Eprosartan

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Eprosartan
Clinical data
Trade namesTeveten
AHFS/Drugs.comMonograph
MedlinePlusa601237
Routes of
administration		Oral
ATC code
Pharmacokinetic data
Bioavailability15% (Eprosartan mesylate)
Metabolismnot metabolized
Elimination half-life5 to 9 hours
ExcretionRenal 10%, biliary 90%
Identifiers
  • 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
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H24N2O4S
Molar massEprosartan mesylate: 520.625 g/mol g·mol−1
3D model (JSmol)
  • O=C(O)\C(=C\c1cnc(n1Cc2ccc(C(=O)O)cc2)CCCC)Cc3sccc3
  • 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+ checkY
  • Key:OROAFUQRIXKEMV-LDADJPATSA-N checkY
  (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]

Synthesis

The following is a medicinal chemistry (early discovery stage) synthesis of eprosartan from Merck research into QSAR of this class of drug, which represents an approach to the construction of its carbon skeleton (though which is not necessarily related to the actual manufacturing synthesis of the on-market drug). Note, the reagents indicated alongside the arrows are a summary list, and are not complete for what is required in each transformation:

Example of an eprosartan discovery-stage chemical (organic) synthesis, from chemists at Merck.[2] Abbreviations: Bu, n-butyl functional group; Ac, acetyl group; Me, methyl group, Tf, trifluoromethylsulfonyl group, -SO2CF3; NaOH, the base, sodium hydroxide; MnO2, the oxidant, manganese dioxide; LDA, the strong base lithium diisopropylamide; BOC, the tert-butyloxycarbonyl protecting group; Ac2O, acetylating agent acetic anhydride; BDU, the non-nucleophilic base, 1,8-Diazabicycloundec-7-ene; HCl, hydrochloric acid.

See also

References

  1. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jm00047a009, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/jm00047a009 instead.

External links

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