Quetiapine sulfoxide
(Synonyms: 喹硫平磺酸盐,Quetiapine S-oxide) 目录号 : GC37056
Quetiapine sulfoxide (Quetiapine S-oxide) 是 Quetiapinem 的主要代谢产物。Quetiapinem 是第二代抗精神病药。
Cas No.:329216-63-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Quetiapine sulfoxide (Quetiapine S-oxide) is a main metabolite of Quetiapinem. Quetiapine is a second-generation antipsychotic[1].
The Cmax value (mean±SD) is estimated for Quetiapine sulfoxide (77.3±32.4 ng/mL). The AUClast value is estimated for Quetiapine sulfoxide (1,286±458 ng•h/mL). For Quetiapine sulfoxide, metabolic ratio decreases with time, from 119% on average 2 hours after dosing to 30% on average 72 hours after dosing[1].
[1]. Remmerie B, et al. Comparison of Capillary and Venous Drug Concentrations After Administration of a Single Dose of Risperidone, Paliperidone, Quetiapine, Olanzapine, or Aripiprazole. Clin Pharmacol Drug Dev. 2016 Nov;5(6):528-537.
| Cas No. | 329216-63-9 | SDF | |
| 别名 | 喹硫平磺酸盐,Quetiapine S-oxide | ||
| Canonical SMILES | OCCOCCN(CC1)CCN1C2=NC(C=CC=C3)=C3S(C4=C2C=CC=C4)=O | ||
| 分子式 | C21H25N3O3S | 分子量 | 399.51 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.5031 mL | 12.5153 mL | 25.0307 mL |
| 5 mM | 0.5006 mL | 2.5031 mL | 5.0061 mL |
| 10 mM | 0.2503 mL | 1.2515 mL | 2.5031 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Quetiapine Carboxylic Acid and Quetiapine sulfoxide Prevalence in Patient Urine
J Anal Toxicol 2016 Oct;40(8):687-693.PMID:27562964DOI:10.1093/jat/bkw078.
Treatment adherence is often an issue with mental health patients. For those prescribed quetiapine (Seroquel®), the low levels of parent drug and plasma metabolite(s) (e.g., 7-hydroxyquetiapine) typically used in urine drug monitoring can result in false negatives with concomitant unfavorable impacts on patient care. Literature review coupled with liquid chromatography/time-of-flight mass spectrometry analysis of patient positive urine samples indicated the presence of quetiapine carboxylic acid and Quetiapine sulfoxide as significant urinary metabolites of quetiapine. Analysis of these two metabolites determined that they are abundant in the urine of quetiapine patients and can result in apparent adherence rates that are improved relative to those determined using only quetiapine and 7-hydroxyquetiapine. For example, analysis of a random set of 114 patients who were prescribed quetiapine exhibited an apparent adherence rate of 47% using the quetiapine carboxylic acid and Quetiapine sulfoxide metabolites. Traditional metabolite testing with quetiapine and 7-hydroxyquetiapine yielded apparent adherence rates of ~31% while all four analytes resulted in apparent adherence of 48%. The prevalence of these metabolites suggests that quetiapine urine drug testing would be more consistent with prescriptions when they are included in the analysis.
Plasma concentrations of quetiapine, N-desalkylquetiapine, o-desalkylquetiapine, 7-hydroxyquetiapine, and Quetiapine sulfoxide in relation to quetiapine dose, formulation, and other factors
Ther Drug Monit 2012 Aug;34(4):415-21.PMID:22777152DOI:10.1097/FTD.0b013e3182603f62.
Background: N-Desalkylquetiapine may be a pharmacologically active quetiapine metabolite. However, information on plasma concentrations of N-desalkylquetiapine and other quetiapine metabolites attained during quetiapine therapy is scant. The aim of this study was to investigate plasma concentrations of quetiapine, N-desalkylquetiapine, O-desalkylquetiapine, 7-hydroxyquetiapine, and Quetiapine sulfoxide attained during therapy and analyze the data with respect to prescribed dose and other variables. Method: Quetiapine and its metabolites were measured in plasma samples submitted for quetiapine therapeutic drug monitoring (2009-2011). Concentration, metabolic ratio, and concentration corrected for dose (C/D) were investigated against quetiapine dose, age, sex, and formulation. Sample results were excluded if nonadherence with therapy was queried. Results: There were 99 samples from 59 patients. N-Desalkylquetiapine plasma concentrations showed the strongest correlation with dose of all analytes, but O-desalkylquetiapine and Quetiapine sulfoxide were strongly correlated to plasma quetiapine concentrations. There was no significant difference in C/D for any analyte between males and females and no correlation to age. Quetiapine and Quetiapine sulfoxide C/D were significantly different (P < 0.01) between patients prescribed immediate- and extended-release formulations. Quetiapine, 7-hydroxyquetiapine and Quetiapine sulfoxide C/D showed significant variation (P < 0.02) between those samples taken 10-14 hours postdose as compared with that of 16-24 hours postdose, but there was no significant effect as regards N-desalkylquetiapine. Conclusions: Plasma quetiapine, O-desalkylquetiapine, 7-hydroxyquetiapine, and Quetiapine sulfoxide concentrations were significantly affected by formulation and/or time since last dose. Plasma N-desalkylquetiapine concentrations were not affected by either factor therefore may be a better marker for quetiapine exposure than plasma quetiapine concentrations.
Measurement of quetiapine and four quetiapine metabolites in human plasma by LC-MS/MS
Biomed Chromatogr 2012 Sep;26(9):1125-32.PMID:22241669DOI:10.1002/bmc.2672.
There is interest in monitoring plasma concentrations of N-desalkylquetiapine in relation to antidepressant effect. A simple LC-MS/MS method for quetiapine and four metabolites in human plasma (50 μL) has been developed to measure concentrations of these compounds attained during therapy. Analytes and internal standard (quetiapine-d8) were extracted into butyl acetate-butanol (10:1, v/v) and a portion of the extract analysed by LC-MS/MS (100 × 2.1 mm i.d. Waters Spherisorb S5SCX; eluent: 50 mmol/L methanolic ammonium acetate, pH* 6.0; flow-rate 0.5 mL/min; positive ion APCI-SRM, two transitions per analyte). Assay calibration (human plasma calibrators) was linear across the ranges studied (quetiapine and N-desalkylquetiapine 5-800, Quetiapine sulfoxide 100-15,000, others 2-100 µg/L). Assay validation was as per FDA guidelines. Quetiapine sulfone was found to be unstable and to degrade to Quetiapine sulfoxide. In 47 plasma samples from patients prescribed quetiapine (prescribed dose 200-950 mg/day), the (median, range) concentrations found (µg/L) were: quetiapine 83 (7-748), N-desalkylquetiapine, 127 (7-329), O-desalkylquetiapine 12 (2-37), 7-hydroxyquetiapine 3 (<1-48), and Quetiapine sulfoxide 3,379 (343-21,704). The analyte concentrations found were comparable to those reported by others except that the concentrations of the sulfoxide were markedly higher. The reason for this discrepancy in unclear.
Multiple dose pharmacokinetics of quetiapine and some of its metabolites in Chinese suffering from schizophrenia
Acta Pharmacol Sin 2004 Mar;25(3):390-4.PMID:15000896doi
Aim: To study the multiple dose pharmacokinetics of quetiapine and its sulfoxide-, 7-hydroxy-, 7-hydroxy-N-dealkyl-metabolites in Chinese suffering from schizophrenia. Methods: Twenty-one patients (11 females and 10 males) were given quetiapine twice daily to control the symptoms. After the dose reached 200 mg twice daily, blood were sampled to study the pharmacokinetics. The plasma concentrations of quetiapine and its metabolites were assayed by HPLC-MS. Results: The main pharmacokinetic parameters of quetiapine, 7-hydroxy-N-dealkyl-quetiapine, Quetiapine sulfoxide, and 7-hydroxy-quetiapine were as follows: tmax were 2.0 (0.3-5.0), 4.0 (1.5-6.0), 3.0 (0.5-5.0), and 3.0 (0.5-5.0) h respectively; t1/2 were (7+/-3), (9.4+/-2.7), (7+/-3), and (8+/-5) h, respectively; Cmax(SS) were (678+/-325), (19+/-5), (451+/-216), and (58+/-22) microg/L, respectively; Cmin(SS) were (51+/-68), (3.3+/-1.6), (35+/-36), and (5+/-4) microg/L, respectively; Cav(SS) were (295+/-144), (13+/-4), (209+/-71), and (28+/-9) micro/L, respectively; AUC(0-12)(SS) were (3,538+/-1 728), (153+/-44), (2,512+/-854), and (335+/-104) microg.h.L(-1), respectively; AUC(0-infinite)(SS) were (5,534+/-4 198), (287+/-107), (3,858+/-2 012), and (529+/-262) microg.h.L(-1), respectively; Ke were (0.11+/-0.03), (0.079+/-0.019), (0.11+/-0.03), and (0.103+/-0.028) h(-1), respectively; CL/F and V/F of quetiapine were (67+/-25) L.h(-1) and (672+/-394) L, respectively. The plasma concentrations for the four compounds reached a steady state within 48 h at the dose of 200 mg initiation. These parameters were not statistically different between genders. Conclusions: Quetiapine was absorbed quickly, distributed widely, and metabolized mainly to be Quetiapine sulfoxide. The elimination speeds of quetiapine and its three metabolites were similar. Gender had no effect on the pharmacokinetics of quetiapine and its metabolites. The clinical dosage regime caused no drug accumulation.
Metabolism of quetiapine by CYP3A4 and CYP3A5 in presence or absence of cytochrome B5
Drug Metab Dispos 2009 Feb;37(2):254-8.PMID:19022943DOI:10.1124/dmd.108.023291.
The antipsychotic drug quetiapine is extensively metabolized by CYP3A4, but little is known about the possible influence of the polymorphic enzyme CYP3A5. This in vitro study investigated the relative importance of CYP3A4 and CYP3A5 in the metabolism of quetiapine and compared the metabolic pattern by the two enzymes, in the presence or absence of cytochrome b(5). Intrinsic clearance (CL(int)) of quetiapine was determined by the substrate depletion approach in CYP3A4 and CYP3A5 insect cell microsomes with or without coexpressed cytochrome b(5). Formation of the metabolites Quetiapine sulfoxide, N-desalkylquetiapine, O-desalkylquetiapine, and 7-hydroxyquetiapine by CYP3A4 and CYP3A5 were compared in the different microsomal preparations. CL(int) of quetiapine by CYP3A5 was less than 35% relative to CYP3A4. CL(int) was higher (3-fold) in CYP3A4 microsomes without cytochrome b(5) compared with CYP3A4 microsomes with coexpressed cytochrome b(5), whereas in CYP3A5 microsomes CL(int) was similar for both microsomal preparations. Metabolism of quetiapine by CYP3A5 revealed a different metabolic pattern compared with CYP3A4. The results indicated that O-desalkylquetiapine constituted a higher proportion of the formed metabolites by CYP3A5 compared with CYP3A4. In conclusion, the present study indicates that CYP3A5 is of minor importance for the overall metabolism of quetiapine, regardless of the presence of cytochrome b(5). However, a different metabolic pattern by CYP3A5 compared with CYP3A4 could possibly result in different pharmacological and/or toxicological effects of quetiapine in patients expressing CYP3A5.