Eprosartan

Eprosartan is an angiotensin II receptor antagonist used for the treatment of high blood pressure. It is marketed in the United States as Teveten by Abbvie, the spin-off of the pharmaceutical discovery division of Abbott Laboratories; it is marketed as Eprozar by Intas Pharmaceuticals in India, and by Abbott Laboratories elsewhere. The compound came into the Abbott Laboratories cardiovascular pipeline with its acquisition of Kos Pharmaceuticals in 2006, which had licensed it, along with "a range of hypertensive treatments", from the Biovail Corporation.[1]

Eprosartan
Clinical data
Trade namesTeveten
AHFS/Drugs.comMonograph
MedlinePlusa601237
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability15% (Eprosartan mesylate)
Metabolismnot metabolized
Elimination half-life5 to 9 hours
ExcretionKidney 10%, bile duct 90%
Identifiers
IUPAC name
  • 4-({2-Butyl-5-[2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H24N2O4S
Molar mass424.52 g·mol−1
3D model (JSmol)
SMILES
  • O=C(O)\C(=C\c1cnc(n1Cc2ccc(C(=O)O)cc2)CCCC)Cc3sccc3
InChI
  • 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+ Y
  • Key:OROAFUQRIXKEMV-LDADJPATSA-N Y
  (verify)

Eprosartan is sometimes paired with hydrochlorothiazide, whereupon it is marketed in the US as Teveten HCT and elsewhere as Teveten Plus.

The drug acts on the renin–angiotensin system to decrease total peripheral resistance in two ways. 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.

As with other angiotensin II receptor antagonists, eprosartan is generally better tolerated than enalapril (an ACE inhibitor), especially among the elderly.[2]

Structure activity Relationship

One feature that compares in Eprosartan versus other molecules is that Eprosartan is dosed relatively high at 400 to 800 mg/day. Eprosartan has an alpha-beta unsaturated hydrocarbon group which makes the compound difficult to absorb and contributes to its instability, thus there is a need for higher doses. The lipophilic aspects of the molecule also contribute to its low bioavailibility.

See also

References
  1. Anon., 2006, Abbott Laboratories: Kos Pharmaceuticals a wise buy, Datamonitor ResearchStore (online), November 8, 2006, see , accessed 29 January 2015.
  2. Ruilope L, Jäger B, Prichard B (2001). "Eprosartan versus enalapril in elderly patients with hypertension: a double-blind, randomized trial". Blood Press. 10 (4): 223–9. doi:10.1080/08037050152669747. PMID 11800061. S2CID 13063704.
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