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Showing drug card for Eprosartan (DB00876)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:07:52
Primary Accession Number DB00876
Secondary Accession Number
  • APRD00950
Name Eprosartan
Drug Type
  • Approved
  • Small Molecule
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 vascular smooth muscle, causing vascular dilatation. Second, it inhibits sympathetic norepinephrine production, further reducing blood pressure.
Synonyms Not Available
Brand Names
  1. Teveten
Brand Mixtures
  1. Teveten Plus (Eprosartan Mesylate + Hydrochlorothiazide)
Chemical IUPAC Name 4-[[2-butyl-5-[3-hydroxy-3-oxo-2-(thiophen-2-ylmethyl)prop-1-enyl]imidazol-1-yl]methyl]benzoic acid
Chemical Formula C23H24N2O4S
Chemical Structure Structure
CAS Registry Number 133040-01-4
InChI Identifier InChI=1/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)/f/h26,28H
InChI Key OROAFUQRIXKEMV-SKKVRFOWCP
KEGG Drug D04040 Link Image
KEGG Compound C07467 Link Image
PubChem Compound 60879 Link Image
PubChem Substance 9670 Link Image
ChEBI ID Not Available
PharmGKB ID PA449481 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02243942 Link Image
RxList Link http://www.rxlist.com/cgi/generic3/eprosartan.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/tev1538.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Eprosartan Link Image
FDA Label
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 424.5130
Monoisotopic Molecular Weight 424.1457
State Solid
Melting Point 248-250oC (mesylate form)
Experimental Water Solubility Insoluble (mesylate form) Source: PhysProp
Predicted Water Solubility 8.66e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.9 Source: PhysProp
Predicted LogP 3.58 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.69 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCCCC1=NC=C(\C=C(\CC2=CC=CS2)C(O)=O)N1CC1=CC=C(C=C1)C(O)=O
Canonical SMILES CCCCC1=NC=C(C=C(CC2=CC=CS2)C(O)=O)N1CC1=CC=C(C=C1)C(O)=O
Drug Category
  • Angiotensin II Type 1 Receptor Blockers
  • Antihypertensive Agents
ATC Codes
AHFS Codes
  • 24:32.08
Indication For the treatment of hypertension.
Pharmacology Eprosartan inhibits the pharmacologic effects of angiotensin II. As angiotensin II is a vasoconstrictor, this inhibition effectively lowers blood pressure.
Mechanism of Action Angiotensin II (formed from angiotensin I in a reaction catalyzed by angiotensin-converting enzyme [kininase II], a potent vasoconstrictor, is the principal pressor agent of the renin-angiotensin system. Angiotensin II also stimulates aldosterone synthesis and secretion by the adrenal cortex, cardiac contraction, renal resorption of sodium, activity of the sympathetic nervous system, and smooth muscle cell growth. Eprosartan blocks the vasoconstrictor and aldosterone-secreting effects of angiotensin II by selectively blocking the binding of angiotensin II to the AT1 receptor found in many tissues (e.g., vascular smooth muscle, adrenal gland). There is also an AT2 receptor found in many tissues but it is not known to be associated with cardiovascular homeostasis. Eprosartan does not exhibit any partial agonist activity at the AT1 receptor. Its affinity for the AT1 receptor is 1,000 times greater than for the AT2 receptor. In vitro binding studies indicate that eprosartan is a reversible, competitive inhibitor of the AT1 receptor.
Absorption Absolute bioavailability following a single 300 mg oral dose of eprosartan is approximately 13%. Administering eprosartan with food delays absorption.
Toxicity There was no mortality in rats and mice receiving oral doses of up to 3000 mg eprosartan/kg and in dogs receiving oral doses of up to 1000 mg eprosartan/kg.
Protein Binding Plasma protein binding of eprosartan is high (approximately 98%) and constant over the concentration range achieved with therapeutic doses.
Biotransformation Eprosartan is not metabolized by the cytochrome P450 system. It is mainly eliminated as unchanged drug. Less than 2% of an oral dose is excreted in the urine as a glucuronide.
Half Life The terminal elimination half-life of eprosartan following oral administration is typically 5 to 9 hours.
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Amiloride Increased risk of hyperkaliemia
Drospirenone Increased risk of hyperkaliemia
Lithium The ARB increases serum levels of lithium
Potassium Increased risk of hyperkaliemia
Spironolactone Increased risk of hyperkaliemia
Triamterene Increased risk of hyperkaliemia
Food Interactions
  • Take without regard to meals.
Pathways Not Available
General References
  1. 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 Link Image]
  2. Wikipedia Link Image
  3. RxList Link Image
  4. PDRhealth Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Type-1 angiotensin II receptor
Drug Target 1 [top]
Target 1 ID 70
Target 1 Name Type-1 angiotensin II receptor
Target 1 Synonyms
  1. AT1
  2. AT1AR
  3. AT1BR
Target 1 Gene Name AGTR1
Target 1 Protein Sequence >Type-1 angiotensin II receptor 
MILNSSTEDGIKRIQDDCPKAGRHNYIFVMIPTLYSIIFVVGIFGNSLVVIVIYFYMKLK
TVASVFLLNLALADLCFLLTLPLWAVYTAMEYRWPFGNYLCKIASASVSFNLYASVFLLT
CLSIDRYLAIVHPMKSRLRRTMLVAKVTCIIIWLLAGLASLPAIIHRNVFFIENTNITVC
AFHYESQNSTLPIGLGLTKNILGFLFPFLIILTSYTLIWKALKKAYEIQKNKPRNDDIFK
IIMAIVLFFFFSWIPHQIFTFLDVLIQLGIIRDCRIADIVDTAMPITICIAYFNNCLNPL
FYGFLGKKFKRYFLQLLKYIPPKAKSHSNLSTKMSTLSYRPSDNVSSSTKKPAPCFEVE
Target 1 Number of Residues 364
Target 1 Molecular Weight 41062
Target 1 Theoretical pI 9.71
Target 1 GO Classification
Function
G-protein chemoattractant receptor activity
chemokine receptor activity
C-X-C chemokine receptor activity
bradykinin receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
peptide receptor activity, G-protein coupled
angiotensin receptor activity
angiotensin type II receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in angiotensin type II receptor activity
Target 1 Specific Function Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 28-52
  • 65-87
  • 103-124
  • 143-162
  • 193-214
  • 241-262
  • 276-296
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 179122 Link Image
Target 1 UniProtKB/Swiss-Prot ID P30556 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name AGTR1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1080 bp 
ATGATTCTCAACTCTTCTACTGAAGATGGTATTAAAAGAATCCAAGATGATTGTCCCAAA
GCTGGAAGGCATAATTACATATTTGTCATGATTCCTACTTTATACAGTATCATCTTTGTG
GTGGGAATATTTGGAAACAGCTTGGTGGTGATAGTCATTTACTTTTATATGAAGCTGAAG
ACTGTGGCCAGTGTTTTTCTTTTGAATTTAGCACTGGCTGACTTATGCTTTTTACTGACT
TTGCCACTATGGGCTGTCTACACAGCTATGGAATACCGCTGGCCCTTTGGCAATTACCTA
TGTAAGATTGCTTCAGCCAGCGTCAGTTTCAACCTGTACGCTAGTGTGTTTCTACTCACG
TGTCTCAGCATTGATCGATACCTGGCTATTGTTCACCCAATGAAGTCCCGCCTTCGACGC
ACAATGCTTGTAGCCAAAGTCACCTGCATCATCATTTGGCTGCTGGCAGGCTTGGCCAGT
TTGCCAGCTATAATCCATCGAAATGTATTTTTCATTGAGAACACCAATATTACAGTTTGT
GCTTTCCATTATGAGTCCCAAAATTCAACCCTCCCGATAGGGCTGGGCCTGACCAAAAAT
ATACTGGGTTTCCTGTTTCCTTTTCTGATCATTCTTACAAGTTATACTCTTATTTGGAAG
GCCCTAAAGAAGGCTTATGAAATTCAGAAGAACAAACCAAGAAATGATGATATTTTTAAG
ATAATTATGGCAATTGTGCTTTTCTTTTTCTTTTCCTGGATTCCCCACCAAATATTCACT
TTTCTGGATGTATTGATTCAACTAGGCATCATACGTGACTGTAGAATTGCAGATATTGTG
GACACGGCCATGCCTATCACCATTTGTATAGCTTATTTTAACAATTGCCTGAATCCTCTT
TTTTATGGCTTTCTGGGGAAAAAATTTAAAAGATATTTTCTCCAGCTTCTAAAATATATT
CCCCCAAAAGCCAAATCCCACTCAAACCTTTCAACAAAAATGAGCACGCTTTCCTACCGC
CCCTCAGATAATGTAAGCTCATCCACCAAGAAGCCTGCACCATGTTTTGAGGTTGAGTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID AGTR1 Link Image
Target 1 GenAtlas ID AGTR1 Link Image
Target 1 HGNC ID HGNC:336 Link Image
Target 1 Chromosome Location 3
Target 1 Locus 3q21-q25
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Mauzy CA, Hwang O, Egloff AM, Wu LH, Chung FZ: Cloning, expression, and characterization of a gene encoding the human angiotensin II type 1A receptor. Biochem Biophys Res Commun. 1992 Jul 15;186(1):277-84. [PubMed Link Image]
  2. Curnow KM, Pascoe L, White PC: Genetic analysis of the human type-1 angiotensin II receptor. Mol Endocrinol. 1992 Jul;6(7):1113-8. [PubMed Link Image]
  3. Furuta H, Guo DF, Inagami T: Molecular cloning and sequencing of the gene encoding human angiotensin II type 1 receptor. Biochem Biophys Res Commun. 1992 Feb 28;183(1):8-13. [PubMed Link Image]
  4. Takayanagi R, Ohnaka K, Sakai Y, Nakao R, Yanase T, Haji M, Inagami T, Furuta H, Gou DF, Nakamuta M, et al.: Molecular cloning, sequence analysis and expression of a cDNA encoding human type-1 angiotensin II receptor. Biochem Biophys Res Commun. 1992 Mar 16;183(2):910-6. [PubMed Link Image]
  5. Bergsma DJ, Ellis C, Kumar C, Nuthulaganti P, Kersten H, Elshourbagy N, Griffin E, Stadel JM, Aiyar N: Cloning and characterization of a human angiotensin II type 1 receptor. Biochem Biophys Res Commun. 1992 Mar 31;183(3):989-95. [PubMed Link Image]
  6. Nawata H, Takayanagi R, Ohnaka K, Sakai Y, Imasaki K, Yanase T, Ikuyama S, Tanaka S, Ohe K: Type 1 angiotensin II receptors of adrenal tumors. Steroids. 1995 Jan;60(1):28-34. [PubMed Link Image]
  7. Konishi H, Kuroda S, Inada Y, Fujisawa Y: Novel subtype of human angiotensin II type 1 receptor: cDNA cloning and expression. Biochem Biophys Res Commun. 1994 Mar 15;199(2):467-74. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]
  3. 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 Link Image]
  4. 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 Link Image]
  5. 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 Link Image]
  6. 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 Link Image]

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