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

• ChemBase ID: 792
• Molecular Formular: C6H9N3O3
• Molecular Mass: 171.15396
• Monoisotopic Mass: 171.06439116
• SMILES: OCCn1c(ncc1[N+](=O)[O-])C
• Canonical SMILES: OCCn1c(C)ncc1[N+](=O)[O-]
• InChI: InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
• InChIKey: VAOCPAMSLUNLGC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
• IUPAC Traditional name: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol; metronidazole
• Brand Name: Acromona; Anagiardil; Apo-Metronidazole; Arilin; Atrivyl; Bayer 5360; Bexon; Clont; Cont; Danizol; Deflamon; Deflamon-Wirkstoff; Efloran; Elyzol; Entizol; Eumin; Flagemona; Flagesol; Flagil; Flagyl; Flagyl ER; Flagyl I.V.; Flegyl; Fossyol; Giatricol; Gineflavir; Klion; Klont; Meronidal; Metric 21; Metro Cream; Metro I.V.; Metro I.V. In Plastic Container; Metrocream; Metrogel; Metrogel-Vaginal; Metrolag; Metrolotion; Metrolyl; Metromidol; Metronidaz; Metrotop; Mexibol; Monagyl; Monasin; Nalox; Neo-Tric; Nida; Nidagel; Noritate; Novonidazol; Orvagil; Protostat; Rathimed; Sanatrichom; Satric; Takimetol; Trichazol; Trichex; Tricho Cordes; Tricho-Gynaedron; Trichocide; Trichomol; Trichopal; Trichopol; Tricocet; Tricom; Tricowas B; Trikacide; Trikamon; Trikojol; Trikozol; Trimeks; Trivazol; Vagilen; Vagimid; Vertisal; Wagitran; Zadstat; Flagyl, Filmet
• Synonyms: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol; lagyl; Nidagyl; Mepagyl; Anagiardil; Metronidaz; Metronidazole; 2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethanol; Flagyl; Metrotop; Midazol; Torgyl; Zadstat; 2-Methyl-5-nitro-1H-imidazole-1-ethanol; Arilin; Bayer 5360; Cimetrol 500LPCI; Clont; Deflamon; Dentamet gel; Efloran; Elyzol; Entizol; Flagesol; Flagil; 1-(2-Hydroxyethyl)-2-methyl-5-nitroimidazole; NSC 50364; NSC 69587; Nidazole; Metronidazole in Plastic Container; Metronidazole Hcl; Metronidazole Benzoate; Metronidazol; Metronidazolo; Methronidazole; Metronidazole; 2-Methyl-5-nitroimidazole-1-ethanol; 2-甲基-5-硝基咪唑-1-乙醇; 甲硝唑

Database IDs

• CAS Number: 443-48-1
• EC Number: 207-136-1
• MDL Number: MFCD00009750
• Beilstein Number: 611683
• PubChem SID: 160964255; 24897314; 24870198; 24896667; 46508911; 24896871
• PubChem CID: 4173
• CHEBI ID: 6909
• ATC CODE: D06BX01; P01AB01; A01AB17; G01AF01; J01XD01; QP51AA01
• CHEMBL: 137
• Chemspider ID: 4029
• DrugBank ID: DB00916
• KEGG ID: D00409
• Unique Ingredient Identifier: 140QMO216E
• Wikipedia Title: Metronidazole

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.436296
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.46084404
• LogD (pH = 7.4): -0.45932958
• Log P: -0.45931023
• Molar Refractivity: 41.2205 cm^3
• Polarizability: 15.170468 Å^3
• Polar Surface Area: 83.87 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.15
• LOG S: -1.46
• Solubility (Water): 5.92e+00 g/l

PROPERTIES

Physical Property

• Solubility: <0.1g/100mL; acetic acid: soluble0.1 M, clear, faintly yellow; DMSO
• Apperance: crystalline; Off-White to Pale Yellow Solid
• Melting Point: 159-161 °C; 159-161 °C(lit.); 159-161°C; 159-163 °C (318.2-325.4°F); 160-162°C
• Hydrophobicity(logP): -0.1

Safety Information

• Storage Condition: -20°C; 2-8°C; Refrigerator
• RTECS: NI5600000
• European Hazard Symbols: Toxic (T); X; Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40; R:36-45
• Safety Statements: 36/37; 36/37-60; S:26-28-36/37/39-45-53
• TSCA Listed: 否
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351; H351-H303
• GHS Precautionary statements: P281; P281-P201-P312-P308+P313-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: oral, topical, rectal, IV, vaginal
• Bioavailability: 100% (oral); 59–94% (rectal)
• Excretion: Renal (60-80%), biliary (6–15%)
• Half Life: 6–7 hours
• Metabolism: Hepatic
• Legal Status: POM (UK); Rx-only (US); S4 (Australia)
• Pregnancy Category: B (US); B2 (Au)
• Mechanism of Action: After diffusing into the organism, 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: ≥98.0% (HPLC); ≥99.0%; 95+%; 97%; 99%
• Grade: analytical standard; purum; SAJ first grade; VETRANAL™, analytical standard
• Salt Data: Free Base
• Packaging: vial of 200 mg
• Ignition Residue: ≤0.1%
• Impurities: ≤0.0005% Phosphorus (P); ≤0.1% Insoluble matter
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.005%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.0005%; Na: ≤0.005%; Pb: ≤0.001%; Zn: ≤0.0005%
• Antion Traces: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• Application(s): Amebiasis, symptomatic and asymptomatic trichomoniasis; skin and skin structure infections; CNS infections; intra-abdominal infections (as part of combination regimen);; Antiprotozoal, antibacterial and amoebicidal agent; as part of a multidrug regimen for H. pylorieradication to reduce the risk of duodenal ulcer recurrence; systemic anaerobic infections; treatment of antibiotic-associated pseudomembranous colitis (AAPC), bacterial vaginosis; Treatment of susceptible anaerobic bacterial and protozoal infections in the following conditions:
• Pharmacopeia Traceability: traceable to BP 603; traceable to PhEur M1850000; traceable to USP 1442009
• Empirical Formula (Hill Notation): C6H9N3O3

DETAILS

MP Biomedicals - 02155710

(2-Methyl-5-nitroimidazole-1-ethanol)

DrugBank - DB00916

• Drug Groups: approved
• Description: A nitroimidazole used to treat amebiasis; vaginitis; trichomonas infections; giardiasis; anaerobic bacteria; and treponemal infections. It has also been proposed as a radiation sensitizer for hypoxic cells. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985, p133), this substance may reasonably be anticipated to be a carcinogen (Merck, 11th ed).
• Indication: For the treatment of anaerobic infections and mixed infections, surgical prophylaxis requiring anaerobic coverage, Clostridium difficile-associated diarrhea and colitis, Helicobacter pylori infection and duodenal ulcer disease, bacterial vaginosis, Giardia lamblia gastro-enteritis, amebiasis caused by Entamoeba histolytica, acne rosacea (topical treatment), and Trichomonas infections.
• Pharmacology: Metronidazole, a synthetic antibacterial and antiprotozoal agent of the nitroimidazole class, is used against protozoa such as Trichomonas vaginalis, amebiasis, and giardiasis. Metronidazole is extremely effective against anaerobic bacterial infections and is also used to treat Crohn's disease, antibiotic-associated diarrhea, and rosacea.
• Toxicity: LD50=500 mg/kg/day (orally in rat). Adverse effects include reversible peripheral neuropathy with prolonged therapy, CNS toxicity, disulfiram effect with alcohol, dark red-brown urine, metallic taste, nausea, epigastric distress, dizziness, vertigo and paresthesias associated with high doses, and neutropenia (reversible and mild).
• Affected Organisms: Bacteria and protozoa
• Biotransformation: Hepatic metabolism by hydroxylation, oxidation, and glucuronidation.
• Absorption: Well absorbed (at least 80%) with peak plasma concentrations achieved in 1-3 hours following oral administration of therapeutic doses of immediate release formulation.
• Half Life: 6-8 hours
• Protein Binding: Less than 20% bound to plasma proteins.
• References: Shennan A, Crawshaw S, Briley A, Hawken J, Seed P, Jones G, Poston L: A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: the PREMET Study. BJOG. 2006 Jan;113(1):65-74. [Pubmed] ; Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. [Pubmed] ; Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. [Pubmed] ; Visapaa JP, Tillonen JS, Kaihovaara PS, Salaspuro MP: Lack of disulfiram-like reaction with metronidazole and ethanol. Ann Pharmacother. 2002 Jun;36(6):971-4. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1907

Research Area: Infection
Biological Activity:
Metronidazole(Flagyl)is a nitroimidazole antibiotic medication used particularly for anaerobic bacteria and protozoa. Metronidazole, taken up by diffusion, is selectively absorbed by anaerobic bacteria and sensitive protozoa. Once taken up by anaerobes, it is non-enzymatically reduced by reacting with reduced ferredoxin, which is generated by pyruvate oxido-reductase. This reduction causes the production of toxic products to anaerobic cells, and allows for selective accumulation in anaerobes. [1]

Sigma Aldrich - M1547

Application
Metronidazole is a nitroimidazole used to treat amebiasis, vaginitis, Trichomonas infections, giardiasis, anaerobic bacteria and treponemal infections. Metronidazole is used to study DNA damage and repair and has been found to induce the gene transfer agent VSH-1 in Brachyspira hyodysenteriae. It is commonly used for treatment of periodontitis and is used in bioavailability studies.
Biochem/physiol Actions
Metronidazole induces DNA strand breaks. Metronidazole is used to study DNA damage and repair and has been found to induce the gene transfer agent VSH-1 in Brachyspira hyodysenteriae.
Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce metronidazole to its active form. Reduced metronidazole covalently binds to DNA which disrupts its helical structure, induces DNA strand breaks and inhibits bacterial nucleic acid synthesis. Bacterial cell death results.

Sigma Aldrich - M9036

包装
Supplied in amber screw-cap vials

Sigma Aldrich - 46461

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - M3761

包装
5, 25, 100 g in poly bottle

Toronto Research Chemicals - M338880

Used as an antibacterial in the treatment of rosacea. Antiprotozoal (trichomonas). A potential human carcinogen.

REFERENCES

• Shennan A, Crawshaw S, Briley A, Hawken J, Seed P, Jones G, Poston L: A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: the PREMET Study. BJOG. 2006 Jan;113(1):65-74. Pubmed
• Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. Pubmed
• Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. Pubmed
• Visapaa JP, Tillonen JS, Kaihovaara PS, Salaspuro MP: Lack of disulfiram-like reaction with metronidazole and ethanol. Ann Pharmacother. 2002 Jun;36(6):971-4. Pubmed
• http://en.wikipedia.org/wiki/Metronidazole
• Carballo, M., et al.: J. App. Toxicol., 29, 248 (2009)
• Leitsch, D., et al.: Mol. Microbiol., 72, 518 (2009)
• Sanderson, H., et al.: Toxicol. Lett., 187, 84 (2009)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 619B, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 84B, (nmr)
• Cossar, B.C. et al., Arzneim.-Forsch., 1966, 16, 23, (synth)
• Stambaugh, J.E. et al., Can. J. Spectrosc., 1968, 13, 134, (ir, nmr)
• Ross, W.J. et al., J. Med. Chem., 1972, 15, 1035, (pharmacol)
• Wearley, L.L. et al., Anal. Profiles Drug Subst., 1976, 5, 327, (rev)
• IARC Monog., 1977, 13, 113; Suppl. 7, 250; Suppl. 6, 399, (rev, tox)
• Ger. Pat., 1978, BASF, 2 718 192; CA, 90, 87453e
• Phillips, I. et al., Int. Congr. Symp. Ser. R. Soc. Med., (Eds.), No. 18: Metronidazole, Academic Press, N.Y., 1979, (book)
• Edwards, D.I., Antibiotics (N.Y.), 1983, 6, 121, (rev, pharmacol)
• McKillop, A. et al., Tetrahedron, 1983, 39, 3797, (cmr)
• Rosenblatt, J.E. et al., Mayo Clin. Proc., 1987, 62, 1013, (rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 480; 2721, (synonyms)
• Scully, B.E., Med. Clin. North Am., 1988, 72, 613, (rev, pharmacol)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 516
• Freeman, C.D. et al., Drugs, 1997, 54, 679-708, (rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MMN250