Fosinopril (CHEM022119)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:20:46 UTC
Update Date2016-11-09 01:17:25 UTC
Accession NumberCHEM022119
Identification
Common NameFosinopril
ClassSmall Molecule
DescriptionFosinopril is a phosphinic acid-containing ester prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly hydrolyzed to fosinoprilat, its principle active metabolite. Fosinoprilat inhibits 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). Fosinopril may be used to treat mild to moderate hypertension, as an adjunct in the treatment of congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acidChEBI
(2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acidChEBI
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acidChEBI
(2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylateGenerator
(2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylateGenerator
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylateGenerator
Fosinopril sodiumHMDB
MonoprilHMDB
NewaceHMDB
Squibb brand OF fosinopril sodiumHMDB
StarilHMDB
Bristol-myers squibb brand OF fosinopril sodiumHMDB
DynacilHMDB
FosenoprilHMDB
Fosinopril, (1(s*(r*)),2 alpha,4 beta)-isomerHMDB
Fosinopril, (1(s*(s*)),2 alpha,4 beta)-isomerHMDB
FositensHMDB
Sanol brand OF fosinopril sodiumHMDB
Sodium, fosinoprilHMDB
TensocardilHMDB
Bristol myers squibb brand OF fosinopril sodiumHMDB
Ferrer brand OF fosinopril sodiumHMDB
FosinilHMDB
FosinormHMDB
Schwarz brand OF fosinopril sodiumHMDB
Esteve brand OF fosinopril sodiumHMDB
Fosinopril, (1(s*(r*)),2 alpha,4 alpha)-(D-pro)-isomerHMDB
FozitecHMDB
HiperlexHMDB
Merck lipha santé brand OF fosinoprilHMDB
Tenso stopHMDB
Chemical FormulaC30H46NO7P
Average Molecular Mass563.663 g/mol
Monoisotopic Mass563.301 g/mol
CAS Registry Number98048-97-6
IUPAC Name(2S,4S)-4-cyclohexyl-1-(2-{[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylic acid
Traditional Namefosinopril
SMILESCCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C
InChI IdentifierInChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30?,39?/m1/s1
InChI KeyBIDNLKIUORFRQP-FKDWWROVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Proline or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Carboxylic acid ester
  • Carboxamide group
  • Phosphinic acid ester
  • Organoheterocyclic compound
  • Carboxylic acid
  • Azacycle
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility0.001 g/LALOGPS
logP4.71ALOGPS
logP5.49ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area110.21 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity149.12 m³·mol⁻¹ChemAxon
Polarizability61.17 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9211610000-94f1646db6bff331382dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-052f-9011161000-d47389b6092a1bdbc108Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Fosinopril,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0000900000-f61a6a8a62cc0c92102bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0000900000-ed280398ec57e4a02dceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0090300000-4e1c300644a39a64aefeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0090000000-85f8c80f83290feea35cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0090000000-e28a43e299ff58e3a6bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0010900000-a142ed389f6652d197f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-1090000000-833fa43a37b31e08737cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-1090000000-cda46913f10b57e39204Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-2290000000-8627963d14d5d091e338Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0229-7890000000-a5186e8ef5fa038d0a91Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03k9-9720000000-ff0242177e3d4ef6c38aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000f-0000900000-a2e65cd39ca7266f3a02Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0000900000-0eee13fe1a605e98c985Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00ku-0105900000-1253dd1cea86dcfde7f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udl-0908200000-59ff4955c6e6b2d36435Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0901000000-e2b0d1bb8bfd4d6f7595Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0000900000-f625a00c8eb75cbf317dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f6x-0409200000-5a18b8096c457898aa5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0900000000-28e69824d7a0442561b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052g-8501940000-1921bd0fb11f89e7ac6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9742100000-b1fe493a8ecd28a1063bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300100000-2565c33f04881158cfa2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9001350000-645f2ba1f7eb05f66e9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adj-8956210000-4bf1693483e47cacee67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001a-1690000000-5349ec5626e3dd64f38dSpectrum
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 IDDB00492
HMDB IDHMDB0014635
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFosinopril
Chemspider ID50469
ChEBI ID5163
PubChem Compound ID55891
Kegg Compound IDC07016
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sharma S, Deitchman D, Eni JS, Gelperin K, Ilgenfritz JP, Blumenthal M: The hemodynamic effects of long-term ACE inhibition with fosinopril in patients with heart failure. Fosinopril Hemodynamics Study Group. Am J Ther. 1999 Jul;6(4):181-9.
2. David D, Jallad N, Germino FW, Willett MS, de Silva J, Weidner SM, Mills DJ: A Comparison of the Cough Profile of Fosinopril and Enalapril in Hypertensive Patients with a History of ACE Inhibitor-Associated Cough. Am J Ther. 1995 Oct;2(10):806-813.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11937741
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18209565
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22729889
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=8285178
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=9195116