苯哌利多

苯哌利多
臨床資料
商品名（英語：Drug nomenclature）	Anquil, Frenactil
AHFS/Drugs.com	國際藥品名稱
給藥途徑	口服
ATC碼	N05AD07 (WHO) ;
法律規範狀態
法律規範	澳：S4 (Prescription only); 美：處方藥（℞-only）;
藥物動力學數據
生物半衰期	8小時
識別資訊
	IUPAC命名法 11-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl1,3-dihydro-2H-benzimidazol-2-one; 1-(1-(4-(4-氟苯基)-4-氧代丁基)哌啶-4-基)-1,3-二氫-2H-苯並咪唑-2-酮; ;
CAS號	2062-84-2
PubChem CID	16363;
DrugBank	DB12867 ;
ChemSpider	15521 ;
UNII	97O6X78C53;
KEGG	D02627;
ChEBI	CHEBI:93403;
ChEMBL	ChEMBL297302 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID7045364 ;
ECHA InfoCard	100.016.521
化學資訊
化學式	C22H24FN3O2
摩爾質量	381.45 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	SMILES Fc1ccc(cc1)C(=O)CCCN4CCC(N3c2ccccc2NC3=O)CC4;
	InChI InChI=1S/C22H24FN3O2/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-10,18H,3,6,11-15H2,(H,24,28) ; Key:FEBOTPHFXYHVPL-UHFFFAOYSA-N ;

苯哌利多（INN：benperidol）,商品名Anquil等^[1]。為第一代抗精神病藥物，主要用於治療性慾亢進^[2]和精神分裂症^[3]。苯哌利多為一種強效丁酰苯衍生物，是歐洲市場上的強效神經安定藥，氯丙嗪當量達75-100%（約每劑量氟哌啶醇效力的150-200%）^[4]。有時被作為色普龍等抗雄激素藥的替代方案，作為假釋條件開給性罪犯者^[5]。

苯哌利多於1961年由比利時楊森製藥公司發現，並於1966年投入市場。主要銷往德國，在比利時、希臘、意大利、荷蘭和英國也可獲得^[6]。

藥理學

藥效動力學

苯哌利多是強效多巴胺受體激動劑（D₂，K_i=0.027 nM; D₄，K_i=0.066 nM）,對血清素受體激動性很弱（5-HT_2A, K_i= 3.75 nM）^[7]。在高劑量下，具有抗組胺和α-腎上腺素能特性。其具有最小的抗膽鹼性能^[8]。

苯哌利多受體抑制常數^[9]
作用位點	抑制常數K_i (nM)	作用	參考文獻
5-羥色胺受體2A（5-HT_2A）	3.75	拮抗作用	^[7]
多巴胺受體D₁	4,100	拮抗作用	^[7]
多巴胺受體D₂	0.027	拮抗作用	^[7]
多巴胺受體D₄	0.06	拮抗作用	^[7]

藥代動力學

苯哌利多吸收良好，並經過廣泛的首過代謝。1%的藥物經腎臟以從尿液排出。生物半衰期為8小時^[8]。

合成

苯哌利多由4-（2-酮酸-1-苯並咪唑）哌啶(1)與4-氯對氟苯丁酮(2)經烷基化反應得到^[10]^[11]。

圖中 MIBK=甲基異丁基酮，KI=碘化鉀、TM=目標分子，即苯哌利多

參考文獻

^ Council A, Kuenssberg V. Benperidol - a drug for sexual offenders?. Drug and Therapeutics Bulletin (BMJ Publishing Group Ltd). 1974-02-01, 12 (3): 12. PMID 4457302. S2CID 44581451. doi:10.1136/dtb.12.3.12.
^ British National Formulary (49th), British Medical Association 2005 p 183
^ Bobon J, Collard J, Lecoq R. [Benperidol and promazine: a "double blind" comparative study in mental geriatrics]. Acta Neurologica et Psychiatrica Belgica. October 1963, 63: 839–43. PMID 14092279 （法語）.
^ Möller HJ, Müller WE, Bandelow. Neuroleptika: pharmakologische Grundlagen, klinisches Wissen und therapeutisches Vorgehen; mit 136 Tabellen.. Wiss. Verlag-Ges. 2001. ISBN 3-8047-1773-X （德語）.
^ Murray MA, Bancroft JH, Anderson DC, Tennent TG, Carr PJ. Endocrine changes in male sexual deviants after treatment with anti-androgens, oestrogens or tranquillizers. The Journal of Endocrinology. November 1975, 67 (2): 179–88. PMID 1107462. doi:10.1677/joe.0.0670179.
^ NCATS Inxight Drugs — BENPERIDOL. [13 March 2022].
^ ^7.0 ^7.1 ^7.2 ^7.3 ^7.4 Li P, Snyder GL, Vanover KE. Dopamine Targeting Drugs for the Treatment of Schizophrenia: Past, Present and Future. Current Topics in Medicinal Chemistry. December 2016, 16 (29): 3385–3403. PMC 5112764  . PMID 27291902. doi:10.2174/1568026616666160608084834.
^ ^8.0 ^8.1 Leucht S, Hartung B. Benperidol for schizophrenia. The Cochrane Database of Systematic Reviews. April 2005, 2005 (2): CD003083. PMC 7017029  . PMID 15846648. doi:10.1002/14651858.CD003083.pub2.
^ Roth BL, Driscol J. PDSP K_i Database. Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. [11 March 2022].
^ Thieme
^ BE 626307 (1963 to Janssen), C.A. 60, 10690c (1964), corresp. to GB 989755,「1-(1-aroylpropyl-4-piperidyl)-2-benzimidazolinones and related compounds」,發表於1965-04-22,指定於Janssen Pharmaceuticals#History

[1] Council A, Kuenssberg V. Benperidol - a drug for sexual offenders?. Drug and Therapeutics Bulletin (BMJ Publishing Group Ltd). 1974-02-01, 12 (3): 12. PMID 4457302. S2CID 44581451. doi:10.1136/dtb.12.3.12.

[2] British National Formulary (49th), British Medical Association 2005 p 183

[pmid14092279-3] Bobon J, Collard J, Lecoq R. [Benperidol and promazine: a "double blind" comparative study in mental geriatrics]. Acta Neurologica et Psychiatrica Belgica. October 1963, 63: 839–43. PMID 14092279 （法語）.

[4] Möller HJ, Müller WE, Bandelow. Neuroleptika: pharmakologische Grundlagen, klinisches Wissen und therapeutisches Vorgehen; mit 136 Tabellen.. Wiss. Verlag-Ges. 2001. ISBN 3-8047-1773-X （德語）.

[pmid1107462-5] Murray MA, Bancroft JH, Anderson DC, Tennent TG, Carr PJ. Endocrine changes in male sexual deviants after treatment with anti-androgens, oestrogens or tranquillizers. The Journal of Endocrinology. November 1975, 67 (2): 179–88. PMID 1107462. doi:10.1677/joe.0.0670179.

[6] NCATS Inxight Drugs — BENPERIDOL. [13 March 2022].

[:1-7] 7.0 ^7.1 ^7.2 ^7.3 ^7.4 Li P, Snyder GL, Vanover KE. Dopamine Targeting Drugs for the Treatment of Schizophrenia: Past, Present and Future. Current Topics in Medicinal Chemistry. December 2016, 16 (29): 3385–3403. PMC 5112764  . PMID 27291902. doi:10.2174/1568026616666160608084834.

[:0-8] 8.0 ^8.1 Leucht S, Hartung B. Benperidol for schizophrenia. The Cochrane Database of Systematic Reviews. April 2005, 2005 (2): CD003083. PMC 7017029  . PMID 15846648. doi:10.1002/14651858.CD003083.pub2.

[PDSP-9] Roth BL, Driscol J. PDSP K_i Database. Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. [11 March 2022].

[10] Thieme

[:2-11] BE 626307 (1963 to Janssen), C.A. 60, 10690c (1964), corresp. to GB 989755,「1-(1-aroylpropyl-4-piperidyl)-2-benzimidazolinones and related compounds」,發表於1965-04-22,指定於Janssen Pharmaceuticals#History

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