Misonidazole

Base Information

• Chemical Name: Misonidazole
• CAS No.: 13551-87-6
• Molecular Formula: C7H11 N3 O4
• Molecular Weight: 201.182
• Hs Code.: 2933290090
• European Community (EC) Number: 236-931-6
• NSC Number: 261037
• UNII: 8FE7LTN8XE
• DSSTox Substance ID: DTXSID80864420
• Nikkaji Number: J2.739A
• Wikipedia: Misonidazole
• Wikidata: Q6875874
• NCI Thesaurus Code: C657
• Metabolomics Workbench ID: 152827
• ChEMBL ID: CHEMBL42161
• Mol file: 13551-87-6.mol

Synonyms:alpha-(Methoxymethyl)-2-nitro-1H-imidazole-1-ethanol;Misonidazole;Ro 07 0582;Ro 07-0582;Ro 070582;Ro 7 0582;Ro 7-0582;Ro 70582

Chemical Property of Misonidazole

Chemical Property:

• Vapor Pressure: 1.83E-08mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 438.5°C at 760 mmHg
• Flash Point: 219°C
• PSA: 93.10000
• Density: 1.43g/cm³
• LogP: 0.32180
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly, Heated), Methanol (Slightly, Sonicated)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 201.07495584
• Heavy Atom Count: 14
• Complexity: 196

Purity/Quality:

99%, ^*data from raw suppliers

Misonidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCC(CN1C=CN=C1[N+](=O)[O-])O
• Recent EU Clinical Trials: Do Selective Radiation Dose Escalation and Tumor Hypoxia Status Impact the Locoregional Tumor Control after Radiochemotherapy of Head & Neck Tumors?
• Description: Misonidazole is a nitroimidazole with radiosensitizing and antineoplastic properties. Nitroimidazoles, including misonidazole, specifically accumulate as nitro anion radicals and their metabolites in hypoxic cells. The metabolites of misonidazole can themselves be cytotoxic or they can increase the chemosensitivity and radiosensitivity of the target cells. Misonidazole and derivatives, including fluoromisonidazole, are used in the imaging of hypoxic regions in tumors and in the cardiovascular system.
• Uses: Antiprotozoal (Trichomonas). Misonidazole can be used as a potential hypoxic cancer cell radiosensitizer and DNA binding and nicking agent. The metabolites of misonidazole can themselves be cytotoxic or they can increase the chemosensitivity and radiosensitivity of the target cells

Technology Process of Misonidazole

There total 1 articles about Misonidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ 2-nitroimidazole-1-(2-methoxymethyl)ethanol (13551-87-6)

Guidance literature:

2-Nitroimidazol + 1,2-Epoxy-3-methoxypropan.;

Reference yield: 94.5%

2-nitroimidazole-1-(2-methoxymethyl)ethanol (13551-87-6) → α-(Methoxymethyl)-2-amino-1H-imidazole-1-ethanol (76620-73-0)

Guidance literature:

With hydrazine hydrate; palladium on activated charcoal; In tetrahydrofuran; ethanol; at 52 ℃; for 3.5h;

DOI:10.1021/jo00179a037

Reference yield: 65.0%

potassium amminetrichloroplatinate + 2-nitroimidazole-1-(2-methoxymethyl)ethanol (13551-87-6) → cis-amminedichloro(1-(2-nitro-1-imidazolyl)-3-methoxy-2-propanol)platinum(II) (112198-62-6)

Guidance literature:

In water; byproducts: KCl; mixed solution is stirred overnight at room temp.; soln. is evapd. to dryness to give an orange oil, the oil is dissolved in acetone and filtered, then dried over CaSO4, soln. is filtered and evapd., addn. of ether, a solid is filtered off, washed with ether and dried., elem. anal.;

Downstream raw materials:

α-(Methoxymethyl)-2-amino-1H-imidazole-1-ethanol

C₇H₁₂N₄O₄

1-{2-[1-(2-Hydroxy-3-methoxy-propyl)-1H-imidazol-2-ylazo]-imidazol-1-yl}-3-methoxy-propan-2-ol

1-{2-[1-(2-Hydroxy-3-methoxy-propyl)-1H-imidazol-2-yl-NNO-azoxy]-imidazol-1-yl}-3-methoxy-propan-2-ol