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

General Information of Drug (ID: DR1330)
Drug Name
Prazosin
Synonyms
Prazocin; Prazosin [INN:BAN]; Prazosina; Prazosina [INN-Spanish]; Prazosine; Prazosine [INN-French]; Prazosinum; Prazosinum [INN-Latin]; Furazosin; Lentopres; Minipress; prazosin; (4-(4-Amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)(furan-2-yl)methanone; 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)piperazine; 19216-56-9; 2-(4-(2-Furoyl)piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline; C19H21N5O4; CHEMBL2; HSDB 3298; UNII-XM03YJ541D; [3H]-Prazosin
Indication Prostatic hyperplasia [ICD11: GA90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 383.4 Topological Polar Surface Area 107
Heavy Atom Count 28 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
4893
PubChem SID
9572 ; 841974 ; 4500854 ; 7980376 ; 8153011 ; 11112649 ; 11112650 ; 11113367 ; 11120245 ; 11120733 ; 11121221 ; 11121703 ; 11122183 ; 11335550 ; 11360789 ; 11362790 ; 11363716 ; 11365352 ; 11366278 ; 11367914 ; 11368840 ; 11370831 ; 11370832 ; 11371821 ; 11373515 ; 11374104 ; 11376076 ; 11377002 ; 11406810 ; 11461761 ; 11466975 ; 11468095 ; 11485033 ; 11486809 ; 11489105 ; 11490367 ; 11492298 ; 11494636 ; 14804776 ; 26751613 ; 26751614 ; 29223971 ; 46508594 ; 47364941 ; 47364942 ; 47588782 ; 47662032 ; 47662033 ; 47662034 ; 47662035
ChEBI ID
ChEBI:8364
CAS Number
19216-56-9
TTD Drug ID
D0WV3U
Formula
C19H21N5O4
Canonical SMILES
COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4=CC=CO4)N)OC
InChI
1S/C19H21N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22)
InChIKey
IENZQIKPVFGBNW-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
6-O-demethyl prazosin DM002920
90673655
Oxidation - O-Demethylation 1 [3]
7-O-demethyl prazosin DM002922
136498753
Oxidation - O-Demethylation 1 [3]
Doxazosin Metabolite M7 DM002918
4122435
Unclear 1 [4]
Doxazosin Metabolite M8 DM002919
616267
Unclear 1 [4]
Prazosin metabolite M1 DM002915 N. A. Unclear 1 [3]
Prazosin metabolite M15 DM002928 N. A. Unclear 1 [3]
Prazosin metabolite M16 DM002917 N. A. Unclear 1 [3]
Prazosin metabolite M2 DM002924 N. A. Unclear 1 [3]
Prazosin metabolite M5 DM002916
6603972
Unclear 1 [3]
Prazosin N-glucuronide DM002914
154731637
Conjugation - Glucuronidation 1 [3]
Prazosin 6-O-glucuronide DM002921
154731571
Conjugation - Glucuronidation 2 [3]
Prazosin 7-O-glucuronide DM002923
154731632
Conjugation - Glucuronidation 2 [3]
Prazosin metabolite M20 DM002926 N. A. Unclear 2 [3]
Prazosin metabolite M21 DM002927 N. A. Unclear 2 [3]
Prazosin metabolite M4 DM002929
154731613
Unclear 2 [3]
Prazosin metabolite M8 DM002925
154731575
Unclear 2 [3]
Prazosin metabolite M7 DM002930
154731614
Unclear 3 [3]
Prazosin metabolite M19 DM002931 N. A. Unclear 4 [3]
⏷ Show the Full List of 18  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002747 Prazosin Prazosin N-glucuronide Conjugation - Glucuronidation Unclear [3]
MR002748 Prazosin Prazosin metabolite M1 Unclear Unclear [3]
MR002749 Prazosin Prazosin metabolite M5 Unclear Unclear [3]
MR002750 Prazosin Prazosin metabolite M16 Unclear Unclear [3]
MR002751 Prazosin 2,4-diamino-6,7-dimethoxyquinazoline Unclear Unclear [4]
MR002752 Prazosin 2-(l-Piperazinyl)- 4-amino-6,7 - dimethoxyquinazoline Unclear Unclear [4]
MR002753 Prazosin 6-O-demethyl prazosin Oxidation - O-Demethylation Unclear [3]
MR002754 Prazosin 7-O-demethyl prazosin Oxidation - O-Demethylation Unclear [3]
MR002755 Prazosin Prazosin metabolite M2 Unclear Unclear [3]
MR002756 Prazosin Prazosin metabolite M15 Unclear Unclear [3]
MR002739 6-O-demethyl prazosin Prazosin 6-O-glucuronide Conjugation - Glucuronidation Unclear [3]
MR002740 7-O-demethyl prazosin Prazosin 7-O-glucuronide Conjugation - Glucuronidation Unclear [3]
MR002744 Prazosin metabolite M15 Prazosin metabolite M4 Unclear Unclear [3]
MR002741 Prazosin metabolite M2 Prazosin metabolite M8 Unclear Unclear [3]
MR002742 Prazosin metabolite M2 Prazosin metabolite M20 Unclear Unclear [3]
MR002743 Prazosin metabolite M2 Prazosin metabolite M21 Unclear Unclear [3]
MR002745 Prazosin metabolite M4 Prazosin metabolite M7 Unclear Unclear [3]
MR002746 Prazosin metabolite M7 Prazosin metabolite M19 Unclear Unclear [3]
⏷ Show the Full List of 18 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
References
1 Prazosin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Role of adrenoceptor-linked signaling pathways in the regulation of CYP1A1 gene expression. Biochem Pharmacol. 2005 Jan 15;69(2):277-87.
3 Metabolism of prazosin in rat and characterization of metabolites in plasma, urine, faeces, brain and bile using liquid chromatography/mass spectrometry (LC/MS) Xenobiotica. 2008 May;38(5):540-58. doi: 10.1080/00498250802001826.
4 DrugBank(Pharmacology-Metabolism)Prazosin

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