Basic information Safety Supplier Related

Azumolene

Basic information Safety Supplier Related

Azumolene Basic information

Product Name:
Azumolene
Synonyms:
  • Azumolene
  • 1-[[[5-(4-Bromophenyl)-2-oxazolyl]methylene]amino]hydantoin
  • 2,4-Imidazolidinedione, 1-[[[5-(4-bromophenyl)-2-oxazolyl]methylene]amino]-
  • EU4093 free base
  • SOCE,inhibit,Azumolene,EU-4093,ryanodine,Inhibitor,Ca channels,EU 4093,Calcium Channel,relaxant,Ca2+ channels,muscle,EU4093,receptor,calcium
CAS:
64748-79-4
MF:
C13H9BrN4O3
MW:
349.14
Mol File:
64748-79-4.mol
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Azumolene Chemical Properties

storage temp. 
Store at -20°C
solubility 
DMSO: 13.89 mg/mL (39.78 mM)
form 
Solid
color 
White to light brown
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Azumolene Usage And Synthesis

Originator

Azumolene sodium,ZYF Pharm Chemical

Uses

Relaxant (skeletal muscle).

Definition

ChEBI: Azumolene is a 1,3-oxazole which is substituted by a [(2,4-dioxoimidazolidin-1-yl)imino]methyl group at position 2 and a 4-bromophenyl group at position 5. It is a muscle relaxant used for the treatment/prevention of malignant hyperthermia. It has a role as a ryanodine receptor modulator and a muscle relaxant. It is a member of 1,3-oxazoles, a member of bromobenzenes and an imidazolidine-2,4-dione. It is a conjugate acid of an azumolene(1-).

Manufacturing Process

To a stirred solution of 2-bromo-4'-bromoacetophenone (100.0 g, 0.36 mole) in chloroform (500 ml) was added hexamethylenetetramine (50.0 g, 0.36 mole). The mixture was stirred for 2.5 h and 143.0 g of the product was collected by filtration (100%).
The product above was combined with a solution of methanol (300 ml) and conc. HCl (410 ml), and the mixture was stirred for 52 h. The solid was collected by filtration and was washed with isopropanol. The product was recrystallized from methanol (Darco) to give 55.0 g (61%, in three crops), melting point 284°-287°C.
To a stirred mixture of the above amine hydrochloride (55.0 g, 0.22 mole) and [[(2,4-dioxo-1-imidazolidinyl)imino]methyl]formyl chloride (42.0 g, 0.22 mole) was added a solution of 440 ml of dimethylformamide and 44 ml of pyridine. The mixture was stirred for 20 h and poured into 2 L of water. The solid was collected by filtration and washed with ethanol and ether to give 36.0 g (28%) of N-[2-(4-bromophenyl)-2-oxoethyl]-[[(2,4-dioxo-1-imidazolidinyl)- imino]methyl]formamide, melting point 267°-269°C (recrystallization from 2200 ml acetic acid).
The of N-[2-(4-bromophenyl)-2-oxoethyl]-[[(2,4-dioxo-1-imidazolidinyl) imino]methyl]formamide (22.0 g, 0.061 mole) was combined with phosphorus oxychloride (310 ml) and the mixture was stirred and refluxed for 7 h. The solid was filtered off and stirred into an ice and water mixture (1 L). The 15.0 g (70%) of 1-[[[5-(4-bromophenyl)-2-oxazolyl]methylene]amino]-2,4- imidazolidinedione was collected by filtration, melting point 290°-292°C (recrystallization from 700 ml acetic acid).

Therapeutic Function

Muscle relaxant

Biochem/physiol Actions

Azumolene, a more water-soluble analog of dantrolene, is a potent inhibitor of sarcoplasmic reticulum (SR) ryanodine receptor (RyR) that inhibits skeletal muscle SR Ca2+ release. Azumolene is a direct acting skeletal muscle relaxant that induces effective blockade of skeletal muscle RyR1.

AzumoleneSupplier

Shanghai EFE Biological Technology Co., Ltd.
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021-65675885 18964387627
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info@efebio.com
Beijing Solarbio Science & Tecnology Co., Ltd.
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010-50973130 4009686088
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TargetMol Chemicals Inc.
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+1-781-999-5354 +1-00000000000
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InvivoChem
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+1-708-310-1919 +1-13798911105
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DC Chemicals
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021-58447131 13564518121
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sales@dcchemicals.com
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