Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01254)
Name
Mirabegron
Synonyms    Click to Show/Hide the Synonyms of This API
Mirabegron; 223673-61-8; Myrbetriq; Betanis; Betmiga; Mirabegron (YM178); YM 178; YM178; YM-178; UNII-MVR3JL3B2V; MVR3JL3B2V; CHEBI:65349; 2-Amino-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-4-thiazoleacetamide; 2-(2-amino-1,3-thiazol-4-yl)-N-[4-(2-{[(2R)-2-hydroxy-2-phenylethyl]amino}ethyl)phenyl]acetamide; Myrbetriq (TN); Mirabegron [USAN:INN]; 2-(2-amino-1,3-thiazol-4-yl)-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]acetamide; Mirabegron (USAN/JAN); SCHEMBL904788; GTPL7445; CHEMBL2095212; AMY1800; HMS3714I09; HMS3885M16; EX-A1050; ZINC1996784; MFCD11100356; s4009; AKOS016340341; CCG-268611; CS-0915; DB08893; KS-1398; SB17018; (R)-2-(2-aminothiazol-4-yl)-N-(4-(2-((2-hydroxy-2-phenylethyl)amino)ethyl)phenyl)acetamide; 2-(2-Aminothiazol-4-yl)-4'-(2-((2-hydroxy-2-phenylethyl)amino)ethyl)acetanilide; N-(4-(2-(2-hydroxy-2-phenylethylamino)ethyl)phenyl)-2-(2-aminothiazol-4-yl)acetamide; NCGC00386239-01; HY-14773; SW220301-1; Y1125; D09535; W-5473; AB01565808_02; A816162; AR-270/43507997; Q3702534; (R)-2-(2-aminothiazol-4-yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetanilide; (R)-2-(2-aminothiazol-4-yl)-4-{2-[(2-hydroxy-2-phenylethyl)amino]ethyl}acetanilide; (R)-2-(2-aminothiazol-4-yl)-N-(4-(2-(2-hydroxy-2-phenylethylamino)ethyl)phenyl)acetamide; 4-Thiazoleacetamide, 2-amino-N-(4-(2-(((2R)-2-hydroxy-2-phenylethyl)amino)ethyl)phenyl)-; 2-(2-amino-4-thiazolyl)-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]acetamide; 2-(2-azanyl-1,3-thiazol-4-yl)-N-[4-[2-[[(2R)-2-oxidanyl-2-phenyl-ethyl]amino]ethyl]phenyl]ethanamide
Clinical Status
Approved
PubChem CID
9865528
Formula
C21H24N4O2S
Canonical SMILES
C1=CC=C(C=C1)[C@H](CNCCC2=CC=C(C=C2)NC(=O)CC3=CSC(=N3)N)O
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
InChIKey
PBAPPPCECJKMCM-IBGZPJMESA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=9865528"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 396.5 Topological Polar Surface Area 129
XlogP 2.1 Complexity 467
Heavy Atom Count 28 Rotatable Bond Count 9
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Mirabegron 8mg/ml extended release for suspension Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Acesulfame Potassium; Diluted Hydrochloric Acid; Ethylparaben; Hypromellose; Magnesium Stearate; Mannitol; Methylparaben; Silicon Dioxide; Simethicone; Sodium Polystyrene Sulfonate; Xanthan Gum
                   Dosage Form Extended Release For Suspension
                   Company Apgdi
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Simethicone DIG Info Opioid receptor mu (IC50 = 1.5 nM) [1]
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [2]
Ethylparaben DIG Info Estrogen receptor beta (EC50 = 1860 nM) [3]
Acesulfame DIG Info Carbonic anhydrase IX (Ki = 2400 nM) [4]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [5]
Hydrochloric acid DIG Info Carbonic anhydrase V (Ki = 156 nM) [6]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
          Mirabegron 25mg extended release tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated Hydroxytoluene; Hydroxypropyl Cellulose; Hypromellose; Magnesium Stearate; Polyethylene Glycol; Polyethylene Oxide; Yellow Ferric Oxide; Red Ferric Oxide
                   Dosage Form Extended Release Tablet
                   Company Apgdi
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [9]
Hydroxypropyl cellulose DIG Info Mephenytoin 4-hydroxylase (EC50 = 89.5 uM) [7]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [10]
          Mirabegron 50mg extended release tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated Hydroxytoluene; Hydroxypropyl Cellulose; Hypromellose; Magnesium Stearate; Polyethylene Glycol; Polyethylene Oxide; Yellow Ferric Oxide
                   Dosage Form Extended Release Tablet
                   Company Apgdi
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [9]
Hydroxypropyl cellulose DIG Info Mephenytoin 4-hydroxylase (EC50 = 89.5 uM) [7]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [10]
References
1 From hit to lead. Combining two complementary methods for focused library design. Application to mu opiate ligands. J Med Chem. 2001 Oct 11; 44(21):3378-90.
2 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
3 Discovery of natural estrogen receptor modulators with structure-based virtual screening. Bioorg Med Chem Lett. 2013 Jun 1; 23(11):3329-33.
4 Sweet Binders: Carbonic Anhydrase IX in Complex with Sucralose. ACS Med Chem Lett. 2018 May 10; 9(7):657-661.
5 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
6 Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1; 14(21):5435-9.
7 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
8 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
9 Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem. 2009 Apr 15; 17(8):3207-11.
10 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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