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

General Information of Drug (ID: DR0573)
Drug Name
Enalapril
Prodrug Info Enalapril is the prodrug of Enalaprilat
Synonyms
Enalapril (INN); Enalapril (TN); Enalapril Richet; Enalapril [INN:BAN]; Enalapril maleate; Enalaprila; Enalaprila [INN-Spanish]; Enalaprilum; Enalaprilum [INN-Latin]; Epaned; GBXSMTUPTTWBMN-XIRDDKMYSA-N; Vasotec; enalapril; 1-(N-((S)-1-Carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl ester; 69PN84IO1A; 75847-73-3; C20H28N2O5; CHEBI:4784; CHEMBL578; DSSTox_CID_2982; DSSTox_GSID_22982; DSSTox_RID_76817; L-Proline, N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-; NCGC00021569-04; UNII-69PN84IO1A
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 376.4 Topological Polar Surface Area 95.9
Heavy Atom Count 27 Rotatable Bond Count 10
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5388962
PubChem SID
9191 ; 7979157 ; 11112847 ; 11335583 ; 11360822 ; 11364201 ; 11366763 ; 11369325 ; 11372634 ; 11373494 ; 11377487 ; 11461794 ; 11485085 ; 11489271 ; 11491293 ; 11491823 ; 11495121 ; 14779899 ; 14877707 ; 17185069 ; 29214998 ; 39404326 ; 46507920 ; 47365119 ; 47588933 ; 47588934 ; 47810682 ; 48110391 ; 48184936 ; 48415941 ; 49698433 ; 50073899 ; 50103938 ; 50103939 ; 53787340 ; 57362754 ; 75931775 ; 89736144 ; 92309084 ; 93166909 ; 96024588 ; 99313640 ; 103179319 ; 103928457 ; 113955320 ; 127931871 ; 134358398 ; 135012773 ; 137100856 ; 140098266
ChEBI ID
CHEBI:4784
CAS Number
75847-73-3
TTD Drug ID
D00SEB
Formula
C20H28N2O5
Canonical SMILES
CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CCCC2C(=O)O
InChI
1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1
InChIKey
GBXSMTUPTTWBMN-XIRDDKMYSA-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
Enalapril demethylation DM006390 N. A. Oxidation - N-Demethylation 1 [2]
Enalaprilat DM006389 N. A. Oxidation - Hydrolyzationn 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006865 Enalapril Enalaprilat Oxidation - Hydrolyzationn CES1 [2]
MR006866 Enalapril Enalapril demethylation Oxidation - N-Demethylation CYP3A4 [2]
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]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Dipeptidase (pepV) DME1002 Lactococcus lactis
Q84BU9_LACLH
3.4.13.-
[4]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [5]
⏷ Show the Full List of 6  DME(s)
References
1 Hydralazine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Absorption and cleavage of enalapril, a carboxyl ester prodrug, in the rat intestine: in vitro, in situ intestinal perfusion and portal vein cannulation models. Biopharm Drug Dispos. 2015 Sep;36(6):385-397.
3 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
4 Characterization and kinetic analysis of enzyme-substrate recognition by three recombinant lactococcal PepVs. Arch Biochem Biophys. 2006 Oct 15;454(2):137-45.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.