苯酰甲硝唑 | 13182-89-3

• 物质功能分类: 原料药 - 抗寄生虫病药 - 抗阿米巴病及抗滴虫病药
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯酰甲硝唑
• 中文别名: 1-(2-苯甲酰氧乙基)-5-硝基-2-甲基咪唑；1-(2-苯甲酰氧乙基)-2-甲基-5-硝基咪唑；苯甲酸甲硝唑；灭滴灵
• 英文名称: metronidazole benzoate
• 英文别名: benzoyl metronidazole；2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate；2-(2-methyl-5-nitroimidazol-1-yl)ethyl benzoate
• CAS: 13182-89-3
• 化学式: C₁₃H₁₃N₃O₄
• 分子量: 275.264
• InChiKey: CUUCCLJJOWSASK-UHFFFAOYSA-N

物化性质

• 熔点：
  100 °C
• 沸点：
  487.7±25.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  几乎不溶于水，易溶于二氯甲烷，溶于丙酮，微溶于乙醇。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090
• 危险品运输编号：
  NONH for all modes of transport
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放温度：0-10°C；应存放在惰性气体中，并避免与空气接触和加热。

SDS

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Section 1. Chemical Product and Company Identification
Metronidazole benzoate Catalog
M1357, M1183
Common Name/
Number(s).
Trade Name
CAS# 13182-89-3
Manufacturer
RTECS Not available.
SPECTRUM CHEMICAL MFG. CORP.
TSCA TSCA 8(b) inventory: No
products were found.
Commercial Name(s) Not available.
CI# Not available.
Synonym 2-Methyl-5-nitroimidazole-1-ethanol benzoate
IN CASE OF EMERGENCY
Not available.
Chemical Name
Chemical Family Not available. CALL [phone]
C13H13N3O4
Chemical Formula
SPECTRUM CHEMICAL MFG. CORP.

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Section 2.Composition and Information on Ingredients
Exposure Limits
TWA (mg/m3) STEL (mg/m3) CEIL (mg/m3)
Name CAS # % by Weight
1) Metronidazole benzoate 13182-89-3 100
Toxicological Data Metronidazole benzoate
on Ingredients LD50: Not available.
LC50: Not available.

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Section 3. Hazards Identification
Potential Acute Health Effects Hazardous in case of skin contact (irritant), of eye contact (irritant), of ingestion, of inhalation.
Potential Chronic Health CARCINOGENIC EFFECTS: Not available.
Effects MUTAGENIC EFFECTS: Not available.
TERATOGENIC EFFECTS: Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure is not known to aggravate medical condition.
Metronidazole benzoate

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Section 4. First Aid Measures
Eye Contact Check for and remove any contact lenses. Do not use an eye ointment. Seek medical attention.
Skin Contact After contact with skin, wash immediately with plenty of water. Gently and thoroughly wash the contaminated skin
with running water and non-abrasive soap. Be particularly careful to clean folds, crevices, creases and groin.
Cover the irritated skin with an emollient. If irritation persists, seek medical attention. Wash contaminated
clothing before reusing.
Serious Skin Contact Wash with a disinfectant soap and cover the contaminated skin with an anti-bacterial cream. Seek medical
attention.
Inhalation Allow the victim to rest in a well ventilated area. Seek immediate medical attention.
Serious Inhalation Not available.
Ingestion Do not induce vomiting. Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not
breathing, perform mouth-to-mouth resuscitation. Seek immediate medical attention.
Serious Ingestion Not available.

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Section 5. Fire and Explosion Data
Flammability of the Product May be combustible at high temperature.
Auto-Ignition Temperature Not available.
Flash Points Not available.
Flammable Limits Not available.
These products are carbon oxides (CO, CO2), nitrogen oxides (NO, NO2...).
Products of Combustion
Fire Hazards in Presence of Not available.
Various Substances
Explosion Hazards in Presence Risks of explosion of the product in presence of mechanical impact: Not available.
of Various Substances Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media SMALL FIRE: Use DRY chemical powder.
and Instructions LARGE FIRE: Use water spray, fog or foam. Do not use water jet.
Special Remarks on Not available.
Fire Hazards
Special Remarks on Explosion Not available.
Hazards

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Section 6. Accidental Release Measures
Small Spill Use appropriate tools to put the spilled solid in a convenient waste disposal container. Finish cleaning by
spreading water on the contaminated surface and dispose of according to local and regional authority
requirements.
Large Spill
Use a shovel to put the material into a convenient waste disposal container. Finish cleaning by spreading water
on the contaminated surface and allow to evacuate through the sanitary system.
Metronidazole benzoate

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Section 7. Handling and Storage
Precautions Keep away from heat. Keep away from sources of ignition. Empty containers pose a fire risk, evaporate the
residue under a fume hood. Ground all equipment containing material. Do not breathe dust. Wear suitable
protective clothing In case of insufficient ventilation, wear suitable respiratory equipment If you feel unwell, seek
medical attention and show the label when possible. Avoid contact with skin and eyes
Storage Keep container dry. Keep in a cool place. Ground all equipment containing material. Keep container tightly
closed. Keep in a cool, well-ventilated place. Combustible materials should be stored away from extreme heat
and away from strong oxidizing agents.

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Section 8. Exposure Controls/Personal Protection
Engineering Controls Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal Protection Splash goggles. Lab coat. Dust respirator. Be sure to use an approved/certified respirator or equivalent.
Gloves.
Personal Protection in Case of Splash goggles. Full suit. Dust respirator. Boots. Gloves. A self contained breathing apparatus should be used
a Large Spill to avoid inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist
BEFORE handling this product.
Exposure Limits Not available.

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Section 9. Physical and Chemical Properties
Physical state and appearance Solid. Odor Not available.
Taste Not available.
275.3 g/mole
Molecular Weight
Color Not available.
pH (1% soln/water) Not available.
Boiling Point Not available.
Melting Point Not available.
Critical Temperature Not available.
Specific Gravity Not available.
Not applicable.
Vapor Pressure
Vapor Density Not available.
Volatility Not available.
Odor Threshold Not available.
Water/Oil Dist. Coeff. Not available.
Not available.
Ionicity (in Water)
Dispersion Properties Not available.
Not available.
Solubility

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Section 10. Stability and Reactivity Data
The product is stable.
Stability
Instability Temperature Not available.
Not available.
Conditions of Instability
Incompatibility with various Not available.
substances
Metronidazole benzoate
Corrosivity Non-corrosive in presence of glass.
Special Remarks on Not available.
Reactivity
Special Remarks on Not available.
Corrosivity
Polymerization No.

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Section 11. Toxicological Information
Routes of Entry Eye contact. Inhalation. Ingestion.
Toxicity to Animals LD50: Not available.
LC50: Not available.
Chronic Effects on Humans Not available.
Other Toxic Effects on Hazardous in case of skin contact (irritant), of ingestion, of inhalation.
Humans
Special Remarks on Not available.
Toxicity to Animals
Special Remarks on Not available.
Chronic Effects on Humans
Special Remarks on other Not available.
Toxic Effects on Humans

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Section 12. Ecological Information
Ecotoxicity Not available.
BOD5 and COD Not available.
Products of Biodegradation Possibly hazardous short term degradation products are not likely. However, long term degradation products may
arise.
Toxicity of the Products The products of degradation are more toxic.
of Biodegradation
Special Remarks on the Not available.
Products of Biodegradation

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Section 13. Disposal Considerations
Waste Disposal

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Section 14. Transport Information
DOT Classification Not a DOT controlled material (United States).
Identification Not applicable.
Special Provisions for Not applicable.
Transport
Metronidazole benzoate
DOT (Pictograms)

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Section 15. Other Regulatory Information and Pictograms
No products were found.
Federal and State
Regulations
California California prop. 65: This product contains the following ingredients for which the State of California has found
to cause cancer which would require a warning under the statute: No products were found.
Proposition 65
Warnings
California prop. 65: This product contains the following ingredients for which the State of California has found
to cause birth defects which would require a warning under the statute: No products were found.
Other Regulations Not available..
WHMIS (Canada) Not controlled under WHMIS (Canada).
Other Classifications
DSCL (EEC) R36/38- Irritating to eyes and skin.
Health Hazard
HMIS (U.S.A.) 2 National Fire Protection
1 Flammability
1 Association (U.S.A.)
Fire Hazard
2 0 Reactivity
Health
Reactivity
0
Specific hazard
Personal Protection
E
WHMIS (Canada)
(Pictograms)
DSCL (Europe)
(Pictograms)
TDG (Canada)
(Pictograms)
ADR (Europe)
(Pictograms)
Protective Equipment
Gloves.
Lab coat.
Dust respirator. Be sure to use an
approved/certified respirator or
equivalent.
Metronidazole benzoate

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Metronidazole Benzoate（苯甲酸甲硝唑）是metronidazole的苯甲酸酯形式。Metronidazole是一种合成的硝基咪唑衍生物，具有抗原生动物和抗细菌活性。

靶点

• 抗菌
• 抗微生物
• 抗寄生虫
• 抗滴虫

体外研究

Metronidazole Benzoate 适用于治疗由多种厌氧、原生动物及拟杆菌引起的感染，包括滴虫病、阿米巴病、阴道炎和牙龈炎。

用途

抗寄生虫药。用于治疗阿米巴、滴虫及厌氧菌感染。

反应信息

• 作为反应物：
  描述：

  苯酰甲硝唑 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 NSC302323
  参考文献：
  名称：

  甲硝唑酯：一类新的抗糖化剂。

  摘要：

  已经合成了一系列甲硝唑酯衍生物1-34，目的是开发具有抗糖基化活性的新的前导物。体外抗糖化能力为1-34的评估表明，酯衍生物28、16和3的IC（50）值分别为218.97±2.5、245.3±5.1和278.6±0.8 µM，与标准药物相当，芦丁（IC（50）= 294.5±1.50 µM）。该研究确定了一类新的有效抗糖化剂。构效关系也得到了评估。所有化合物均使用光谱技术进行了表征，包括（1）H NMR，IR和EI-MS。

  DOI：

  10.2174/157340612802084360
• 作为产物：
  描述：

  甲硝唑 在 吡啶 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 苯酰甲硝唑
  参考文献：
  名称：

  甲硝唑芳氧基，羧基和吡咯衍生物：合成，抗肿瘤活性，QSAR，分子对接和动力学研究

  摘要：

  已经合成了一系列新颖的甲硝唑芳氧基，羧基和唑衍生物，并通过MTT分析评估了它们对三种癌细胞系的细胞毒活性。化合物4m，4l和4d表现出最强的细胞毒活性（IC 50小于100 µg / mL）。还通过流式细胞术检测了这些化合物的凋亡。进行了对接研究以提出可能的靶蛋白。下一步，对与化合物4m结合的拟议目标蛋白粘着斑激酶（FAK，PDB代码：2ETM）进行了分子动力学模拟。As，4m 提示其具有强力的细胞毒活性和可接受的凋亡作用，它可能是潜在的抗癌候选药物，可以通过抑制FAK发挥作用。

  DOI：

  10.1016/j.bmc.2018.12.003

文献信息

• Amphiphilic block copolymer and polymeric composition comprising the same for drug delivery
  申请人：Seo Hyo Min

  公开号：US20050201972A1

  公开（公告）日：2005-09-15

  The present invention relates to an amphiphilic block copolymer of a hydrophilic block and a hydrophobic block with a terminal hydroxyl group wherein the terminal hydroxyl group of the hydrophobic bock is substituted with a tocopherol or cholesterol group. It also relates to polymeric compositions capable of forming stable micelles in an aqueous solution, comprising the amphiphilic block copolymer and a polylactic acid derivative wherein one or more ends of the polylactic acid are covalently bound to at least one carboxyl group.

  本发明涉及一种两性块共聚物，包括亲水性块和疏水性块，其末端羟基团与生育酚或胆固醇基团取代的疏水性块。还涉及能在水溶液中形成稳定胶束的聚合物组合物，包括该两性块共聚物和聚乳酸衍生物，其中聚乳酸的一个或多个末端与至少一个羧基共价结合。
• A highly green approach towards aromatic nitro group substitutions: catalyst free reactions of nitroimidazoles with carbon nucleophiles in water
  作者：Syed Raza Shah、Muhammad Ali、Muhammad U. Anwar、Ahmed Al-Harrasi

  DOI：10.1039/d0ra03640d

  日期：——

  approach for the formation of a carbon–carbon bond by the reaction of highly-enolizable carbanions (mostly derived from 1,3-dicarbonyl compounds) with an aromatic carbon bearing a nitro group. The key step involves a nucleophilic displacement reaction. All newly synthesized compounds were unambiguously characterized via various spectroscopic techniques including NMR, mass spectrometry and single-crystal

  我们已经成功开发出一种灵活的绿色水性方法，通过高度烯醇化的碳负离子（主要衍生自 1,3-二羰基化合物）与带有硝基的芳族碳反应形成碳-碳键。关键步骤涉及亲核置换反应。所有新合成的化合物都通过各种光谱技术明确表征，包括核磁共振、质谱和单晶 X 射线衍射（如适用）。我们相信我们的研究将有助于为无催化剂水介导的亲核取代反应提供新的见解。
• Visible-light-promoted late-stage direct fluoroalkylation of nitroimidazoles
  作者：Hezhen Wang、Zhiyuan Wang、Chunyong Wei、Guohui Bai、Yongzheng Chen、Jing Wang、Lei Zhang

  DOI：10.1016/j.tetlet.2021.153484

  日期：2021.11

  nitroimidazoles through visible-light-prompted direct radical reaction with commercially available materials is described. The strategy proceeds smoothly under mild conditions to afford the fluoroalkyl nitroimidazoles under mild conditions. In addition, control experiments have been performed, revealing a radical process involved in the reaction mechanism. Preliminary evaluations on some products display

  将氟烷基并入生物活性化合物可以显着改变其理化和生理特性，并进一步改善其药代动力学和药理特性。因此，氟烷基化已被公认为药物化学中用于药物发现的重要策略。在这项研究中，描述了一种通过可见光促进的直接自由基反应与市售材料制备氟烷基化硝基咪唑的有效和方便的方法。该策略在温和条件下顺利进行，在温和条件下得到氟烷基硝基咪唑。此外，还进行了对照实验，揭示了反应机理中涉及的自由基过程。
• GAMMA-AAPEPTIDES WITH POTENT AND BROAD-SPECTRUM ANTIMICROBIAL ACTIVITY
  申请人：Cai Jianfeng

  公开号：US20150274782A1

  公开（公告）日：2015-10-01

  The present invention is directed to a novel class of antimicrobial agents called γ-AApeptides. The current invention provides various categories of γ-AApeptides, for example, linear γ-AApeptides, cyclic γ-AApeptides, and lipidated γ-AApeptides. γ-AApeptides of the current invention are designed to exert antimicrobial activity while being stable and non-toxic. γ-AApeptides also do not appear to lead to the development of microbial resistance in treated microorganisms. Thus, the disclosed γ-AApeptides can be used for the treatment of various medical conditions associated with pathogenic microorganisms.

  本发明涉及一种新型类别的抗微生物药物，称为γ-AA肽。当前发明提供了各种类别的γ-AA肽，例如线性γ-AA肽、环状γ-AA肽和脂质化γ-AA肽。本发明的γ-AA肽被设计为具有抗微生物活性，同时稳定且无毒。γ-AA肽似乎也不会导致被治疗微生物体内微生物产生抗药性。因此，所披露的γ-AA肽可用于治疗与病原微生物相关的各种医疗状况。
• Processes for preparing
  申请人：Schering Aktiengesellschaft

  公开号：US03952007A1

  公开（公告）日：1976-04-20

  1-SUBSTITUTED 5-NITRO-2-(2-DIALKYLAMINOVINYL)-IMIDAZOLES HAVING TRICHOMONACIDAL ACTIVITY OF THE FORMULA: ##SPC1## Wherein R is H, CH.sub.3 or C.sub.2 H.sub.5 and X is hydrocarbon or hydrocarbon substituted with a halogen or a hydroxy, ether, ester or amino group, are produced by reacting the 1-substituted-5-nitro-2-alkyl-imidazoles with an aminal ester or amidoacetal of orthoformic acid or like functionally reactive derivative thereof.

  具有滴虫杀活性的1-取代5-硝基-2-(2-二烷基氨基乙烯基)-咪唑的化学式如下：##SPC1## 其中R为H、CH3或C2H5，X为烃或烃基，烃基上取代有卤素、羟基、醚、酯或氨基，通过将1-取代5-硝基-2-烷基-咪唑与邻甲酸氨基酯或酰胺乙醛或类似的功能反应衍生物反应而制得。