UC431 Sigma


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

  • CAS Number 59468-85-8

  • Empirical Formula (Hill Notation) C18H13ClFN3O

  • Molecular Weight 341.77

  •  MDL number MFCD00871459

  •  PubChem Substance ID 24724656



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
mp   186-187 °C
storage temp.   2-8°C


Biochem/physiol Actions

CYP3A4 metabolite of midazolam.

4′-Hydroxymidazolam is the minor hydroxylated metabolite of Midazolam (MDZ). The product contributes in the pharmacological impact of MDZ.1


Bottomless glass bottle. Contents are inside inserted fused cone.


4′-Hydroxymidazolam can be used in cell biology studies. It can also be used for studying cell signaling and neuroscience.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. UC431.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit

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Safety Information

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Protocols & Articles

Peer-Reviewed Papers


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1. 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)


Determination of midazolam and two of its metabolites in human plasma by high-performance liquid chromatography. Mastey V, Panneton AC, Donati F, et al. J. Chromatogr. B, Biomed. Appl. 655(2), 305-10, (1994)


Determination of midazolam and its hydroxy metabolites in human plasma and oral fluid by liquid chromatography/electrospray ionization ion trap tandem mass spectrometry. Link B, Haschke M, Wenk M, et al. Rapid Commun. Mass Spectrom. 21(9), 1531-40, (2007)


Determination of picogram levels of midazolam, and 1- and 4-hydroxymidazolam in human plasma by gas chromatography-negative chemical ionization-mass spectrometry. Eap CB, Bouchoux G, Powell Golay K, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 802(2), 339-45, (2004)


In vitro forecasting of drugs which may interfere with the biotransformation of midazolam. Gascon MP and Dayer P Eur. J. Clin. Pharmacol. 41(6), 573-8, (1991)


Pharmacokinetics of midazolam in CYP3A4- and CYP3A5-genotyped subjects. Eap CB, Buclin T, Hustert E, et al. Eur. J. Clin. Pharmacol. 60(4), 231-6, (2004)


Oral administration of a low dose of midazolam (75 microg) as an in vivo probe for CYP3A activity. Eap CB, Buclin T, Cucchia G, et al. Eur. J. Clin. Pharmacol. 60(4), 237-46, (2004)


Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Gorski JC, Hall SD, Jones DR, et al. Biochem. Pharmacol. 47(9), 1643-53, (1994)


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)


Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human, and cdna-expressed human cytochrome P450. Ghosal A, Satoh H, Thomas PE, et al. Drug Metab. Dispos. 24(9), 940-7, (1996)


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)


Simultaneous determination of midazolam and its metabolites 1-hydroxymidazolam and 4-hydroxymidazolam in human serum using gas chromatography-mass spectrometry. Martens J and Banditt P J. Chromatogr. B. Biomed. Sci. Appl. 692(1), 95-100, (1997)


Expression of the human CYP3A4 gene in the small intestine of transgenic mice: in vitro metabolism and pharmacokinetics of midazolam. Granvil CP, Yu AM, Elizondo G, et al. Drug Metab. Dispos. 31(5), 548-58, (2003)


Ultrafast liquid chromatography/tandem mass spectrometry bioanalysis of polar analytes using packed silica columns. Shou WZ, Chen YL, Eerkes A, et al. Rapid Commun. Mass Spectrom. 16(17), 1613-21, (2002)


Decreased CYP3A2 expression and activity in senescent male Wistar rats: is there a role for HNF4alpha? Wauthier V, Verbeeck RK, and Calderon PB Exp. Gerontol. 41(9), 846-54, (2006)


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)


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)


The CYP3A4*18 allele, the most frequent coding variant in asian populations, does not significantly affect the midazolam disposition in heterozygous individuals. Lee SJ, Lee SS, Jeong HE, et al. Drug Metab. Dispos. 35(11), 2095-101, (2007)


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)


Cooperative binding of midazolam with testosterone and alpha-naphthoflavone within the CYP3A4 active site: a NMR T1 paramagnetic relaxation study. Cameron MD, Wen B, Allen KE, et al. Biochemistry 44(43), 14143-51, (2005)


Quantitation by gas chromatography of the 1- and 4-hydroxy metabolites of midazolam in human plasma. Arendt RM, Greenblatt DJ, and Garland WA Pharmacology 29(3), 158-64, (1984)


Inhibition of CYP3A by erythromycin: in vitro-in vivo correlation in rats. Zhang X, Galinsky RE, Kimura RE, et al. Drug Metab. Dispos. 38(1), 61-72, (2010)


Midazolam withdrawal and discriminative motor control: effects of FG 7142 and Ro 15-1788. Vigorito M, Lau CE, Tang M, et al. Pharmacol. Biochem. Behav. 39(2), 351-9, (1991)


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