Azumolene
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MedKoo CAT#: 330058

CAS#: 64748-79-4 (free)

Description: Azumolene is a muscle relaxant that inhibits the release of calcium from skeletal muscle sarcoplasmic reticulum. Azumolene inhibits a component of store-operated calcium entry coupled to the skeletal muscle ryanodine receptor. Azumolene, an equipotent dantrolene analog, inhibits a component of SOCE coupled to activation of RyR1 by caffeine and ryanodine, whereas the SOCE component induced by thapsigargin is not affected.


Chemical Structure

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Azumolene
CAS# 64748-79-4 (free)

Theoretical Analysis

MedKoo Cat#: 330058
Name: Azumolene
CAS#: 64748-79-4 (free)
Chemical Formula: C13H9BrN4O3
Exact Mass: 347.99
Molecular Weight: 349.144
Elemental Analysis: C, 44.72; H, 2.60; Br, 22.89; N, 16.05; O, 13.75

Price and Availability

Size Price Availability Quantity
50mg USD 750 2 Weeks
100mg USD 1250 2 Weeks
200mg USD 1850 2 Weeks
500mg USD 3650 2 Weeks
1g USD 5650 2 Weeks
2g USD 8950 2 Weeks
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Related CAS #: 64748-79-4 (free)   105336-14-9 (sodium)    

Synonym: Azumolene; EU4093; EU-4093; EU 4093;

IUPAC/Chemical Name: 2,4-Imidazolidinedione, 1-(((5-(4-bromophenyl)-2-oxazolyl)methylene)amino)-

InChi Key: SEGCNGONCZQFDW-OMCISZLKSA-N

InChi Code: InChI=1S/C13H9BrN4O3/c14-9-3-1-8(2-4-9)10-5-15-12(21-10)6-16-18-7-11(19)17-13(18)20/h1-6H,7H2,(H,17,19,20)/b16-6+

SMILES Code: O=C1NC(CN1/N=C/C2=NC=C(C3=CC=C(Br)C=C3)O2)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 349.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Si D, Chakraborty P, Azam MA, Nair MKK, Massé S, Lai PFH, Labos C, Riazi S, Nanthakumar K. Synchronizing systolic calcium release with azumolene in an experimental model. Heart Rhythm O2. 2022 Jun 15;3(5):568-576. doi: 10.1016/j.hroo.2022.06.001. PMID: 36340488; PMCID: PMC9626747.


2: Chakraborty P, Massé S, Azam MA, Thollon C, Niri A, Lai PFH, Bouly M, Riazi S, Nanthakumar K. Effects of azumolene on arrhythmia substrate in a model of recurrent long-duration ventricular fibrillation. Biochem Biophys Res Commun. 2022 Apr 16;600:123-129. doi: 10.1016/j.bbrc.2022.02.031. Epub 2022 Feb 16. PMID: 35219100.


3: Dershwitz M, Sréter FA. Azumolene reverses episodes of malignant hyperthermia in susceptible swine. Anesth Analg. 1990 Mar;70(3):253-5. doi: 10.1213/00000539-199003000-00004. PMID: 2305975.


4: Sudo RT, Carmo PL, Trachez MM, Zapata-Sudo G. Effects of azumolene on normal and malignant hyperthermia-susceptible skeletal muscle. Basic Clin Pharmacol Toxicol. 2008 Mar;102(3):308-16. doi: 10.1111/j.1742-7843.2007.00156.x. Epub 2007 Nov 28. PMID: 18047479.


5: Zhang Y, Rodney GG, Schneider MF. Effects of azumolene on Ca2+ sparks in skeletal muscle fibers. J Pharmacol Exp Ther. 2005 Jul;314(1):94-102. doi: 10.1124/jpet.105.084046. Epub 2005 Apr 14. PMID: 15831441.


6: Thota S, Rodrigues DA, Pinheiro PSM, Lima LM, Fraga CAM, Barreiro EJ. N-Acylhydrazones as drugs. Bioorg Med Chem Lett. 2018 Sep 15;28(17):2797-2806. doi: 10.1016/j.bmcl.2018.07.015. Epub 2018 Jul 9. PMID: 30006065.


7: Zhao X, Weisleder N, Han X, Pan Z, Parness J, Brotto M, Ma J. Azumolene inhibits a component of store-operated calcium entry coupled to the skeletal muscle ryanodine receptor. J Biol Chem. 2006 Nov 3;281(44):33477-86. doi: 10.1074/jbc.M602306200. Epub 2006 Aug 31. PMID: 16945924.


8: Tian Q, Katz AM, Kim DH. Effects of azumolene on doxorubicin-induced Ca2+ release from skeletal and cardiac muscle sarcoplasmic reticulum. Biochim Biophys Acta. 1991 Aug 13;1094(1):27-34. doi: 10.1016/0167-4889(91)90022-p. PMID: 1883852.


9: do Carmo PL, Zapata-Sudo G, Trachez MM, das Graças Fernandes Sales M, Sudo RT. Toxicological evaluation of azumolene after repeated intraperitoneal administration in rats. Fundam Clin Pharmacol. 2010 Aug;24(4):491-500. doi: 10.1111/j.1472-8206.2009.00787.x. Epub 2009 Nov 3. PMID: 19889027.


10: Talbert EE, Smuder AJ, Kwon OS, Sollanek KJ, Wiggs MP, Powers SK. Blockage of the Ryanodine Receptor via Azumolene Does Not Prevent Mechanical Ventilation- Induced Diaphragm Atrophy. PLoS One. 2016 Feb 5;11(2):e0148161. doi: 10.1371/journal.pone.0148161. PMID: 26849371; PMCID: PMC4744044.


11: Si D, Azam MA, Lai PFH, Zamiri N, Kichigina G, Asta J, Massé S, Bokhari MM, Porta-Sánchez A, Labos C, Sun H, Yang P, Nanthakumar K. Essential role of ryanodine receptor 2 phosphorylation in the effect of azumolene on ventricular arrhythmia vulnerability in a rabbit heart model. J Cardiovasc Electrophysiol. 2018 Dec;29(12):1707-1715. doi: 10.1111/jce.13737. Epub 2018 Oct 31. PMID: 30203424.


12: do Carmo PL, Zapata-Sudo G, Trachez MM, Antunes F, Guimarães SE, Debom R, Rizzi MD, Sudo RT. Intravenous administration of azumolene to reverse malignant hyperthermia in swine. J Vet Intern Med. 2010 Sep-Oct;24(5):1224-8. doi: 10.1111/j.1939-1676.2010.0556.x. Epub 2010 Jun 24. PMID: 20584138.


13: Leslie GC, Part NJ. The effect of EU4093 (azumolene sodium) on the contraction of intrafusal muscle in the soleus muscle of the anaesthetized rat. Br J Pharmacol. 1989 Aug;97(4):1151-6. doi: 10.1111/j.1476-5381.1989.tb12573.x. PMID: 2790379; PMCID: PMC1854609.


14: Foster PS, Hopkinson KC, Payne N, Denborough MA. The effect of azumolene on hypercontractility and sarcoplasmic reticulum Ca(2+)-dependent ATPase activity of malignant hyperpyrexia-susceptible porcine skeletal muscle. Clin Exp Pharmacol Physiol. 1991 Jul;18(7):489-95. doi: 10.1111/j.1440-1681.1991.tb01482.x. PMID: 1833102.


15: Zhao X, Min CK, Ko JK, Parness J, Kim DH, Weisleder N, Ma J. Increased store-operated Ca2+ entry in skeletal muscle with reduced calsequestrin-1 expression. Biophys J. 2010 Sep 8;99(5):1556-64. doi: 10.1016/j.bpj.2010.06.050. PMID: 20816068; PMCID: PMC2931717.


16: el-Hayek R, Parness J, Valdivia HH, Coronado R, Hogan K. Dantrolene and azumolene inhibit [3H]PN200-110 binding to porcine skeletal muscle dihydropyridine receptors. Biochem Biophys Res Commun. 1992 Sep 16;187(2):894-900. doi: 10.1016/0006-291x(92)91281-t. PMID: 1326958.


17: Kindler CH, Eilers H, Donohoe P, Ozer S, Bickler PE. Volatile anesthetics increase intracellular calcium in cerebrocortical and hippocampal neurons. Anesthesiology. 1999 Apr;90(4):1137-45. doi: 10.1097/00000542-199904000-00029. PMID: 10201687.


18: Yarotskyy V, Protasi F, Dirksen RT. Accelerated activation of SOCE current in myotubes from two mouse models of anesthetic- and heat-induced sudden death. PLoS One. 2013 Oct 15;8(10):e77633. doi: 10.1371/journal.pone.0077633. PMID: 24143248; PMCID: PMC3797063.


19: Hotchkiss RS, Osborne DF, Lappas GD, Karl IE. Calcium antagonists decrease plasma and tissue concentrations of tumor necrosis factor-alpha, interleukin-1 beta, and interleukin-1 alpha in a mouse model of endotoxin. Shock. 1995 May;3(5):337-42. PMID: 7648334.


20: Michelucci A, Paolini C, Boncompagni S, Canato M, Reggiani C, Protasi F. Strenuous exercise triggers a life-threatening response in mice susceptible to malignant hyperthermia. FASEB J. 2017 Aug;31(8):3649-3662. doi: 10.1096/fj.201601292R. Epub 2017 May 2. PMID: 28465322; PMCID: PMC5503704.