59468-85-8

Basic information

• Product Name: 4-HYDROXYMIDAZOLAM
• Synonyms: 8-Chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-4-o;8-Chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-4-ol;8-Chloro-6-(2-fluorophenyl)-4-hydroxy-4H-imidazo[1,5a][1,4]bezodiazepine;4-Hydroxymidazolam,8-Chloro-6-(2-fluorophenyl)-4-hydroxy-4H-imidazo[1,5a][1,4]bezodiazepine
• CAS NO: 59468-85-8
• Molecular Formula: C₁₈H₁₃ClFN₃O
• Molecular Weight: 341.77
• EINECS: 200-323-9
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Aromatics;Heterocycles;Intermediates
• Mol File: 59468-85-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 186-187 °C
• Boiling Point: 550.6°C at 760 mmHg
• Flash Point: 286.8°C
• Appearance: white to off-white/
• Density: 1.44g/cm³
• Vapor Pressure: 5.9E-13mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: 2-8°C
• PKA: 12.69±0.40(Predicted)
• CAS DataBase Reference: 4-HYDROXYMIDAZOLAM(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXYMIDAZOLAM(59468-85-8)
• EPA Substance Registry System: 4-HYDROXYMIDAZOLAM(59468-85-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 59468-85-8(Hazardous Substances Data)

Usage

Description

4-HYDROXYMIDAZOLAM, also known as 4′-Hydroxymidazolam, is a metabolite of Midazolam (M343000). It is an off-white solid with significant applications in various scientific fields, particularly in cell biology, cell signaling, and neuroscience.

Uses

Used in Cell Biology Studies:
4-HYDROXYMIDAZOLAM is used as a research compound for studying cellular processes and functions. It aids in understanding the intricate mechanisms and interactions within cells, which is crucial for advancing our knowledge of cellular biology.
Used in Cell Signaling Research:
In the field of cell signaling, 4-HYDROXYMIDAZOLAM is employed as a tool to investigate the complex network of signaling pathways that regulate cellular responses to external stimuli. This helps in unraveling the molecular basis of various biological processes and potential therapeutic targets.
Used in Neuroscience:
4-HYDROXYMIDAZOLAM is used as a research compound in neuroscience to explore the intricate workings of the nervous system. It can be utilized to study the effects of various factors on neuronal function, synaptic transmission, and overall brain activity, contributing to a better understanding of neurological disorders and potential treatments.
Used in Pharmaceutical Development:
As a metabolite of Midazolam, 4-HYDROXYMIDAZOLAM may also have potential applications in the development of new pharmaceuticals, particularly those targeting the central nervous system. Its chemical properties and biological activities can be harnessed to design more effective and safer drugs for various medical conditions.

Biochem/physiol Actions

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

InChI:InChI=1/C18H13ClFN3O/c1-10-21-9-16-18(24)22-17(12-4-2-3-5-14(12)20)13-8-11(19)6-7-15(13)23(10)16/h2-9,18,24H,1H3

Upstream product

• 59467-70-8 Midazolam 
• 59468-84-7 4-acetoxymidazolam 
• 59468-83-6 8-Chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepine 5-oxide 

Downstream Products

• 81256-82-8 4-Hydroxymidazolam O-glucuronide 

Relevant articles and documents

Impurity A and impurity B of midazolam or pharmaceutical composition thereof and application thereof

The invention belongs to the field of medical chemistry, and particularly relates to an impurity A and an impurity B of midazolam or a pharmaceutical composition of midazolam and a preparation methodthereof, and application of the impurity A and the impur

Differential induction of midazolam metabolism in the small intestine and liver by oral and intravenous dexamethasone pretreatment in rat

1. Midazolam is metabolized in the rat by CYP3A enzymes to 4-OH-midazolam (4-OH-MDZ) and 1′-OH-midazolam (1′-OH-MDZ). The induction of midazolam metabolism was studied in male Wistar rats treated with dexamethasone (50mg kg-1 day-1) during 4 days via the oral or intravenous routes. Microsomes were prepared from the liver and the proximal small intestine and in vitro metabolism of midazolam was determined. In addition, CYP3A1- and CYP3A2-like protein levels were measured by gel electrophoresis and immunoblotting. 2. The Vmax's (mean SEM) for 4-OH-MDZ and 1′-OH-MDZ formation were much lower in intestinal (0.078 ± 0.002 and 0.074 ± 0.002 μM min-1 mg-1 protein, respectively) compared with hepatic microsomes prepared from the uninduced rat (0.870 ± 0.007 and 0.310 ± 0.020 μmin-1 mg-1 protein, respectively). Induction by oral or intravenous dexamethasone pretreatment led to significant increases in Vmax for 4-OH-MDZ and 1′-OH-MDZ by both intestinal and hepatic microsomes. Oral dexamethasone pretreatment via the oral route resulted in a more pronounced increase in Vmax compared with intravenous administration of the inducer. 3. CYP3A1 and CYP3A2 protein levels in liver microsomes were significantly increased following oral (3.7- and 3.2-fold, respectively) or intravenous (2.6- and 2.1-fold, respectively) pretreatment with dexamethasone. On the contrary, only oral dexamethasone pretreatment resulted in a significant change in intestinal CYP3A2-like protein (7.3-fold). A slight difference in the migration distance of the immunoreactive band for CYP3A2 was also observed for intestinal microsomes. 4. These results suggest that intestinal CYP3A enzymes in the rat differ from hepatic CYP3A1 and CYP3A2. They also demonstrate that systemic dexamethasone administration can induce intestinal microsome activity.

Simultaneous determination and pharmacokinetics of midazolam and its hydroxymetabolites in plasma and urine of man and dog by means of high-performance liquid chromatography

A HPLC (high performance liquid chromatography) method for the determination of 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepine (midazolam, Ro 21-3981, Dormicum) and its hydroxy metabolites has been developed. The half-life of elimination of midazolam and the glucuronides of the metabolites 1-hydroxymethyl-midazolam, 4-hydroxy-midazolam and 1-hydroxymethyl-4-hydroxy-midazolam are identical, 53 min in dogs and 90 min in man.