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

General Information of Drug (ID: DR2648)
Drug Name
Ramipril
Prodrug Info Ramipril is the prodrug of Ramiprilat
Synonyms
Ramipril; Ramace; Ramipril (USP/INN); Ramipril [USAN:INN:BAN]; Ramiprilum; Ramiprilum [Latin]; Triatec; Tritace; Tritace (TN); Vesdil; Zabien; Acovil; Almirall Brand of Ramipril; Altace; Altace (TN); Astra Brand of Ramipril; AstraZeneca Brand of Ramipril; Aventis Brand of Ramipril; Aventis Pharma Brand of Ramipril; Carasel; Cardace; Hoechst Brand of Ramipril; Hypren; Hytren; Lostapres; Monarch Brand of Ramipril; Naprix; Pramace; Pramace (discontinued); Promed Brand of (2 S ,3 aS,6 aS)-1[(S)-N-[(S)-1-Carboxy-3-phenylpropyl] alanyl] octahydrocyclopenta [ b ]pyrrole-2-carboxylic acid, 1-ethyl ester; (2S,3aS,6aS)-1-((S)-2-((S)-1-ethoxy-1-oxo-4-phenylbutan-2-ylamino)propanoyl) octahydrocyclopenta[b]pyrrole-2-carboxylic acid; (2S,3aS,6aS)-1-((S)-N-((S)-1-Carboxy-3-phenylpropyl)alanyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid, 1-ethyl ester; (2S,3aS,6aS)-1-((S)-N-((S)-1-Ethoxycarbonyl-3-phenylpropyl)alanyl)octahydrocyclopenta(b)pyrrol-2-carbonsaeure; (2S,3aS,6aS)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid; (2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-ethoxycarbonyl-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid; (2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name); (2S-(1(R*(R*)),2alpha,3abeta,6abeta))-1-(2-((1-(Ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid; (2s,3as,6as)-1((s)-n-((s)-1-carboxy-3-phenylpropyl)alanyl)octahydrocyclopenta(b)pyrrole-2-carboxylic; (2s,3as,6as)-1-((s)-2-((s)-1-ethoxy-1-oxo-4-phenylbutan-2-ylamino)propanoyl)-octahydrocyclopenta[b]p; (2s,3as,6as)-1-[(s)-2-((s)-1-ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-cyclopenta[b]; Delix; HOE 498; HOE498; Hoe-498; N-(1S-carboethoxy-3-phenylpropyl)-S-alanyl-cis,endo-2-azabicyclo[3.3.0]octane-3S-carboxylic Acid; Quark; Ramipro, Tritace, Altace, Prilace, Ramipril; [2S,3aS,6aS]-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid; [2s,3as,6as]-1-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopen
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 416.5 Topological Polar Surface Area 95.9
Heavy Atom Count 30 Rotatable Bond Count 10
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5362129
PubChem SID
7847487 ; 7980483 ; 11364914 ; 11367476 ; 11370038 ; 11372946 ; 11374996 ; 11378208 ; 11491609 ; 11493083 ; 11495772 ; 11528643 ; 11533329 ; 12012944 ; 14904601 ; 14929182 ; 17184929 ; 24724586 ; 26612834 ; 26719894 ; 39384402 ; 46386770 ; 46506390 ; 47721705 ; 48244488 ; 48416510 ; 49664947 ; 49681721 ; 50122729 ; 53787042 ; 57362088 ; 76755897 ; 81093204 ; 85279379 ; 92308080 ; 92308314 ; 92309227 ; 92712074 ; 93166961 ; 103339774 ; 103984211 ; 104170125 ; 104179208 ; 104253384 ; 114149719 ; 117664421 ; 121362522 ; 124658840 ; 124757502 ; 124799903
ChEBI ID
ChEBI:8774
CAS Number
87333-19-5
TTD Drug ID
D01STB
Formula
C23H32N2O5
Canonical SMILES
CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2C3CCCC3CC2C(=O)O
InChI
1S/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1
InChIKey
HDACQVRGBOVJII-JBDAPHQKSA-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
Diketopiperazine acid DM017961 N. A. Unclear - Unclear 1 [3]
Diketopiperazine ester DM017962 N. A. Unclear - Unclear 1 [3]
Ramipril glucuronide DM017963 N. A. Unclear - Unclear 1 [4]
Ramiprilat DM015459
5464096
Hydrolysis - De-esterification 1 [5]
Ramiprilat glucuronide DM017960 N. A. Unclear - Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009700 Ramipril Ramiprilat Hydrolysis - De-esterification CES [5]
MR009702 Ramipril Diketopiperazine acid Unclear - Unclear Unclear [3]
MR009703 Ramipril Diketopiperazine ester Unclear - Unclear Unclear [3]
MR009704 Ramipril Ramipril glucuronide Unclear - Unclear Unclear [4]
MR009701 Ramiprilat Ramiprilat glucuronide Unclear - Unclear Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [2]
⏷ Show the Full List of 6  DME(s)
References
1 Atorvastatin Calcium was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
3 LABEL: RAMIPRIL
4 Pharmacokinetics and pharmacodynamics of ramipril and piretanide administered alone and in combination
5 The analysis of ramipril/ramiprilat concentration in human serum with liquid chromatography-tandem mass spectrometry - interpretation of high concentrations for the purposes of forensic toxicology

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