Eprosartan

Title: Eprosartan
CAS Registry Number: 133040-01-4
CAS Name: (aE)-a-[[2-Butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-2-thiophenepropanoic acid
Additional Names: (E)-3-[2-butyl-1-[(4-carboxyphenyl)methyl]-imidazol-5-yl]-2-(2-thienylmethyl)-2-propenoic acid
Manufacturers' Codes: SKF-108566
Molecular Formula: C23H24N2O4S
Molecular Weight: 424.51
Percent Composition: C 65.07%, H 5.70%, N 6.60%, O 15.08%, S 7.55%
Literature References: Prototype of the imidazoleacrylic acid angiotensin II receptor antagonists. Prepn: J. A. Finkelstein et al., EP 403159 (1990 to SmithKline Beckman); eidem, US 5185351 (1993 to SmithKline Beecham); J. Weinstock et al., J. Med. Chem. 34, 1514 (1991); R. M. Keenan et al., ibid. 36, 1880 (1993). Pharmacology: R. M. Edwards et al., J. Pharmacol. Exp. Ther. 260, 175 (1992). Receptor binding study: H. T. Schambye et al., Mol. Pharmacol. 47, 425 (1995). Clinical pharmacokinetics: D. Tenero et al., Biopharm. Drug Dispos. 19, 351 (1998). Clinical trial in hypertension: W. J. Elliott et al., J. Hum. Hypertens. 13, 413 (1999). Review of clinical experience: L. Ruilope, B. Jäger, Expert Opin. Pharmacother. 4, 107-114 (2003).
Properties: Crystals from methanol, mp 260-261°.
Melting point: mp 260-261°
Derivative Type: Monomethanesulfonate
CAS Registry Number: 144143-96-4
Additional Names: Eprosartan mesylate
Manufacturers' Codes: SKF-108566J
Trademarks: Teveten (Solvay)
Molecular Formula: C23H24N2O4S.CH3SO3H
Molecular Weight: 520.62
Percent Composition: C 55.37%, H 5.42%, N 5.38%, O 21.51%, S 12.32%
Properties: White to off-white crystalline powder, mp 248-250°. Insol in water. Freely sol in ethanol.
Melting point: mp 248-250°
Therap-Cat: Antihypertensive.
Keywords: Angiotensin II Receptor Antagonist; Antihypertensive; Imidazoleacrylic Acid Derivatives.
Eprozinol epsilon-Acetamidocaproic Acid epsilon-Aminocaproic Acid Epsiprantel Eptastigmine

Eprosartan
Eprosartan.svg
Systematic (IUPAC) name
4-({2-Butyl-5-[2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid
Clinical data
Trade names Teveten
AHFS/Drugs.com monograph
MedlinePlus a601237
Legal status  ?
Routes Oral
Pharmacokinetic data
Bioavailability 15% (Eprosartan mesylate)
Metabolism not metabolized
Half-life 5 to 9 hours
Excretion Renal 10%, biliary 90%
Identifiers
CAS number 133040-01-4 YesY
ATC code C09CA02
PubChem CID 5281037
DrugBank DB00876
ChemSpider 4444504 YesY
UNII 2KH13Z0S0Y YesY
KEGG D04040 YesY
ChEBI CHEBI:4814 YesY
ChEMBL CHEMBL813 YesY
Chemical data
Formula C23H24N2O4S 
Mol. mass Eprosartan mesylate: 520.625 g/mol
 YesY (what is this?)  (verify)

Eprosartan is an angiotensin II receptor antagonist used for the treatment of high blood pressure. It is marketed as Teveten by Abbvie in the United States.It is marketed as Eprozar by INTAS Pharmaceuticals in India and by Abbott Laboratories elsewhere. It is sometimes paired with hydrochlorothiazide, marketed in the US as Teveten HCT and elsewhere as Teveten Plus.

The drug 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.

As with other angiotensin II receptor antagonists, eprosartan is generally better tolerated than enalapril (an ACE inhibitor), especially among the elderly.[1]