Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1097)
Drug Name
Mirabegron
Synonyms
Mirabegron; Mirabegron (YM178); Mirabegron [USAN:INN]; Myrbetriq; Myrbetriq (TN); YM 178; YM-178; mirabegron-ym178; Betanis; Betmiga; MVR3JL3B2V; (R)-2-(2-aminothiazol-4-yl)-N-(4-(2-((2-hydroxy-2-phenylethyl)amino)ethyl)phenyl)acetamide; 2-(2-amino-1,3-thiazol-4-yl)-N-[4-(2-{[(2R)-2-hydroxy-2-phenylethyl]amino}ethyl)phenyl]acetamide; 2-Amino-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-4-thiazoleacetamide; 223673-61-8; CHEBI:65349; UNII-MVR3JL3B2V; YM178
Indication Overactive bladder [ICD11: GC50] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 396.5 Topological Polar Surface Area 129
Heavy Atom Count 28 Rotatable Bond Count 9
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
9865528
PubChem SID
14830284 ; 15100038 ; 24157536 ; 45287794 ; 80776075 ; 96026215 ; 104179241 ; 131305973 ; 135262850 ; 135264045 ; 137204503 ; 141480260 ; 152258601 ; 160644771 ; 160647435 ; 160708387 ; 164178021 ; 164230555 ; 164763064 ; 172914174 ; 175267526 ; 175427137 ; 178104017 ; 186007037 ; 187072486 ; 188932513 ; 218903013 ; 223541479 ; 223664787 ; 223701034 ; 223917501 ; 227170942 ; 242060285 ; 248359277 ; 249867219 ; 251963956 ; 251971077 ; 252160992 ; 252227885 ; 252448538 ; 252553766
ChEBI ID
ChEBI:65349
CAS Number
223673-61-8
TTD Drug ID
D0X5UN
Formula
C21H24N4O2S
Canonical SMILES
C1=CC=C(C=C1)C(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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Mirabegron M11 metabolite DM004452
91810672
Conjugation - O-glucuronidation 1 [4]
Mirabegron M12 metabolite DM004454
91810673
Multi-steps Reaction - Glucuronidation; oxidation 1 [4]
Mirabegron M13 metabolite DM004453
91810674
Conjugation - Glucuronidation 1 [4]
Mirabegron M14 metabolite DM004450
91810675
Conjugation - N-glucuronidation 1 [4]
Mirabegron M15 metabolite DM004451
91810676
Multi-steps Reaction - N-oxidation; glucuronidation 1 [2]
Mirabegron M16 metabolite DM004447
52953008
Oxidation - Amide Hydrolyzation 1 [2]
Mirabegron M8 metabolite DM004445
62799987
Multi-steps Reaction - Carboxylic acid formation; dealkylation 1 [2]
Mirabegron M17 metabolite DM004448 N. A. Conjugation - Glucuronidation 2 [2]
Mirabegron M5 metabolite DM004449 N. A. Unclear 2 [2]
Mirabegron M9 metabolite DM004446
2018
Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004775 Mirabegron Mirabegron M8 metabolite Multi-steps Reaction - Carboxylic acid formation; dealkylation Unclear [2]
MR004777 Mirabegron Mirabegron M16 metabolite Oxidation - Amide Hydrolyzation BCHE [2]
MR004780 Mirabegron Mirabegron M14 metabolite Conjugation - N-glucuronidation UGT1A8 [4]
MR004781 Mirabegron Mirabegron M15 metabolite Multi-steps Reaction - N-oxidation; glucuronidation Unclear [2]
MR004782 Mirabegron Mirabegron M11 metabolite Conjugation - O-glucuronidation UGT2B7 [4]
MR004783 Mirabegron Mirabegron M13 metabolite Conjugation - Glucuronidation UGT1A3 [4]
MR004784 Mirabegron Mirabegron M12 metabolite Multi-steps Reaction - Glucuronidation; oxidation Unclear [4]
MR004778 Mirabegron M16 metabolite Mirabegron M17 metabolite Conjugation - Glucuronidation Unclear [2]
MR004779 Mirabegron M16 metabolite Mirabegron M5 metabolite Unclear Unclear [2]
MR004776 Mirabegron M8 metabolite Mirabegron M9 metabolite Unclear Unclear [2]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Butyrylcholine esterase (BCHE) DME0069 Homo sapiens
CHLE_HUMAN
3.1.1.8
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[4]
⏷ Show the Full List of 6  DME(s)
References
1 Mirabegron was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Absorption, metabolism and excretion of [(14)C]mirabegron (YM178), a potent and selective (3)-adrenoceptor agonist, after oral administration to healthy male volunteers
3 Role of cytochrome p450 isoenzymes 3A and 2D6 in the in vivo metabolism of mirabegron, a beta-3-adrenoceptor agonist. Clin Drug Investig. 2013 Jun;33(6):429-40.
4 Identification of Uridine 5'-Diphosphate-Glucuronosyltransferases Responsible for the Glucuronidation of Mirabegron, a Potent and Selective (3)-Adrenoceptor Agonist, in Human Liver Microsomes

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