1-chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol

• ChemBase ID: 53482
• Molecular Formular: C7H10ClN3O3
• Molecular Mass: 219.6256
• Monoisotopic Mass: 219.04106888
• SMILES: c1(n(c(nc1)C)CC(O)CCl)[N+](=O)[O-]
• Canonical SMILES: ClCC(Cn1c(C)ncc1[N+](=O)[O-])O
• InChI: InChI=1S/C7H10ClN3O3/c1-5-9-3-7(11(13)14)10(5)4-6(12)2-8/h3,6,12H,2,4H2,1H3
• InChIKey: IPWKIXLWTCNBKN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol
• IUPAC Traditional name: ornidazole; madelen; 1-chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol
• Synonyms: 1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)-2-propanol; 1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole; Ornidazole; α-(Chloromethyl)-2-methyl-5-nitro-1H-imidazole-1-ethanol; Madelen; NSC 95075; Ornidal; Ro 7-0207; Tiberal; 1-[3-Chloro-2-hydroxypropyl]-2-methyl-5-nitroimidazole; ORNIDAZOLE; 1-chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol; Betiral; Biteral; Danubial; Kolpicid; Tibal; Tinerol; 1(3-chloro-2-hydroxypropyl)-2-methyl-5-nitro imidazole; 1-(3-氯-2-羟丙基)-2-甲基-5-硝基咪唑; 奥硝唑

Database IDs

• CAS Number: 16773-42-5
• EC Number: 240-826-0
• MDL Number: MFCD00057960
• PubChem SID: 162058245; 24898028
• PubChem CID: 28061

CALCULATED PROPERTIES

• Acid pKa: 13.874782
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.26448184
• LogD (pH = 7.4): 0.26494068
• Log P: 0.2649467
• Molar Refractivity: 49.2298 cm^3
• Polarizability: 18.90888 Å^3
• Polar Surface Area: 81.19 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 84-86°C; 88-91°C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: NI5460000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: S:36/37/39
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302

Pharmacology Properties

• Target: Others
• 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

• Purity: 97%; 98%
• Grade: analytical standard
• Salt Data: Free Base
• Application(s): Active against anaerobic bacteria; Antiprotozoal agent
• Linear Formula: C7H10N3O3Cl

DETAILS

MP Biomedicals - 02155999

(1-[3-Chloro-2-hydroxypropyl]-2-methyl-5-nitroimidazole)

Toronto Research Chemicals - O688500

Anti-infective.

REFERENCES

• Grunberg, E, et al.: Proc. Soc. Exp. Biol. Med., 133, 490 (1970)
• Hoffer, M., et al.: J. Med. Chem., 17, 1019 (1970)
• Schwartz, D.E., et al.: Chemotherapy, 22, 19 (1970)
• Hoffer, M. et al., J. Med. Chem., 1974, 17, 1019, (synth, pharmacol)
• Nagarajan, K. et al., Indian J. Chem., Sect. B, 1982, 21, 1006, (cmr, pmr, uv, ms)
• Chen, B.C. et al., Helv. Chim. Acta, 1983, 66, 1537, (N-15 nmr)
• McClain, R.M. et al., Toxicol. Appl. Pharmacol., 1988, 92, 488, (tox)
• Yeung, C.H. et al., J. Reprod. Fertil., 1995, 103, 257; 1996, 106, 231, (tox)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 626
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, OJS000