1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol

• ChemBase ID: 73071
• Molecular Formular: C7H11N3O3
• Molecular Mass: 185.18054
• Monoisotopic Mass: 185.08004123
• SMILES: n1(CC(C)O)c(cnc1C)[N+](=O)[O-]
• Canonical SMILES: CC(Cn1c(C)ncc1[N+](=O)[O-])O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol
• IUPAC Traditional name: secnidazole; 1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol
• Synonyms: PM 185184, RP 14539; 1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol; PM 185184; RP 14539; Sindose; Secnil; Secnidazole; α,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol; 1-(2-Methyl-5-nitroimidazol-1-yl)-2-propanol; Flagentyl; PM 185184; RP 14539; Apex; Daksol; Famide; Flow; Secnidal; Secnidazole

Database IDs

• CAS Number: 3366-95-8
• PubChem SID: 162037991
• PubChem CID: 71815
• ATC CODE: P01AB07
• CHEMBL: 498847
• Chemspider ID: 64839
• KEGG ID: D07353
• Unique Ingredient Identifier: R3459K699K
• Wikipedia Title: Secnidazole

CALCULATED PROPERTIES

• H Donor: 1
• LogD (pH = 5.5): -0.0442613
• LogD (pH = 7.4): -0.04275446
• Log P: -0.0427352
• Molar Refractivity: 45.6393 cm^3
• Polarizability: 16.981556 Å^3
• Polar Surface Area: 83.87 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 15.158427
• H Acceptors: 4

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 70-72°C

Safety Information

• Storage Condition: -20°C; Refrigerator

Pharmacology Properties

• Admin Routes: Oral
• Mechanism of Action: Interacts with DNA to cause a loss of helical DNA structure and strand breakage resulting in inhibition of protein synthesis and cell death in susceptible organisms

Product Information

• Salt Data: Free Base
• Application(s): Amoebicide; Antimicrobial agent; Protozoacide; Trichomonacide

DETAILS

Selleck Chemicals - S2537

Research Area: Infection
Biological Activity:
Secnidazole (Flagentyl) is a nitroimidazole anti-infective. Secnidazole (Flagentyl) is effective in the treatment of dientamoebiasis. Secnidazole (Flagentyl) has also been tested against Atopobium vaginae. An MIC range for secnidazole (Flagentyl) is 4-128 mg/L. The MIC50 for secnidazole (Flagentyl) is 16 mg/L. The MIC90 for secnidazole (Flagentyl) is 64 mg/L. Secnidazole (Flagentyl) is highly effective in achieving parasitologic. [1][2][3]

Toronto Research Chemicals - S225000

Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas).

REFERENCES

• http://en.wikipedia.org/wiki/Secnidazole
• Cosar, C., et al.: Arzneim.-Forsch., 16, 23 (1966)
• Videau, D., et al.: Br. J. Vener. Dis., 54, 77 (1966)
• Symonds, J., et al.: J. Antimicrob. Chemother., 5, 484 (1966)
• Cosar, C. et al., Arzneim.-Forsch., 1966, 16, 23, (synth, pharmacol)
• Nagarajan, K. et al., Indian J. Chem., Sect. B, 1982, 21, 1006, (uv, pmr, ms)
• Bhatia, S.C. et al., J. Chromatogr., 1984, 305, 325, (gc)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 526
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 875, (synonyms)