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Azomycin (2-Nitroimidazole)

Alias: Amicin; 2-Nitroimidazole;
Cat No.:V1979 Purity: ≥98%
Azomycin(2-Nitroimidazole) is an antimicrobial antibiotic extracted from a strain of Nocardia mesenterica andan unidentified Streptomyces.
Azomycin (2-Nitroimidazole)
Azomycin (2-Nitroimidazole) Chemical Structure CAS No.: 527-73-1
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
10g
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description
Azomycin (2-Nitroimidazole) is an antimicrobial antibiotic extracted from a strain of Nocardia mesenterica and an unidentified Streptomyces. Azomycin is active against aerobic Gram-positive and Gram-negative bacteria. The structure of azomycinis a 2-nitroimidazole. Reduction of azomycin abolish the bacteriostatic activities. Also the closely related analog, 4-nitroimidazole does not exhibit bacteriostatic effects.


azomycin is a nitroimidazole antibiotic first isolated from a strain resembling Nocardia mesenterica and also from Streptomyces eurocidicus. In this study, it was isolated from the culture broth of a bacterial strain identified as Pseudomonas fluorescens (PB-6282). It is an acidic substance obtained as colorless prisms, decomposing above 250°C, soluble in aqueous alcohols and DMSO, slightly soluble in methanol and ethanol, and insoluble in acetone, ethyl acetate, chloroform, and water. Its molecular formula is C3H3N3O2 with a molecular weight of 113. [1]
Biological Activity I Assay Protocols (From Reference)
Targets
Bacterial
ln Vitro
An antibiotic called azomycin has the ability to combat both aerobic Gram-positive and Gram-negative bacteria. Azomycin has been shown to be effective against a range of anaerobic bacteria[1].
azomycin was found to be active against a variety of anaerobic bacteria. The minimum inhibitory concentrations (MICs) against tested anaerobic strains are as follows: Peptococcus asaccharolyticus ATCC14963: 3.13 μg/ml; P. prevotii ATCC9321: 6.25 μg/ml; Peptostreptococcus micros VPI 5464-1: 1.56 μg/ml; Streptococcus constellatus ATCC27823: >100 μg/ml; Eubacterium limosum ATCC8486: 3.13 μg/ml; E. aerofaciens ATCC25986: 6.25 μg/ml; Propionibacterium acnes ATCC11827: 50 μg/ml; Bifidobacterium adolescentis JCM1250: 6.25 μg/ml; B. bifidum JCM1122: 6.25 μg/ml; B. longum ATCC15707: 12.5 μg/ml; Clostridium perfringens ATCC13124: 0.78 μg/ml; C. difficile ATCC17857: 0.78 μg/ml; Veillonella parvula ATCC10790: 1.56 μg/ml; Bacteroides fragilis GM7000: 3.13 μg/ml; B. fragilis ATCC25285: 3.13 μg/ml; B. thetaiotaomicron WAL3304: 6.25 μg/ml; B. vulgatus ATCC29327: 0.39 μg/ml; B. melaninogenicus GAI0413: 0.39 μg/ml; Fusobacterium varium ATCC8501: 1.56 μg/ml; F. necrophorum ATCC25286: 0.78 μg/ml; F. nucleatum ATCC25586: 1.56 μg/ml; F. mortiferum ATCC9817: 0.78 μg/ml. [1]
It is mentioned that azomycin has been previously reported to be active against aerobic Gram-positive and Gram-negative bacteria. [1]
Cell Assay
The antibacterial activity of azomycin against anaerobic bacteria was evaluated using an agar dilution method. The test medium was GAM agar. The inoculum size was one loopful of a bacterial suspension adjusted to 10^6 colony-forming units per milliliter (cfu/ml). The minimum inhibitory concentration (MIC) was determined as the lowest concentration of azomycin that prevented visible growth after incubation. [1]
References

[1]. Isolation of azomycin from Pseudomonas fluorescens. J Antibiot (Tokyo). 1989 Oct;42(10):1513-4.

Additional Infomation
2-Nitroimidazole is an imidazole compound with a nitro group substituted at the 2-position of 1H-imidazole. It possesses anti-tuberculosis activity. 2-Nitroimidazole is a C-nitro compound belonging to the imidazole class. Its function is similar to that of 1H-imidazole. 2-Nitroimidazole has been reported to exist in Pseudomonas fluorescens, and relevant data are available for reference.
Azomycin (2-nitroimidazole) was isolated from Pseudomonas fluorescens PB-6282. The fermentation medium contained starch 2.0%, glycerol 0.5%, Bacto Soytone 1.5%, corn steep liquor 0.5%, NaCl 0.3%, CaCO3 0.3% (pH 7.0). The culture was incubated at 23°C for 2 days on a rotary shaker (180 rpm, 70 mm stroke). The isolation procedure involved pH adjustment to 2.0 with HCl, extraction with BuOH, back-extraction into aqueous NaHCO3, re-extraction at pH 2.0, followed by Sephadex LH-20 column chromatography with MeOH, silica gel column chromatography with CHCl3-MeOH (20:1), and crystallization from MeOH to yield colorless prisms. [1]
The UV absorption spectrum of azomycin in 95% EtOH showed λmax (ε) 219 (3,900) and 315 (8,600); in 0.1 N HCl-95% EtOH: 219 (3,900) and 315 (8,400); in 0.1 N NaOH-95% EtOH: 223 (3,500) and 365 (10,700). The IR spectrum (KBr) was consistent with reported data for azomycin. No optical activity was detected by CD measurement. 1H NMR (DMSO-d6, TMS): δ 7.41 (s, 4-H, 5-H); 13C NMR: δ 126.3 (d, 1JCH=195 Hz, long range coupling 2JCH=12 Hz, C-4 and C-5), δ 146.1 (s, C-2). EI-MS: m/z 113 (M+). Elemental analysis: Calcd for C3H3N3O2: C 31.86, H 2.67, N 37.16; Found: C 31.86, H 2.92, N 37.10. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C3H3N3O2
Molecular Weight
113.07
Exact Mass
113.022
Elemental Analysis
C, 31.87; H, 2.67; N, 37.16; O, 28.30
CAS #
527-73-1
Related CAS #
527-73-1
PubChem CID
10701
Appearance
White to yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
373.6±25.0 °C at 760 mmHg
Melting Point
287 °C (dec.)(lit.)
Flash Point
179.7±23.2 °C
Vapour Pressure
0.0±0.8 mmHg at 25°C
Index of Refraction
1.612
LogP
0.15
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
8
Complexity
99.2
Defined Atom Stereocenter Count
0
SMILES
O=[N+]([O-])C1=NC=CN1
InChi Key
YZEUHQHUFTYLPH-UHFFFAOYSA-N
InChi Code
InChI=1S/C3H3N3O2/c7-6(8)3-4-1-2-5-3/h1-2H,(H,4,5)
Chemical Name
2-nitro-1H-imidazole
Synonyms
Amicin; 2-Nitroimidazole;
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : 22~50 mg/mL ( 194.56~442.20 mM )
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.67 mg/mL (23.61 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 26.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.67 mg/mL (23.61 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 26.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 3: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.67 mg/mL (23.61 mM)


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 8.8441 mL 44.2204 mL 88.4408 mL
5 mM 1.7688 mL 8.8441 mL 17.6882 mL
10 mM 0.8844 mL 4.4220 mL 8.8441 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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