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

General Information of Drug (ID: DR2415)
Drug Name
Quinapril
Prodrug Info Quinapril is the prodrug of Quinaprilat
Synonyms
Quinaprilum; QUINAPRIL HCL; Quinaprilum [Latin]; Accupril (TN); Quinapril [INN:BAN]; Quinapril (USP/INN); [3S-[2[R*(R*)],3R*]]-2-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-Isoquinolinecarboxylic acid; (3S)-2-(N-{(1S)-1-[(ethyloxy)carbonyl]-3-phenylpropyl}-L-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; (3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid; (3S)-2-{(2S)-2-[(1S)-1-ethoxycarbonyl-3-phenylpropylamino]propanoyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; (3S)-2-{N-((S)-1-Ethoxycarbonyl-3-phenylpropyl)-L-alanyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; Ectren; Koretic
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 438.5 Topological Polar Surface Area 95.9
Heavy Atom Count 32 Rotatable Bond Count 10
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
54892
PubChem SID
9602 ; 7980446 ; 8145927 ; 8149893 ; 8183841 ; 11335885 ; 11361124 ; 11364491 ; 11367053 ; 11369615 ; 11372621 ; 11374133 ; 11377777 ; 11462096 ; 11484485 ; 11488641 ; 11491366 ; 11492542 ; 11495411 ; 14759220 ; 14881354 ; 17397841 ; 34718828 ; 46506309 ; 47589015 ; 48035134 ; 48259244 ; 48416506 ; 49835285 ; 50065313 ; 50113005 ; 50113006 ; 50744269 ; 85787397 ; 92309221 ; 93166955 ; 99301798 ; 103590286 ; 104306102 ; 117576967 ; 121264493 ; 124893433 ; 126683866 ; 127334979 ; 127334980 ; 127334981 ; 127334982 ; 127334983 ; 127334984 ; 127334985
ChEBI ID
ChEBI:8713
CAS Number
85441-61-8
TTD Drug ID
D0I7SZ
Formula
C25H30N2O5
Canonical SMILES
CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CC3=CC=CC=C3CC2C(=O)O
InChI
1S/C25H30N2O5/c1-3-32-25(31)21(14-13-18-9-5-4-6-10-18)26-17(2)23(28)27-16-20-12-8-7-11-19(20)15-22(27)24(29)30/h4-12,17,21-22,26H,3,13-16H2,1-2H3,(H,29,30)/t17-,21-,22-/m0/s1
InChIKey
JSDRRTOADPPCHY-HSQYWUDLSA-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
Quinapril metabolite PD109488 DM003035 N. A. Other reaction - Dehydration 1 [4]
Quinaprilat DM003034
107994
Other reaction - Deesterification 1 [5]
Quinapril metabolite PD113413 DM003036 N. A. Oxidation - O-Deethylation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002790 Quinapril Quinaprilat Other reaction - Deesterification CES1 [5]
MR002791 Quinapril Quinapril metabolite PD109488 Other reaction - Dehydration Unclear [4]
MR002789 Quinapril metabolite PD109488 Quinapril metabolite PD113413 Oxidation - O-Deethylation Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1439 Marvinbryantia formatexigens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1462 Salmonella enterica Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1467 Subdoligranulum variabile Not Available Not Available [3]
⏷ Show the Full List of 24  DME(s)
References
1 Quinapril Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of carboxylesterase 1 c.428G?>?A single nucleotide variation on the pharmacokinetics of quinapril and enalapril Br J Clin Pharmacol. 2015 Nov;80(5):1131-8. doi: 10.1111/bcp.12667.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Quinapril: a new second-generation ACE inhibitor
5 Simultaneous determination of quinapril and its active metabolite quinaprilat in human plasma using high-performance liquid chromatography with ultraviolet detection

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