Azomycin | CAS#527-73-1

MedKoo Cat#: 462918 | Name: Azomycin

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Azomycin is a natural antimicrobial antibiotic produced by a strain of Streptomyces eurocidicus. It has been used to combat anaerobic bacterial and parasitic infections.

Chemical Structure

Azomycin

CAS#527-73-1

Theoretical Analysis

MedKoo Cat#: 462918

Name: Azomycin

CAS#: 527-73-1

Chemical Formula: C3H3N3O2

Exact Mass: 113.0225

Molecular Weight: 113.08

Elemental Analysis: C, 31.87; H, 2.67; N, 37.16; O, 28.30

Price and Availability

Size	Price	Availability
5g	USD 250.00	2 Weeks
10g	USD 400.00	2 Weeks
25g	USD 750.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Amicin; 2-Nitroimidazole;

IUPAC/Chemical Name

2-nitro-1H-imidazole

InChi Key

YZEUHQHUFTYLPH-UHFFFAOYSA-N

InChi Code

InChI=1S/C3H3N3O2/c7-6(8)3-4-1-2-5-3/h1-2H,(H,4,5)

SMILES Code

[O-][N+](C1=NC=CN1)=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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 113.08 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.

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

1: Kallitsakis MG, Ioannou DI, Terzidis MA, Kostakis GE, Lykakis IN. Selective Photoinduced Reduction of Nitroarenes to N-Arylhydroxylamines. Org Lett. 2020 Jun 5;22(11):4339-4343. doi: 10.1021/acs.orglett.0c01367. Epub 2020 May 26. PMID: 32453579. 2: Meißner R, Feketeová L, Ribar A, Fink K, Limão-Vieira P, Denifl S. Electron Ionization of Imidazole and Its Derivative 2-Nitroimidazole. J Am Soc Mass Spectrom. 2019 Dec;30(12):2678-2691. doi: 10.1007/s13361-019-02337-w. Epub 2019 Oct 30. PMID: 31667709; PMCID: PMC6914720. 3: Abinaya M, Rajakumaran R, Chen SM, Karthik R, Muthuraj V. In Situ Synthesis, Characterization, and Catalytic Performance of Polypyrrole Polymer-Incorporated Ag2MoO4 Nanocomposite for Detection and Degradation of Environmental Pollutants and Pharmaceutical Drugs. ACS Appl Mater Interfaces. 2019 Oct 16;11(41):38321-38335. doi: 10.1021/acsami.9b13682. Epub 2019 Oct 3. PMID: 31549800. 4: Hedges JB, Ryan KS. In vitro Reconstitution of the Biosynthetic Pathway to the Nitroimidazole Antibiotic Azomycin. Angew Chem Int Ed Engl. 2019 Aug 19;58(34):11647-11651. doi: 10.1002/anie.201903500. Epub 2019 Jul 17. PMID: 31231913. 5: Nakata N, Kiriu M, Okumura Y, Zhao S, Nishijima KI, Shiga T, Tamaki N, Kuge Y, Matsumoto H. Comparative evaluation of [18F]DiFA and its analogs as novel hypoxia positron emission tomography and [18F]FMISO as the standard. Nucl Med Biol. 2019 Mar;70:39-45. doi: 10.1016/j.nucmedbio.2019.01.008. Epub 2019 Feb 8. PMID: 30836255. 6: Maier FC, Schweifer A, Damaraju VL, Cass CE, Bowden GD, Ehrlichmann W, Kneilling M, Pichler BJ, Hammerschmidt F, Reischl G. 2-Nitroimidazole-Furanoside Derivatives for Hypoxia Imaging-Investigation of Nucleoside Transporter Interaction, 18F-Labeling and Preclinical PET Imaging. Pharmaceuticals (Basel). 2019 Feb 15;12(1):31. doi: 10.3390/ph12010031. PMID: 30781409; PMCID: PMC6469291. 7: Sun W, Falzon C, Naimi E, Akbari A, Wiebe LI, Tandon M, Kumar P. Synthesis of [18F]FAZA Using Nosyl and Iodo Precursors for Nucleophilic Radiofluorination. Curr Radiopharm. 2019;12(1):49-57. doi: 10.2174/1874471011666181019105947. PMID: 30338747. 8: Ficociello G, Zonfrilli A, Cialfi S, Talora C, Uccelletti D. Yeast-Based Screen to Identify Natural Compounds with a Potential Therapeutic Effect in Hailey-Hailey Disease. Int J Mol Sci. 2018 Jun 20;19(6):1814. doi: 10.3390/ijms19061814. PMID: 29925776; PMCID: PMC6032253. 9: Dingsdag SA, Hunter N. Metronidazole: an update on metabolism, structure- cytotoxicity and resistance mechanisms. J Antimicrob Chemother. 2018 Feb 1;73(2):265-279. doi: 10.1093/jac/dkx351. PMID: 29077920. 10: Busk M, Munk OL, Jakobsen SS, Horsman MR. Hypoxia positron emission tomography imaging: combining information on perfusion and tracer retention to improve hypoxia specificity. Acta Oncol. 2017 Nov;56(11):1583-1590. doi: 10.1080/0284186X.2017.1355114. Epub 2017 Aug 25. PMID: 28840765. 11: Kumar P, Roselt P, Reischl G, Cullinane C, Beiki D, Ehrlichmann W, Binns D, Naimi E, Yang J, Hicks R, Machulla HJ, Wiebe LI. β -[18F]Fluoro Azomycin Arabinoside (β -[18F]FAZA): Synthesis, Radiofluorination and Preliminary PET Imaging of Murine A431 Tumors. Curr Radiopharm. 2017;10(2):93-101. doi: 10.2174/1874471010666170313120540. PMID: 28294075. 12: Schweifer A, Maier F, Ehrlichmann W, Lamparter D, Kneilling M, Pichler BJ, Hammerschmidt F, Reischl G. [18F]Fluoro-azomycin-2´-deoxy-β-d- ribofuranoside - A new imaging agent for tumor hypoxia in comparison with [18F]FAZA. Nucl Med Biol. 2016 Dec;43(12):759-769. doi: 10.1016/j.nucmedbio.2016.08.005. Epub 2016 Aug 9. PMID: 27693670. 13: Wanek T, Kreis K, Križková P, Schweifer A, Denk C, Stanek J, Mairinger S, Filip T, Sauberer M, Edelhofer P, Traxl A, Muchitsch VE, Mereiter K, Hammerschmidt F, Cass CE, Damaraju VL, Langer O, Kuntner C. Synthesis and preclinical characterization of 1-(6'-deoxy-6'-[18F]fluoro-β-d- allofuranosyl)-2-nitroimidazole (β-6'-[18F]FAZAL) as a positron emission tomography radiotracer to assess tumor hypoxia. Bioorg Med Chem. 2016 Nov 1;24(21):5326-5339. doi: 10.1016/j.bmc.2016.08.053. Epub 2016 Aug 29. PMID: 27614920. 14: Kumar P, Elsaidi HR, Zorniak B, Laurens E, Yang J, Bacchu V, Wang M, Wiebe LI. Synthesis and Biological Evaluation of Iodoglucoazomycin (I-GAZ), an Azomycin-Glucose Adduct with Putative Applications in Diagnostic Imaging and Radiotherapy of Hypoxic Tumors. ChemMedChem. 2016 Aug 5;11(15):1638-45. doi: 10.1002/cmdc.201600213. Epub 2016 Jul 5. PMID: 27377671; PMCID: PMC5095876. 15: Aksoy Gökmen A, Girginkardeşler N, Kilimcioğlu AA, Şirin MC, Özbilgin A. Trichomonas vaginalis'in metronidazol, ornidazol ve proton pompa inhibitörleri pantoprazol ve esomeprazole karşı in vitro duyarlılığı [In vitro susceptibility of Trichomonas vaginalis to metronidazole, ornidazole and proton pump inhibitors pantoprazole and esomeprazole]. Mikrobiyol Bul. 2016 Jan;50(1):133-9. Turkish. PMID: 27058337. 16: Zhou F, Zanganeh S, Mohammad I, Dietz C, Abuteen A, Smith MB, Zhu Q. Targeting tumor hypoxia: a third generation 2-nitroimidazole-indocyanine dye- conjugate with improved fluorescent yield. Org Biomol Chem. 2015 Dec 14;13(46):11220-7. doi: 10.1039/c5ob01460c. PMID: 26403518; PMCID: PMC4651866. 17: Quan S, Wang Y, Zhou A, Kumar P, Narain R. Galactose-based Thermosensitive Nanogels for Targeted Drug Delivery of Iodoazomycin Arabinofuranoside (IAZA) for Theranostic Management of Hypoxic Hepatocellular Carcinoma. Biomacromolecules. 2015 Jul 13;16(7):1978-86. doi: 10.1021/acs.biomac.5b00576. Epub 2015 Jun 3. PMID: 25996799. 18: Lewin J, Khamly KK, Young RJ, Mitchell C, Hicks RJ, Toner GC, Ngan SY, Chander S, Powell GJ, Herschtal A, Te Marvelde L, Desai J, Choong PF, Stacker SA, Achen MG, Ferris N, Fox S, Slavin J, Thomas DM. A phase Ib/II translational study of sunitinib with neoadjuvant radiotherapy in soft-tissue sarcoma. Br J Cancer. 2014 Dec 9;111(12):2254-61. doi: 10.1038/bjc.2014.537. Epub 2014 Oct 16. PMID: 25321190; PMCID: PMC4264446. 19: Leitsch D, Schlosser S, Burgess A, Duchêne M. Nitroimidazole drugs vary in their mode of action in the human parasite Giardia lamblia. Int J Parasitol Drugs Drug Resist. 2012 May 12;2:166-70. doi: 10.1016/j.ijpddr.2012.04.002. PMID: 24533278; PMCID: PMC3862438. 20: Wuest M, Kumar P, Wang M, Yang J, Jans HS, Wiebe LI. In vitro and in vivo evaluation of [(18)F]F-GAZ, a novel oxygen-mimetic azomycin-glucose conjugate, for imaging hypoxic tumor. Cancer Biother Radiopharm. 2012 Oct;27(8):473-80. doi: 10.1089/cbr.2011.1148. Epub 2012 Jun 29. PMID: 22746267.