3-羥基芬納西泮

3-羥基芬納西泮
臨床資料
ATC碼	未分配;
法律規範狀態
法律規範	加：Schedule IV; 德：NpSG; 英：PSA;
識別資訊
	IUPAC命名法 7-Bromo-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one; ;
CAS號	70030-11-4
PubChem CID	125820;
ChemSpider	111897;
UNII	1KJ8MP77JK;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID10990281 ;
化學資訊
化學式	C15H10BrClN2O2
摩爾質量	365.61 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	SMILES c1ccc(c(c1)C2=NC(C(=O)Nc3c2cc(cc3)Br)O)Cl;
	InChI InChI=1S/C15H10BrClN2O2/c16-8-5-6-12-10(7-8)13(19-15(21)14(20)18-12)9-3-1-2-4-11(9)17/h1-7,15,21H,(H,18,20); Key:KRJKJUWAZOWXNV-UHFFFAOYSA-N;

3-羥基芬納西泮（英語：3-Hydroxyphenazepam），或叫3-羥基苯那西泮，是一種苯二氮䓬類藥物，具有催眠、鎮靜、抗焦慮和抗驚厥作用。^[1]它是芬納西泮的活性代謝物，^[1]^[2]也是苯二氮䓬類藥物前藥西那西泮的活性代謝物。^[3]相對於芬納西泮，3-羥基芬納西泮具有微弱的肌肉鬆弛特性，但在大多數其他方面大致相當。^[1]與其他苯二氮卓類藥物一樣，3-羥基芬納西泮可作為GABA_A受體苯二氮䓬類位點的正向變構調節劑，EC₅₀值為10.3nM。^[4]^[5]^[6]它曾作為設計師藥物在網上銷售。^[7]^[8]^[9]^[10]

參見

參考資料

^ ^1.0 ^1.1 ^1.2 Artur Viktorovich Valʹdman. Drug dependence and emotional behavior: neurophysiological and neurochemical approaches. Consultants Bureau. 31 May 1986. ISBN 978-0-306-10984-3.
^ Lukasz Komsta; Monika Waksmundzka-Hajnos; Joseph Sherma. Thin Layer Chromatography in Drug Analysis. CRC Press. 20 December 2013: 299–. ISBN 978-1-4665-0715-9.
^ Schukin SI, Zinkovsky VG, Zhuk OV. Elimination kinetics of the novel prodrug cinazepam possessing psychotropic activity in mice (PDF). Pharmacol Rep. 2011, 63 (5): 1093–100 [2023-02-14]. PMID 22180351. doi:10.1016/s1734-1140(11)70628-4. （原始內容存檔 (PDF)於2022-10-12）.
^ Phenazepam Pre-Review Report (PDF). World Health Organization (WHO). November 2015 [2023-02-14]. （原始內容存檔 (PDF)於2022-01-20）.
^ Kopanitsa, M. V.; Zbarska, S. M.; Boychuk, Ya. A.; Krishtal, O. A. Modulation of GABA-activated currents by phenazepam and its metabolites in isolated rat purkinje neurons. Neurophysiology. 2000, 32 (3): 192. ISSN 0090-2977. S2CID 32313668. doi:10.1007/BF02506568.
^ Golovenko, N. Ya; Larionov, V. B. Pharmacodynamical and Neuroreceptor Analysis of the Permeability of the Blood-Brain Barrier for Derivatives of 1,4-Benzodiazepine. Neurophysiology. 2014, 46 (3): 199–205. ISSN 0090-2977. S2CID 33732669. doi:10.1007/s11062-014-9429-2.
^ 3-hydroxyphenazepam. New Synthetic Drugs Database. [2016-05-30]. （原始內容存檔於2016-09-28）.
^ Madeleine Pettersson Bergstrand; Anders Helander; Therese Hansson; Olof Beck. Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays. Drug Testing and Analysis. 2016, 9 (4): 640–645. PMID 27366870. doi:10.1002/dta.2003.
^ Moosmann, Bjoern; Bisel, Philippe; Franz, Florian; Huppertz, Laura M.; Auwärter, Volker. Characterization and in vitro phase I microsomal metabolism of designer benzodiazepines – an update comprising adinazolam, cloniprazepam, fonazepam, 3-hydroxyphenazepam, metizolam, and nitrazolam. Journal of Mass Spectrometry. 2016, 51 (11): 1080–1089. Bibcode:2016JMSp...51.1080M. ISSN 1096-9888. PMID 27535017. doi:10.1002/jms.3840.
^ Manchester, Kieran R.; Maskell, Peter D.; Waters, Laura. Experimental versus theoretical log D_7.4, pK_a and plasma protein binding values for benzodiazepines appearing as new psychoactive substances (PDF). Drug Testing and Analysis. 2018, 10 (8): 1258–1269 [2023-02-14]. ISSN 1942-7611. PMID 29582576. doi:10.1002/dta.2387. （原始內容存檔 (PDF)於2021-08-02）.

[Valʹdman1986-1] 1.0 ^1.1 ^1.2 Artur Viktorovich Valʹdman. Drug dependence and emotional behavior: neurophysiological and neurochemical approaches. Consultants Bureau. 31 May 1986. ISBN 978-0-306-10984-3.

[KomstaWaksmundzka-Hajnos2013-2] Lukasz Komsta; Monika Waksmundzka-Hajnos; Joseph Sherma. Thin Layer Chromatography in Drug Analysis. CRC Press. 20 December 2013: 299–. ISBN 978-1-4665-0715-9.

[pmid22180351-3] Schukin SI, Zinkovsky VG, Zhuk OV. Elimination kinetics of the novel prodrug cinazepam possessing psychotropic activity in mice (PDF). Pharmacol Rep. 2011, 63 (5): 1093–100 [2023-02-14]. PMID 22180351. doi:10.1016/s1734-1140(11)70628-4. （原始內容存檔 (PDF)於2022-10-12）.

[4] Phenazepam Pre-Review Report (PDF). World Health Organization (WHO). November 2015 [2023-02-14]. （原始內容存檔 (PDF)於2022-01-20）.

[KopanitsaZbarska2000-5] Kopanitsa, M. V.; Zbarska, S. M.; Boychuk, Ya. A.; Krishtal, O. A. Modulation of GABA-activated currents by phenazepam and its metabolites in isolated rat purkinje neurons. Neurophysiology. 2000, 32 (3): 192. ISSN 0090-2977. S2CID 32313668. doi:10.1007/BF02506568.

[GolovenkoLarionov2014-6] Golovenko, N. Ya; Larionov, V. B. Pharmacodynamical and Neuroreceptor Analysis of the Permeability of the Blood-Brain Barrier for Derivatives of 1,4-Benzodiazepine. Neurophysiology. 2014, 46 (3): 199–205. ISSN 0090-2977. S2CID 33732669. doi:10.1007/s11062-014-9429-2.

[7] 3-hydroxyphenazepam. New Synthetic Drugs Database. [2016-05-30]. （原始內容存檔於2016-09-28）.

[8] Madeleine Pettersson Bergstrand; Anders Helander; Therese Hansson; Olof Beck. Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays. Drug Testing and Analysis. 2016, 9 (4): 640–645. PMID 27366870. doi:10.1002/dta.2003.

[9] Moosmann, Bjoern; Bisel, Philippe; Franz, Florian; Huppertz, Laura M.; Auwärter, Volker. Characterization and in vitro phase I microsomal metabolism of designer benzodiazepines – an update comprising adinazolam, cloniprazepam, fonazepam, 3-hydroxyphenazepam, metizolam, and nitrazolam. Journal of Mass Spectrometry. 2016, 51 (11): 1080–1089. Bibcode:2016JMSp...51.1080M. ISSN 1096-9888. PMID 27535017. doi:10.1002/jms.3840.

[10] Manchester, Kieran R.; Maskell, Peter D.; Waters, Laura. Experimental versus theoretical log D_7.4, pK_a and plasma protein binding values for benzodiazepines appearing as new psychoactive substances (PDF). Drug Testing and Analysis. 2018, 10 (8): 1258–1269 [2023-02-14]. ISSN 1942-7611. PMID 29582576. doi:10.1002/dta.2387. （原始內容存檔 (PDF)於2021-08-02）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

臨床資料


ATC碼	未分配
法律規範狀態
法律規範	加：Schedule IV 德：NpSG 英：PSA
識別資訊
IUPAC命名法 7-Bromo-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one
CAS號	70030-11-4
PubChem CID	125820
ChemSpider	111897
UNII	1KJ8MP77JK
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID10990281
化學資訊
化學式	C₁₅H₁₀BrClN₂O₂
摩爾質量	365.61 g·mol⁻¹
3D模型（JSmol（英語：JSmol））	交互式圖像
SMILES c1ccc(c(c1)C2=NC(C(=O)Nc3c2cc(cc3)Br)O)Cl
InChI InChI=1S/C15H10BrClN2O2/c16-8-5-6-12-10(7-8)13(19-15(21)14(20)18-12)9-3-1-2-4-11(9)17/h1-7,15,21H,(H,18,20) Key:KRJKJUWAZOWXNV-UHFFFAOYSA-N