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Eprosartan

July 24, 2017
Common Name

Eprosartan Description

Eprosartan is an angiotensin II receptor antagonist used for the treatment of high blood pressure. It acts on the renin-angiotensin system in two ways to decrease total peripheral resistance. First, it blocks the binding of angiotensin II to AT1 receptors in vascliar smooth muscle, causing vascliar dilatation. Second, it inhibits sympathetic norepinephrine production, further reducing blood pressure. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (e)-2-Butyl-1-(P-carboxybenzyl)-alpha-2-thenylimidazole-5-acrylic acidChEBI (e)-3-[2-N-Butyl-1-{(4-carboxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic acidChEBI (e)-Alpha{[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazole-5-yl]methylene}-2-thiopheneproprionic acidChEBI (e)-2-Butyl-1-(P-carboxybenzyl)-a-2-thenylimidazole-5-acrylateGenerator (e)-2-Butyl-1-(P-carboxybenzyl)-a-2-thenylimidazole-5-acrylic acidGenerator (e)-2-Butyl-1-(P-carboxybenzyl)-alpha-2-thenylimidazole-5-acrylateGenerator (e)-2-Butyl-1-(P-carboxybenzyl)-α-2-thenylimidazole-5-acrylateGenerator (e)-2-Butyl-1-(P-carboxybenzyl)-α-2-thenylimidazole-5-acrylic acidGenerator (e)-3-[2-N-Butyl-1-{(4-carboxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoateGenerator (e)-Alpha{[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazole-5-yl]methylene}-2-thiopheneproprionateGenerator SK And F 108566MeSH TevetenMeSH

Chemical Formlia

C23H24N2O4S Average Molecliar Weight

424.513 Monoisotopic Molecliar Weight

424.145677956 IUPAC Name

4-({2-butyl-5-[(1E)-2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid Traditional Name

eprosartan CAS Registry Number

133040-01-4 SMILES

CCCCC1=NC=C(C=C(/CC2=CC=CS2)C(O)=O)N1CC1=CC=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C23H24N2O4S/c1-2-3-6-21-24-14-19(12-18(23(28)29)13-20-5-4-11-30-20)25(21)15-16-7-9-17(10-8-16)22(26)27/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29)/b18-12+

InChI Key

OROAFUQRIXKEMV-LDADJPATSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Benzoic acids Alternative Parents

  • Imidazolyl carboxylic acids and derivatives
  • Benzoyl derivatives
  • 1,2,5-trisubstituted imidazoles
  • N-substituted imidazoles
  • Dicarboxylic acids and derivatives
  • Thiophenes
  • Heteroaromatic compounds
  • Carboxylic acids
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Benzoic acid
  • 1,2,5-trisubstituted-imidazole
  • Benzoyl
  • Imidazolyl carboxylic acid derivative
  • Trisubstituted imidazole
  • Dicarboxylic acid or derivatives
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Thiophene
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • imidazoles (CHEBI:4814 )
  • thiophenes (CHEBI:4814 )
  • dicarboxylic acid (CHEBI:4814 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Angiotensin II Type 1 Receptor Blockers
  • Antihypertensive Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point248 – 250 °C (mesylate form)Not Available Boiling PointNot AvailableNot Available Water Solubility8.66e-03 g/LNot Available LogP3.9Not Available

    Predicted Properties

    Property Value Source Water Solubility0.0087 mg/mLALOGPS logP3.57ALOGPS logP3.8ChemAxon logS-4.7ALOGPS pKa (Strongest Acidic)3.63ChemAxon pKa (Strongest Basic)6.93ChemAxon Physiological Charge-2ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area92.42 Å2ChemAxon Rotatable Bond Count10ChemAxon Refractivity117.02 m3·mol-1ChemAxon Polarizability45.29 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-004i-0009000000-fa421ee23b907968b800View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-00di-0002900000-694c481f9555295f9426View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-004u-0289000000-647b9ea41a7a812dea66View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-00kg-0290000000-08e189bdaeb9c6af3b4fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-014j-1290000000-e8207e65f017389d706fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-00lr-9260000000-7b844b75045cf89e145eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-001i-9100000000-f49fc8384f38dc7b6e3bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-00di-0002900000-e62e6d74d830487d0954View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-002u-0198000000-d571b7bcdbe9e3f7e69fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-00kp-0290000000-0b7c3fe664812ce51596View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-014j-1090000000-85f4ee357273ee0268c0View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-001i-9240000000-8ed6c4fadafd173a2579View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-001i-9400000000-81bd0b20c45458b1bdecView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-004i-0009000000-0333ac2f95788dceda2cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4l-0196300000-c2476723863e5584d7e8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-004i-0000900000-a93af7ff9cf5786971d0View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-056r-0171900000-4a8d34412967af4cbf35View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-052r-1971000000-ee85641cdce897ab6693View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-052r-1920000000-282ecc38e7c0c6cbefefView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Eprosartan Action PathwaySMP00159Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00876

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00876

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00876 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4444504 KEGG Compound ID

    C07467 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Eprosartan NuGOwiki Link

    HMDB15014 Metagene Link

    HMDB15014 METLIN ID

    Not Available PubChem Compound

    5281037 PDB ID

    Not Available ChEBI ID

    4814

    Product: SA4504

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Hedner T: The clinical profile of the angiotensin II receptor blocker eprosartan. J Hypertens Suppl. 2002 Jun;20(5):S33-8. [PubMed:12184062 ]
    2. Puig JG, Lopez MA, Bueso TS, Bernardino JI, Jimenez RT: Clinical profile of eprosartan. Cardiovasc Drugs Ther. 2002 Dec;16(6):543-9. [PubMed:12766389 ]
    3. Ruilope L, Jager B: Eprosartan for the treatment of hypertension. Expert Opin Pharmacother. 2003 Jan;4(1):107-14. [PubMed:12517247 ]
    4. de la Sierra A, Ram CV: Introduction: The pharmacological profile of eprosartan–implications for cerebrovascular and cardiovascular risk reduction. Curr Med Res Opin. 2007 Nov;23 Suppl 5:S1-3. doi: 10.1185/030079907X260692. [PubMed:18093407 ]
    5. Ruilope L, Jager B, Prichard B: Eprosartan versus enalapril in elderly patients with hypertension: a double-blind, randomized trial. Blood Press. 2001;10(4):223-9. [PubMed:11800061 ]
    6. Blankestijn PJ, Rupp H: Clinical profile of eprosartan: a different angiotensin II receptor blocker. Cardiovasc Hematol Agents Med Chem. 2008 Oct;6(4):253-7. [PubMed:18855637 ]

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
    Gene Name:
    CYP2C9
    Uniprot ID:
    P11712
    Molecular weight:
    55627.365
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
    Gene Name:
    AGTR1
    Uniprot ID:
    P30556
    Molecular weight:
    41060.5
    References
    1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    2. Heusser K, Vitkovsky J, Schmieder RE, Schobel HP: AT1 antagonism by eprosartan lowers heart rate variability and baroreflex gain. Auton Neurosci. 2003 Aug 29;107(1):45-51. [PubMed:12927226 ]
    3. Gremmler B, Kunert M, Schleiting H, Ulbricht LJ: Improvement of cardiac output in patients with severe heart failure by use of ACE-inhibitors combined with the AT1-antagonist eprosartan. Eur J Heart Fail. 2000 Jun;2(2):183-7. [PubMed:10856732 ]
    4. Suzuki G, Mishima T, Tanhehco EJ, Sharov VG, Todor A, Rostogi S, Gupta RC, Chaudhry PA, Anagnostopoulos PV, Nass O, Goldstein S, Sabbah HN: Effects of the AT1-receptor antagonist eprosartan on the progression of left ventricular dysfunction in dogs with heart failure. Br J Pharmacol. 2003 Jan;138(2):301-9. [PubMed:12540520 ]
    5. Ilson BE, Martin DE, Boike SC, Jorkasky DK: The effects of eprosartan, an angiotensin II AT1 receptor antagonist, on uric acid excretion in patients with mild to moderate essential hypertension. J Clin Pharmacol. 1998 May;38(5):437-41. [PubMed:9602957 ]
    6. Nap A, Mathy MJ, Balt JC, Pfaffendorf M, van Zwieten PA: Pre- and postsynaptic inhibitory potencies of the angiotensin AT1 receptor antagonists eprosartan and candesartan. Eur J Pharmacol. 2003 May 23;469(1-3):117-24. [PubMed:12782193 ]
    7. Hedner T: The clinical profile of the angiotensin II receptor blocker eprosartan. J Hypertens Suppl. 2002 Jun;20(5):S33-8. [PubMed:12184062 ]
    8. Puig JG, Lopez MA, Bueso TS, Bernardino JI, Jimenez RT: Clinical profile of eprosartan. Cardiovasc Drugs Ther. 2002 Dec;16(6):543-9. [PubMed:12766389 ]
    9. Ruilope L, Jager B: Eprosartan for the treatment of hypertension. Expert Opin Pharmacother. 2003 Jan;4(1):107-14. [PubMed:12517247 ]
    10. de la Sierra A, Ram CV: Introduction: The pharmacological profile of eprosartan–implications for cerebrovascular and cardiovascular risk reduction. Curr Med Res Opin. 2007 Nov;23 Suppl 5:S1-3. doi: 10.1185/030079907X260692. [PubMed:18093407 ]
    11. Murdoch DR, McDonagh TA, Farmer R, Morton JJ, McMurray JJ, Dargie HJ: ADEPT: Addition of the AT1 receptor antagonist eprosartan to ACE inhibitor therapy in chronic heart failure trial: hemodynamic and neurohormonal effects. Am Heart J. 2001 May;141(5):800-7. [PubMed:11320369 ]

    Transporters

    General function:
    Involved in ATP binding
    Specific function:
    Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
    Gene Name:
    ABCC2
    Uniprot ID:
    Q92887
    Molecular weight:
    174205.6
    References
    1. Weiss J, Sauer A, Divac N, Herzog M, Schwedhelm E, Boger RH, Haefeli WE, Benndorf RA: Interaction of angiotensin receptor type 1 blockers with ATP-binding cassette transporters. Biopharm Drug Dispos. 2010 Mar;31(2-3):150-61. doi: 10.1002/bdd.699. [PubMed:20222053 ]

    PMID: 3174627

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