Perindopril (CHEM016827)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:44:50 UTC
Update Date2016-11-09 01:15:28 UTC
Accession NumberCHEM016827
Identification
Common NamePerindopril
ClassSmall Molecule
DescriptionPerindopril is a nonsulfhydryl prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly metabolized in the liver to perindoprilat, its active metabolite, following oral administration. Perindoprilat 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). Perindopril may be used to treat mild to moderate essential hypertension, mild to moderate congestive heart failure, and to reduce the cardiovascular risk of individuals with hypertension or post-myocardial infarction and stable coronary disease.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,3AS,7as)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]octahydro-1H-indole-2-carboxylic acidChEBI
PerindoprilumChEBI
(2S,3AS,7as)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]octahydro-1H-indole-2-carboxylateGenerator
Perindopril erbumineHMDB
Erbumine, perindoprilHMDB
PerstariumHMDB
PirindoprilHMDB
Chemical FormulaC19H32N2O5
Average Molecular Mass368.468 g/mol
Monoisotopic Mass368.231 g/mol
CAS Registry Number82834-16-0
IUPAC Name(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid
Traditional Nameperindopril
SMILES[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O
InChI IdentifierInChI=1S/C19H32N2O5/c1-4-8-14(19(25)26-5-2)20-12(3)17(22)21-15-10-7-6-9-13(15)11-16(21)18(23)24/h12-16,20H,4-11H2,1-3H3,(H,23,24)/t12-,13-,14-,15-,16-/m0/s1
InChI KeyIPVQLZZIHOAWMC-QXKUPLGCSA-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
  • Indole or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • 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
  • Organopnictogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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 Solubility1.22 g/LALOGPS
logP0.56ALOGPS
logP0.63ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.79ChemAxon
pKa (Strongest Basic)5.48ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity95.69 m³·mol⁻¹ChemAxon
Polarizability40 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-9432000000-cd5a3e77250a4c168d5fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9717300000-83b70572a2f77f254c1fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-c0f0dd0396757c3cf0ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00dj-7900000000-6fb82e41c5f7509bf2d9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-0911000000-bcbd5878353663a0becfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-9100000000-b7ff9447b924f0855be0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00dj-7900000000-06fd81d1ed4113d2ccedSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-5c07491310faaef3dcb5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-9100000000-f50db0738e177a896742Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0309000000-24875256bb05cbaf7142Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0002-9000000000-4d9452d99f1522107772Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-0419000000-0e51e0565dc044821214Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2911000000-f881afe8478f809812e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-7900000000-499eef769e6c62234d00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-1019000000-651b3131d4943a27d13dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-3869000000-63563bd6f1750d029d0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ba-7920000000-49269668d5fb9b6e35b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0109000000-4e9eb37e2b101ab0d328Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0092-2933000000-3aebf3a627740b77e5adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-8900000000-f0eeabeb32b9b945d9e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-75ed3bac35742770931bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v6r-2932000000-efd1b65151e2c1476ba7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1901000000-b8ee2f14b02c83d2d921Spectrum
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 IDDB00790
HMDB IDHMDB0014928
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPerindopril
Chemspider ID96956
ChEBI ID8024
PubChem Compound ID107807
Kegg Compound IDC07706
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yoshiji H, Kuriyama S, Kawata M, Yoshii J, Ikenaka Y, Noguchi R, Nakatani T, Tsujinoue H, Fukui H: The angiotensin-I-converting enzyme inhibitor perindopril suppresses tumor growth and angiogenesis: possible role of the vascular endothelial growth factor. Clin Cancer Res. 2001 Apr;7(4):1073-8.
2. Hurst M, Jarvis B: Perindopril: an updated review of its use in hypertension. Drugs. 2001;61(6):867-96.
3. Simpson D, Noble S, Goa KL: Perindopril: in congestive heart failure. Drugs. 2002;62(9):1367-77; discussion 1378-9.
4. Yasumatsu R, Nakashima T, Masuda M, Ito A, Kuratomi Y, Nakagawa T, Komune S: Effects of the angiotensin-I converting enzyme inhibitor perindopril on tumor growth and angiogenesis in head and neck squamous cell carcinoma cells. J Cancer Res Clin Oncol. 2004 Oct;130(10):567-73. Epub 2004 Jul 27.
5. Jastrzebskal M, Widecka K, Naruszewicz M, Ciechanowicz A, Janczak-Bazan A, Foltynska A, Goracy I, Chetstowski K, Wesotowska T: Effects of perindopril treatment on hemostatic function in patients with essential hypertension in relation to angiotensin converting enzyme (ACE) and plasminogen activator inhibitor-1 (PAI-1) gene polymorphisms. Nutr Metab Cardiovasc Dis. 2004 Oct;14(5):259-69.
6. Parker E, Aarons L, Rowland M, Resplandy G: The pharmacokinetics of perindoprilat in normal volunteers and patients: influence of age and disease state. Eur J Pharm Sci. 2005 Sep;26(1):104-13.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24291100
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24324048
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24357222
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24511479
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24515310
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24554346
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24590580
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24602481
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24664905