UC430
1′-Hydroxymidazolam
≥97% (HPLC), powder
Synonym(s):
8-Chloro-6-(2-fluorophenyl)-1-hydroxymethyl-4H-imidazo[1,5a][1,4]benzodiazepine
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About This Item
Empirical Formula (Hill Notation):
C18H13ClFN3O
CAS Number:
Molecular Weight:
341.77
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
1′-Hydroxymidazolam,
SMILES string
OCc1ncc2CN=C(c3ccccc3F)c4cc(Cl)ccc4-n12
InChI key
QHSMEGADRFZVNE-UHFFFAOYSA-N
InChI
1S/C18H13ClFN3O/c19-11-5-6-16-14(7-11)18(13-3-1-2-4-15(13)20)22-9-12-8-21-17(10-24)23(12)16/h1-8,24H,9-10H2
form
powder
drug control
regulated under CDSA - not available from Sigma-Aldrich Canada
color
white to off-white
storage temp.
2-8°C
Quality Level
Related Categories
Application
1′-Hydroxymidazolam (1′-OHMDZ) can be used for assessing Cyp3a11 enzyme activity as well as for pharmacokinetic (PK) study of midazolam.
CYP3A4 metabolite of midazolam.
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.
Features and Benefits
This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
General description
1′-Hydroxymidazolam is the metabolite of midazolam.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Sussan Ghassabian et al.
The AAPS journal, 21(2), 15-15 (2019-01-11)
The multi-kinase inhibitor sorafenib (SOR) is clinically important in the treatment of hepatocellular and renal cancers and undergoes CYP3A4-dependent oxidation in liver to the pharmacologically active N-oxide metabolite (SNO). There have been reports that kinase inhibitors such as SOR may
Alexander J Kvist et al.
Biochemical pharmacology, 155, 124-140 (2018-06-29)
Primary human hepatocytes (PHH), HepaRG™, HepG2, and two sources of induced pluripotent stem cell (iPSC) derived hepatocytes were characterized regarding gene expression and function of key hepatic proteins, important for the metabolic fate of drugs. The gene expression PCA analysis
A S Gandhi et al.
British journal of pharmacology, 166(7), 2176-2187 (2012-03-08)
Gene expression of Cyp3a11 is reduced by activation of Toll-like receptors (TLRs) by Gram-negative or Gram-positive bacterial components, LPS or lipoteichoic acid (LTA) respectively. The primary adaptor protein in the TLR signalling pathway, TIRAP, plays differential roles in LPS- and
Yukiko Toba et al.
PloS one, 15(2), e0229654-e0229654 (2020-02-28)
Human hepatocytes are essential materials in pharmaceutical researches. Not only primary human hepatocytes (PHH) but also human iPS cell-derived hepatocyte-like cells (human iPS-HLCs) are expected to be applied as materials for pharmaceutical researches. To date, several culture media have been
Kar Lai Poon et al.
Archives of toxicology, 91(3), 1187-1197 (2016-08-04)
Understanding and predicting whether new drug candidates will be safe in the clinic is a critical hurdle in pharmaceutical development, that relies in part on absorption, distribution, metabolism, excretion and toxicology studies in vivo. Zebrafish is a relatively new model
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