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

General Information of Drug (ID: DR1530)
Drug Name
Tamsulosin
Synonyms
Tamsolusin; Tamsulosin [INN:BAN]; Tamsulosina; Tamsulosina [INN-Spanish]; Tamsulosine; Tamsulosine [INN-French]; Tamsulosinum; Tamsulosinum [INN-Latin]; YM-617; Flomax; Flomax (TN); Flowmax; TAMSULOSIN; (-)-Tamsulosin; (R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide; 106133-20-4; 5-[(2R)-2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide; 5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzenesulfonamide; CHEBI:9398; CHEMBL836; G3P28OML5I; UNII-G3P28OML5I
Indication Prostatic hyperplasia [ICD11: GA90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 408.5 Topological Polar Surface Area 108
Heavy Atom Count 28 Rotatable Bond Count 11
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
129211
PubChem SID
9334 ; 7978548 ; 10242264 ; 14855214 ; 14855215 ; 29308096 ; 46507763 ; 48416590 ; 49658919 ; 49881530 ; 50112696 ; 57342917 ; 77491402 ; 92309311 ; 93166419 ; 94568973 ; 96025245 ; 103219988 ; 103956570 ; 104369951 ; 117870725 ; 118048890 ; 124772213 ; 124893313 ; 126662035 ; 127253628 ; 127253629 ; 127253630 ; 127253631 ; 127253632 ; 127253633 ; 127253634 ; 127775697 ; 131293768 ; 131322925 ; 131549270 ; 134223415 ; 134337414 ; 135047731 ; 135651350 ; 137001370 ; 142769217 ; 143493354 ; 152164201 ; 152235887 ; 160826144 ; 160964050 ; 163092709 ; 163388355 ; 164786761
ChEBI ID
ChEBI:9398
CAS Number
106133-20-4
TTD Drug ID
D05MBZ
Formula
C20H28N2O5S
Canonical SMILES
CCOC1=CC=CC=C1OCCNC(C)CC2=CC(=C(C=C2)OC)S(=O)(=O)N
InChI
1S/C20H28N2O5S/c1-4-26-17-7-5-6-8-18(17)27-12-11-22-15(2)13-16-9-10-19(25-3)20(14-16)28(21,23)24/h5-10,14-15,22H,4,11-13H2,1-3H3,(H2,21,23,24)/t15-/m1/s1
InChIKey
DRHKJLXJIQTDTD-OAHLLOKOSA-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
Tamsulosin AM-1 metabolite DM000445 N. A. Oxidation - Oxidative Deamination 1 [4] , [5]
Tamsulosin M-1 metabolite DM000435 N. A. Oxidation - Deacetylation 1 [4] , [5]
Tamsulosin M-2 metabolite DM000443 N. A. Oxidation - Hydroxylation 1 [4] , [5]
Tamsulosin M-3 metabolite DM000438 N. A. Oxidation - Hydroxylation 1 [4] , [5]
Tamsulosin M-4 metabolite DM000441 N. A. Oxidation - Demethylation 1 [4] , [5]
Tamsulosin M-1-Glu metabolite DM000437
154731584
Conjugation - O-Glucuronidation 2 [5]
Tamsulosin M-1-Sul metabolite DM000436
154731599
Conjugation - Sulfation 2 [5]
Tamsulosin M-2-Glu metabolite DM000444 N. A. Conjugation - O-Glucuronidation 2 [5]
Tamsulosin M-3-Glu metabolite DM000440 N. A. Conjugation - O-Glucuronidation 2 [5]
Tamsulosin M-3-Sul metabolite DM000439 N. A. Conjugation - Sulfation 2 [5]
Tamsulosin M-4-Glu metabolite DM000442 N. A. Conjugation - O-Glucuronidation 2 [5]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003423 Tamsulosin Tamsulosin M-1 metabolite Oxidation - Deacetylation CYP3A4 [4], [5]
MR003424 Tamsulosin Tamsulosin M-3 metabolite Oxidation - Hydroxylation CYP2D6 [4], [5]
MR003425 Tamsulosin Tamsulosin M-4 metabolite Oxidation - Demethylation CYP2D6 [4], [5]
MR003426 Tamsulosin Tamsulosin M-2 metabolite Oxidation - Hydroxylation Unclear [4], [5]
MR003427 Tamsulosin Tamsulosin AM-1 metabolite Oxidation - Oxidative Deamination CYP3A4 [4], [5]
MR003417 Tamsulosin M-1 metabolite Tamsulosin M-1-Sul metabolite Conjugation - Sulfation Unclear [5]
MR003418 Tamsulosin M-1 metabolite Tamsulosin M-1-Glu metabolite Conjugation - O-Glucuronidation Unclear [5]
MR003422 Tamsulosin M-2 metabolite Tamsulosin M-2-Glu metabolite Conjugation - O-Glucuronidation Unclear [5]
MR003419 Tamsulosin M-3 metabolite Tamsulosin M-3-Sul metabolite Conjugation - Sulfation Unclear [5]
MR003420 Tamsulosin M-3 metabolite Tamsulosin M-3-Glu metabolite Conjugation - O-Glucuronidation Unclear [5]
MR003421 Tamsulosin M-4 metabolite Tamsulosin M-4-Glu metabolite Conjugation - O-Glucuronidation Unclear [5]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[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
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Tamsulosin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of cytochrome P450 isozymes involved in metabolism of the alpha1-adrenoceptor blocker tamsulosin in human liver microsomes. Xenobiotica. 1998 Oct;28(10):909-22.
3 Physiologically based pharmacokinetic (PBPK) modelling of tamsulosin related to CYP2D6*10 allele
4 Pharmacokinetics and plasma protein binding of tamsulosin hydrochloride in rats, dogs, and humans Drug Metab Dispos. 1998 Mar;26(3):240-5.
5 Absorption, metabolism and excretion of tamsulosin hydrochloride in man Xenobiotica. 1996 Jun;26(6):637-45. doi: 10.3109/00498259609046739.

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