胆影脒 | 5587-89-3

• 物质功能分类: 化学试剂 - 有机试剂 - 亚氨、脒
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 胆影脒
• 中文别名: 碘泊酸
• 英文名称: Ipodic acid
• 英文别名: 3-<2.4.6-Triiod-3-dimethylaminomethylenamino-phenyl>-propionsaeure；3-<3-(Dimethylamino-methylenamino)-2,4,6-trijod-phenyl>-propionsaeure；Ipodat-saeure, 3-(Dimethylamino-methylenamino)-2,4,6-trijod-hydrozimtsaeure, Oragrafin；Iopodate；3-{[(dimethylamino)methylene]amino}-3-(2,4,6-triiodophenyl)propionic acid；ipodate；3-[3-(dimethylaminomethylideneamino)-2,4,6-triiodophenyl]propanoic acid
• CAS: 5587-89-3
• 化学式: C₁₂H₁₃I₃N₂O₂
• 分子量: 597.961
• InChiKey: YQNFBOJPTAXAKV-UHFFFAOYSA-N

物化性质

• 熔点：
  168-169° (dec 225°)
• 沸点：
  579.8±60.0 °C(Predicted)
• 密度：
  2.2000 (rough estimate)
• 颜色/状态：
  CRYSTALS
• 溶解度：
  Insoluble

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

5位无取代基有利于肝细胞优先摄取。一旦进入肝脏，代谢主要通过葡萄糖醛酸苷结合进行，与胆红素的代谢途径相同。

The absence of a substituent at position 5 facilitates for preferential hepatocyte uptake. Once taken in the liver, the metabolism is mainly performed by glucuronide conjugation in the same pathway as bilirubin.

来源:DrugBank

毒理性

• 人类毒性摘录

急性碘中毒的开始可能立即发生或在给药后几小时发生。血管性水肿是突出的症状，喉部肿胀可能导致窒息。可能出现多处皮肤出血。还可能表现出类似血清病型超敏反应的表现，如发热、关节痛、淋巴结肿大和嗜酸性粒细胞增多。已经描述了由于对碘的超敏反应引起的血栓性血小板减少性紫癜和致命的结节性多动脉炎。/碘制剂/

ONSET OF ACUTE IODIDE POISONING MAY OCCUR IMMEDIATELY OR SEVERAL HR AFTER ADMIN. ANGIOEDEMA IS OUTSTANDING SYMPTOM, & SWELLING OF LARYNX MAY LEAD TO SUFFOCATION. MULTIPLE CUTANEOUS HEMORRHAGES MAY BE PRESENT. ALSO MANIFESTATIONS OF SERUM-SICKNESS TYPE HYPERSENSITIVITY, SUCH AS FEVER, ARTHRALGIA, LYMPH NODE ENLARGEMENT, & EOSINOPHILIA, MAY APPEAR. THROMBOTIC THROMBOCYTOPENIC PURPURA & FATAL PERIARTERITIS NODOSA ATTRIBUTED TO HYPERSENSITIVITY TO IODIDE HAS BEEN DESCRIBED. /IODINE PREPN/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

用于胃肠道X光造影的介质和口服给药可能会引起恶心、呕吐和腹泻。急性肾小管坏死被报告为摄入某些胆囊染料的后果。/碘化对比剂/

MEDIA USED FOR GI ROENTGENOGRAPHY & AGENTS ADMIN ORALLY MAY CAUSE NAUSEA, VOMITING, & DIARRHEA. ACUTE TUBULAR NECROSIS HAS BEEN REPORTED TO BE THE CONSEQUENCE OF INGESTION OF CERTAIN GALLBLADDER DYES. /IODINATED CONTRAST MEDIA/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

水溶性化合物负责两种严重反应：（1）不常见...严重的呼吸急促伴有喘息、支气管和喉部痉挛、嘴唇和眼睑肿胀以及巨大荨麻疹。...（2）更常见的是...心血管崩溃，其中血压下降、心动过速、呼吸困难、混乱和发绀进展到失去意识。/水溶性碘化对比剂/

THE WATER-SOLUBLE COMPOUNDS ARE RESPONSIBLE FOR 2 TYPES OF SEVERE REACTIONS: (1) INFREQUENTLY...SEVERE RESPIRATORY DIFFICULTY WITH WHEEZING, BRONCHIAL & LARYNGEAL SPASM, SWELLING OF LIPS & EYELIDS, & GIANT URTICARIA. ... (2) SOMEWHAT MORE FREQUENT IS...CARDIOVASCULAR COLLAPSE IN WHICH THERE IS FALL IN BLOOD PRESSURE, TACHYCARDIA, DYSPNEA, & CONFUSION & CYANOSIS PROGRESSING TO UNCONSCIOUSNESS. /WATER-SOLUBLE IODINATED CONTRAST MEDIA/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

报告了包括腹痛、腹泻、恶心、呕吐、尿痛、荨麻疹、头痛、胃灼热和上腹痛等不良反应。尽管罕见，但也报告了低血压和循环衰竭。/碘帕醇钙和钠/

UNTOWARD EFFECTS REPORTED INCL ABDOMINAL CRAMPING, DIARRHEA, NAUSEA, VOMITING, DYSURIA, URTICARIA, HEADACHE, HEARTBURN, & EPIGASTRIC PAIN. ALTHOUGH RARE, HYPOTENSION & CIRCULATORY COLLAPSE HAVE BEEN REPORTED. /IPODATE CALCIUM & SODIUM/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 蛋白质结合

5号位上没有取代基，这使得该化合物能够与血清白蛋白结合。这就是为什么一旦被吸收，碘潘酸进入血液后，它会与白蛋白结合并被运输到肝脏的原因。

The absence of a substituent at position 5 allows the compound to bind to serum albumin. This is the reason why immediately after absorption, iopanoic acid enters the bloodstream it binds to albumin and it is transported to the liver.

来源:DrugBank

吸收、分配和排泄

• 吸收

碘番酸(ipodate)的亲脂性足以通过胃肠粘膜。摄入后，碘番酸通过被动扩散迅速被小肠粘膜吸收。胆盐在十二指肠的存在对于它通过肠壁的扩散至关重要，而高脂肪饮食对于提高吸收效果也很重要。最大效果在初始剂量后的5小时达到，并且效果可以保持超过60小时。

The lipophilicity of ipodate is sufficient for passage through the gastrointestinal mucosa. After ingestion, iopodic acid is promptly absorbed by passive diffusion in the small intestinal mucosa. The presence of bile salts in the duodenum is essential for its diffusion through the intestine wall and a high-fat diet is important in order to increase the absorption effectivity. The maximum effect is showed to be attained 5 hours after the initial dosage and the effect were retained for more than 60 hours.

来源:DrugBank

吸收、分配和排泄

• 消除途径

碘番酸的代谢产物容易排入胆汁中，随胆汁流动填充胆囊，然后通过胆道系统随粪便排出。这种排泄方式占总消除剂量的65%，而肾脏负责剩余35%的消除。

The metabolism products of ipodate are readily excreted into the bile, follow the bile flow to fill up the gallbladder and then excreted by the biliary system in the feces. This mode of excretion accounts for 65% of the eliminated dose whereas the kidneys are responsible for the remaining 35% of the elimination.

来源:DrugBank

吸收、分配和排泄

...迅速从胃肠道吸收并在胆汁中排泄... /碘番酸钙/

...RAPIDLY ABSORBED FROM GI TRACT & EXCRETED IN BILE... /IPODATE CALCIUM/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

...与碘帕醇钙相比，从胃肠道吸收较慢.../碘帕醇钠/

...SOMEWHAT LESS RAPIDLY ABSORBED FROM GI TRACT.../WHEN COMPARED WITH IPODATE CALCIUM/. /IPODATE SODIUM/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2925290090

制备方法与用途

化学性质

磺泊酸是一种白色结晶。熔点为168-169℃，225℃时分解。它溶于甲醇、乙醇、丙酮和稀硫酸。其钠盐为磺泊酸钠（C₁₂H₁₂I₃N₂NaO₂），也被称为Ipodate sodium或Biloptin，Oragrafin sodium。该钠盐是白色叶状结晶，熔点在303-304℃（分解）。它易溶于水和甲醇、乙醇，但在二甲基甲酰胺中易溶，在丙酮和乙醚中不溶解。

用途

磺泊酸是一种口服胆囊、胆管造影药。其毒性较低，极少产生副作用，并且在正常剂量下对肝病、骨肠病及胆道疾病患者都是安全的。它可以提供良好的显影效果，无需经过胆囊浓缩即可清晰显示胆管与胆囊。对于需要快速胆囊造影的情况，在服药2.5-3小时后，即可达到所需的显影程度。

生产方法

磺泊酸的生产方法包括由间硝基苯甲醛与乙酐缩合、用铝镍合金催化氢化还原、碘化以及与DMF缩合而成盐而制得碘泊酸钠。

反应信息

• 作为产物：
  描述：

  3-(3-氨基-2,4,6-三碘-苯基)丙酸 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 邻二氯苯 为溶剂， 生成 胆影脒
  参考文献：
  名称：

  CASSEBAUM; DIERBACH, Pharmazie, 1961, vol. 16, p. 389 - 395

  摘要：

  DOI：

文献信息

• CASSEBAUM; DIERBACH, Pharmazie, 1961, vol. 16, p. 389 - 395
  作者：CASSEBAUM、DIERBACH

  DOI：——

  日期：——