Nebentan , Endothelin receptor ET-A antagonist, CAS No.403604-85-3, Endothelin receptor ET-A antagonist

CAS: 403604-85-3 Cat. No.: N646223 Molecular Weight: 491.52 PubChem CID: 9957262

Synonyms

SCHEMBL5272291 | DTXSID50193350 | UNII-IJ670B0H4A | Nebentan [INN] | Ethenesulfonamide, N-[6-methoxy-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-2-phenyl-, (1E)- | Nebentan potassium | (E)-N-(6-Methoxy-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)-2-phenyl

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Nebentan (YM598 free base) is a potent, selective and orally active non-peptide endothelin ET A receptor antagonist through the modification of Bosentan . Nebentan inhibits [ 125 I] endothelin-1 binding to cloned human endothelin ETA and ETB receptor, with K i of 0.697 nM and 569 nM, respectively YM598 can ameliorate the progression of cor pulmonale and myocardial infarction in vivo .

In Vitro

Nebentan inhibits the specific binding of [ 125 I] endothelin-1 to endothelin ET A and ET B receptors in a concentration dependent manner, K i values are 0.697 nM and 1.53 nM for human and rat endothelin ETA receptors, respectively. In contrast, YM598 exhibits low affinities for human and rat endothelin ET B receptors, with K i values of 569 nM and 155 nM,respectively. In measurement of intracellular Ca 2+ concentration, Nebentan concentration-dependently inhibits the increase in [Ca 2+ ]i induced by 10 nM endothelin-1 in both CHO cells and A10 cells, the IC 50 values are 26.2 nM for CHO cells and 26.7 nM for A10 cells, respectively. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Nebentan (oral administration; 0.1-1 mg/kg; 4 weeks) significantly inhibits the progression of pulmonary hypertension and the development of right ventricular hypertrophy. Nebentan (oral administration; 1 mg/kg; 30 weeks) significantly ameliorates the poor survival rate of CHF rats, it markedly reduces the hypertrophy of both ventricles as well as pulmonary congestion. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:ET A 0.697 nM (Ki) ET B 569 nM (Ki)

Specifications

Synonyms

SCHEMBL5272291 | DTXSID50193350 | UNII-IJ670B0H4A | Nebentan [INN] | Ethenesulfonamide, N-[6-methoxy-5-(2-methoxyphenoxy)[2, 2'-bipyrimidin]-4-yl]-2-phenyl-, (1E)- | Nebentan potassium | (E)-N-(6-Methoxy-5-(2-methoxyphenoxy)-2, 2'-bipyrimidin-4-yl)-2-phenyl

Biochemical and Physiological Mechanisms

Nebentan (YM598 free base) is a potent, selective and orally active non-peptide endothelin ET A receptor antagonist through the modification of Bosentan ( HY-A0013 ). Nebentan inhibits [ 125 I] endothelin-1 binding to cloned human endothelin ETA and ETB r

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

ANTAGONIST

Mechanism of action

Endothelin receptor ET-A antagonist

Product Properties

• ALogP: 3.3

Names and Identifiers

• Canonical Smiles: COC1=CC=CC=C1OC2=C(N=C(N=C2OC)C3=NC=CC=N3)NS(=O)(=O)C=CC4=CC=CC=C4
• IUPAC Name: (E)-N-[6-methoxy-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]-2-phenylethenesulfonamide
• InChIKey: LONWRQOYFPYMQD-DTQAZKPQSA-N
• INCHI: 1S/C24H21N5O5S/c1-32-18-11-6-7-12-19(18)34-20-21(29-35(30,31)16-13-17-9-4-3-5-10-17)27-23(28-24(20)33-2)22-25-14-8-15-26-22/h3-16H,1-2H3,(H,27,28,29)/b16-13+
• Isomeric SMILES: COC1=CC=CC=C1OC2=C(N=C(N=C2OC)C3=NC=CC=N3)NS(=O)(=O)/C=C/C4=CC=CC=C4
• Alternate CAS: 403604-85-3
• PubChem CID: 9957262
• Molecular Weight: 491.52

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrimidines and pyrimidine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrimidines and pyrimidine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Bipyrimidines and oligopyrimidines
• Alternative Parents: Diarylethers Anisoles Styrenes Methoxybenzenes Phenoxy compounds Alkyl aryl ethers Organic sulfonamides Imidolactams Organosulfonamides Heteroaromatic compounds Aminosulfonyl compounds Azacyclic compounds Organic oxides Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Bipyrimidine - Diaryl ether - Styrene - Methoxybenzene - Phenol ether - Phenoxy compound - Anisole - Alkyl aryl ether - Organic sulfonic acid amide - Imidolactam - Benzenoid - Monocyclic benzene moiety - Organosulfonic acid amide - Organic sulfonic acid or derivatives - Aminosulfonyl compound - Sulfonyl - Heteroaromatic compound - Organosulfonic acid or derivatives - Ether - Azacycle - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organosulfur compound - Organic oxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as bipyrimidines and oligopyrimidines. These are organic compounds containing two or more pyrimidine rings directly linked to each other. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 125 mg/mL (254.31 mM; Need ultrasonic)
• Molecular Weight: 491.500 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 491.126 Da
• Monoisotopic Mass: 491.126 Da
• Topological Polar Surface Area: 134.000 Ų
• Heavy Atom Count: 35
• Formal Charge: 0
• Complexity: 767.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1