磺胺米隆 | 138-39-6

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 磺胺类药及增效剂
• 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: 磺胺米隆
• 中文别名: 4-氨甲基苯磺酰胺；磺胺苄胺；磺胺灭脓
• 英文名称: 4-homosulfanilamide
• 英文别名: 4-(aminomethyl)benzenesulfonamide；mafenide
• CAS: 138-39-6
• 化学式: C₇H₁₀N₂O₂S
• mdl: MFCD00072084
• 分子量: 186.235
• InChiKey: TYMRLRRVMHJFTF-UHFFFAOYSA-N

物化性质

• 熔点：
  177-178℃ (decomposition)
• 沸点：
  382.0±44.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

代谢

代谢成碳酸酐酶抑制剂。

Metabolized to a carbonic anhydrase inhibitor.

来源:DrugBank

吸收、分配和排泄

• 吸收

甲芬尼德在局部给药后通过去血管化区域被吸收进入系统性循环。

Mafenide is absorbed through devascularized areas into the systemic circulation following topical administration.

来源:DrugBank

吸收、分配和排泄

• 消除途径

肾脏 - 代谢物在尿液中以高浓度迅速排泄；然而，未在尿液中检测到母化合物。

Renal—Metabolite rapidly excreted in urine in high concentrations; however, the parent compound has not been detected in urine.

来源:DrugBank

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2935009090
• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Aminomethylbenzenesulfonamide
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Aminomethylbenzenesulfonamide
CAS number: 138-39-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C7H10N2O2S
Molecular weight: 186.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Mafenide 是一种有效的磺酰胺类抗菌剂，可用于烧伤创面。它能够通过抑制核苷酸合成来对抗革兰氏阳性和阴性生物（包括铜绿假单胞菌）。

化学性质

Mafenide 的熔点为151-152℃，能溶于稀酸和稀碱。其盐酸盐是一种无色结晶性粉末，熔点为256℃。

用途

它主要用于医药中间体以及磺胺类药物的生产，特别是针对绿脓杆菌及金黄色葡萄球菌感染。

生产方法

Mafenide 的制备是从乙酰苄胺出发，经氯磺化、氨化和水解得到。具体步骤如下：首先将乙酰苄胺在35℃下加入到氯磺酸中，并保持温度在55-60℃反应2小时。然后将反应物倒入冰水中并用氯仿萃取，弃去水层，保留氯仿层以制备对乙酰苄胺基磺酰氯的氯仿溶液。接下来，在30℃下将该氯仿液滴入氯水中，并在室温条件下继续反应2小时后过滤，得到对乙酰苄胺磺酰胺。接着将其加入到20%氢氧化钠溶液中，并于100-102℃回流5小时，加水及活性炭脱色20分钟后进行过滤。滤液冷却结晶并过滤，随后将滤饼用适量的水溶解，在50-60℃下调节pH值至9.5-10并加入活性炭回流20分钟后再进行过滤。最后得到对氨甲苯磺酰胺。

反应信息

• 作为反应物：
  描述：

  磺胺米隆 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 三氟甲磺酸酐 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到4-(azidomethyl)benzenesulfonamide
  参考文献：
  名称：

  基于带有4-氨基取代的苯磺酰胺臂的2-吡啶基-1,2,3-三唑衍生物的新型Re（I）三羰基配位化合物：合成，晶体结构，计算研究和对碳酸酐酶I，II和IX同工型†

  摘要：

  抽象的 在这项工作中，通过经典的点击化学方法制备了两个含有4-取代的苯磺酰胺药效基团的二齿2-吡啶基-1,2,3-三唑配体（3a和3b），以及它们相应的rh配合物，一般为4a和4b。制备了[ReCl（CO）3（L）]（L  =  3a或3b）式，并通过光谱方法（IR，NMR，MS，UV-Vis），元素分析，X射线衍射和使用DFT和TD-DFT方法。尤其是，我们表明，在固态下，3b的吡啶和三唑环采用罕见的源于分子间氢键的顺式构型。初步测定表明，对碳酸酐酶同工型IX的配体和复合物都具有极好的纳摩尔抑制活性，对配体3a的亲和力K i为2.8 nM 。更有趣的是，复合物4b对脱靶的hCA I和hCA II表现出明显的针对hCA IX的选择性，这使该化合物成为有希望的潜在抗癌药物候选物。

  DOI：

  10.1080/14756366.2019.1585835
• 作为产物：
  描述：

  N-[4-(氨基磺酰基)苄基]乙酰胺 在 sodium hydroxide 作用下， 生成 磺胺米隆
  参考文献：
  名称：

  DE726386

  摘要：

  公开号：

文献信息

• [EN] DERIVATIVES OF AMANITA TOXINS AND THEIR CONJUGATION TO A CELL BINDING MOLECULE<br/>[FR] DÉRIVÉS DE TOXINES D'AMANITES ET LEUR CONJUGAISON À UNE MOLÉCULE DE LIAISON CELLULAIRE
  申请人：HANGZHOU DAC BIOTECH CO LTD

  公开号：WO2017046658A1

  公开（公告）日：2017-03-23

  Derivatives of Amernita toxins of Formula (I), wherein, formula (a) R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10, X, L, m, n and Q are defined herein. The preparation of the derivatives. The therapeutic use of the derivatives in the targeted treatment of cancers, autoimmune disorders, and infectious diseases.

  Amernita毒素的衍生物的化学式（I），其中，化学式（a）中的R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8、R 9、R 10、X、L、m、n和Q在此处被定义。这些衍生物的制备。这些衍生物在靶向治疗癌症、自身免疫性疾病和传染病中的治疗用途。
• [EN] A CONJUGATE OF A CYTOTOXIC AGENT TO A CELL BINDING MOLECULE WITH BRANCHED LINKERS<br/>[FR] CONJUGUÉ D'UN AGENT CYTOTOXIQUE À UNE MOLÉCULE DE LIAISON CELLULAIRE AVEC DES LIEURS RAMIFIÉS
  申请人：HANGZHOU DAC BIOTECH CO LTD

  公开号：WO2020257998A1

  公开（公告）日：2020-12-30

  Provided is a conjugation of cytotoxic drug to a cell-binding molecule with a side-chain linker. It provides side-chain linkage methods of making a conjugate of a cytotoxic molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and immunological disorders.

  提供了一种将细胞毒性药物与一个侧链连接分子结合的共轭物。它提供了制备细胞毒性分子与细胞结合配体的共轭物的侧链连接方法，以及在靶向治疗癌症、感染和免疫性疾病中使用该共轭物的方法。
• [EN] CROSS-LINKED PYRROLOBENZODIAZEPINE DIMER (PBD) DERIVATIVE AND ITS CONJUGATES<br/>[FR] DÉRIVÉ DE DIMÈRE DE PYRROLOBENZODIAZÉPINE RÉTICULÉ (PBD) ET SES CONJUGUÉS
  申请人：HANGZHOU DAC BIOTECH CO LTD

  公开号：WO2020006722A1

  公开（公告）日：2020-01-09

  A novel cross-linked cytotoxic agents, pyrrolobenzo-diazepine dimer (PBD) derivatives, and their conjugates to a cell-binding molecule, a method for preparation of the conjugates and the therapeutic use of the conjugates.

  一种新型的交联细胞毒剂，吡咯苯并二氮杂环二聚体（PBD）衍生物，以及它们与细胞结合分子的结合物，一种制备这些结合物的方法以及这些结合物的治疗用途。
• [EN] ANTIBACTERIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS
  申请人：MASSACHUSETTS GEN HOSPITAL

  公开号：WO2019199979A1

  公开（公告）日：2019-10-17

  The present application provides compounds of formula: Methods of using these compounds for killing bacterial growth and treating bacterial infections are also provided.

  本申请提供了以下化合物的公式：还提供了使用这些化合物杀灭细菌生长和治疗细菌感染的方法。
• [EN] FUSED POLYCYCLIC 2-PYRIDINONE ANTIBACTERIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS DE 2-PYRIDINONE POLYCYCLIQUE
  申请人：PTC THERAPEUTICS INC

  公开号：WO2016109706A1

  公开（公告）日：2016-07-07

  The present description relates to fused polycyclic 2-pyridinone compounds and forms and pharmaceutical compositions thereof and methods of using such compounds, forms or compositions thereof for treating or ameliorating a wild-type or drug-resistant form of N. gonorrhoeae or N. meningitides. A compound of Formula (la), Formula (lb) or Formula (Ic), or a form thereof, wherein the dashed lines represent one or more double bonds optionally present where allowed by available valences.

  本描述涉及融合的多环2-吡啶酮化合物及其形式和药物组合物，以及使用这些化合物、形式或组合物治疗或改善N. gonorrhoeae或N. meningitides的野生型或耐药型的方法。其中，化合物的化学式为（la）、（lb）或（Ic），或其形式，其中虚线代表一个或多个双键，根据可用的价键允许的情况下可选择地存在。

表征谱图