8-羟基卡替洛尔 | 59826-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 8-羟基卡替洛尔
• 中文别名: 肼,[(3-甲基-2-噻嗯基)甲基]-
• 英文名称: 8-Hydroxycarteolol
• 英文别名: 5-(3-tert-butylamino-2-hydroxy-propoxy)-8-hydroxy-3,4-dihydro-1H-quinolin-2-one；5-(3'-tert-Butylamino-2'-hydroxy)propoxy-8-hydroxy-3,4-dihydrocarbostyril；8-hydroxy-5-(3-t-butylamino-2-hydroxypropoxy)-3,4-dihydrocarbostyril；5-(3-tert-Butylamino-2-hydroxypropoxy)-8-hydroxy-3,4-dihydrocarbostyril；5-[3-(tert-butylamino)-2-hydroxypropoxy]-8-hydroxy-3,4-dihydro-1H-quinolin-2-one
• CAS: 59826-22-1
• 化学式: C₁₆H₂₄N₂O₄
• 分子量: 308.378
• InChiKey: TVZJLAKRXHGVOK-UHFFFAOYSA-N

物化性质

• 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)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  90.8
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-羟基卡替洛尔 、 3-溴丙烯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 8-Allyloxy-5-(2-hydroxy-3-tert-butylamino)propoxy-3,4-dihydrocarbostyril hydrochloride
  参考文献：
  名称：

  Carbostyril compounds

  摘要：

  碳基喹啉化合物由以下公式（I）表示：其中R.sub.1代表氢原子、烷基或苯基烷基，R.sub.2代表烯基、烷氧基烷基、羟基烷基、羧基烷基、烷基羰基、环烷基羰基、烷基羰基烷基、烷氧基羰基烷基、炔基或氨基烷基，R.sub.3和R.sub.4（可以相同也可以不同）分别代表氢原子、烷基、环烷基、烷氧基烷基、烯基、苯基烷基、苯氧基烷基或苯基，而碳基喹啉核的3,4-键代表单键或双键，以及其药用可接受盐，以及制备该化合物的方法。

  公开号：

  US04289883A1
• 作为产物：
  描述：

  盐酸卡替洛尔 在 rat liver microsomes 作用下， 以 phosphate buffer 为溶剂， 生成 8-羟基卡替洛尔
  参考文献：
  名称：

  Involvement of CYP2D1 in the metabolism of carteolol by male rat liver microsomes

  摘要：

  1. The metabolism of carteolol, a beta-adrenoceptor blocking drug, was investigated in male Sprague-Dawley rat liver microsomes.2. The formation of 8-hydroxycarteolol was the principal metabolic pathway of carteolol in vitro and followed Michaelis-Menten kinetics with a K-m = 11.0+/-5.4 mu M and a V-max = 1.58 +/- 0.64 nmol/min/nmol P450 respectively (mean +/-SD, n = 5). Eadie-Hofstee plot analysis of carteolol 8-hydroxylase activity confirmed single-enzyme Michaelis-Menten kinetics.3. The cytochrome P450 isoforms involved in B-hydroxylation of carteolol were investigated using selective chemical inhibitors and polyclonal anti-P450 antibodies. Quinine (K-i = 0.06 mu M) and quinidine (K-i = 2.0 mu M), selective inhibitors of CYP2D1, competitively inhibited 8-hydroxycarteolol formation. Furthermore, only anti-human CYP2D6 antibody inhibited this reaction.4. These results suggest that carteolol is metabolized to 8-hydroxycarteolol by CYP2D1. The K-m of carteolol for CYP2D1 in male rat liver microsomes was much greater than those of propranolol or bunitrolol, indicating that carteolol has a lower affinity for CYP2D1 compared with these other beta-adrenoceptor blocking drugs.

  DOI：

  10.1080/004982597239886

文献信息

• US4072683A
  申请人：——

  公开号：US4072683A

  公开（公告）日：1978-02-07
• US4210753A
  申请人：——

  公开号：US4210753A

  公开（公告）日：1980-07-01
• US4289883A
  申请人：——

  公开号：US4289883A

  公开（公告）日：1981-09-15
• Carbostyril compounds
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04289883A1

  公开（公告）日：1981-09-15

  Carbostyril compounds represented by the formula (I) ##STR1## wherein R.sub.1 represents a hydrogen atom, an alkyl group or a phenylalkyl group, R.sub.2 represents an alkenyl group, an alkoxyalkyl group, a hydroxyalkyl group, a carboxyalkyl group, an alkylcarbonyl group, a cycloalkylcarbonyl group, an alkylcarbonylalkyl group, an alkoxycarbonylalkyl group, an alkynyl group or a carbamoylalkyl group, R.sub.3 and R.sub.4, which may be the same or different, each represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxyalkyl group, an alkenyl group, a phenylalkyl group, a phenoxyalkyl group or a phenyl group, and the 3,4-bond of the carbostyril nucleus represents a single or double bond, pharmaceutically acceptable salts thereof, and a process for preparing the same.

  碳基喹啉化合物由以下公式（I）表示：其中R.sub.1代表氢原子、烷基或苯基烷基，R.sub.2代表烯基、烷氧基烷基、羟基烷基、羧基烷基、烷基羰基、环烷基羰基、烷基羰基烷基、烷氧基羰基烷基、炔基或氨基烷基，R.sub.3和R.sub.4（可以相同也可以不同）分别代表氢原子、烷基、环烷基、烷氧基烷基、烯基、苯基烷基、苯氧基烷基或苯基，而碳基喹啉核的3,4-键代表单键或双键，以及其药用可接受盐，以及制备该化合物的方法。
• Involvement of CYP2D1 in the metabolism of carteolol by male rat liver microsomes
  作者：K. UMEHARA、S. KUDO、M. ODOMI

  DOI：10.1080/004982597239886

  日期：1997.1

  1. The metabolism of carteolol, a beta-adrenoceptor blocking drug, was investigated in male Sprague-Dawley rat liver microsomes.2. The formation of 8-hydroxycarteolol was the principal metabolic pathway of carteolol in vitro and followed Michaelis-Menten kinetics with a K-m = 11.0+/-5.4 mu M and a V-max = 1.58 +/- 0.64 nmol/min/nmol P450 respectively (mean +/-SD, n = 5). Eadie-Hofstee plot analysis of carteolol 8-hydroxylase activity confirmed single-enzyme Michaelis-Menten kinetics.3. The cytochrome P450 isoforms involved in B-hydroxylation of carteolol were investigated using selective chemical inhibitors and polyclonal anti-P450 antibodies. Quinine (K-i = 0.06 mu M) and quinidine (K-i = 2.0 mu M), selective inhibitors of CYP2D1, competitively inhibited 8-hydroxycarteolol formation. Furthermore, only anti-human CYP2D6 antibody inhibited this reaction.4. These results suggest that carteolol is metabolized to 8-hydroxycarteolol by CYP2D1. The K-m of carteolol for CYP2D1 in male rat liver microsomes was much greater than those of propranolol or bunitrolol, indicating that carteolol has a lower affinity for CYP2D1 compared with these other beta-adrenoceptor blocking drugs.