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

• ChemBase编号: 792
• 分子式: C6H9N3O3
• 平均质量: 171.15396
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
• IUPAC传统名: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol; metronidazole
• 商标名: 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
• 别名: 2-甲基-5-硝基咪唑-1-乙醇; 甲硝唑; 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

登记号

• CAS号: 443-48-1
• EC号: 207-136-1
• MDL号: MFCD00009750
• Beilstein号: 611683
• PubChem SID: 160964255; 24897314; 46508911; 24896871; 24870198; 24896667
• PubChem CID: 4173
• CHEBI ID: 6909
• ATC码: P01AB01; J01XD01; QP51AA01; A01AB17; G01AF01; D06BX01
• CHEMBL: 137
• Chemspider ID: 4029
• DrugBank ID: DB00916
• KEGG ID: D00409
• 美国药典/FDA物质标识码: 140QMO216E
• 维基百科标题: Metronidazole

理论计算性质

JChem

• Acid pKa: 15.436296
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): -0.46084404
• LogD (pH = 7.4): -0.45932958
• Log P: -0.45931023
• 摩尔折射率: 41.2205 cm^3
• 极化性: 15.170468 Å^3
• 极化表面积: 83.87 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.15
• LOG S: -1.46
• 溶解度: 5.92e+00 g/l

分子性质

理化性质

• 溶解度: <0.1g/100mL; acetic acid: soluble0.1 M, clear, faintly yellow; DMSO
• 外观: crystalline; Off-White to Pale Yellow Solid
• 熔点: 159-161 °C; 159-161 °C(lit.); 159-161°C; 159-163 °C (318.2-325.4°F); 160-162°C
• 疏水性(logP): -0.1

安全信息

• 保存条件: -20°C; 2-8°C; Refrigerator
• RTECS编号: NI5600000
• 欧盟危险性物质标志: 有毒(Toxic) (T); X; 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 40; R:36-45
• 安全公开号: 36/37; 36/37-60; S:26-28-36/37/39-45-53
• TSCA收录: 否
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H351; H351-H303
• GHS警示性声明: P281; P281-P201-P312-P308+P313-P405-P501A
• 个人保护装置: 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
• 保存温度: 2-8°C

药理学性质

• 给药途径: oral, topical, rectal, IV, vaginal
• 生物利用度: 100% (oral); 59–94% (rectal)
• 排泄: Renal (60-80%), biliary (6–15%)
• 半衰期: 6–7 hours
• 代谢: Hepatic
• 法定药品分级: POM (UK); Rx-only (US); S4 (Australia)
• 妊娠期药物分类: B (US); B2 (Au)
• 生物活性机理: 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

产品相关信息

• 纯度: ≥98.0% (HPLC); ≥99.0%; 95+%; 97%; 99%
• 级别: analytical standard; purum; SAJ first grade; VETRANAL™, analytical standard
• 成盐信息: Free Base
• 包装: vial of 200 mg
• 燃烧残渣: ≤0.1%
• 杂质: ≤0.0005% Phosphorus (P); ≤0.1% Insoluble matter
• 痕量阳离子: 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%
• 痕量阴离子: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• 应用领域: 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

详细说明

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

法律信息
VETRANAL 商标 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.

参考文献

• 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)
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• 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