Chlorzoxazone

Manufactured by Merck Group

Sourced in United States, China, Germany, United Kingdom, Czechia

Chlorzoxazone is a laboratory chemical used as a reference standard. It is a crystalline solid with a molecular formula of C7H5ClNO. Chlorzoxazone is primarily used for analytical purposes and quality control in various industries.

Automatically generated - may contain errors

Lab products found in correlation

Phenacetin, by Merck Group (34 mentions) Acetaminophen, by Merck Group (24 mentions) 6 hydroxychlorzoxazone, by Merck Group (21 mentions) Dextromethorphan, by Merck Group (20 mentions) Quinidine, by Merck Group (18 mentions) 7 hydroxycoumarin, by Merck Group (18 mentions) Coumarin, by Merck Group (18 mentions) Glucose 6 phosphate dehydrogenase, by Merck Group (17 mentions) Tolbutamide, by Merck Group (17 mentions) Sulfaphenazole, by Merck Group (16 mentions) Furafylline, by Merck Group (16 mentions) Paclitaxel, by Merck Group (16 mentions) Clomethiazole, by Merck Group (14 mentions) Testosterone, by Merck Group (14 mentions) Tranylcypromine, by Merck Group (13 mentions) 4 hydroxymephenytoin, by Merck Group (13 mentions) 6β hydroxytestosterone, by Merck Group (13 mentions) Midazolam, by Merck Group (13 mentions) D glucose 6 phosphate, by Merck Group (12 mentions) Bupropion, by Merck Group (12 mentions)

Spelling variants of this product

6-hydroxyl chlorzoxazone (3 citations) Chlorzoxazone (CZX), (2 citations)

70 protocols using chlorzoxazone

In Vitro Metabolism of Pinocembrin

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Pinocembrin
(≥95%), tacrine hydrochloride (≥98%), hydroxytacrine
maleate, i.e., 1-hydroxytacrine (≥98%), and
paracetamol (≥98%) were obtained from Cayman Chemical. Fluvoxamine
maleate (≥97%), phenacetin (≥98%), diazepam (∼98%),
chlorzoxazone (≥98%), nicotinamide adenine dinucleotide phosphate
(NADPH) (≥98%), and Tween 20 were procured from Sigma-Aldrich.
Caffeine was obtained from the Indian Pharmacopoeia Commission. RLM
(lot no. RT059-D) and HLM (pool of 50 donors; lot no. PL050D-A) were
procured from Gibco. MS-grade acetonitrile and formic acid as well
as HPLC-grade methanol and acetonitrile were obtained from Thermo
Fisher Scientific. Magnesium chloride and monobasic potassium phosphate
were purchased from Rankem. PEG-400 and dimethylsulfoxide (DMSO) were
procured from Loba Chemie. Ultrapure water was obtained from a water
purification system (Direct-Q 3, Merck-Millipore). Characterization
data of the test candidate (pinocembrin) are presented in Figures S1–S4.

Bhatt S., Dhiman S., Kumar V., Gour A., Manhas D., Sharma K., Ojha P.K, & Nandi U. (2022). Assessment of the CYP1A2 Inhibition-Mediated Drug Interaction Potential for Pinocembrin Using In Silico, In Vitro, and In Vivo Approaches. ACS Omega, 7(23), 20321-20331.

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Characterization of Kurarinone Metabolism

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Kurarinone (>98%) was purchased from BioBioPha Co., Ltd. (Kunming, China). Glucose-6-phosphate, Glucose-6-phosphate dehydrogenase, NADP⁺, D-Glucose-6-phosphate, Tris-HCl, 7-hydroxycoumarin, 4-methylumbelliferone (4-MU), 4-methylumbelliferone-β-D-glucuronide, uridine 5′-diphosphoglucuronic acid (UDPGA; trisodium salt), phenacetin, diclofenac, dextromethorphan, chlorzoxazone, testosterone, (S)-mephenytoin, sulfaphenazole, quinidine, clomethiazole, furafylline, ketoconazole, and omeprazole were purchased from Sigma Aldrich (St. Louis, MO, USA). Metabolites of the probe substrates including 6-hydroxylated chlorzoxazone (2E1), O-deethylated phenacetin (CYP1A2), 4′-hydroxylated diclofenac (2C9), 4′-hydroxylated (S)-mephenytoin (2C19), O-demethylated dextromethorphan (2D6), and 6β-hydroxylated testosterone (3A4) were provided from the Research Institute for Liver Disease Co., Ltd. (Shanghai, China). Pooled liver microsomes from humans (HLMs), monkeys (MLMs), rabbits (RAMs), rats (RLMs), mouse (MOMs), dogs (DLMs), and minipigs (PLMs) were provided by the Research Institute for Liver Disease Co., Ltd. (Shanghai, China). Recombinant human supersomes (UGT1A1, UGT1A3, UGT1A6, UGT1A7, UGT1A8, UGT1A9, UGT1A10, UGT2B4, UGT2B7, UGT2B15, CYP1A2, CYP2C9, CYP2D6, CYP2E1, CYP3A4, and CYP2C19) were obtained from BD Gentest Corp. (Woburn, MA, USA).

Qin Y., Zhu Y., Xue X., Zhou G., Li H, & Wang J. (2020). An In Vitro Study for Evaluating Permeability and Metabolism of Kurarinone. Evidence-based Complementary and Alternative Medicine : eCAM, 2020, 5267684.

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Lysionotin and Testosterone Characterization

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Lysionotin (≥98%) and testosterone (≥98%) were obtained from the National Institute for the Control of Pharmaceutical and Biological Products (Beijing, China). The chemical structure of lysionotin is shown in Figure 1. d-Glucose-6-phosphate, glucose-6-phosphate dehydrogenase, corticosterone (≥98%), NADP⁺, phenacetin (≥98%), acetaminophen (≥98%), 4-hydroxymephenytoin (≥98%), 7-hydroxy Coumarin (≥98%), 4′-hydroxy diclofenac (≥98%), sulfaphenazole (≥98%), quinidine (≥98%), tranylcypromine (≥98%), chlorzoxazone (≥98%), 6-hydroxychlorzoxazone (≥98%), paclitaxel (≥98%), 6β-hydroxytestosterone (≥98%), clomethiazole (≥98%), and furafylline (≥98%) were obtained from Sigma Chemical Co. Montelukast (≥98%) was obtained from Beijing Aleznova Pharmaceutical (Beijing, China). Coumarin (≥98%), diclofenac (≥98%), dextromethorphan (≥98%), and ketoconazole (≥98%) were purchased from ICN Biomedicals. Pooled HLMs were purchased from BD Biosciences Discovery Labware. All other reagents and solvents were of analytical reagent grade.

Li Y., Qin J., Wu H., Xu Y., Zhang L., Su K., Cui Y, & Wang H. (2020). In vitro inhibitory effect of lysionotin on the activity of cytochrome P450 enzymes. Pharmaceutical Biology, 58(1), 695-700.

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In Vitro Metabolic Profiling

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Sch B, phenobarbital sodium, and carbamazepine were provided by the National Institute for the Control of Pharmaceutical and Biological Products (Beijing, China). Phenacetin, paracetamol, tolbutamide, 4-hydroxytolbutamide, dextromethorphan, dextrorphan, chlorzoxazone, 6-hydroxychlorzoxazone, midazolam, 1-hydroxymidazolam, and β-nicotinamide adenine dinucleotide phosphate (NADPH) were purchased from Sigma-Aldrich Co. (St Louis, MO, USA). Mice liver microsomes and human liver microsomes were purchased from the Research Institute for Liver Diseases Co., Ltd (Shanghai, China). LC–MS grade m ethanol, ethanol, and acetonitrile were obtained from Thermo Fisher Scientific, Inc. (Waltham, MA, USA). All other regents were of analytical grade.

Feng S., Qiu B., Zou L., Liu K., Xu X, & Zhu H. (2018). Schisandrin B elicits the Keap1-Nrf2 defense system via carbene reactive metabolite which is less harmful to mice liver. Drug Design, Development and Therapy, 12, 4033-4046.

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Xanthotoxol Cytochrome P450 Inhibition

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Xanthotoxol (purity > 98%) was purchased from Sichuan Weikeqi Biotechnology Co. Ltd. (Sichuan, China). Paclitaxel, 1-aminobenzotriazole (ABT), phenacetin, sulfaphenazole, chlorzoxazone, quinidine, clomethiazole, furafylline, 8-methoxypsoralen, coumarin, diclofenac, quercetin, dextromethorphan, ketoconazole, testosterone, S-mephenytoin, omeprazole, glucose-6-phosphate dehydrogenase, NADP⁺, and D-glucose-6-phosphate were obtained from Sigma-Aldrich (St. Louis, MO, USA). All other reagents were the highest purity commercially available or HPLC grade.

Ma Z., Shi X., Zhang G., Guo F., Shan L, & Cai J. (2016). Metabolism and Metabolic Inhibition of Xanthotoxol in Human Liver Microsomes. Evidence-based Complementary and Alternative Medicine : eCAM, 2016, 5416509.

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CYP-Mediated Metabolism of Ginsenoside Compound K

Cited 1 time

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The enzymes and chemicals ware prepared according to our previous study with some modifications [14 (link)]. Pooled human liver microsomes, recombinant human CYP enzymes, and NADPH were purchased from Cypex Ltd. (U.K.) and stored at -80°C until use. Ginsenoside compound K (CK, C₃₆H₆₂O₈, MW:622.873, assay≥99.2%, Lot: P1201-1) was provided by Zhejiang Hisun Pharmaceutical Company Limited (Zhejiang, China). Furafylline, tranylcypromine, ketoconazole,sulfaphenazole, quinidine, chlormethiazole hydrochloride, and ticlopidine hydrochloride were purchased from the National Institutes for Food and Drug Control (Beijing, China). Phenacetin, coumarin, midazolam, tolbutamide, S-Mephenytoin, metoprolol, chlorzoxazone, and the standards for their metabolites, including acetaminophen, 7-hydroxyl coumarin, 1-hydroxyl midazolam, 4-hydroxyl tolbutamide, 4-hydroxyl mephenytoin, α-hydroxyl metoprolol, 6-hydroxyl chlorzoxazone, and irbesartan (the internal standard), were purchased from Sigma-Aldrich (Shanghai, China). All other chemicals and solvents were of high-performance liquid chromatography (HPLC) grade.

Xiao J., Chen D., Lin X.X., Peng S.F., Xiao M.F., Huang W.H., Wang Y.C., Peng J.B., Zhang W., Ouyang D.S, & Chen Y. (2016). Screening of Drug Metabolizing Enzymes for the Ginsenoside Compound K In Vitro: An Efficient Anti-Cancer Substance Originating from Panax Ginseng. PLoS ONE, 11(2), e0147183.

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Inhibition of Human Liver Enzymes

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Anemarsaponin BII (≥98%) and testosterone (≥98%) were purchased from the National Institute for the Control of Pharmaceutical and Biological Products (Beijing, China). d-Glucose-6-phosphate, glucose-6-phosphate dehydrogenase, corticosterone (≥98%), NADP⁺, phenacetin (≥98%), acetaminophen (≥98%), 4-hydroxymephenytoin (≥98%), 7-hydroxy Coumarin (≥98%), 4′-hydroxy diclofenac (≥98%), sulfaphenazole (≥98%), quinidine (≥98%), tranylcypromine (≥98%), chlorzoxazone (≥98%), 6-hydroxychlorzoxazone (≥98%), paclitaxel (≥98%), 6β-hydroxytestosterone (≥98%), clomethiazole (≥98%) and furafylline (≥98%) were obtained from Sigma Chemical Co. Montelukast (≥98%) was obtained from Beijing Aleznova Pharmaceutical (Beijing, China). Coumarin (≥98%), diclofenac (≥98%), dextromethorphan (≥98%), and ketoconazole (≥98%) were purchased from ICN Biomedicals. Pooled HLMs were purchased from BD Biosciences Discovery Labware. All other reagents and solvents were of analytical reagent grade.

Wang M., Jiang W., Zhou J., Xue X, & Yin C. (2020). Anemarsaponin BII inhibits the activity of CYP3A4, 2D6, and 2E1 with human liver microsomes. Pharmaceutical Biology, 58(1), 1064-1069.

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Quantification of Acetaminophen Metabolites

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APAP, APAP-d4, APAP glucuronide, APAP sulfate, 2-benzoxazolinone, chlorzoxazone, ethoxy resorufin, and protease type XIV enzyme were purchased from Sigma-Aldrich (St. Louis, MO). APAP-d3 glucuronide and APAP-d3 sulfate were from Santa Cruz Biotechnology (Dallas, TX). APAP-cysteine was purchased from Toronto Research Chemicals (North Rock, Canada). 6-Hydroxychlorzoxazone and resorufin were purchased from Cayman chemicals (Ann Arbor, MI) and Life Technologies (Eugene, OR), respectively.

Cho S., Tripathi A., Chlipala G., Green S., Lee H., Chang E.B, & Jeong H. (2017). Fructose diet alleviates acetaminophen-induced hepatotoxicity in mice. PLoS ONE, 12(8), e0182977.

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Hepatocyte Cell Line Cultivation Protocol

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Undifferentiated human HepaRG cells (HPR101) were purchased from Biopredic International (Rennes, France) and human normal immortalized THLE2 and hepatoma Huh7 cells were obtained from American Type Culture Collection. William’s E medium with no glutamine, bronchial epithelium growth medium (BEGM) medium with complete supplement, Dulbecco’s modified Eagle medium (DMEM), fetal bovine serum (FBS), fibronectin, phosphate buffered saline (PBS), L-glutamine, penicillin/streptomycin, and trypsin-EDTA were purchased from Thermo Fisher Scientific (Rockford, IL, USA). Collagen type I was purchased from Advanced Biomatrix (San Diego, CA, USA). Insulin, hydrocortisone hemisuccinate, dimethyl sulfoxide (DMSO), methanol, acetonitrile anhydrous, CHIR, 30% wt H₂O₂ solution, and agarose (low gelling temperature) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Chlorzoxazone, tamoxifen, isoniazid, bromobenzene, and APAP were acquired from Sigma-Aldrich (USA).

Ahn J., Ahn J.H., Yoon S., Nam Y.S., Son M.Y, & Oh J.H. (2019). Human three-dimensional in vitro model of hepatic zonation to predict zonal hepatotoxicity. Journal of Biological Engineering, 13, 22.

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Peucedanol Metabolism Assay Protocol

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Peucedanol (≥98%, Figure 1) and testosterone (≥98%) were purchased from the National Institute for the Control of Pharmaceutical and Biological Products (Beijing, China). d-Glucose-6-phosphate, glucose-6-phosphate dehydrogenase, corticosterone (≥98%), NADP⁺, phenacetin (≥98%), acetaminophen (≥98%), 4-hydroxymephenytoin (≥98%), 7-hydroxy Coumarin (≥98%), 4′-hydroxy diclofenac (≥98%), sulfaphenazole (≥98%), quinidine (≥98%), tranylcypromine (≥98%), chlorzoxazone (≥98%), 6-hydroxychlorzoxazone (≥98%), paclitaxel (≥98%), 6β-hydroxytestosterone (≥98%), clomethiazole (≥98%), and furafylline (≥98%) were obtained from Sigma Chemical Co. Montelukast (≥98%) was obtained from Beijing Aleznova Pharmaceutical (Beijing, China). Coumarin (≥98%), diclofenac (≥98%), dextromethorphan (≥98%), and ketoconazole (≥98%) were purchased from ICN Biomedicals. Pooled HLMs were purchased from BD Biosciences Discovery Labware. All other reagents and solvents were of analytical reagent grade.

Zhang C., Li Y., Yin C., Zheng J, & Liu G. (2021). In vitro study on the effect of peucedanol on the activity of cytochrome P450 enzymes. Pharmaceutical Biology, 59(1), 935-940.

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