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

General Information of Drug (ID: DR0542)
Drug Name
Doxazosin
Synonyms
Doxazosin [INN:BAN]; Doxazosina; Doxazosina [Spanish]; Doxazosine; Doxazosine [French]; Doxazosinum; Doxazosinum [Latin]; RUZYUOTYCVRMRZ-UHFFFAOYSA-N; UK 33274; doxazosin; 1-(4-Amino-6,7-Dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcarbonyl)piperazin; 1-(4-Amino-6,7-dimethoxy-2-chinazolinyl)-4-(2,3-dihydro-1,4-benzodioxixin-2-ylcarbonyl)piperazin; 2-[4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine; 74191-85-8; C23H25N5O5; CHEBI:4708
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 451.5 Topological Polar Surface Area 112
Heavy Atom Count 33 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
3157
PubChem SID
9184 ; 4407398 ; 7979127 ; 8152011 ; 11222167 ; 11466886 ; 11468006 ; 11486532 ; 14784191 ; 24278398 ; 29222299 ; 46506825 ; 47298998 ; 47298999 ; 47299000 ; 47670375 ; 47744452 ; 47744453 ; 47818609 ; 48415923 ; 49698667 ; 50011218 ; 50105246 ; 50308562 ; 56311128 ; 56311129 ; 56313874 ; 56464101 ; 57321640 ; 85209457 ; 85787347 ; 90341261 ; 90342475 ; 92241035 ; 92309056 ; 92710466 ; 96024570 ; 103194429 ; 103930616 ; 104170183 ; 104302690 ; 106228658 ; 117488203 ; 117498461 ; 121362602 ; 124671348 ; 124883381 ; 124883382 ; 124883384 ; 125357054
ChEBI ID
ChEBI:4708
CAS Number
74191-85-8
TTD Drug ID
D03MIR
Formula
C23H25N5O5
Canonical SMILES
COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4COC5=CC=CC=C5O4)N)OC
InChI
1S/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)
InChIKey
RUZYUOTYCVRMRZ-UHFFFAOYSA-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
Demethylated metabolite of Doxazosin DM006204 N. A. Oxidation - O-demethylation 1 [5]
Doxazosin Metabolite M2 DM006207 N. A. Unclear 1 [6]
Doxazosin Metabolite M3 DM006206 N. A. Unclear 1 [6]
Doxazosin Metabolite M5 DM006211 N. A. Unclear 1 [6]
Doxazosin Metabolite M6 DM006210 N. A. Unclear 1 [6]
Doxazosin Metabolite M7 DM002918
4122435
Unclear 1 [6]
Doxazosin Metabolite M8 DM002919
616267
Unclear 1 [6]
Hydroxylated metabolite of Doxazosin DM006205 N. A. Oxidation - Hydrolyzationn 1 [5]
N-glucuronide Doxazosin DM006212 N. A. Unclear 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006652 Doxazosin Demethylated metabolite of Doxazosin Oxidation - O-demethylation Unclear [5]
MR006653 Doxazosin Hydroxylated metabolite of Doxazosin Oxidation - Hydrolyzationn Unclear [5]
MR006654 Doxazosin Doxazosin Metabolite M3 Unclear Unclear [6]
MR006655 Doxazosin Doxazosin Metabolite M2 Unclear Unclear [6]
MR006656 Doxazosin Doxazosin Metabolite M8 Unclear Unclear [6]
MR006657 Doxazosin Doxazosin Metabolite M7 Unclear Unclear [6]
MR006658 Doxazosin Doxazosin Metabolite M6 Unclear Unclear [6]
MR006659 Doxazosin Doxazosin Metabolite M5 Unclear Unclear [6]
MR006660 Doxazosin N-glucuronide Doxazosin Unclear Unclear [6]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_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
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [4]
⏷ Show the Full List of 7  DME(s)
References
1 Doxazosin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Product monograph: CARDURA (Doxazosin mesylate).
3 Priapism induced by boceprevir-CYP3A4 inhibition and alpha-adrenergic blockade: case report. Clin Infect Dis. 2014 Jan;58(1):e35-8.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Pharmacokinetic overview of doxazosin
6 The metabolism and kinetics of doxazosin in man, mouse, rat and dog

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