Corwin

Base Information

• Chemical Name: Corwin
• CAS No.: 73210-73-8
• Molecular Formula: C₄H₄O₄*C₁₆H₂₅N₃O₅
• Molecular Weight: 455.465
• European Community (EC) Number: 277-319-9
• NCI Thesaurus Code: C152925
• ChEMBL ID: CHEMBL2104466
• Mol file: 73210-73-8.mol

Synonyms:Carwin;Corwin;Fumarate, Xamoterol;Hemifumarate, Xamoterol;ICI 118587;ICI-118587;ICI118587;Monohydrobromide, Xamoterol;Monohydrochloride, Xamoterol;Xamoterol;Xamoterol Fumarate;Xamoterol Hemifumarate;Xamoterol Maleate (2:1);Xamoterol Monohydrobromide;Xamoterol Monohydrochloride;Xamoterol, (S)-Isomer;Xamtol

Chemical Property of Corwin

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 7.41E-18mmHg at 25°C
• Melting Point: 168-169° (dec)
• Boiling Point: 651.4 °C at 760 mmHg
• Flash Point: 347.7 °C
• PSA: 103.29000
• LogP: 0.48300
• Storage Temp.: Store at RT
• Solubility.: H2O: 10 mg/mL at 60 °C, soluble
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 455.19037951
• Heavy Atom Count: 32
• Complexity: 477

Purity/Quality:

99% ^*data from raw suppliers

XamoterolHemifumarate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1C(=O)NCCNCC(COC2=CC=C(C=C2)O)O.C(=CC(=O)O)C(=O)O
• Isomeric SMILES: C1COCCN1C(=O)NCCNCC(COC2=CC=C(C=C2)O)O.C(=C/C(=O)O)\C(=O)O
• Description: Xamoterol fumarate is a cardioselective partial beta-agonist, the first of its class to be developed for use in heart failure. The main advantage of xamoterol fumarate as a cardiotonic lies in the fact that its beta-blocking effect exerted during high sympathetic drive will protect the heart from overstimulation. It is claimed to be a viable but safer alternative to digoxin. Xamoterol is a partial agonist of β1-adrenergic receptors (β1-ARs) with an EC50 value of 80 nM for the generation of cyclic AMP (cAMP) in neonatal rat cardiomyocyte cultures. It increases spontaneous contraction of isolated rat right atria (EC50 = 4.67 nM). In vivo, xamoterol increases heart rate in beagle dogs (ED50 = 3.2 μg/kg) and in a rat model of spontaneous heart failure (ED50 = 6 μg/kg), an effect that is reversed by the selective β1-AR antagonist betaxolol but not the selective β2-AR antagonist ICI 118551 . Formulations containing xamoterol have been used in the treatment of heart failure.
• Uses: Xamoterol Hemifumarate, is a β1-adrenoceptor-selective partial agonist. Stimulant (cardiac).

Technology Process of Corwin

There total 12 articles about Corwin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.7%

(S)-N-(2-(3-(4-(benzyloxy)phenoxy)-2-hydroxypropylamino)ethyl)morpholine-4-carboxamide (122715-70-2,69630-21-3) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2) → (S)-xamoterol hemifumarate (73210-73-8,90730-93-1)

Guidance literature:

(S)-N-(2-(3-(4-(benzyloxy)phenoxy)-2-hydroxypropylamino)ethyl)morpholine-4-carboxamide; With hydrogen; acetic acid; In ethanol; under 2844.39 Torr;

(2E)-but-2-enedioic acid; In ethanol;

DOI:10.1371/journal.pone.0180319

Reference yield:

(R)-N-(2-(3-(4-(benzyloxy)phenoxy)-2-hydroxypropylamino)ethyl)morpholine-4-carboxamide (69630-21-3) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2) → (R)-xamoterol hemifumarate (73210-73-8,90730-93-1)

Guidance literature:

(R)-N-(2-(3-(4-(benzyloxy)phenoxy)-2-hydroxypropylamino)ethyl)morpholine-4-carboxamide; With hydrogen; acetic acid; In ethanol; under 2844.39 Torr;

(2E)-but-2-enedioic acid; In ethanol;

DOI:10.1371/journal.pone.0180319

Reference yield:

1-p-benzyloxyphenoxy-3-(beta-morpholinocarbonamidoethyl)amino-2-propanol hydrochloride + (2E)-but-2-enedioic acid (110-17-8,26099-09-2) → 1-p-hydroxyphenoxy-3-beta-(morpholinocarbonamido)ethyl-amino-2-propanol fumerate (73210-73-8,90730-93-1)

Guidance literature:

1-p-benzyloxyphenoxy-3-(beta-morpholinocarbonamidoethyl)amino-2-propanol hydrochloride; With palladium on activated charcoal; hydrogen; acetic acid; In ethanol;

(2E)-but-2-enedioic acid; In ethanol; at 5 ℃; for 12h;

upstream raw materials:

(2E)-but-2-enedioic acid

4-(phenyloxycarbonyl)morpholine

tert-butyl 2-(3-(morpholine-4-carboxamido)ethyl)carbamate

(S)-{[4-(Phenylmethoxy)phenoxy]methyl}-oxirane

Refernces

• 1、 -. "METHOD OF IMPROVING COGNITION AND SOCIAL BEHAVIOR IN HUMANS HAVING DEFICITS THEREIN DUE TO NEURODEGENERATIVE DISORDERS AND COMPOUNDS AND COMPOSITIONS THEREFOR". Paragraph 0146. . Retrieved 2016/08/03.