Marvin 06011015382D 32 34 0 0 1 0 999 V2000 7.7581 -7.2907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4726 -6.8782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0436 -6.8782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1789 -7.2858 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7581 -8.1157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3292 -7.2907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1781 -8.1108 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0436 -8.5282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8922 -8.5240 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3292 -8.1157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1766 -9.7608 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.8914 -9.3490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4633 -8.5226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4726 -6.0532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4625 -9.3476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6147 -8.5282 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.0436 -9.3532 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 7.0436 -6.0532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.4634 -9.7650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6071 -8.1122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0337 -10.5886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1783 -9.3532 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 12.7493 -9.3517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4626 -10.5899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0345 -9.7636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7477 -11.0018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1758 -10.5858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8899 -10.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3188 -11.0004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6047 -10.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3292 -5.6407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3211 -8.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 3 1 1 0 0 0 0 5 1 2 0 0 0 0 4 2 1 0 0 0 0 14 2 2 0 0 0 0 6 3 2 0 0 0 0 18 3 1 0 0 0 0 7 4 1 1 0 0 0 8 5 1 0 0 0 0 10 6 1 0 0 0 0 9 7 1 0 0 0 0 13 7 1 0 0 0 0 10 8 2 0 0 0 0 17 8 1 0 0 0 0 12 9 1 0 0 0 0 9 20 1 1 0 0 0 16 10 1 0 0 0 0 15 11 1 0 0 0 0 27 11 1 0 0 0 0 12 11 1 0 0 0 0 15 13 1 0 0 0 0 31 18 1 0 0 0 0 24 19 1 0 0 0 0 22 19 1 0 0 0 0 23 19 2 0 0 0 0 32 20 1 0 0 0 0 29 21 1 0 0 0 0 25 21 2 0 0 0 0 26 21 1 0 0 0 0 25 23 1 0 0 0 0 26 24 2 0 0 0 0 28 27 1 0 0 0 0 30 28 1 0 0 0 0 30 29 1 0 0 0 0 M END > CHEBI:3720 > cisapride > The amide resulting from formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-amine. It has been used (as its monohydrate or as its tartrate) for the treatment of gastro-oesophageal reflux disease and for non-ulcer dyspepsia, but its propensity to cause cardiac arrhythmias resulted in its complete withdrawal from many countries, including the U.K., and restrictions on its use elsewhere. > 3 > CHEBI:151790; CHEBI:221485; CHEBI:143545; CHEBI:657397; CHEBI:657741 > Cisapride; cis-4-amino-5-chloro-N-{1-[3-(p-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-o-anisamide; cis-4-amino-5-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-methoxybenzamide; cis-4-amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-o-anisamide; 4-Amino-5-chloro-N-{1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-methoxy-benzamide; 4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamide; (+-)-cisapride > 4-amino-5-chloro-N-{cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl}-2-methoxybenzamide > cisapridum; cisapride; cisaprida > C23H29ClFN3O4 > 465.94500 > 465.18306 > 0 > CO[C@H]1CN(CCCOc2ccc(F)cc2)CC[C@H]1NC(=O)c1cc(Cl)c(N)cc1OC > InChI=1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(14-22(20)31-2)9-3-11-32-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)/t20-,22+/m1/s1 > DCSUBABJRXZOMT-IRLDBZIGSA-N > 81098-60-4 > 81098-60-4 > DB00604 > C06910 > D00274 > LSM-2133 > 10891117; 12190308; 1995885; 2139471; 19663444; 19110341 $$$$