安非他酮
此条目可参照英语维基百科相应条目来扩充,此条目在对应语言版为高品质条目。 |
临床资料 | |
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读音 | /bjuːˈproʊpi.ɒn/ bew-PROH-pee-on |
商品名 | Wellbutrin, Elontril, Zyban |
其他名称 | 3-Chloro-N-tert-butyl-β-keto-α-methylphenethylamine; 3-Chloro-N-tert-butylcathinone |
AHFS/Drugs.com | Monograph |
MedlinePlus | a695033 |
核准状况 | |
怀孕分级 |
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依赖性 | 几乎没有 |
成瘾性 | 几乎没有 |
给药途径 | 医疗用途: 口服 娱乐: 鼻腔内, 静脉注射 |
ATC码 | |
法律规范状态 | |
法律规范 |
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药物动力学数据 | |
血浆蛋白结合率 | 84% (安非他酮), 77% (羟安非他酮代谢产物), 42% (苏氨酸氢化安非他酮代谢物)[1] |
药物代谢 | 肝脏 (大部分是CYP2B6-介导的羟化, 但有时候也是CYP1A2, CYP2A6, CYP2C9, CYP3A4, CYP2E1和CYP2C19)[1][6][3][7] |
生物半衰期 | 11小时(短期给药;母体化合物)[2] 14–21小时(长期给药; 母体化合物 - 取决于形式),[1][3][4] 20小时(羟安非他酮), 33小时(赤藓糖氢化安非他酮), 37小时(苏氨酸氢化安非他酮)[1][3][4][5] |
排泄途径 | 肾脏 (87%; 0.5% 原型), 粪便 (10%)[6][3][4] |
识别信息 | |
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CAS号 | 34841-39-9 |
PubChem CID | |
IUPHAR/BPS | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
化学信息 | |
化学式 | C13H18ClNO |
摩尔质量 | 239.74 g·mol−1 |
3D模型(JSmol) | |
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安非他酮(国际非专利药品名称:Bupropion,旧名:amfebutamone) 或盐酸安非他酮,商品名威博隽(Wellbutrin),是一种主要作为抗抑郁药和戒烟药使用的药物、也可用作治疗注意力不足过动症的第二线药品(second-line medication)与中枢神经刺激剂合并使用,或作为中枢神经刺激剂的替代方案。[8][9][10] [11][12] 安非他酮在美国是最常用的抗抑郁药之一,在其他许多英语国家亦是如此。[13][14] 以商品名载班(Zyban)出售的安非他酮缓释片用作戒烟药使用,并且使用十分广泛。[13] 安非他酮以片剂使用,并且在大部分国家仅可凭处方使用。[13] 在台湾有经卫生福利部食品药物管理署核准由瑞安大药厂推出的医师处方学名药必博宁(Buporin)。[15]化学上,安非他酮属于氨基酮类化合物。不能用于有过癫痫病史的病人身上,否则会增加癫痫发作的风险。
此药由Burroughs Wellcome药厂(葛兰素史克(GSK)前身)的有机化学暨药学家纳里曼·梅达(Nariman Mehta)于1969年所发明,并于1974年取得美国专利3819706号[16]。
医疗用途
抑郁
现有证据表明,安非他酮在治疗抑郁症方面比安慰剂更有效。[17][18]不过,有些研究认为这些证据的质量较低。一些荟萃分析认为,安非他酮对抑郁症的效果并不一致。[19][20][21]但也有荟萃分析认为称其效果较好。[22]然而,该分析在方法上存在一定局限性,比如只用了五项试验的数据来计算效果,且不同试验间的效果差异较大,因此作者声明要对这一结果要“非常谨慎”地解读。此外,该荟萃分析中没有包含未发表的试验,而这些研究通常得出负面结果。其他荟萃分析则包含了未发表的试验。[23][20]总体而言,安非他酮在治疗抑郁症方面的效果与其他抗抑郁药相似。
在秋冬季节,安非他酮能够预防季节性情感障碍患者的抑郁发作:使用安非他酮的患者中有15%出现了重度抑郁症状,而使用安慰剂的患者则有27%出现了类似症状。[24]对于双相障碍,安非他酮也能有效改善抑郁症状,其疗效和引发情感转换的风险与其他抗抑郁药相似。[25]
安非他酮有几个不同于其他抗抑郁药的特点:与大多数抗抑郁药不同,它通常不会引起性功能障碍,该副作用的发生率与安慰剂无差异。[22][26]安非他酮不会引起体重增加,反而大多数研究发现服用安非他酮的患者体重显著下降。[22]安非他酮不会像其他抗抑郁药那样引发嗜睡。 [27]对于伴有嗜睡和疲劳症状的抑郁患者,安非他酮的疗效优于选择性血清素再摄取抑制剂(SSRIs)。[28]和一般认知相反,安非他酮在治疗伴有焦虑的抑郁中同样有效,且不会加重焦虑。[29][30]对于伴有中度以下的焦虑的抑郁,安非他酮的疗效与SSRIs相当,而SSRIs对伴有高度焦虑的患者在缓解率上有一定的疗效优势。[29]
戒烟
安非他酮是一种辅助戒烟的药物,可以减轻对尼古丁的渴望和戒断症状的严重程度。[31][32][33]例如抑郁、易怒、注意力难以集中以及食欲增加。[34]安非他酮在治疗初期能够减缓体重增加。但是随着时间推移,这种效果会变得不再显著。[34]
安非他酮用于戒烟的疗程一般持续7到12周,患者在疗程开始十天后停止使用烟草。[34][35]疗程结束后,安非他酮维持戒烟的效果会随着时间的推移而下降。从三个月内的37%戒烟成功率下降到一年的20%[36]。目前尚不清楚延长安非他酮治疗是否有助于预防复吸。[37]
经过六个月的治疗后,和安慰剂对比,安非他酮使戒烟成功率增加了约60%。在这方面,安非他酮和尼古丁取代疗法同样有效。但不如伐尼克兰。同时使用尼古丁替代疗法不能提高成功率。[38]
对于儿童和青少年而言,使用安非他酮戒烟似乎没有任何明显的益处。[39]使用其帮助孕妇戒烟的证据也不充分。[40]
注意缺陷多动障碍
在美国,安非他酮未被用于批准用于治疗注意缺陷多动障碍(ADHD)。也未在美国儿科学会的现行(2019)ADHD治疗指南中提及。[41]针对安非他酮用于成人和儿童ADHD治疗的系统性综述表明,安非他酮可能对ADHD有效,但由于临床试验规模较小且存在偏倚风险,相关结论应谨慎对待。[42][43][44][45]和托莫西汀类似,安非他酮需要需要数周才会起效。[42][46]与安非他明和哌甲酯等兴奋剂不同,它们会立刻起效。[46]
体重增加
安非他酮用于治疗长期体重增加(6-12个月)时,平均比安慰剂组减轻2.7公斤。[47]这与其他几种减肥药物(如西布曲明或奥利司他)的效果差距不大。[47]复方药物纳曲酮/安非他酮已被美国食品药品监督管理局(FDA)批准用于治疗成人慢性肥胖。
药理
药效学
安非他酮用于治疗抑郁症和其他适应症的作用机制尚不明确,据信与安非他酮作为去甲肾上腺素-多巴胺再吸收抑制剂(NDRI)和几种烟碱型乙酰胆碱受体的负变构调节剂的特性有关。[48]安非他酮不诱导释放多巴胺或去甲肾上腺素。[49]其的药理作用很大程度上归功于它的活性代谢物,这些代谢物在血浆中的含量相当或高于安非他酮本身。因此安非他酮可视为这些代谢物的前药。
这些代谢物,尤其是瑞达法辛的作用,也表现为抑制去甲肾上腺素和多巴胺的再摄取,和同时抑制烟碱受体。安非他酮在多种受体上没有显著的直接活性,包括α-和β-肾上腺素受体、多巴胺受体、血清素受体、组胺受体以及毒蕈碱型乙酰胆碱受体。[27]此外,安非他酮也不抑制单胺氧化酶。
药代动力学
口服给药后,安非他酮被迅速且完全吸收,在1.5个小时后达到最大血药浓度。缓释(SR)和长效(XL)制剂设计用于减缓吸收,分别在3小时和5小时内达到峰值浓度。[50]安非他酮的绝对生物利用度未知,但估计较低,为5%至20%,和首过效应有关。至于不同制剂的相对生物利用度,XL制剂的利用度(68%)低于SR制剂和速释的安非他酮。[51]
安非他酮通过多种途径在体内代谢。氧化途径包括由细胞色素P450同工酶CYP2B6代谢生成R,R-羟基安非他酮和(S,S)-羟基安非他酮(瑞达法辛),并在较小程度上通过CYP2C19产生 4'-羟基安非他酮。还原途径包括由肝脏中的11β-羟基类固醇脱氢酶1型和肠道中的AKR7A2和AKR7A3生成苏氨酸氢化安非他酮。[52]11β-羟基类固醇脱氢酶1型通过还原安非他酮的酮基形成赤藓氯化安非他酮,也有部分由醛酮还原酶产生。[53]
安非他酮的代谢变化较大,不同个体在服用相同剂量时,其有效剂量可能相差多达5.5倍,半衰期为12至30小时。而羟基安非他酮的有效剂量差异则可能达到7.5倍,半衰期为15至25小时。[54]由于这些显著的代谢差异,一些研究者建议监测安非他酮及其羟基代谢物的血药浓度。[55]
副作用
安非他酮与安慰剂相比,最常见的不良反应是口干、恶心、便秘、失眠、焦虑、震颤和多汗。除去甲文拉法辛外,安非他酮是所有二代抗抑郁药中失眠发生率最高的药物。[56]其还与约20%的头痛风险增加有关。[57]
癫痫发作是安非他酮的严重但罕见的不良反应之一。其风险具有显著的剂量依赖性。在每日300至450毫克的速释制剂剂量下,癫痫发作的发生率约为0.4%;当剂量超过600毫克时,癫痫发作的发生率增加约十倍。相比之下,一般人群中自发性癫痫发作的发生率为0.07%至0.09%,而大多数其他抗抑郁药物在推荐剂量下引发癫痫发作的风险通常在0%至0.5%之间。[58]
与九种选择性血清素再摄取抑制剂(SSRI)和血清素去甲肾上腺素再摄取抑制剂(SNRI)相比,安非他酮的脱发风险最高,导致脱发的原因可能与多巴胺能有关。其所致的脱发通常是可逆的。[59]
精神副作用
FDA要求包括安非他酮在内所有抗抑郁药必须附有黑框警告,警告这些药物可能会增加25岁以下人群的自杀风险。该警告基于FDA进行的统计分析,其发现儿童和青少年中自杀意念和行为的风险增加了2倍,而18–24岁人群的风险增加了1.5倍。在此分析中,FDA结合了295项针对11种抗抑郁药的试验结果,以获得统计学上显著的结果。单独考虑时,安非他酮与安慰剂之间在统计学上并无显著差异。[60]
用于戒烟的安非他酮会使精神副作用的风险增加25%,特别是焦虑(约增加40%)和失眠(约增加80%)。证据不足所以无法确定安非他酮是否与自杀或自杀行为相关。[32]
在少数情况下,可能会出现安非他酮引发的精神病。和使用高剂量安非他酮有关;其中的很多案例服用剂量都超过了推荐剂量。联合使用抗精神病药物似乎有保护作用。在大多数情况下,降低剂量、停止治疗或添加抗精神病药物可以消除精神病症状。[61]
尽管缺乏研究,但少量病例报告表明,突然停用安非他酮可能导致抗抑郁药停药综合症。[62]
药物相互作用
由于安非他酮通过CYP2B6酶代谢为羟基安非他酮,因此可能与CYP2B6抑制剂发生相互作用,包括帕罗西汀、舍曲林、去甲氟西汀(氟西汀的活性代谢物)、地西泮、氯吡格雷和奥芬那君。这些药物可能会导致安非他酮血药浓度升高,而羟基安非他酮血药浓度下降。相反,CYP2B6诱导剂(如卡马西平、克霉唑、利福平、利托那韦、贯叶连翘和苯巴比妥)则可能导致安非他酮血药浓度下降、羟基安非他酮浓度上升。[50]例如,卡马西平能使安非他酮的暴露量减少90%,而羟基安非他酮的暴露量增加94%。[63]研究表明,利托那韦、洛匹那韦/利托那韦和依法韦仑均可降低安非他酮及其代谢物的浓度。[64]氯吡格雷和噻氯匹定这两种强效的CYP2B6抑制剂已被发现能显著增加安非他酮的水平,同时减少其代谢物羟基安非他酮的水平。[64]
安非他酮及其代谢物是CYP2D6的强抑制剂,羟基安非他酮导致大部分作用。此外,安非他酮及其代谢物可能会减少肝脏中CYP2D6的表达,其最终结果是显著减慢其他由该酶代谢的药物的清除速度。例如,研究发现安非他酮可使地昔帕明(CYP2D6的底物)的曲线下面积增加5倍。[64]安非他酮还可使托莫西汀的浓度增加5.1倍,同时使其主要代谢物的暴露量减少1.5倍。[65]另外,当右美沙芬(主要由CYP2D6代谢的药物)与每日300毫克的安非他酮合用时,其主要代谢物右啡烷与右美沙芬的比率增加了大约35倍。[50]同时使用MDMA时,二者的暴露量都会增加约30%,MDMA导致的精神作用增强,但对心率的影响减小。[66]与其他CYP2D6底物(如美托洛尔、丙咪嗪、去甲替林、[67]文拉法辛和[[奈必洛尔)也已报道过相互作用。值得注意的是,安非他酮似乎并不会影响CYP2D6底物氟西汀和帕罗西汀的浓度。[68]
安非他酮降低癫痫发作阈值,因此可能与其他也降低阈值的药物(如抗精神病药、三环类抗抑郁药、茶碱和全身性皮质类固醇)发生相互作用。处方信息建议尽量减少饮酒,因为安非他酮在极少数情况下会降低酒精耐受性。[69]
在将安非他酮与单胺氧化酶抑制剂(MAOI)联用时应谨慎,因为可能会引发高血压危象。[70]
过量
安非他酮在过量时被认为具有中度危险性。[71]根据美国毒物中心的分析,按处方剂量调整后,安非他酮和文拉法辛是第二代抗抑郁药(不包括三环类抗抑郁药)中导致死亡率和发病率最高的两种药物。[72]对于严重过量,约三分之一的病例报告出现癫痫发作;其他严重影响包括幻觉、意识丧失和心律异常。当安非他酮与其他多种药物一起过量时,已有报告体温升高、肌肉僵硬、肌肉损伤、高血压或低血压、昏迷、昏厥以及呼吸衰竭。[73]
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