| Identification | More | [Name]
alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol | [CAS]
3366-95-8 | [Synonyms]
alpha,2-dimethyl-5-nitro-1h-imidazole-1-ethanol
SECNIDAZOLE
SECNIDAZOLE, MM(CRM STANDARD)
1-(2-Methyl-5-nitroimidazol-1-yl)-2-propanol
a,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol
Flagentyl
PM 185184
RP 14539
1-(2-Methyl-5-nitroimidazol-1-yl)propan-2-ol
1H-Imidazole-1-ethanol, alpha,2-dimethyl-5-nitro-
α,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol | [EINECS(EC#)]
222-134-0 | [Molecular Formula]
C7H11N3O3 | [MDL Number]
MFCD00864656 | [Molecular Weight]
185.18 | [MOL File]
3366-95-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
76°C | [Boiling point ]
396.1±22.0 °C(Predicted) | [density ]
1.39±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Sparingly), Methanol (Sparingly) | [form ]
Solid | [pka]
14.50±0.20(Predicted) | [color ]
White to Light Yellow | [Water Solubility ]
H2O: 2mg/mL, clear (warmed) | [Usage]
Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas) | [λmax]
319nm(H2O)(lit.) | [Merck ]
14,8419 | [InChI]
InChI=1S/C7H11N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3,5,11H,4H2,1-2H3 | [InChIKey]
KPQZUUQMTUIKBP-UHFFFAOYSA-N | [SMILES]
C(N1C(=NC=C1N(=O)=O)C)C(O)C | [CAS DataBase Reference]
3366-95-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline Solid | [Uses]
Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas) | [Uses]
Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas). | [Uses]
antiameobic, antitrichomonas | [Definition]
ChEBI: Secnidazole is a C-nitro compound that is 5-nitroimidazole in which the hydrogens at positions 1 and 2 are replaced by 2-hydroxypropyl and methyl groups, respectively. It has a role as an epitope. It is a C-nitro compound, a member of imidazoles and a secondary alcohol. | [Pharmaceutical Applications]
A 5-nitroimidazole with properties similar to those of metronidazole. It is rapidly absorbed after oral administration and is distinguished by having the longest plasma half-life (18 h) of clinically used nitroimidazole drugs. It is used in the treatment of intestinal amebiasis, giardiasis, trichomoniasis and bacterial vaginosis. | [Biological Activity]
Secnidazole is a nitroimidazole anti-microbial selective against many anaerobic Gram-positive and Gram-negative bacteria and protozoa. It has been approved for the treatment of bacterial vaginosis. Secnidazole is a prodrugwhose nitro group is reduced by bacterial enzymes to radical anions th at interfere with bacterial DNA synthesis. | [Synthesis]
In a 10 L glass reactor, 2-methyl-5-nitroimidazole (635 g), 1-bromo-2-propanol (2070 g), potassium carbonate (2114 g) and acetone (7.1 L) were added in a molar ratio of 1:3:3:20. The reaction mixture was heated to 70 °C and refluxed for 5 h under stirring conditions. The progress of the reaction was monitored by TLC (GF254 silica gel plate, unfolding agent was chloroform:ethanol=85:15) to confirm the completion of the reaction to obtain the reaction mixture A. Acetone was recovered by distillation under reduced pressure to obtain the reaction mixture B. 9 L of water was added to the reaction mixture B, cooled down to 0 °C and centrifuged to obtain the wet product. The wet product was washed with cold water and centrifuged again after stirring at 1 °C for 3 h to obtain 1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol crude product. The crude product was transferred to a 5L reactor, 40% ethanol (3L) and activated carbon (30g) were added, heated to 70°C refluxed to dissolve and then hot filtered. The filtrate was cooled to 0°C for crystallization for 3 h. After centrifugal separation, the product was dried under vacuum at 40°C to obtain the pure Secnidazole. After weighing, the mass of the final product was 820 g, and the total yield was 89.1%. | [References]
[1] Patent: CN103772289, 2016, B. Location in patent: Paragraph 0036-0042 |
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