Ramipril (CHEM016861)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:45:47 UTC
Update Date2026-04-13 20:29:04 UTC
Accession NumberCHEM016861
Identification
Common NameRamipril
ClassSmall Molecule
DescriptionRamipril is a prodrug belonging to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is metabolized to ramiprilat in the liver and, to a lesser extent, kidneys. Ramiprilat is a potent, competitive inhibitor of ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Ramipril may be used in the treatment of hypertension, congestive heart failure, nephropathy, and to reduce the rate of death, myocardial infarction and stroke in individuals at high risk of cardiovascular events.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S-(1(R*(r*)),2alpha,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acidChEBI
AltaceChEBI
RamiprilumChEBI
TritaceChEBI
(2S-(1(R*(r*)),2a,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylateGenerator
(2S-(1(R*(r*)),2a,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acidGenerator
(2S-(1(R*(r*)),2alpha,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylateGenerator
(2S-(1(R*(r*)),2α,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylateGenerator
(2S-(1(R*(r*)),2α,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acidGenerator
Almirall brand OF ramiprilHMDB
DelixHMDB
Hoechst brand OF ramiprilHMDB
Monarch brand OF ramiprilHMDB
ZabienHMDB
Aventis brand OF ramiprilHMDB
CaraselHMDB
HOE 498HMDB
HOE-498HMDB
TriatecHMDB
VesdilHMDB
Astra brand OF ramiprilHMDB
Promed brand OF ramiprilHMDB
AcovilHMDB
AstraZeneca brand OF ramiprilHMDB
Aventis pharma brand OF ramiprilHMDB
RamaceHMDB
Chemical FormulaC23H32N2O5
Average Molecular Mass416.511 g/mol
Monoisotopic Mass416.231 g/mol
CAS Registry Number87333-19-5
IUPAC Name(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid
Traditional Nameramipril
SMILES[H][C@@]12CCC[C@]1([H])N([C@@H](C2)C(O)=O)C(=O)[C@H](C)N[C@@H](CCC1=CC=CC=C1)C(=O)OCC
InChI IdentifierInChI=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
InChI KeyHDACQVRGBOVJII-JBDAPHQKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Alpha-amino acid ester
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Fatty acid ester
  • Aralkylamine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Fatty acyl
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Amino acid
  • Azacycle
  • Secondary aliphatic amine
  • Carboxylic acid
  • Organoheterocyclic compound
  • Secondary amine
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP0.92ALOGPS
logP1.47ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity111.19 m³·mol⁻¹ChemAxon
Polarizability44.78 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9154000000-0fd268c0fd4553ce3ab0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-5111900000-7df272465d895b3cfd2bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-1897100000-b1c2f0fcf086f6260572Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-02ai-3951000000-05bdaffd016f2d5b5d42Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-3930000000-ea57777ac9a14b1e9083Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0300900000-971088f84d244b7183feSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-0792400000-eb2eba23ddd5b9b9b1ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0568900000-ddc98c0a9a0a339f0dd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053u-3982000000-245405250f246de18bfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r6-3910000000-a34aa1853535d9227376Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1019400000-6df2aca7d66607a7a4e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0i91-2529100000-4d27b82aeecd981101c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udj-3911000000-0756695a4b95e60fd11cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-0339700000-452e8e2b82c270cd994fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-1978200000-050e9a36f1e4e960836aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-5911000000-74a534a7b59ef1f2a03cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009700000-a71f2ed8451e5e6d162aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-1889000000-8f9e12a4e55869c7da6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-2931000000-820a55e837269565502bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00178
HMDB IDHMDB0014324
FooDB IDFDB009079
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRamipril
Chemspider ID4514937
ChEBI ID8774
PubChem Compound ID5362129
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Cacciapuoti F, Capasso A, Mirra G, De Nicola A, Minicucci F, Gentile S: Prevention of left ventricular hypertrophy by ACE-inhibitor, ramipril in comparison with calcium-channel antagonist, felodipine. Int J Cardiol. 1998 Jan 31;63(2):175-8.
2. Kleinert S: HOPE for cardiovascular disease prevention with ACE-inhibitor ramipril. Heart Outcomes Prevention Evaluation. Lancet. 1999 Sep 4;354(9181):841.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11095026
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11575208
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12076194
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12768220
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15110900
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16144510
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16734081
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=17004100
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17192135
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=17496463
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=17903031
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=20122169
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22799880
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23557551
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23713675
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23747952
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23842688
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23842829
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23951921
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=24048485
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=24090393
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=24191305
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=24397981
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=24435506
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=24452090
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=24509355