbetriq CoA (Certificate of Analysis) is a formal document that attests to Myrbetriq's compliance with Myrbetriq specifications and serves as a tool for batch-level quality control.

Myrbetriq CoA mostly includes findings from lab analyses of a specific batch. For each Myrbetriq CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Myrbetriq may be tested according to a variety of international standards, such as European Pharmacopoeia (Myrbetriq EP), Myrbetriq JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Myrbetriq USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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