Stable under recommended storage conditions. /Citalopram hydrobromide/
西酞普兰(Citalopram),是选择性五羟色胺回收抑制剂的一种。抑郁症作为精神科常见的精神疾病,其患者常伴有焦虑症状。这种抑郁与焦虑的共病现象在年轻和老年患者中尤为常见,甚至成为患者的就医原因之一。
西酞普兰治疗伴随焦虑症状的老年抑郁症患者效果显著,因其作用温和、药物相互作用较少及安全性好,在老年人群中的应用较为广泛。此外,它对其他神经递质的影响较小,特别适用于老年人。西酞普兰是首个在丹麦获准用于临床的五羟色胺再摄取抑制剂,并于1998年在美国成功上市。
药理作用西酞普兰通过选择性地抑制突触前膜对五羟色胺(5-HT)的再吸收,增加脑内5-HT水平,从而发挥抗抑郁效果。它主要用于治疗抑郁症、老年性痴呆及多发梗死性痴呆等。
化学性质与用途西酞普兰为油状物,沸点175~181℃/4.00Pa;其氢溴酸盐(Citalopram Hydmbmmide)熔点为182--183℃,从异丙醇结晶而成;草酸盐(Citalopram Oxalate)熔点为164~166℃。
生产方法 氢溴酸西酞普兰的合成在通氮气、温度控制在60-70℃下,将21g 50%氢化钠(溶于矿物油中)溶于90ml二甲亚砜中制得甲亚磺酰甲基钠溶液。冷却条件下滴入96g的1-(4-氟苯基)-1-二氢-S-异苯并呋喃腈(溶于150ml二甲亚砜),保持反应液温度为25℃,维持10min。随后快速加入53g的3-二甲氨基丙基氯(溶于25ml二亚砜中)加热至40℃,继续搅拌50min。
将上述混合物倾入冰水中进行萃取后,乙醚提取液再用20%乙酸水溶液处理。随后碱化乙酸水溶液并再次使用乙醚进行萃取。最终经无水碳酸钾干燥、真空浓缩等步骤制得西酞普兰。
药理作用与临床应用中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
1-(4-氟苯基)-1,3-二氢-1-[3-(甲基氨基)丙基]异苯并呋喃-5-甲腈 | rac-desmethylcitalopram | 62498-67-3 | C19H19FN2O | 310.371 |
1-(3-氨基丙基)-1-(4-氟苯基)-1,3-二氢-5-异苯并呋喃甲腈 | didesmethylcitalopram | 62498-69-5 | C18H17FN2O | 296.344 |
—— | 1-(4-fluorophenyl)-1-(3-oxopropyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 211800-31-6 | C18H14FNO2 | 295.313 |
—— | 3-(5-(aminomethyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | 125803-03-4 | C20H25FN2O | 328.43 |
西酞普兰羧酸杂质 | 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acid | 440121-09-5 | C20H22FNO3 | 343.398 |
—— | 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-isobenzofuran | —— | C19H22FNO | 299.388 |
1-[3-(二甲基氨基)丙基]-1-(4-氟苯基)-1,3-二氢-5-异苯并呋喃甲酰胺 | 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide | 64372-56-1 | C20H23FN2O2 | 342.413 |
1-(4-氟苯基)-1-(3-二甲基氨基丙基)-5-氯二氢异苯并呋喃 | Lu 10-134-C | 64169-45-5 | C19H21ClFNO | 333.833 |
4-(4-二甲胺基-1-对氟苯基-1-羟基丁基)-3-(羟甲基)苯腈 | 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile | 103146-25-4 | C20H23FN2O2 | 342.413 |
(-)4[4-(二甲胺基)-1-(4-氟苯基)-1-(羟基丁基)-3-(羟基 甲基)氰苯.氢溴酸盐 | (-)-(S)-4-(4-dimethylamino-1-(4'-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)-benzonitrile | 488787-59-3 | C20H23FN2O2 | 342.413 |
—— | 3-(1-(4-fluorophenyl)-5-iodo-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | —— | C19H21FINO | 425.285 |
3-(5-溴-1-(4-氟苯基)-1,3-二氢异苯并呋喃-1-基)-N,N-二甲基丙烷-1-胺 | {3-[5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl]-propyl}-dimethylamine | 64169-39-7 | C19H21BrFNO | 378.284 |
—— | 5-bromo-1-(4-fluorophenyl)-1-(3-methylaminopropyl)phthalane | 945543-92-0 | C18H19BrFNO | 364.257 |
—— | 5-Amino-1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran | —— | C19H23FN2O | 314.403 |
—— | 1-(4-fluorophenyl)-1-[(3-p-toluenesulfonyloxy)propyl]-1,3-dihydro-5-isobenzo-furancarbonitrile | 345663-50-5 | C25H22FNO4S | 451.518 |
—— | (±)-1-(4-fluorophenyl)-1-formyl-1,3-dihydroisobenzofuran-5-carbonitrile | —— | C16H10FNO2 | 267.259 |
—— | 4,4-dimethyl-[2-[3-hydroxymethyl-4-[4-fluoro-a-hydroxy-a-(dimethylamino)propyl]benzyl]phenyl]oxazoline | 265137-38-0 | C24H31FN2O3 | 414.52 |
1-(4-氟苯基)-1,3-二氢异苯并呋喃-5-腈 | 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 64169-67-1 | C15H10FNO | 239.249 |
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
(R)-西酞普兰 | (S)-1-[3-(dimethylamino)propyl]-1-(4-flouorphenyl)-1,3-dihydro-5-isobenzofuran carbonitrile | 128196-02-1 | C20H21FN2O | 324.398 |
依他普仑 | escitalopram | 128196-01-0 | C20H21FN2O | 324.398 |
1-(4-氟苯基)-1,3-二氢-1-[3-(甲基氨基)丙基]异苯并呋喃-5-甲腈 | rac-desmethylcitalopram | 62498-67-3 | C19H19FN2O | 310.371 |
—— | (-)-Desmethylcitalopram | —— | C19H19FN2O | 310.371 |
—— | 1-(4-fluorophenyl)-1-(3-(methyl(4-phenylbutyl)amino)propyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507401-91-3 | C29H31FN2O | 442.576 |
—— | 1-(3-(butyl(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507401-89-9 | C23H27FN2O | 366.479 |
—— | 1-(4-fluorophenyl)-1-(3-(methyl(propyl)amino)propyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507401-88-8 | C22H25FN2O | 352.452 |
—— | 1-(3-((2-aminoethyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507402-16-5 | C21H24FN3O | 353.439 |
—— | 1-(3-((cyclopropylmethyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507401-87-7 | C23H25FN2O | 364.463 |
艾司西酞普兰 E | Citalopram N-Oxide | 63284-72-0 | C20H21FN2O2 | 340.397 |
—— | 1-(4-fluorophenyl)-1-(3-(methyl(phenethyl)amino)propyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507401-90-2 | C27H27FN2O | 414.523 |
—— | 1-(4-fluorophenyl)-1-(3-(methyl(pyridin-4-yl)amino)propyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507401-96-8 | C25H24FN3O | 401.483 |
—— | 3-(5-(aminomethyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | 125803-03-4 | C20H25FN2O | 328.43 |
西酞普兰甲醛 | 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde | 227954-87-2 | C20H22FNO2 | 327.399 |
—— | 1-(4-fluorophenyl)-1-(3-(methyl(4-oxocyclohexyl)amino)propyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507402-21-2 | C25H27FN2O2 | 406.5 |
—— | 1-(3-(((1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-yl)methyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507402-05-2 | C39H41F2N3O2 | 621.77 |
—— | 1-(4-fluorophenyl)-1-(3-(methyl(naphthalen-2-ylmethyl)amino)-propyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507402-01-8 | C30H27FN2O | 450.556 |
—— | 3-(5-((((1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-yl)methyl)amino)methyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | 1507401-72-0 | C40H47F2N3O2 | 639.829 |
西酞普兰羧酸杂质 | 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acid | 440121-09-5 | C20H22FNO3 | 343.398 |
—— | 1-(3-((4-(dimethylamino)benzyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507401-94-6 | C28H30FN3O | 443.564 |
—— | methyl 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylate | 1507401-62-8 | C21H24FNO3 | 357.425 |
—— | 3-(1-(4-fluorophenyl)-5-(piperidin-1-ylmethyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | 1507401-63-9 | C25H33FN2O | 396.548 |
1-[3-(二甲基氨基)丙基]-1-(4-氟苯基)-1,3-二氢-5-异苯并呋喃甲酰胺 | 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide | 64372-56-1 | C20H23FN2O2 | 342.413 |
—— | 3-(1-(4-fluorophenyl)-5-(morpholinomethyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | 1507401-64-0 | C24H31FN2O2 | 398.521 |
—— | 3-(1-(4-fluorophenyl)-5-(((naphthalen-2-ylmethyl)amino)-methyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | 1507401-70-8 | C31H33FN2O | 468.614 |
—— | 1-(4-fluorophenyl)-1-(3-(methyl(1,4-dioxaspiro[4.5]decan-8-yl)-amino)propyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507402-18-7 | C27H31FN2O3 | 450.553 |
1-[3-(二甲基氨基)丙基]-1-(4-氟苯基)-1,3-二氢-3-氧代-5-异苯并呋喃甲腈 | 3-oxocitalopram | 372941-54-3 | C20H19FN2O2 | 338.381 |
—— | N'-benzoyl-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzo furan-5-carbohydrazide | —— | C27H28FN3O3 | 461.536 |
—— | N'-(4-methylbenzoyl)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbohydrazide | —— | C28H30FN3O3 | 475.563 |
—— | 1-(3-(((9H-fluoren-2-yl)methyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507402-03-0 | C33H29FN2O | 488.604 |
—— | 1-(4-fluorophenyl)-1-(3-(methyl(quinolin-4-ylmethyl)amino)-propyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507401-98-0 | C29H26FN3O | 451.543 |
—— | 1-(3-(((1H-indol-3-yl)methyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507402-09-6 | C28H26FN3O | 439.532 |
—— | 3-(1-(4-fluorophenyl)-5-((4-phenylpiperazin-1-yl)methyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | 1507401-65-1 | C30H36FN3O | 473.634 |
—— | N'-(2-iodobenzoyl)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro isobenzofuran-5-carbohydrazide | —— | C27H27FIN3O3 | 587.433 |
—— | 1-(3-((benzo[b]thiophen-3-yl-methyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507401-93-5 | C28H25FN2OS | 456.584 |
—— | N'-(2-bromobenzoyl)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbohydrazide | —— | C27H27BrFN3O3 | 540.432 |
—— | 1-(3-((benzofuran-3-yl-methyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507401-92-4 | C28H25FN2O2 | 440.517 |
—— | 3-(5-((((9H-fluoren-2-yl)methyl)amino)methyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | 1507401-71-9 | C34H35FN2O | 506.663 |
—— | 1-(3-((2-(1,3-dioxoisoindolin-2-yl)ethyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507402-14-3 | C29H26FN3O3 | 483.542 |
—— | N'-(2-methoxybenzoyl)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbohydrazide | —— | C28H30FN3O4 | 491.562 |
—— | 3-(5-(((benzofuran-3-ylmethyl)amino)methyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | 1507401-68-4 | C29H31FN2O2 | 458.576 |
—— | N'-(4-hydroxy-3-methoxybenzoyl)-1-[3-(dimethylamino)propyl]-1-(4-fluoro phenyl)-1,3-dihydroisobenzofuran-5-carbohydrazide | —— | C28H30FN3O5 | 507.562 |
—— | 1-(4-fluorophenyl)-1-(3-(((5-methoxy-1H-indol-3-yl)methyl)-(methyl)amino)propyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507402-13-2 | C29H28FN3O2 | 469.559 |
—— | 3-(5-((4-(2,3-dichlorophenyl)piperazin-1-yl)methyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | 1507401-67-3 | C30H34Cl2FN3O | 542.524 |
—— | 3-(1-(4-fluorophenyl)-5-((4-(2-methoxyphenyl)piperazin-1-yl)-methyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine | 1507401-66-2 | C31H38FN3O2 | 503.66 |
—— | 1-(3-((4-(1H-indol-3-yl)cyclohex-3-en-1-yl)(methyl)amino)-propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | 1507402-22-3 | C33H32FN3O | 505.635 |
—— | tert-butyl-3-(((3-(5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)propyl)(methyl)amino)methyl)-1H-indole-1-carboxylate | 1507402-07-4 | C33H34FN3O3 | 539.65 |
—— | tert-butyl-3-(((3-(5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)propyl)(methyl)amino)methyl)-5-methoxy-1H-indole-1-carboxylate | 1507402-11-0 | C34H36FN3O4 | 569.676 |