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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C29H30O8.C2H8N2
Molecular Weight 1073.1857
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENRASENTAN EDAMINE

SMILES

NCCN.CCCOC1=CC=C2[C@@H]([C@H]([C@@H](C2=C1)C3=CC=C(OC)C=C3OCCO)C(O)=O)C4=CC=C5OCOC5=C4.CCCOC6=CC=C7[C@@H]([C@H]([C@@H](C7=C6)C8=CC=C(OC)C=C8OCCO)C(O)=O)C9=CC=C%10OCOC%10=C9

InChI

InChIKey=WWCIKXJATPIKHK-HTFWYUNBSA-N
InChI=1S/2C29H30O8.C2H8N2/c2*1-3-11-34-19-6-7-20-22(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;3-1-2-4/h2*4-9,13-15,26-28,30H,3,10-12,16H2,1-2H3,(H,31,32);1-4H2/t2*26-,27+,28+;/m00./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
Molecular Formula C2H8N2
Molecular Weight 60.0983
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 1.1 nM [Ki]
Antagonist
2849
 111.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
ABI Chem
AC1L4363
eNovation Chemicals
D675285
https://www.enovationchem.com/ProductDetails.asp?ProductID=D675285
MuseChem
I006676
https://www.musechem.com/product/I006676.html
Smolecule
S527193
http://www.smolecule.com/products/s527193
THE BioTek
bt-267340
https://www.thebiotek.com/product/inhibitors/bt-267340
PubMed

PubMed

TitleDatePubMed
Endothelin receptor antagonists.
2006-06
Comparison of the dual receptor endothelin antagonist enrasentan with enalapril in asymptomatic left ventricular systolic dysfunction: a cardiovascular magnetic resonance study.
2006-06
Enrasentan, an antagonist of endothelin receptors.
2003
The endothelin receptor antagonist SB 217242 reduces cerebral focal ischemic brain injury.
1995
Patents

Patents

06274737
68

Sample Use Guides

In Vivo Use Guide
60-90 mg once daily
Route of Administration: Oral
In Vitro Use Guide
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 Mon Mar 31 18:05:53 GMT 2025
Edited
by admin
on Mon Mar 31 18:05:53 GMT 2025
Record UNII
W4N3HUS9UW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1H-INDENE-2-CARBOXYLIC ACID, 1-(1,3-BENZODIOXOL-5-YL)-2,3-DIHYDRO-3-(2-(2-HYDROXYETHOXY)-4-METHOXYPHENYL)-5-PROPOXY-, (1S,2R,3S)-, COMPD. WITH 1,2-ETHANEDIAMINE (2:1)
Preferred Name English
ENRASENTAN EDAMINE
Common Name English
1H-INDENE-2-CARBOXYLIC ACID, 1-(1,3-BENZODIOXOL-5-YL)-2,3-DIHYDRO-3-(2-(2-HYDROXYETHOXY)-4-METHOXYPHENYL)-5-PROPOXY-, (1S-(1.ALPHA.,2.BETA.,3.ALPHA.))-, COMPD. WITH 1,2-ETHANEDIAMINE (2:1)
Common Name English
Code System Code Type Description
PUBCHEM
15886604
Created by admin on Mon Mar 31 18:05:53 GMT 2025 , Edited by admin on Mon Mar 31 18:05:53 GMT 2025
PRIMARY
FDA UNII
W4N3HUS9UW
Created by admin on Mon Mar 31 18:05:53 GMT 2025 , Edited by admin on Mon Mar 31 18:05:53 GMT 2025
PRIMARY
CAS
183507-63-3
Created by admin on Mon Mar 31 18:05:53 GMT 2025 , Edited by admin on Mon Mar 31 18:05:53 GMT 2025
PRIMARY
Related Record Type Details
Structure of ENRASENTAN
PARENT -> SALT/SOLVATE
Structure of Ethylenediamine
PARENT -> SALT/SOLVATE
NIH
NCATS
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