CHEBI:156258 - enrasentan

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ChEBI Name enrasentan
ChEBI ID CHEBI:156258
Definition A member of the class of indanes that is 2,3-dihydro-1H-indene which is substituted by a 1,3-benzodioxol-5-yl group, carboxy group, 2-(2-hydroxyethoxy)-4-methoxyphenyl group and a propoxy group at positions 1S, 2R, 3S and 5, respectively. It is an orally active mixed endothelin A/B receptor antagonist with a 100-fold greater affinity for the endothelin A receptor. The drug was being developed by GSK for the treatment of congestive heart failure and pulmonary hypertension (clinical trials discontinued).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Stan Laulederkind
Supplier Information
Download Molfile XML SDF
Formula C29H30O8
Net Charge 0
Average Mass 506.551
Monoisotopic Mass 506.19407
InChI InChI=1S/C29H30O8/c1-3-11-34-19-6-7-20-22(14-19)27(21-8-5-18(33-2)15-24(21)35-12-10-30)28(29(31)32)26(20)17-4-9-23-25(13-17)37-16-36-23/h4-9,13-15,26-28,30H,3,10-12,16H2,1-2H3,(H,31,32)/t26-,27+,28+/m0/s1
InChIKey GLCKXJLCYIJMRB-UPRLRBBYSA-N
SMILES [C@@]1([C@]([C@@](C=2C=C(C=CC12)OCCC)(C=3C(=CC(=CC3)OC)OCCO)[H])(C(=O)O)[H])(C=4C=C5OCOC5=CC4)[H]
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): endothelin receptor antagonist
A hormone antagonist that blocks endothelin receptors.
Application(s): endothelin receptor antagonist
A hormone antagonist that blocks endothelin receptors.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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ChEBI Ontology
Outgoing enrasentan (CHEBI:156258) has role antihypertensive agent (CHEBI:35674)
enrasentan (CHEBI:156258) has role endothelin receptor antagonist (CHEBI:51451)
enrasentan (CHEBI:156258) is a aromatic ether (CHEBI:35618)
enrasentan (CHEBI:156258) is a benzodioxoles (CHEBI:38298)
enrasentan (CHEBI:156258) is a indanes (CHEBI:46940)
enrasentan (CHEBI:156258) is a monocarboxylic acid (CHEBI:25384)
enrasentan (CHEBI:156258) is a monomethoxybenzene (CHEBI:25235)
enrasentan (CHEBI:156258) is a primary alcohol (CHEBI:15734)
IUPAC Name
(1S,2R,3S)-1-(1,3-benzodioxol-5-yl)-3-[2-(2-hydroxyethoxy)-4-methoxyphenyl]-5-propoxy-2,3-dihydro-1H-indene-2-carboxylic acid
INNs Sources
enrasentán ChemIDplus
enrasentan WHO MedNet
enrasentan WHO MedNet
enrasentanum WHO MedNet
Synonyms Sources
(1S,2R,3S)-3-(2-(2-hydroxyethoxy)-4-methoxyphenyl)-1-(3,4-(methylenedioxy)phenyl)-5-propoxy-2-indancarboxylic acid ChemIDplus
SB 217242 ChemIDplus
SB-217242 ChemIDplus
SB217242 ChEBI
Manual Xref Database
DB06460 DrugBank
View more database links
Registry Number Type Source
167256-08-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10208832 PubMed citation Europe PMC
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Last Modified
28 July 2020