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UC430 Sigma

1′-Hydroxymidazolam

Synonym: 8-Chloro-6-(2-fluorophenyl)-1-hydroxymethyl-4H-imidazo[1,5a][1,4]benzodiazepine

  • CAS Number 59468-90-5

  • Empirical Formula (Hill Notation) C18H13ClFN3O

  • Molecular Weight 341.77

  •  MDL number MFCD00871458

  •  PubChem Substance ID 24724655

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Drug and Xenobiotic Metabolism,
drug control   regulated under CDSA - not available from Sigma-Aldrich Canada
color   white to off-white
storage temp.   2-8°C

Description

Application

CYP3A4 metabolite of midazolam.

1′-Hydroxymidazolam (1′-OHMDZ) can be used for assessing Cyp3a11 enzyme activity as well as for pharmacokinetic (PK) study of midazolam.1

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Biochem/physiol Actions

1′-Hydroxymidazolam is the major hydroxylated metabolite of Midazolam (MDZ), forms due to rapid and extensive metabolization of MDZ by the CYP 450 3A isoenzymes in the liver. The product contributes to the pharmacological impact of MDZ.2

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. UC430.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

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Safety & Documentation

Safety Information

WGK Germany 
3

Protocols & Articles

Articles

Discover Bioactive Small Molecules for ADME/Tox

A significant number of drugs that fail in clinical trials have been associated with safety issues, including unexpected drug-drug interactions (DDI) or lack of efficacy due to poor pharmacokinetics....
Keywords: Absorption, Bioactive small molecules, Clinical, Metabolism

Peer-Reviewed Papers

References

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1. CYP3A-dependent drug metabolism is reduced in bacterial inflammation in mice. Gandhi AS, Guo T, Shah P, et al. Br. J. Pharmacol. 166(7), 2176-87, (2012)

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2. Determination of midazolam and its major metabolite 1'-hydroxymidazolam by high-performance liquid chromatography-electrospray mass spectrometry in plasma from children. Muchohi SN, Ward SA, Preston L, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 821(1), 1-7, (2005)

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Evidence of CYP3A allosterism in vivo: analysis of interaction between fluconazole and midazolam. Yang J, Atkins WM, Isoherranen N, et al. Clin. Pharmacol. Ther. 91(3), 442-9, (2012)

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Population pharmacokinetics of midazolam and its metabolites during venoarterial extracorporeal membrane oxygenation in neonates. Ahsman MJ, Hanekamp M, Wildschut ED, et al. Clin. Pharmacokinet. 49(6), 407-19, (2010)

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Mild hypothermia alters midazolam pharmacokinetics in normal healthy volunteers. Hostler D, Zhou J, Tortorici MA, et al. Drug Metab. Dispos. 38(5), 781-8, (2010)

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The structural basis for homotropic and heterotropic cooperativity of midazolam metabolism by human cytochrome P450 3A4. Roberts AG, Yang J, Halpert JR, et al. Biochemistry 50(50), 10804-18, (2011)

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Proposal of a new limited sampling strategy to predict CYP3A activity using a partial AUC of midazolam. Katzenmaier S, Markert C, and Mikus G Eur. J. Clin. Pharmacol. 66(11), 1137-41, (2010)

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Daily honey consumption does not change CYP3A activity in humans. Fetzner L, Burhenne J, Weiss J, et al. J. Clin. Pharmacol. 51(8), 1223-32, (2011)

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A highly sensitive liquid chromatography tandem mass spectrometry method for simultaneous quantification of midazolam, 1'-hydroxymidazolam and 4-hydroxymidazolam in human plasma. de Loor H, de Jonge H, Verbeke K, et al. Biomed. Chromatogr. 25(10), 1091-8, (2011)

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Effect of telaprevir on the pharmacokinetics of midazolam and digoxin. Garg V, Chandorkar G, Farmer HF, et al. J. Clin. Pharmacol. 52(10), 1566-73, (2012)

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Rapid and simultaneous measurement of midazolam, 1'-hydroxymidazolam and digoxin by liquid chromatography/tandem mass spectrometry: application to an in vivo study to simultaneously measure P-glycoprotein and cytochrome P450 3A activity. Xue X, Huang M, Xiao H, et al. J. Pharm. Biomed. Anal. 55(1), 187-93, (2011)

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Development and validation of a method using supported liquid extraction for the simultaneous determination of midazolam and 1'-hydroxy-midazolam in human plasma by liquid chromatography with tandem mass spectrometry detection. Svanström C, Hansson GP, Svensson LD, et al. J. Pharm. Biomed. Anal. 58, 71-7, (2012)

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Development and validation of a rapid and sensitive assay for simultaneous quantification of midazolam, 1'-hydroxymidazolam, and 4-hydroxymidazolam by liquid chromatography coupled to tandem mass-spectrometry. Dostalek M, Macwan JS, Chitnis SD, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 878(19), 1629-33, (2010)

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Effect of the CYP3A inhibitor ketoconazole on the PXR-mediated induction of CYP3A activity. Fuchs I, Hafner-Blumenstiel V, Markert C, et al. Eur. J. Clin. Pharmacol. 69(3), 507-13, (2013)

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Determination of midazolam and 1-hydroxymidazolam from plasma by gas chromatography coupled to methane negative chemical ionization mass spectrometry after sublingual administration of midazolam. Kaartama R, Jarho P, Savolainen J, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 879(19), 1668-76, (2011)

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Metabolism of 1'- and 4-hydroxymidazolam by glucuronide conjugation is largely mediated by UDP-glucuronosyltransferases 1A4, 2B4, and 2B7. Seo KA, Bae SK, Choi YK, et al. Drug Metab. Dispos. 38(11), 2007-13, (2010)

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High-throughput analysis of in vitro cytochrome p450 inhibition samples using mass spectrometry coupled with an integrated liquid chromatography/autosampler system. Brown A, Bickford S, Hatsis P, et al. Rapid Commun. Mass Spectrom. 24(8), 1207-10, (2010)

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Synthesis of stable isotope labelled internal standards for drug-drug interaction (DDI) studies. Atzrodt J, Blankenstein J, Brasseur D, et al. Bioorg. Med. Chem. 20(18), 5658-67, (2012)

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Development and validation of a LC-MS/MS method for the in vitro analysis of 1-hydroxymidazolam in human liver microsomes: application for determining CYP3A4 inhibition in complex matrix mixtures. Mooiman KD, Maas-Bakker RF, Rosing H, et al. Biomed. Chromatogr. 27(9), 1107-16, (2013)

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Furanocoumarin derivatives in Kampo extract medicines inhibit cytochrome P450 3A4 and P-glycoprotein. Iwanaga K, Hayashi M, Hamahata Y, et al. Drug Metab. Dispos. 38(8), 1286-94, (2010)

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Sex-dependent differences in cytochrome P450 3A activity as assessed by midazolam disposition in humans: a meta-analysis. Hu ZY and Zhao YS Drug Metab. Dispos. 38(5), 817-23, (2010)

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Application of dried blood spot sampling combined with LC-MS/MS for genotyping and phenotyping of CYP450 enzymes in healthy volunteers. de Boer T, Wieling J, Meulman E, et al. Biomed. Chromatogr. 25(10), 1112-23, (2011)

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Pharmacokinetics and metabolism of midazolam in chimeric mice with humanised livers. Samuelsson K, Pickup K, Sarda S, et al. Xenobiotica 42(11), 1128-37, (2012)

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Chronological effects of rifampicin discontinuation on cytochrome P450 activity in healthy Japanese volunteers, using the cocktail method. Inui N, Akamatsu T, Uchida S, et al. Clin. Pharmacol. Ther. 94(6), 702-8, (2013)

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Microbial production of phase I and phase II metabolites of midazolam. Marvalin C, Denoux M, Pérard S, et al. Xenobiotica 42(3), 285-93, (2012)

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Rate of onset of inhibition of gut-wall and hepatic CYP3A by clarithromycin. Quinney SK, Malireddy SR, Vuppalanchi R, et al. Eur. J. Clin. Pharmacol. 69(3), 439-48, (2013)

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Effect of quercetin on CYP3A activity in Chinese healthy participants. Duan KM, Wang SY, Ouyang W, et al. J. Clin. Pharmacol. 52(6), 940-6, (2012)

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The effects of multiple doses of rolofylline on the single-dose pharmacokinetics of midazolam in healthy subjects. Stroh M, Dishy V, Radziszewski W, et al. Am. J. Ther. 17(1), 53-60, (2010)

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Blood concentrations of midazolam in status epilepticus using an appropriate condition of HPLC. Iwasaki T, Nonoda Y, Ishii M, et al. Pediatr. Int. 52(4), 513-9, (2010)

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