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.


Price and Availability

Size Price Shipping out time Quantity
50mg USD 750 2 Weeks
100mg USD 1250 2 Weeks
200mg USD 1850 2 Weeks
500mg USD 2850 2 Weeks
1g USD 3850 2 Weeks
2g USD 5850 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-12-02. Prices are subject to change without notice.

Azumolene is in stock.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 330058
Name: Azumolene
CAS#: 64748-79-4 (free)
Chemical Formula: C13H9BrN4O3
Exact Mass: 347.9858
Molecular Weight: 349.144
Elemental Analysis: C, 44.72; H, 2.60; Br, 22.89; N, 16.05; O, 13.75


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


Technical Data

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


References

1: 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.

2: 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.

3: 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.

4: 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.

5: 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.

6: Bina S, Capacchione J, Muldoon S, Bayarsaikhan M, Bunger R. Lymphocyte-based determination of susceptibility to malignant hyperthermia: a pilot study in swine. Anesthesiology. 2010 Oct;113(4):917-24. doi: 10.1097/ALN.0b013e3181ee2cd0. PMID: 20823761.

7: 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.

8: 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.

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: Silva JH, Gomez MV, Silva JH, Guatimosim C, Gomez RS. Halothane induces vesicular and carrier-mediated release of [3H]serotonin from rat brain cortical slices. Neurochem Int. 2008 May;52(6):1240-6. doi: 10.1016/j.neuint.2008.01.004. Epub 2008 Jan 12. PMID: 18282641.

11: 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.

12: 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.

13: McKinney LC, Butler T, Mullen SP, Klein MG. Characterization of ryanodine receptor-mediated calcium release in human B cells: relevance to diagnostic testing for malignant hyperthermia. Anesthesiology. 2006 Jun;104(6):1191-201. doi: 10.1097/00000542-200606000-00014. PMID: 16732090.

14: 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.

15: 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.

16: Shamash J, Salam AH, Davies DC, Williams A, Joel S, Lister TA. In vitro testing of calcium channel blockers and cytotoxic chemotherapy in B-cell low- grade non-Hodgkin's lymphoma. Br J Cancer. 1998 May;77(10):1598-603. doi: 10.1038/bjc.1998.262. PMID: 9635834; PMCID: PMC2150073.

17: Palnitkar SS, Mickelson JR, Louis CF, Parness J. Pharmacological distinction between dantrolene and ryanodine binding sites: evidence from normal and malignant hyperthermia-susceptible porcine skeletal muscle. Biochem J. 1997 Sep 15;326 ( Pt 3)(Pt 3):847-52. doi: 10.1042/bj3260847. PMID: 9307036; PMCID: PMC1218741.

18: Gallant EM, Lentz LR, Taylor SR. Modulation of caffeine contractures in mammalian skeletal muscles by variation of extracellular potassium. J Cell Physiol. 1995 Nov;165(2):254-60. doi: 10.1002/jcp.1041650206. PMID: 7593203.

19: Parness J, Palnitkar SS. Identification of dantrolene binding sites in porcine skeletal muscle sarcoplasmic reticulum. J Biol Chem. 1995 Aug 4;270(31):18465-72. doi: 10.1074/jbc.270.31.18465. PMID: 7629173.

20: 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.