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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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