安非他酮
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臨床資料 | |
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讀音 | /bjuːˈproʊpi.ɒn/ bew-PROH-pee-on |
商品名 | Wellbutrin, Elontril, Zyban |
其他名稱 | 3-Chloro-N-tert-butyl-β-keto-α-methylphenethylamine; 3-Chloro-N-tert-butylcathinone |
AHFS/Drugs.com | Monograph |
MedlinePlus | a695033 |
核准狀況 | |
懷孕分級 |
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依賴性 | 幾乎沒有 |
成癮性 | 幾乎沒有 |
給藥途徑 | 醫療用途: 口服 娛樂: 鼻腔內, 靜脈注射 |
ATC碼 | |
法律規範狀態 | |
法律規範 |
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藥物動力學數據 | |
血漿蛋白結合率 | 84% (安非他酮), 77% (羥安非他酮代謝產物), 42% (蘇氨酸氫化安非他酮代謝物)[1] |
藥物代謝 | 肝臟 (大部分是CYP2B6-介導的羥化, 但有時候也是CYP1A2, CYP2A6, CYP2C9, CYP3A4, CYP2E1和CYP2C19)[1][6][3][7] |
生物半衰期 | 11小時(短期給藥;母體化合物)[2] 14–21小時(長期給藥; 母體化合物 - 取決於形式),[1][3][4] 20小時(羥安非他酮), 33小時(赤蘚糖氫化安非他酮), 37小時(蘇氨酸氫化安非他酮)[1][3][4][5] |
排泄途徑 | 腎臟 (87%; 0.5% 原型), 糞便 (10%)[6][3][4] |
識別資訊 | |
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CAS號 | 34841-39-9 |
PubChem CID | |
IUPHAR/BPS | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
化學資訊 | |
化學式 | C13H18ClNO |
摩爾質量 | 239.74 g·mol−1 |
3D模型(JSmol) | |
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安非他酮(國際非專利藥品名稱:Bupropion,舊名:amfebutamone) 或鹽酸安非他酮,商品名威博雋(Wellbutrin),是一種主要作為抗抑鬱藥和戒煙藥使用的藥物、也可用作治療注意力不足過動症的第二線藥品(second-line medication)與中樞神經刺激劑合併使用,或作為中樞神經刺激劑的替代方案。[8][9][10] [11][12] 安非他酮在美國是最常用的抗抑鬱藥之一,在其他許多英語國家亦是如此。[13][14] 以商品名載班(Zyban)出售的安非他酮緩釋片用作戒煙藥使用,並且使用十分廣泛。[13] 安非他酮以片劑使用,並且在大部分國家僅可憑處方使用。[13] 在台灣有經衛生福利部食品藥物管理署核准由瑞安大藥廠推出的醫師處方學名藥必博寧(Buporin)。[15]化學上,安非他酮屬於氨基酮類化合物。不能用於有過癲癇病史的病人身上,否則會增加癲癇發作的風險。
此藥由Burroughs Wellcome藥廠(葛蘭素史克(GSK)前身)的有機化學暨藥學家納里曼·梅達(Nariman Mehta)於1969年所發明,並於1974年取得美國專利3819706號[16]。
醫療用途
抑鬱
現有證據表明,安非他酮在治療抑鬱症方面比安慰劑更有效。[17][18]不過,有些研究認為這些證據的質量較低。一些薈萃分析認為,安非他酮對抑鬱症的效果並不一致。[19][20][21]但也有薈萃分析認為稱其效果較好。[22]然而,該分析在方法上存在一定局限性,比如只用了五項試驗的數據來計算效果,且不同試驗間的效果差異較大,因此作者聲明要對這一結果要「非常謹慎」地解讀。此外,該薈萃分析中沒有包含未發表的試驗,而這些研究通常得出負面結果。其他薈萃分析則包含了未發表的試驗。[23][20]總體而言,安非他酮在治療抑鬱症方面的效果與其他抗抑鬱藥相似。
在秋冬季節,安非他酮能夠預防季節性情感障礙患者的抑鬱發作:使用安非他酮的患者中有15%出現了重度抑鬱症狀,而使用安慰劑的患者則有27%出現了類似症狀。[24]對於雙相障礙,安非他酮也能有效改善抑鬱症狀,其療效和引發情感轉換的風險與其他抗抑鬱藥相似。[25]
安非他酮有幾個不同於其他抗抑鬱藥的特點:與大多數抗抑鬱藥不同,它通常不會引起性功能障礙,該副作用的發生率與安慰劑無差異。[22][26]安非他酮不會引起體重增加,反而大多數研究發現服用安非他酮的患者體重顯著下降。[22]安非他酮不會像其他抗抑鬱藥那樣引發嗜睡。 [27]對於伴有嗜睡和疲勞症狀的抑鬱患者,安非他酮的療效優於選擇性血清素再攝取抑制劑(SSRIs)。[28]和一般認知相反,安非他酮在治療伴有焦慮的抑鬱中同樣有效,且不會加重焦慮。[29][30]對於伴有中度以下的焦慮的抑鬱,安非他酮的療效與SSRIs相當,而SSRIs對伴有高度焦慮的患者在緩解率上有一定的療效優勢。[29]
戒煙
安非他酮是一種輔助戒煙的藥物,可以減輕對尼古丁的渴望和戒斷症狀的嚴重程度。[31][32][33]例如抑鬱、易怒、注意力難以集中以及食慾增加。[34]安非他酮在治療初期能夠減緩體重增加。但是隨着時間推移,這種效果會變得不再顯著。[34]
安非他酮用於戒煙的療程一般持續7到12周,患者在療程開始十天後停止使用煙草。[34][35]療程結束後,安非他酮維持戒煙的效果會隨着時間的推移而下降。從三個月內的37%戒煙成功率下降到一年的20%[36]。目前尚不清楚延長安非他酮治療是否有助於預防復吸。[37]
經過六個月的治療後,和安慰劑對比,安非他酮使戒煙成功率增加了約60%。在這方面,安非他酮和尼古丁取代療法同樣有效。但不如伐尼克蘭。同時使用尼古丁替代療法不能提高成功率。[38]
對於兒童和青少年而言,使用安非他酮戒煙似乎沒有任何明顯的益處。[39]使用其幫助孕婦戒煙的證據也不充分。[40]
注意缺陷多動障礙
在美國,安非他酮未被用於批准用於治療注意缺陷多動障礙(ADHD)。也未在美國兒科學會的現行(2019)ADHD治療指南中提及。[41]針對安非他酮用於成人和兒童ADHD治療的系統性綜述表明,安非他酮可能對ADHD有效,但由於臨床試驗規模較小且存在偏倚風險,相關結論應謹慎對待。[42][43][44][45]和托莫西汀類似,安非他酮需要需要數周才會起效。[42][46]與安非他明和哌甲酯等興奮劑不同,它們會立刻起效。[46]
體重增加
安非他酮用於治療長期體重增加(6-12個月)時,平均比安慰劑組減輕2.7公斤。[47]這與其他幾種減肥藥物(如西布曲明或奧利司他)的效果差距不大。[47]複方藥物納曲酮/安非他酮已被美國食品藥品監督管理局(FDA)批准用於治療成人慢性肥胖。
藥理
藥效學
安非他酮用於治療抑鬱症和其他適應症的作用機制尚不明確,據信與安非他酮作為去甲腎上腺素-多巴胺再吸收抑制劑(NDRI)和幾種煙鹼型乙酰膽鹼受體的負變構調節劑的特性有關。[48]安非他酮不誘導釋放多巴胺或去甲腎上腺素。[49]其的藥理作用很大程度上歸功於它的活性代謝物,這些代謝物在血漿中的含量相當或高於安非他酮本身。因此安非他酮可視為這些代謝物的前藥。
這些代謝物,尤其是瑞達法辛的作用,也表現為抑制去甲腎上腺素和多巴胺的再攝取,和同時抑制煙鹼受體。安非他酮在多種受體上沒有顯著的直接活性,包括α-和β-腎上腺素受體、多巴胺受體、血清素受體、組胺受體以及毒蕈鹼型乙酰膽鹼受體。[27]此外,安非他酮也不抑制單胺氧化酶。
藥代動力學
口服給藥後,安非他酮被迅速且完全吸收,在1.5個小時後達到最大血藥濃度。緩釋(SR)和長效(XL)製劑設計用於減緩吸收,分別在3小時和5小時內達到峰值濃度。[50]安非他酮的絕對生物利用度未知,但估計較低,為5%至20%,和首過效應有關。至於不同製劑的相對生物利用度,XL製劑的利用度(68%)低於SR製劑和速釋的安非他酮。[51]
安非他酮通過多種途徑在體內代謝。氧化途徑包括由細胞色素P450同工酶CYP2B6代謝生成R,R-羥基安非他酮和(S,S)-羥基安非他酮(瑞達法辛),並在較小程度上通過CYP2C19產生 4'-羥基安非他酮。還原途徑包括由肝臟中的11β-羥基類固醇脫氫酶1型和腸道中的AKR7A2和AKR7A3生成蘇氨酸氫化安非他酮。[52]11β-羥基類固醇脫氫酶1型通過還原安非他酮的酮基形成赤蘚氯化安非他酮,也有部分由醛酮還原酶產生。[53]
安非他酮的代謝變化較大,不同個體在服用相同劑量時,其有效劑量可能相差多達5.5倍,半衰期為12至30小時。而羥基安非他酮的有效劑量差異則可能達到7.5倍,半衰期為15至25小時。[54]由於這些顯著的代謝差異,一些研究者建議監測安非他酮及其羥基代謝物的血藥濃度。[55]
副作用
安非他酮與安慰劑相比,最常見的不良反應是口乾、噁心、便秘、失眠、焦慮、震顫和多汗。除去甲文拉法辛外,安非他酮是所有二代抗抑鬱藥中失眠發生率最高的藥物。[56]其還與約20%的頭痛風險增加有關。[57]
癲癇發作是安非他酮的嚴重但罕見的不良反應之一。其風險具有顯著的劑量依賴性。在每日300至450毫克的速釋製劑劑量下,癲癇發作的發生率約為0.4%;當劑量超過600毫克時,癲癇發作的發生率增加約十倍。相比之下,一般人群中自發性癲癇發作的發生率為0.07%至0.09%,而大多數其他抗抑鬱藥物在推薦劑量下引發癲癇發作的風險通常在0%至0.5%之間。[58]
與九種選擇性血清素再攝取抑制劑(SSRI)和血清素去甲腎上腺素再攝取抑制劑(SNRI)相比,安非他酮的脫髮風險最高,導致脫髮的原因可能與多巴胺能有關。其所致的脫髮通常是可逆的。[59]
精神副作用
FDA要求包括安非他酮在內所有抗抑鬱藥必須附有黑框警告,警告這些藥物可能會增加25歲以下人群的自殺風險。該警告基於FDA進行的統計分析,其發現兒童和青少年中自殺意念和行為的風險增加了2倍,而18–24歲人群的風險增加了1.5倍。在此分析中,FDA結合了295項針對11種抗抑鬱藥的試驗結果,以獲得統計學上顯著的結果。單獨考慮時,安非他酮與安慰劑之間在統計學上並無顯著差異。[60]
用於戒煙的安非他酮會使精神副作用的風險增加25%,特別是焦慮(約增加40%)和失眠(約增加80%)。證據不足所以無法確定安非他酮是否與自殺或自殺行為相關。[32]
在少數情況下,可能會出現安非他酮引發的精神病。和使用高劑量安非他酮有關;其中的很多案例服用劑量都超過了推薦劑量。聯合使用抗精神病藥物似乎有保護作用。在大多數情況下,降低劑量、停止治療或添加抗精神病藥物可以消除精神病症狀。[61]
儘管缺乏研究,但少量病例報告表明,突然停用安非他酮可能導致抗抑鬱藥停藥綜合症。[62]
藥物相互作用
由於安非他酮通過CYP2B6酶代謝為羥基安非他酮,因此可能與CYP2B6抑制劑發生相互作用,包括帕羅西汀、舍曲林、去甲氟西汀(氟西汀的活性代謝物)、地西泮、氯吡格雷和奧芬那君。這些藥物可能會導致安非他酮血藥濃度升高,而羥基安非他酮血藥濃度下降。相反,CYP2B6誘導劑(如卡馬西平、克霉唑、利福平、利托那韋、貫葉連翹和苯巴比妥)則可能導致安非他酮血藥濃度下降、羥基安非他酮濃度上升。[50]例如,卡馬西平能使安非他酮的暴露量減少90%,而羥基安非他酮的暴露量增加94%。[63]研究表明,利托那韋、洛匹那韋/利托那韋和依法韋侖均可降低安非他酮及其代謝物的濃度。[64]氯吡格雷和噻氯匹定這兩種強效的CYP2B6抑制劑已被發現能顯著增加安非他酮的水平,同時減少其代謝物羥基安非他酮的水平。[64]
安非他酮及其代謝物是CYP2D6的強抑制劑,羥基安非他酮導致大部分作用。此外,安非他酮及其代謝物可能會減少肝臟中CYP2D6的表達,其最終結果是顯著減慢其他由該酶代謝的藥物的清除速度。例如,研究發現安非他酮可使地昔帕明(CYP2D6的底物)的曲線下面積增加5倍。[64]安非他酮還可使托莫西汀的濃度增加5.1倍,同時使其主要代謝物的暴露量減少1.5倍。[65]另外,當右美沙芬(主要由CYP2D6代謝的藥物)與每日300毫克的安非他酮合用時,其主要代謝物右啡烷與右美沙芬的比率增加了大約35倍。[50]同時使用MDMA時,二者的暴露量都會增加約30%,MDMA導致的精神作用增強,但對心率的影響減小。[66]與其他CYP2D6底物(如美托洛爾、丙咪嗪、去甲替林、[67]文拉法辛和[[奈必洛爾)也已報道過相互作用。值得注意的是,安非他酮似乎並不會影響CYP2D6底物氟西汀和帕羅西汀的濃度。[68]
安非他酮降低癲癇發作閾值,因此可能與其他也降低閾值的藥物(如抗精神病藥、三環類抗抑鬱藥、茶鹼和全身性皮質類固醇)發生相互作用。處方信息建議儘量減少飲酒,因為安非他酮在極少數情況下會降低酒精耐受性。[69]
在將安非他酮與單胺氧化酶抑制劑(MAOI)聯用時應謹慎,因為可能會引發高血壓危象。[70]
過量
安非他酮在過量時被認為具有中度危險性。[71]根據美國毒物中心的分析,按處方劑量調整後,安非他酮和文拉法辛是第二代抗抑鬱藥(不包括三環類抗抑鬱藥)中導致死亡率和發病率最高的兩種藥物。[72]對於嚴重過量,約三分之一的病例報告出現癲癇發作;其他嚴重影響包括幻覺、意識喪失和心律異常。當安非他酮與其他多種藥物一起過量時,已有報告體溫升高、肌肉僵硬、肌肉損傷、高血壓或低血壓、昏迷、昏厥以及呼吸衰竭。[73]
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