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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H30O8
Molecular Weight 506.5437
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENRASENTAN

SMILES

CCCOC1=CC2=C(C=C1)[C@@H]([C@H]([C@@H]2C3=CC=C(OC)C=C3OCCO)C(O)=O)C4=CC=C5OCOC5=C4

InChI

InChIKey=GLCKXJLCYIJMRB-UPRLRBBYSA-N
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

HIDE SMILES / InChI

Molecular Formula C29H30O8
Molecular Weight 506.5437
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800004637 | https://www.ncbi.nlm.nih.gov/pubmed/16339819

Enrasentan is an orally active mixed endothelin A/B receptor antagonist with a 100-fold greater affinity for the endothelin A receptor. In an animal model of hypertension and cardiac hypertrophy the drug has reduced blood pressure, prevented cardiac hypertrophy and preserved myocardial function. In rats with hyperinsulinemia and hypertension enrasentan normalized blood pressure and prevented cardiac and renal damage. In rats with stroke the drug reduced the ischemic area in the brain. Enrasentan had been in phase II clinical trial for the treatment of heart failure but the results suggested that enrasentan does not appear to have favorable effects on ventricular remodeling.

Approval Year

PubMed

PubMed

TitleDatePubMed
The endothelin receptor antagonist SB 217242 reduces cerebral focal ischemic brain injury.
1995
Enrasentan, an antagonist of endothelin receptors.
2003 Spring
Endothelin receptor antagonists.
2006 Jun
Comparison of the dual receptor endothelin antagonist enrasentan with enalapril in asymptomatic left ventricular systolic dysfunction: a cardiovascular magnetic resonance study.
2006 Jun
Patents

Patents

Sample Use Guides

60-90 mg once daily
Route of Administration: Oral
The functional activity of enrasentan was evaluated in vitro in rat isolated aorta. In this model enrasentan (10 to 1000 nM) produced concentration-dependent, parallel rightward shifts in the ET-1 concentration-response curve. The Kb value for inhibition of ET-1-induced contraction for enrasentan was 4.4 ± 0.6 nM. The drug was devoid of agonistic activity. In human isolated pulmonary artery enrasentan produced a 7-fold shift to the right of the ET-1 concentration-response curve, with a calculated Kb value of 5.2 nM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:11:23 GMT 2023
Edited
by admin
on Sat Dec 16 17:11:23 GMT 2023
Record UNII
QG16H8A6ZH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENRASENTAN
INN  
INN  
Official Name English
SB-217242
Code English
enrasentan [INN]
Common Name English
(1S,2R,3S)-3-(2-(2-HYDROXYETHOXY)-4-METHOXYPHENYL)-1-(3,4-(METHYLENEDIOXY)PHENYL)-5-PROPOXY-2-INDANCARBOXYLIC ACID
Systematic Name English
Code System Code Type Description
DRUG BANK
DB06460
Created by admin on Sat Dec 16 17:11:24 GMT 2023 , Edited by admin on Sat Dec 16 17:11:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID50168260
Created by admin on Sat Dec 16 17:11:24 GMT 2023 , Edited by admin on Sat Dec 16 17:11:24 GMT 2023
PRIMARY
SMS_ID
300000034155
Created by admin on Sat Dec 16 17:11:24 GMT 2023 , Edited by admin on Sat Dec 16 17:11:24 GMT 2023
PRIMARY
INN
7784
Created by admin on Sat Dec 16 17:11:24 GMT 2023 , Edited by admin on Sat Dec 16 17:11:24 GMT 2023
PRIMARY
FDA UNII
QG16H8A6ZH
Created by admin on Sat Dec 16 17:11:24 GMT 2023 , Edited by admin on Sat Dec 16 17:11:24 GMT 2023
PRIMARY
CAS
167256-08-8
Created by admin on Sat Dec 16 17:11:24 GMT 2023 , Edited by admin on Sat Dec 16 17:11:24 GMT 2023
PRIMARY
MESH
C098288
Created by admin on Sat Dec 16 17:11:24 GMT 2023 , Edited by admin on Sat Dec 16 17:11:24 GMT 2023
PRIMARY
PUBCHEM
178103
Created by admin on Sat Dec 16 17:11:24 GMT 2023 , Edited by admin on Sat Dec 16 17:11:24 GMT 2023
PRIMARY
CHEBI
156258
Created by admin on Sat Dec 16 17:11:24 GMT 2023 , Edited by admin on Sat Dec 16 17:11:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL431651
Created by admin on Sat Dec 16 17:11:24 GMT 2023 , Edited by admin on Sat Dec 16 17:11:24 GMT 2023
PRIMARY
NCI_THESAURUS
C87727
Created by admin on Sat Dec 16 17:11:24 GMT 2023 , Edited by admin on Sat Dec 16 17:11:24 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
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ACTIVE MOIETY