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product summary
company name :
MilliporeSigma
other brands :
FLUKA, Sigma-Aldrich, Roche Applied Science
product type :
chemical
product name :
1,7-Dimethylxanthine
catalog :
D5385
citations: 86
Reference
Suenderhauf C, Berger B, Puchkov M, Schmid Y, Muller S, Huwyler J, et al. Pharmacokinetics and phenotyping properties of the Basel phenotyping cocktail combination capsule in healthy male adults. Br J Clin Pharmacol. 2020;86:352-361 pubmed publisher
Ponce Rodríguez H, García Robles A, Saenz González P, Verdú Andrés J, Campins Falco P. On-line in-tube solid phase microextraction coupled to capillary liquid chromatography-diode array detection for the analysis of caffeine and its metabolites in small amounts of biological samples. J Pharm Biomed Anal. 2020;178:112914 pubmed publisher
Rodríguez Morató J, Goday A, Langohr K, Pujadas M, Civit E, Pérez Mañá C, et al. Short- and medium-term impact of bariatric surgery on the activities of CYP2D6, CYP3A4, CYP2C9, and CYP1A2 in morbid obesity. Sci Rep. 2019;9:20405 pubmed publisher
Redivo L, Anastasiadi R, Pividori M, Berti F, Peressi M, Di Tommaso D, et al. Prediction of self-assembly of adenosine analogues in solution: a computational approach validated by isothermal titration calorimetry. Phys Chem Chem Phys. 2019;21:4258-4267 pubmed publisher
Asprodini E, Tsiokou V, Begas E, Kilindris T, Kouvaras E, Samara M, et al. Alterations in Xenobiotic-Metabolizing Enzyme Activities across Menstrual Cycle in Healthy Volunteers. J Pharmacol Exp Ther. 2019;368:262-271 pubmed publisher
Khatri A, Cheng L, Camez A, Ignatenko S, Pang Y, Othman A. Lack of Effect of 12-Week Treatment with Risankizumab on the Pharmacokinetics of Cytochrome P450 Probe Substrates in Patients with Moderate to Severe Chronic Plaque Psoriasis. Clin Pharmacokinet. 2019;58:805-814 pubmed publisher
Tian D, Natesan S, White J, Paine M. Effects of Common CYP1A2 Genotypes and Other Key Factors on Intraindividual Variation in the Caffeine Metabolic Ratio: An Exploratory Analysis. Clin Transl Sci. 2019;12:39-46 pubmed publisher
Pérez Míguez R, Sánchez López E, Plaza M, Castro Puyana M, Marina M. A non-targeted metabolomic approach based on reversed-phase liquid chromatography-mass spectrometry to evaluate coffee roasting process. Anal Bioanal Chem. 2018;410:7859-7870 pubmed publisher
Lopez Sanchez R, Lara Díaz V, Aranda Gutierrez A, Martinez Cardona J, Hernandez J. HPLC Method for Quantification of Caffeine and Its Three Major Metabolites in Human Plasma Using Fetal Bovine Serum Matrix to Evaluate Prenatal Drug Exposure. J Anal Methods Chem. 2018;2018:2085059 pubmed publisher
Chuang Y, Liu C, Hammerschmidt R, Zhang W, Boyd S, Li H. Metabolic Demethylation and Oxidation of Caffeine during Uptake by Lettuce. J Agric Food Chem. 2018;66:7907-7915 pubmed publisher
Khalilieh S, Hussain A, Montgomery D, Levine V, Shaw P, Bodrug I, et al. Effect of tildrakizumab (MK-3222), a high affinity, selective anti-IL23p19 monoclonal antibody, on cytochrome P450 metabolism in subjects with moderate to severe psoriasis. Br J Clin Pharmacol. 2018;84:2292-2302 pubmed publisher
D Alessio M, Onanong S, Snow D, Ray C. Occurrence and removal of pharmaceutical compounds and steroids at four wastewater treatment plants in Hawai'i and their environmental fate. Sci Total Environ. 2018;631-632:1360-1370 pubmed publisher
Nagai K, Shibata T, Shinkura S, Ohnishi A. Poly(butylene terephthalate) based novel achiral stationary phase investigated under supercritical fluid chromatography conditions. J Chromatogr A. 2018;1549:85-92 pubmed publisher
Jo J, Jo J, Kim S, Lee J, Lee S. Development of a simultaneous LC-MS/MS method to predict in vivo drug-drug interaction in mice. Arch Pharm Res. 2018;41:450-458 pubmed publisher
He K, Echigo S, Asada Y, Itoh S. Determination of Caffeine and Its Metabolites in Wastewater Treatment Plants Using Solid-Phase Extraction and Liquid Chromatography-Tandem Mass Spectrometry. Anal Sci. 2018;34:349-354 pubmed publisher
Rodríguez Gil J, Caceres N, Dafouz R, Valcárcel Y. Caffeine and paraxanthine in aquatic systems: Global exposure distributions and probabilistic risk assessment. Sci Total Environ. 2018;612:1058-1071 pubmed publisher
Shen J, Ye Y, Chang D, Huang M, Heymach J, Roth J, et al. Circulating metabolite profiles to predict overall survival in advanced non-small cell lung cancer patients receiving first-line chemotherapy. Lung Cancer. 2017;114:70-78 pubmed publisher
Li H, Canet M, Clarke J, Billheimer D, Xanthakos S, Lavine J, et al. Pediatric Cytochrome P450 Activity Alterations in Nonalcoholic Steatohepatitis. Drug Metab Dispos. 2017;45:1317-1325 pubmed publisher
Kot M, Haduch A, Papp M, Daniel W. The Effect of Chronic Treatment with Lurasidone on Rat Liver Cytochrome P450 Expression and Activity in the Chronic Mild Stress Model of Depression. Drug Metab Dispos. 2017;45:1336-1344 pubmed publisher
Merlier F, Jellali R, Leclerc E. Online monitoring of hepatic rat metabolism by coupling a liver biochip and a mass spectrometer. Analyst. 2017;142:3747-3757 pubmed publisher
Asimakopoulos A, Kannan P, Higgins S, Kannan K. Determination of 89 drugs and other micropollutants in unfiltered wastewater and freshwater by LC-MS/MS: an alternative sample preparation approach. Anal Bioanal Chem. 2017;409:6205-6225 pubmed publisher
Goday Arno A, Farré M, Rodríguez Morató J, Ramón J, Pérez Mañá C, Papaseit E, et al. Pharmacokinetics in Morbid Obesity: Influence of Two Bariatric Surgery Techniques on Paracetamol and Caffeine Metabolism. Obes Surg. 2017;27:3194-3201 pubmed publisher
Pan X, Kent R, Won K, Jeong H. Cholic Acid Feeding Leads to Increased CYP2D6 Expression in CYP2D6-Humanized Mice. Drug Metab Dispos. 2017;45:346-352 pubmed publisher
Lu Y, Xie T, Zhang Y, Zhou F, Ruan J, Zhu W, et al. Triptolide Induces hepatotoxicity via inhibition of CYP450s in Rat liver microsomes. BMC Complement Altern Med. 2017;17:15 pubmed publisher
Grangeon A, Gravel S, Gaudette F, Turgeon J, Michaud V. Highly sensitive LC-MS/MS methods for the determination of seven human CYP450 activities using small oral doses of probe-drugs in human. J Chromatogr B Analyt Technol Biomed Life Sci. 2017;1040:144-158 pubmed publisher
Ashengroph M. Salinivibrio costicola GL6, a Novel Isolated Strain for Biotransformation of Caffeine to Theobromine Under Hypersaline Conditions. Curr Microbiol. 2017;74:34-41 pubmed publisher
Machnik M, Kaiser S, Koppe S, Kietzmann M, Schenk I, Düe M, et al. Control of methylxanthines in the competition horse: pharmacokinetic/pharmacodynamic studies on caffeine, theobromine and theophylline for the assessment of irrelevant concentrations. Drug Test Anal. 2017;9:1372-1384 pubmed publisher
Scurachio R, Mattiucci F, Santos W, Skibsted L, Cardoso D. Caffeine metabolites not caffeine protect against riboflavin photosensitized oxidative damage related to skin and eye health. J Photochem Photobiol B. 2016;163:277-83 pubmed publisher
Mills D, Gomberawalla A, Gordon E, Tondre J, Nejad M, Nguyen T, et al. Examination of Duct Physiology in the Human Mammary Gland. PLoS ONE. 2016;11:e0150653 pubmed publisher
Ferrer Aguirre A, Romero González R, Vidal J, Frenich A. Simple and quick determination of analgesics and other contaminants of emerging concern in environmental waters by on-line solid phase extraction coupled to liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2016;1446:27-33 pubmed publisher
Timofeeva I, Medinskaia K, Nikolaeva L, Kirsanov D, Bulatov A. Stepwise injection potentiometric determination of caffeine in saliva using single-drop microextraction combined with solvent exchange. Talanta. 2016;150:655-60 pubmed publisher
Dinger J, Woods C, Brandt S, Meyer M, Maurer H. Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class. Toxicol Lett. 2016;241:82-94 pubmed publisher
Rysz M, Bromek E, Daniel W. Activation of brain serotonergic system by repeated intracerebral administration of 5-hydroxytryptophan (5-HTP) decreases the expression and activity of liver cytochrome P450. Biochem Pharmacol. 2016;99:113-22 pubmed publisher
Basińska Ziobroń A, Daniel W, Wójcikowski J. Inhibition of human cytochrome P450 isoenzymes by a phenothiazine neuroleptic levomepromazine: An in vitro study. Pharmacol Rep. 2015;67:1178-82 pubmed publisher
Eichelberger K, Baker A, Woodham P, Haeri S, Strauss R, Stuebe A. Second-Trimester Maternal Serum Paraxanthine, CYP1A2 Activity, and the Risk of Severe Preeclampsia. Obstet Gynecol. 2015;126:725-30 pubmed publisher
Rodriguez A, Costa Bauza A, Sáez Torres C, Rodrigo D, Grases F. HPLC method for urinary theobromine determination: Effect of consumption of cocoa products on theobromine urinary excretion in children. Clin Biochem. 2015;48:1138-43 pubmed publisher
Derungs A, Donzelli M, Berger B, Noppen C, Krähenbühl S, Haschke M. Effects of Cytochrome P450 Inhibition and Induction on the Phenotyping Metrics of the Basel Cocktail: A Randomized Crossover Study. Clin Pharmacokinet. 2016;55:79-91 pubmed publisher
Adehin A, Bolaji O. Polymorphisms of CYP1A2 and CYP2A6 activity: phenotypes and the effect of age and sex in a Nigerian population. Drug Metab Pers Ther. 2015;30:203-10 pubmed publisher
Rysz M, Bromek E, Haduch A, Sadakierska Chudy A, Daniel W. Damage to the Brain Serotonergic System Increases the Expression of Liver Cytochrome P450. Drug Metab Dispos. 2015;43:1345-52 pubmed publisher
De Kesel P, Lambert W, Stove C. Does volumetric absorptive microsampling eliminate the hematocrit bias for caffeine and paraxanthine in dried blood samples? A comparative study. Anal Chim Acta. 2015;881:65-73 pubmed publisher
Pan X, Jeong H. Estrogen-Induced Cholestasis Leads to Repressed CYP2D6 Expression in CYP2D6-Humanized Mice. Mol Pharmacol. 2015;88:106-12 pubmed publisher
Pan X, Lee Y, Jeong H. Farnesoid X Receptor Agonist Represses Cytochrome P450 2D6 Expression by Upregulating Small Heterodimer Partner. Drug Metab Dispos. 2015;43:1002-7 pubmed publisher
Lazenka M, Moeller F, Negus S. Effects of caffeine and its metabolite paraxanthine on intracranial self-stimulation in male rats. Exp Clin Psychopharmacol. 2015;23:71-80 pubmed publisher
Coelho A, Fraichard S, Le Goff G, Faure P, Artur Y, Ferveur J, et al. Cytochrome P450-dependent metabolism of caffeine in Drosophila melanogaster. PLoS ONE. 2015;10:e0117328 pubmed publisher
Leuthold L, Heudi O, Déglon J, Raccuglia M, Augsburger M, Picard F, et al. New microfluidic-based sampling procedure for overcoming the hematocrit problem associated with dried blood spot analysis. Anal Chem. 2015;87:2068-71 pubmed publisher
De Kesel P, Lambert W, Stove C. Paraxanthine/Caffeine Concentration Ratios in Hair: An Alternative for Plasma-Based Phenotyping of Cytochrome P450 1A2?. Clin Pharmacokinet. 2015;54:771-81 pubmed publisher
Koyanagi T, Nakanishi Y, Murayama N, Yamaura Y, Ikeda K, Yano K, et al. Age-related changes of hepatic clearances of cytochrome P450 probes, midazolam and R-/S-warfarin in combination with caffeine, omeprazole and metoprolol in cynomolgus monkeys using in vitro-in vivo correlation. Xenobiotica. 2015;45:312-21 pubmed publisher
Grases F, Rodriguez A, Costa Bauza A. Theobromine inhibits uric acid crystallization. A potential application in the treatment of uric acid nephrolithiasis. PLoS ONE. 2014;9:e111184 pubmed publisher
Nödler K, Tsakiri M, Licha T. The impact of different proportions of a treated effluent on the biotransformation of selected micro-contaminants in river water microcosms. Int J Environ Res Public Health. 2014;11:10390-405 pubmed publisher
De Kesel P, Capiau S, Stove V, Lambert W, Stove C. Potassium-based algorithm allows correction for the hematocrit bias in quantitative analysis of caffeine and its major metabolite in dried blood spots. Anal Bioanal Chem. 2014;406:6749-55 pubmed publisher
Wierzejska R, Jarosz M, Siuba M, Sawicki W. Comparison of maternal and fetal blood levels of caffeine and its metabolite. A pilot study. Ginekol Pol. 2014;85:500-3 pubmed
De Kesel P, Lambert W, Stove C. Why dried blood spots are an ideal tool for CYP1A2 phenotyping. Clin Pharmacokinet. 2014;53:763-71 pubmed publisher
Gassner A, Schappler J, Feinberg M, Rudaz S. Derivation of uncertainty functions from validation studies in biological fluids: application to the analysis of caffeine and its major metabolites in human plasma samples. J Chromatogr A. 2014;1353:121-30 pubmed publisher
Inui N, Akamatsu T, Uchida S, Tanaka S, Namiki N, Karayama M, et al. Chronological effects of rifampicin discontinuation on cytochrome P450 activity in healthy Japanese volunteers, using the cocktail method. Clin Pharmacol Ther. 2013;94:702-8 pubmed publisher
Choi E, Bae S, Park J, Kwon M, Jang S, Zheng Y, et al. Simultaneous quantification of caffeine and its three primary metabolites in rat plasma by liquid chromatography-tandem mass spectrometry. Food Chem. 2013;141:2735-42 pubmed publisher
Ghassabian S, Murray M. Simultaneous in vivo phenotyping of CYP enzymes. Methods Mol Biol. 2013;987:261-7 pubmed publisher
Foster L, Allan M, Khan A, Moore P, Williams D, Hubbard M, et al. Multiple dosing of ephedra-free dietary supplements: hemodynamic, electrocardiographic, and bacterial contamination effects. Clin Pharmacol Ther. 2013;93:267-74 pubmed publisher
Perera V, Gross A, McLachlan A. Diurnal variation in CYP1A2 enzyme activity in South Asians and Europeans. J Pharm Pharmacol. 2013;65:264-70 pubmed publisher
Wang L, Hu Z, Deng X, Wang Y, Zhang Z, Cheng Z. Association between common CYP1A2 polymorphisms and theophylline metabolism in non-smoking healthy volunteers. Basic Clin Pharmacol Toxicol. 2013;112:257-63 pubmed publisher
Kimura M, Shimizu M, Kiyotani K, Nakagawa K, Kamataki T, Yamazaki H. Cytochrome P450 2A6 phenotyping based on dietary caffeine intake in a Japanese population of non-smokers. Drug Metab Lett. 2012;6:67-72 pubmed
Sharmin S, Guan H, Williams A, Yang K. Caffeine reduces 11β-hydroxysteroid dehydrogenase type 2 expression in human trophoblast cells through the adenosine A(2B) receptor. PLoS ONE. 2012;7:e38082 pubmed publisher
Yubero Lahoz S, Pardo R, Farre M, Mathúna B, Torrens M, Mustata C, et al. Changes in CYP1A2 activity in humans after 3,4-methylenedioxymethamphetamine (MDMA, ecstasy) administration using caffeine as a probe drug. Drug Metab Pharmacokinet. 2012;27:605-13 pubmed
Perera V, Gross A, McLachlan A. Measurement of CYP1A2 activity: a focus on caffeine as a probe. Curr Drug Metab. 2012;13:667-78 pubmed
Oh K, Park S, Shinde D, Shin J, Kim D. High-sensitivity liquid chromatography-tandem mass spectrometry for the simultaneous determination of five drugs and their cytochrome P450-specific probe metabolites in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2012;895-896:56-64 pubmed publisher
Filimonova A, Ziganshina L, Ziganshin A, Chichirov A. New specific marker of cytochrome P450 1A2 activity. Bull Exp Biol Med. 2011;150:762-4 pubmed
Pinhancos R, Maass S, Ramanathan D. High-resolution mass spectrometry method for the detection, characterization and quantitation of pharmaceuticals in water. J Mass Spectrom. 2011;46:1175-81 pubmed publisher
Hillebrand O, Nödler K, Licha T, Sauter M, Geyer T. Caffeine as an indicator for the quantification of untreated wastewater in karst systems. Water Res. 2012;46:395-402 pubmed publisher
Perera V, Gross A, Xu H, McLachlan A. Pharmacokinetics of caffeine in plasma and saliva, and the influence of caffeine abstinence on CYP1A2 metrics. J Pharm Pharmacol. 2011;63:1161-8 pubmed publisher
Youngberg M, Karpov I, Begley A, Pollock B, Buysse D. Clinical and physiological correlates of caffeine and caffeine metabolites in primary insomnia. J Clin Sleep Med. 2011;7:196-203 pubmed
Uney K, Tumer I, Tras B. Measurements of caffeine and plasma metabolite/caffeine ratios as a test for hepatic drug-oxidizing capacity in goats. Xenobiotica. 2011;41:585-92 pubmed publisher
Noh K, Seo Y, Lee S, Bista S, Kang M, Jahng Y, et al. Effects of rutaecarpine on the metabolism and urinary excretion of caffeine in rats. Arch Pharm Res. 2011;34:119-25 pubmed publisher
Laughon S, Powers R, Roberts J, Parana S, Catov J. Caffeine and insulin resistance in pregnancy. Am J Perinatol. 2011;28:571-8 pubmed publisher
Arnaud M. Pharmacokinetics and metabolism of natural methylxanthines in animal and man. Handb Exp Pharmacol. 2011;:33-91 pubmed publisher
Perera V, Gross A, McLachlan A. Caffeine and paraxanthine HPLC assay for CYP1A2 phenotype assessment using saliva and plasma. Biomed Chromatogr. 2010;24:1136-44 pubmed publisher
Gómez Martínez L. Disposition kinetics of caffeine and paraxanthine in Nile tilapia (Oreochromis niloticus): characterization of the main metabolites. Arch Environ Contam Toxicol. 2011;60:654-64 pubmed publisher
Wang X, Yeung J. Effects of the aqueous extract from Salvia miltiorrhiza Bunge on caffeine pharmacokinetics and liver microsomal CYP1A2 activity in humans and rats. J Pharm Pharmacol. 2010;62:1077-83 pubmed publisher
Kobayashi T, Homma M, Momo K, Kobayashi D, Kohda Y. A simple chromatographic method for determining norfloxacin and enoxacin in pharmacokinetic study assessing CYP1A2 inhibition. Biomed Chromatogr. 2011;25:435-8 pubmed publisher
Okuro M, Fujiki N, Kotorii N, Ishimaru Y, Sokoloff P, Nishino S. Effects of paraxanthine and caffeine on sleep, locomotor activity, and body temperature in orexin/ataxin-3 transgenic narcoleptic mice. Sleep. 2010;33:930-42 pubmed
Xu K, Xu Y, Chen J, Schwarzschild M. Neuroprotection by caffeine: time course and role of its metabolites in the MPTP model of Parkinson's disease. Neuroscience. 2010;167:475-81 pubmed publisher
Senggunprai L, Kukongviriyapan U, Jetsrisuparb A, Kukongviriyapan V. Drug metabolizing enzyme CYP1A2 status in pediatric patients with hemoglobin E-beta thalassemia. J Med Assoc Thai. 2009;92:1675-80 pubmed
Roy A, Lunn F, Bearne S. Inhibition of CTP synthase from Escherichia coli by xanthines and uric acids. Bioorg Med Chem Lett. 2010;20:141-4 pubmed publisher
Geraets L, Haegens A, Weseler A, Brauers K, Vernooy J, Wouters E, et al. Inhibition of acute pulmonary and systemic inflammation by 1,7-dimethylxanthine. Eur J Pharmacol. 2010;629:132-9 pubmed publisher
Diamandis P, Wildenhain J, Clarke I, Sacher A, Graham J, Bellows D, et al. Chemical genetics reveals a complex functional ground state of neural stem cells. Nat Chem Biol. 2007;3:268-73 pubmed
Shi D, Daly J. Chronic effects of xanthines on levels of central receptors in mice. Cell Mol Neurobiol. 1999;19:719-32 pubmed
Jodynis Liebert J, Matuszewska A. Effect of toluidines and dinitrotoluenes on caffeine metabolic ratio in rat. Toxicol Lett. 1999;104:159-65 pubmed
Ferre S, Guix T, Salles J, Badia A, Parra P, Jane F, et al. Paraxanthine displaces the binding of [3H]SCH 23390 from rat striatal membranes. Eur J Pharmacol. 1990;179:295-9 pubmed
product information
Catalog Number :
D5385
Product Name :
1,7-Dimethylxanthine
Product Type :
SMALL MOLECULES
Product Group :
Protein & Pathway Technologies
Product Description :
~98%, solid
company information
MilliporeSigma
PO Box 14508
St. Louis, MO 63178
https://www.sigmaaldrich.com
1-800-325-3010
headquarters: USA