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Merck

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:
59468-90-5
Molecular Weight:
341.77
UNSPSC Code:
12161501
PubChem Substance ID:
24724655
NACRES:
NA.77
MDL number:
MFCD00871458

Key Documents

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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

200

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)

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Certificates of Analysis (COA)

Lot/Batch Number
0000363972
0000363972
0000230248
0000230251
0000230248

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Pharmacokinetics of midazolam and its main metabolite 1-hydroxymidazolam in intensive care patients
Boulieu R, et al.
Eur. J. Drug Metab. Pharmacokinet., 23(2), 255-258 (1998)
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
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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
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