2-(2-Methyl-5-nitro-1-imidazolyl)ethanol 2-甲基-5-硝基咪唑-1-乙醇

CAS 443-48-1 MFCD00009750

化学结构图

443-48-1
SMILES: Cc1ncc([N+](=O)[O-])n1CCO

化学属性

Mol. FormulaC6H9N3O3
Mol. Weight171.15
Density1.45
Melting Point159-161°C
Solubility<0.1 G/100 ML AT 20 ºC
TSCANo
Appearance crystalline
Boiling Point405.4°C at 760 mmHg

别名和识别编码

Chemical Name2-(2-Methyl-5-nitro-1-imidazolyl)ethanol
CAS Number443-48-1
Synonym Metronidazole {LY} Metronidazole {} {LY} Metronidazole {} {} {LY} Metronidazole {} {} {} {LY} Metronidazole {} {} {} {} {LY} Metronidazole {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {} {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Metronidazole {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00009750
EC Number207-136-1
Beilstein Registry Number611683
PubChem Substance ID87572910
Reaxys-RN611683
Merck Number6157
Chemical Name Translation2-甲基-5-硝基咪唑-1-乙醇
Wiswesser Line NotationT5N CNJ A2Q B1 ENW
LabNetwork Molecule IDLN00196219
InChIInChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
Canonical SMILESOCCN1C([N+]([O-])=O)=CN=C1C
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分类

  • {SNA} Alphabetical Index of Analytical Standards, Analytical Standards, Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics G-M, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics, Antiparasitic / Antiprotozoal / Anthelminthic, Biochemicals and Reagents, Chemical Structure Class, Imidazoles, Interferes with DNA Synthesis, L - Z, M, METI - MZ, Mechanism of Action, Spectrum of Activity, 分析/色谱
  • {SNA} Antibacterial, A
  • {SNA} Antibacterial, Antibiotics A to Z, Antibiotics G-M, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics,

产品应用

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

相关文献及参考

  • Carballo, M., et al.: J. App. Toxicol., 29, 248 (2009),
  • Merck: 14,6157 Beilstein: 23,V,5,63
  • Sanderson, H., et al.: Toxicol. Lett., 187, 84 (2009),
  • Leitsch, D., et al.: Mol. Microbiol., 72, 518 (2009),
  • Merck: 14,6157

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置;
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
  • R45 May cause cancer 可能致癌
  • R46 May cause inheritable genetic damage 可能引起遗传基因损害
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前,切勿操作。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P308+P313
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
RTECSNI5600000
Hazard statements
  • H303 May be harmfully swallowed 吞食可能有害
  • H351 Suspected of causing cancer 怀疑致癌
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
Hazard Codes Xn Xn,T
Storage condition 2-8°C, protect from light {LY} 2-8°C, protect from light 99%室温保存。分析标准品2-8℃保存 {} {LY} 2-8°C, protect from light {} {} {LY} 2-8°C, protect from light {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 181 gm/kg/72W-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Lungs, Thorax, or Respiration - tumors
   Blood - lymphoma, including Hodgkin's disease
REFERENCE :
   JNCIAM Journal of the National Cancer Instit

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 3 gm/kg/14W-C
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Skin and Appendages - tumors
REFERENCE :
   TUMOAB Tumori.  (Casa Editrice Amb

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 219 gm/kg/2Y-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Liver - tumors
   Skin and Appendages - tumors
REFERENCE :
   JJIND8 JNCI, Journal of the National Cancer Institute.  (Washington, DC)
   V.61-79, 1978-87. For publisher information, see JNCIEQ.
   Volume(issue)/page/year: 63,863,1979

TYPE OF TEST            : T

TYPE OF TEST            : TD - Toxic dose (othe

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1680 mg/kg
                          female 1-21 day(s) after conception
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Reproductive - Tumorigenic effects - transplacental tumorigenesis
   Lungs, Thorax, or Respiration - tumors
REFERENCE :
   JCROD7 Journal of Cancer Research and Clinical Oncology.  (Springer-Verlag
   New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094)  V.93-
   1979-  Volume(issue)/page/year: 112,135,1986

TYPE OF TEST            :

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 40 mg/kg
TOXIC EFFECTS :
   Behavioral - hallucinations, distorted perceptions
REFERENCE :
   SMJOAV Southern Medical Journal.  (Southern Medical Assoc., POB 2446,
   Birmingham, AL 35205) V.1-    1908-  Volume(issue)/page/year: 78,627,1985

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 3640 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - tremor
   Behavioral - convulsions or effect on seizure threshold
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 8,1089,1974

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 12 mg/kg
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - effect, not otherwise specified
   Behavioral - tremor
REFERENCE :
   BMJOAE British Medical Journal.  (British Medical Assoc., BMA House,
   Tavistock Sq., London WC1H 9JR, UK)  V.1-    1857- Volume(issue)/page/year:
   292,174,1986

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 3800 mg/kg
TOXIC EFFECTS :
   Biochemical - Enzyme inhibition, induction, or change in blood or tissue
   levels - other oxidoreductases
REFERENCE :
   JMCMAR Journal of Medicinal Chemistry.  (American Chemical Soc.,
   Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC
   20037)  V.6-    1963-  Volume(issue)/page/year: 20

TYPE OF TEST            : DNA repair
TEST SYSTEM             : Bacteria - Bacillus subtilis
DOSE/DURATION           : 200 ug/disc
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 97,1,1982

TYPE OF TEST            : Phage inhibition capacity
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 500 ug/plate
REFERENCE :
   AMPOAX Acta Microbiologica Polonica.  (Ars Polona, POB 1001, 00-068 Warsaw
   1, Poland)  V.1-17(4), 1952-68; V.25-    1976-  Volume(issue)/page/year:
   34,111,1985

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 5 mg/L
REFERENCE :
   BCPCA6 Biochemical Pharmacology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.1-    1958-  Volume(issue)/page/year:
   23,1421,1974

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - rat Liver
DOSE/DURATION           : 3 mmol/L
REFERENCE :
   SinJF# Personal Communication from J.F. Sina, Merck Institute for
   Therapeutic Research, West Point, PA 19486, Oct. 26, 1982
   Volume(issue)/page/year: 26OCT1982

TYPE OF TEST            : Body fluid assay
TEST SYSTEM             : Human Bacteria - Salmonella typhimurium
DOSE/DURATION           : 10 mg/kg
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 77,357,1980

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 1 mg/L
REFERENCE :
   BCPCA6 Biochemical Pharmacology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.1-    1958-  Volume(issue)/page/year:
   23,1421,1974

{hazard_com

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 22400 mg/kg
SEX/DURATION            : male 56 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - spermatogenesis (incl. genetic material,
   sperm morphology, motility, and count)
   Reproductive - Paternal Effects - testes, epididymis, sperm duct
REFERENCE :
   FAATDF Fundamental and Applied Toxicology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1981-  Volume(issue)/page/year:
   12,386,1989

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 60 mg/kg
SEX/DURATION            : female 8-14 day(s) afte

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 750 mg/kg
SEX/DURATION            : female 30 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
   RPHRA6 Recent Progress In Hormone Research.  Proceedings of the Laurentian
   Hormone Conference. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802)
    V.1-    1947-  Volume(issue)/page/year: 20,395,1964

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 16800 mg/kg
SEX/DURATION            : male 42 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Fertility - male fertility index (e.g. # males impregnating
   females per # males exposed to fertile nonpregnant females)
REFERENCE :
   FAATDF Fundamental and Applied Toxicology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1981-  Volume(issue)/page/year:
   12,386,1989

其他信息

  • 稳定性:Stable. Incompatible with strong oxidizing agents.
  • 毒害物质数据:443-48-1(Hazardous Substances Data)
  • MOL 文件:443-48-1.mol
  • RTECS号:NI5600000
  • F:8
  • EPA化学物质信息:1H-Imidazole-1-ethanol, 2-methyl-5-nitro-(443-48-1)
  • 硝基咪唑类抗生素:甲硝唑是一种硝基咪唑类抗生素,又叫灭滴灵、甲硝哒唑、甲硝基羟乙唑、灭滴唑,对厌氧微生物有杀灭作用,它在人体中还原时生成的代谢物也具有抗厌氧菌作用,抑制细菌的脱氧核糖核酸的合成,从而干扰细菌的生长、繁殖,最终致细菌死亡,抗厌氧菌普包括:脆弱拟杆菌、梭形杆菌(由于菌体形态两端尖锐呈梭形而得名)、破伤风杆菌、消化球菌、消化链球菌、贾第鞭毛虫菌。最初被用于治疗阴道滴虫病,临床效果非常显著。后来人们发现,甲硝唑也可以杀灭引起口腔感染的厌氧菌,1978年被世界卫生组织将其确定为抗厌氧菌感染的特效药物,广泛应用于预防和治疗口腔厌氧菌感染。在医院本品也经常被用于预防和治疗因厌氧菌引起的呼吸道,消化道,腹腔及盆腔感染,皮肤软组织及骨关节感染,心膜炎,败血症和脑的治疗。 甲硝唑对体内组织及肠腔内的阿米巴病的疗效显著,也是人体治疗虫病的首选药物,作用机理是通过抑制阿米巴原虫的氧化还原反应,使原虫氮链发生断裂而起作用。体外试验证明,药物浓度为1~2mg/L时,溶组织阿米巴于6 ~20小时即可发生形态改变,24小时内全部被杀灭,浓度为0.2mg/L的,72小时内可杀死溶组织阿米巴,目前已经广泛用于治疗肠道和肠外阿米巴病(如阿米巴肝脓肿、胸膜阿米巴病等)。 由于硝基咪唑类抗生素和乙醇、尼古丁等有相互作用,干扰乙醇的氧化过程,能引起双硫仑反应,导致心率较快、血压降低等症状,所以患者服药期间,应避免接触含酒精的饮品,少抽烟,以避免药物不良反应的发生。
  • 图谱信息:甲硝唑(443-48-1)红外图谱(IR1) 甲硝唑(443-48-1)核磁图( 1 HNMR) 甲硝唑(443-48-1)红外图谱(IR2) 甲硝唑(443-48-1)核磁图( 13 CNMR) 甲硝唑(443-48-1)质谱(MS)
  • 溶于热水,略溶于乙醇,微溶于水或氯仿,极微溶于乙醇。味苦而略咸。
  • NIST化学物质信息:Metronidazole(443-48-1)
  • 生产方法:由2-甲基-5-硝基咪唑(见25010)与环氧乙烷加成而得。将2-甲基-5-硝基咪唑溶解于甲酸中,在30-40℃逐次加入环氧乙烷,并在加料中间加硫酸。加毕,反应1h。减压回收甲酸,加水溶解后冷却至10℃,过滤。滤液用氢氧化钠溶液调至pH=10,放置冷却,过滤,水洗至近中改建。用水重结晶。活性炭脱色,即得甲硝唑。
  • 甲硝唑价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 M0924 2-甲基-5-硝基咪唑-1-乙醇 2-Methyl-5-nitroimidazole-1-ethanol 25G 495元 2014/06/02 M0924 2-甲基-5-硝基咪唑-1-乙醇 2-Methyl-5-nitroimidazole-1-ethanol 500G 4310元 2010/06/21 BTB09707EE 甲硝唑 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol 50 GR 915元
  • 用途:用于治疗阿米巴病、滴虫病及厌氧菌感染

系列性分类


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