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59468-90-5,MFCD00871458
Catalog No.:AA00EB7U

59468-90-5 | 1'-HYDROXYMIDAZOLAM

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00EB7U
Chemical Name:
1'-HYDROXYMIDAZOLAM
CAS Number:
59468-90-5
Molecular Formula:
C18H13ClFN3O
Molecular Weight:
341.7667
MDL Number:
MFCD00871458
SMILES:
OCc1ncc2n1c1ccc(cc1C(=NC2)c1ccccc1F)Cl
Properties
Computed Properties
 
Complexity:
491  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
2.7  

Literature

Title: Relationship between low midazolam metabolism by cytochrome P450 3A in mice and the high incidence of birth defects.

Journal: The Journal of toxicological sciences 20180101

Title: Humanizing the zebrafish liver shifts drug metabolic profiles and improves pharmacokinetics of CYP3A4 substrates.

Journal: Archives of toxicology 20170301

Title: P450 3A-Catalyzed O-Dealkylation of Lapatinib Induces Mitochondrial Stress and Activates Nrf2.

Journal: Chemical research in toxicology 20160516

Title: Interactions of sesquiterpenes zederone and germacrone with the human cytochrome P450 system.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20130901

Title: Direct and metabolism-dependent cytochrome P450 inhibition assays for evaluating drug-drug interactions.

Journal: Journal of applied toxicology : JAT 20130201

Title: Pharmacokinetics and metabolism of midazolam in chimeric mice with humanised livers.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20121101

Title: Effect of telaprevir on the pharmacokinetics of midazolam and digoxin.

Journal: Journal of clinical pharmacology 20121001

Title: Synthesis of stable isotope labelled internal standards for drug-drug interaction (DDI) studies.

Journal: Bioorganic & medicinal chemistry 20120915

Title: Effect of quercetin on CYP3A activity in Chinese healthy participants.

Journal: Journal of clinical pharmacology 20120601

Title: Microbial production of phase I and phase II metabolites of midazolam.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20120301

Title: Evidence of CYP3A allosterism in vivo: analysis of interaction between fluconazole and midazolam.

Journal: Clinical pharmacology and therapeutics 20120301

Title: 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.

Journal: Journal of pharmaceutical and biomedical analysis 20120125

Title: The structural basis for homotropic and heterotropic cooperativity of midazolam metabolism by human cytochrome P450 3A4.

Journal: Biochemistry 20111220

Title: A highly sensitive liquid chromatography tandem mass spectrometry method for simultaneous quantification of midazolam, 1'-hydroxymidazolam and 4-hydroxymidazolam in human plasma.

Journal: Biomedical chromatography : BMC 20111001

Title: Application of dried blood spot sampling combined with LC-MS/MS for genotyping and phenotyping of CYP450 enzymes in healthy volunteers.

Journal: Biomedical chromatography : BMC 20111001

Title: Daily honey consumption does not change CYP3A activity in humans.

Journal: Journal of clinical pharmacology 20110801

Title: Determination of midazolam and 1-hydroxymidazolam from plasma by gas chromatography coupled to methane negative chemical ionization mass spectrometry after sublingual administration of midazolam.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110601

Title: 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.

Journal: Journal of pharmaceutical and biomedical analysis 20110428

Title: Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives.

Journal: Chemical research in toxicology 20101220

Title: Proposal of a new limited sampling strategy to predict CYP3A activity using a partial AUC of midazolam.

Journal: European journal of clinical pharmacology 20101101

Title: Metabolism of 1'- and 4-hydroxymidazolam by glucuronide conjugation is largely mediated by UDP-glucuronosyltransferases 1A4, 2B4, and 2B7.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20101101

Title: Blood concentrations of midazolam in status epilepticus using an appropriate condition of HPLC.

Journal: Pediatrics international : official journal of the Japan Pediatric Society 20100801

Title: Furanocoumarin derivatives in Kampo extract medicines inhibit cytochrome P450 3A4 and P-glycoprotein.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100801

Title: CYP3A4 catalytic activity is induced in confluent Huh7 hepatoma cells.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100601

Title: 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.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100601

Title: Population pharmacokinetics of midazolam and its metabolites during venoarterial extracorporeal membrane oxygenation in neonates.

Journal: Clinical pharmacokinetics 20100601

Title: Sex-dependent differences in cytochrome P450 3A activity as assessed by midazolam disposition in humans: a meta-analysis.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100501

Title: Mild hypothermia alters midazolam pharmacokinetics in normal healthy volunteers.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100501

Title: High-throughput analysis of in vitro cytochrome p450 inhibition samples using mass spectrometry coupled with an integrated liquid chromatography/autosampler system.

Journal: Rapid communications in mass spectrometry : RCM 20100430

Title: CYP3A4*1G genetic polymorphism influences CYP3A activity and response to fentanyl in Chinese gynecologic patients.

Journal: European journal of clinical pharmacology 20100101

Title: The effects of multiple doses of rolofylline on the single-dose pharmacokinetics of midazolam in healthy subjects.

Journal: American journal of therapeutics 20100101

Title: Vitamin E supplementation and hepatic drug metabolism in humans.

Journal: Journal of cardiovascular pharmacology 20091201

Title: Endogenous cortisol 6 beta-hydroxylation clearance is not an accurate probe for overall cytochrome P450 3A phenotyping in humans.

Journal: Clinica chimica acta; international journal of clinical chemistry 20091001

Title: ESRD impairs nonrenal clearance of fexofenadine but not midazolam.

Journal: Journal of the American Society of Nephrology : JASN 20091001

Title: Effect of saquinavir-ritonavir on cytochrome P450 3A4 activity in healthy volunteers using midazolam as a probe.

Journal: Pharmacotherapy 20091001

Title: Evaluation of CYP3A activity in humans using three different parameters based on endogenous cortisol metabolism.

Journal: Acta pharmacologica Sinica 20090901

Title: Effects of statins on the pharmacokinetics of midazolam in healthy volunteers.

Journal: Journal of clinical pharmacology 20090501

Title: The combination of chemical and antibody inhibitors for superior P450 3A inhibition in reaction phenotyping studies.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20081201

Title: Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20080901

Title: Effect of pluronic F68 block copolymer on P-glycoprotein transport and CYP3A4 metabolism.

Journal: International journal of pharmaceutics 20080522

Title: [Effect of polyoxyl ether analogous surfactants on the activity of cytochromes P450 3A in rats in vivo].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20080501

Title: Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes.

Journal: Biochemical pharmacology 20080315

Title: Characterization of 1'-hydroxymidazolam glucuronidation in human liver microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20080201

Title: Impact of the CYP3A5 genotype on midazolam pharmacokinetics and pharmacodynamics during intensive care sedation.

Journal: European journal of clinical pharmacology 20071201

Title: The CYP3A4*18 allele, the most frequent coding variant in asian populations, does not significantly affect the midazolam disposition in heterozygous individuals.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20071101

Title: The effect of multiple-dose, oral rifaximin on the pharmacokinetics of intravenous and oral midazolam in healthy volunteers.

Journal: Pharmacotherapy 20071001

Title: Simultaneous determination of midazolam and 1'-hydroxymidazolam in human plasma by liquid chromatography with tandem mass spectrometry.

Journal: Biomedical chromatography : BMC 20070801

Title: A developed determination of midazolam and 1'-hydroxymidazolam in plasma by liquid chromatography-mass spectrometry: application of human pharmacokinetic study for measurement of CYP3A activity.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070301

Title: Determination of midazolam and its hydroxy metabolites in human plasma and oral fluid by liquid chromatography/electrospray ionization ion trap tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20070101

Title: Quantification of benzodiazepines in whole blood and serum.

Journal: International journal of legal medicine 20061101

Title: Population pharmacodynamic modelling of lorazepam- and midazolam-induced sedation upon long-term continuous infusion in critically ill patients.

Journal: European journal of clinical pharmacology 20060301

Title: Effect of R667, a novel emphysema agent, on the pharmacokinetics of midazolam in healthy men.

Journal: Journal of clinical pharmacology 20060201

Title: Limited sampling models for oral midazolam: midazolam plasma concentrations, not the ratio of 1-hydroxymidazolam to midazolam plasma concentrations, accurately predicts AUC as a biomarker of CYP3A activity.

Journal: Journal of clinical pharmacology 20060201

Title: Cooperative binding of midazolam with testosterone and alpha-naphthoflavone within the CYP3A4 active site: a NMR T1 paramagnetic relaxation study.

Journal: Biochemistry 20051101

Title: Midazolam and its metabolites in brain death diagnosis.

Journal: International journal of clinical pharmacology and therapeutics 20051101

Title: Analysis of omeprazole, midazolam and hydroxy-metabolites in plasma using liquid chromatography coupled to tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050925

Title: A highly sensitive LC-MS-MS assay for analysis of midazolam and its major metabolite in human plasma: applications to drug metabolism.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050805

Title: Determination of midazolam and its major metabolite 1'-hydroxymidazolam by high-performance liquid chromatography-electrospray mass spectrometry in plasma from children.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050705

Title: Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20050501

Title: Variations of CYP3A activity induced by antiretroviral treatment in HIV-1 infected patients.

Journal: European journal of clinical pharmacology 20050201

Title: Differentiating midazolam over-sedation from neurological damage in the intensive care unit.

Journal: Critical care (London, England) 20050101

Title: Between benzodiazepine over-sedation and neurological damage.

Journal: Critical care (London, England) 20050101

Title: Sensitive determination of midazolam and 1'-hydroxymidazolam in plasma by liquid-liquid extraction and column-switching liquid chromatography with ultraviolet absorbance detection and its application for measuring CYP3A activity.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20041125

Title: Oral administration of a low dose of midazolam (75 microg) as an in vivo probe for CYP3A activity.

Journal: European journal of clinical pharmacology 20040601

Title: Pharmacokinetics of midazolam in CYP3A4- and CYP3A5-genotyped subjects.

Journal: European journal of clinical pharmacology 20040601

Title: Determination of picogram levels of midazolam, and 1- and 4-hydroxymidazolam in human plasma by gas chromatography-negative chemical ionization-mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040405

Title: Design and synthesis of a new fluorescent probe for cytochrome P450 3A4 (CYP 3A4).

Journal: Bioorganic & medicinal chemistry letters 20031103

Title: Relationship between CYP3A activity and breast cancer susceptibility in Chinese Han women.

Journal: European journal of clinical pharmacology 20030901

Title: Possibility of influence of midazolam sedation on the diagnosis of brain death: concentrations of active metabolites after cessation of midazolam.

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20030901

Title: Population pharmacokinetics and metabolism of midazolam in pediatric intensive care patients.

Journal: Critical care medicine 20030701

Title: Expression of the human CYP3A4 gene in the small intestine of transgenic mice: in vitro metabolism and pharmacokinetics of midazolam.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20030501

Title: The distribution and gender difference of CYP3A activity in Chinese subjects.

Journal: British journal of clinical pharmacology 20030301

Title: Phenotyping CYP3A using midazolam in cancer and noncancer Asian patients.

Journal: British journal of clinical pharmacology 20030301

Title: A clinical study investigating the pharmacokinetic interaction between NN703 (tabimorelin), a potential inhibitor of CYP3A4 activity, and midazolam, a CYP3A4 substrate.

Journal: European journal of clinical pharmacology 20030201

Title: Determination of midazolam and 1'-hydroxymidazolam by liquid chromatography-mass spectrometry in plasma of patients undergoing methadone maintenance treatment.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20030105

Title: Pharmacokinetics of midazolam and 1'-hydroxymidazolam in Chinese with different CYP3A5 genotypes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20021201

Title: Monolithic silica rod liquid chromatography with ultraviolet or fluorescence detection for metabolite analysis of cytochrome P450 marker reactions.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20021125

Title: [Use of midazolam in postoperative sedation of patients with multiple organ failure treated with hemodiafiltration. Clinical study and pharmacokinetics].

Journal: Annales francaises d'anesthesie et de reanimation 20021101

Title: Single plasma concentrations of 1'-hydroxymidazolam or the ratio of 1'-hydroxymidazolam:midazolam do not predict midazolam clearance in healthy subjects.

Journal: Journal of clinical pharmacology 20021001

Title: Contribution of midazolam and its 1-hydroxy metabolite to preoperative sedation in children: a pharmacokinetic-pharmacodynamic analysis.

Journal: British journal of anaesthesia 20020901

Title: Intestinal first pass metabolism of midazolam in liver cirrhosis --effect of grapefruit juice.

Journal: British journal of clinical pharmacology 20020801

Title: Pharmacokinetics and pharmacodynamics of midazolam administered as a concentrated intranasal spray. A study in healthy volunteers.

Journal: British journal of clinical pharmacology 20020501

Title: Ultrafast liquid chromatography/tandem mass spectrometry bioanalysis of polar analytes using packed silica columns.

Journal: Rapid communications in mass spectrometry : RCM 20020101

Title: Midazolam disposition in patients undergoing continuous venovenous hemodialysis.

Journal: Journal of clinical pharmacology 20010901

Title: Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20010201

Title: Selective inhibition of human cytochrome P450 3A4 by N-[2(R)-hydroxy-1(S)-indanyl]-5-[2(S)-(1, 1-dimethylethylaminocarbonyl)-4-[(furo[2, 3-b]pyridin-5-yl)methyl]piperazin-1-yl]-4(S)-hydroxy-2(R)-phenylmethy lpentanamide and P-glycoprotein by valspodar in gene transfectant systems.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20001001

Title: Prolonged sedation due to accumulation of conjugated metabolites of midazolam.

Journal: Lancet (London, England) 19950715

Title: Hasegawa T, et, al. Increase in the systemic exposure of primary metabolites of Midazolam in rat arising from CYP inhibition or hepatic dysfunction. Drug Metab Pharmacokinet. 2017 Feb; 32(1): 69-76.

Title: Balk M, et, al. Differential depression of neuronal network activity by midazolam and its main metabolite 1-hydroxymidazolam in cultured neocortical slices. Sci Rep. 2017 Jun 14; 7(1): 3503.

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