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

General Information of Drug (ID: DR1482)
Drug Name
Silodosin
Synonyms
Silodosin; Silodosin-d6; Silodyx; Urorec; CUZ39LUY82; KAD 3213; KAD-3213; KMD 3213; KMD-3213; Q-102517; Rapaflo; Rapflo; (R)-1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide; 1-(3-hydroxypropyl)-5-[(2R)-2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]-2,3-dihydroindole-7-carboxamide; 160970-54-7; 160970-64-9; CHEMBL24778; UNII-CUZ39LUY82; Urief
Indication Prostatic hyperplasia [ICD11: GA90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 495.5 Topological Polar Surface Area 97
Heavy Atom Count 35 Rotatable Bond Count 13
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
5312125
PubChem SID
7849027 ; 7979683 ; 11056891 ; 12014894 ; 14810706 ; 14835413 ; 39341745 ; 57359519 ; 80176928 ; 92098546 ; 99299508 ; 103194366 ; 104046714 ; 109693099 ; 114157936 ; 126623000 ; 126665711 ; 128939931 ; 131300819 ; 134339064 ; 134340151 ; 134342132 ; 135252710 ; 135368407 ; 135650458 ; 135916576 ; 137248544 ; 142093997 ; 152258092 ; 152344280 ; 160646931 ; 162011672 ; 162172235 ; 162223757 ; 163884568 ; 164765008 ; 164777753 ; 172085148 ; 174527805 ; 175266679 ; 175427058 ; 175612190 ; 179150028 ; 184816547 ; 187071911 ; 198991703 ; 202821102 ; 211536181 ; 223392962 ; 223484371
ChEBI ID
CHEBI:135929
CAS Number
160970-54-7
TTD Drug ID
D0U0VU
Formula
C25H32F3N3O4
Canonical SMILES
CC(CC1=CC2=C(C(=C1)C(=O)N)N(CC2)CCCO)NCCOC3=CC=CC=C3OCC(F)(F)F
InChI
1S/C25H32F3N3O4/c1-17(30-8-12-34-21-5-2-3-6-22(21)35-16-25(26,27)28)13-18-14-19-7-10-31(9-4-11-32)23(19)20(15-18)24(29)33/h2-3,5-6,14-15,17,30,32H,4,7-13,16H2,1H3,(H2,29,33)/t17-/m1/s1
InChIKey
PNCPYILNMDWPEY-QGZVFWFLSA-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
KMD-3241 DM001317
9891871
Oxidation - Dehydrogenation 1 [4]
KMD-3289 DM001322 N. A. Oxidation - Dealkylation 1 [4]
KMD-3293 DM001321
91799753
Oxidation - Dehydrogenation 1 [4]
Silodosin glucuronide DM001320
72998182
Conjugation - Glucuronidation 1 [4]
Silodosin gluosylated metabolite DM001325 N. A. Conjugation - Glucuronidation 1 [4]
Silodosin hydroxylated metabolite DM001326 N. A. Oxidation - Hydroxylation 1 [4]
Silodosin N-dealkylated metabolite DM001323
22594065
Oxidation - N-Dealkylation 1 [4]
Silodosin sulfated metabolite DM001324 N. A. Conjugation - Sulfation 1 [4]
KMD-3241 glucuronide DM001319 N. A. Conjugation - Glucuronidation 2 [4]
KMD-3295 DM001318
91800092
Oxidation - Oxidation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002256 Silodosin KMD-3241 Oxidation - Dehydrogenation ADH1A ... [4]
MR002257 Silodosin Silodosin glucuronide Conjugation - Glucuronidation UGT2B7 [4]
MR002258 Silodosin KMD-3293 Oxidation - Dehydrogenation ADH1A ... [4]
MR002259 Silodosin KMD-3289 Oxidation - Dealkylation Unclear [4]
MR002260 Silodosin Silodosin N-dealkylated metabolite Oxidation - N-Dealkylation Unclear [4]
MR002261 Silodosin Silodosin sulfated metabolite Conjugation - Sulfation Unclear [4]
MR002262 Silodosin Silodosin gluosylated metabolite Conjugation - Glucuronidation Unclear [4]
MR002263 Silodosin Silodosin hydroxylated metabolite Oxidation - Hydroxylation Unclear [4]
MR002254 KMD-3241 KMD-3295 Oxidation - Oxidation CYP3A4 [4]
MR002255 KMD-3241 KMD-3241 glucuronide Conjugation - Glucuronidation UGT2B7 [4]
⏷ 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
Alcohol dehydrogenase class-I alpha (ADH1A) DME0127 Homo sapiens
ADH1A_HUMAN
1.1.1.1
[2]
Aldehyde dehydrogenase 2 (ALDH2) DME0077 Homo sapiens
ALDH2_HUMAN
1.2.1.3
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
References
1 Silodosin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetics and disposition of silodosin (KMD-3213). Yakugaku Zasshi. 2006 Mar;126 Spec no.:237-45.
3 Silodosin for benign prostatic hyperplasia. Ann Pharmacother. 2010 Feb;44(2):302-10.
4 In vivo metabolic investigation of silodosin using UHPLC-QTOF-MS/MS and in silico toxicological screening of its metabolites J Mass Spectrom. 2016 Oct;51(10):867-882. doi: 10.1002/jms.3795.

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