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Sigma-Aldrich

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
MDL number:
MFCD00871458
UNSPSC Code:
12161501
PubChem Substance ID:
24724655
NACRES:
NA.77

product name

1′-Hydroxymidazolam,

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

white to off-white

storage temp.

2-8°C

SMILES string

OCc1ncc2CN=C(c3ccccc3F)c4cc(Cl)ccc4-n12

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

InChI key

QHSMEGADRFZVNE-UHFFFAOYSA-N

General description

1′-Hydroxymidazolam is the metabolite of midazolam.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Xiao-Yun Liu et al.
Acta pharmacologica Sinica, 41(10), 1366-1376 (2020-04-03)
Alflutinib (AST2818) is a third-generation epidermal growth factor receptor (EGFR) inhibitor that inhibits both EGFR-sensitive mutations and T790M mutations. Previous study has shown that after multiple dosages, alflutinib exhibits nonlinear pharmacokinetics and displays a time- and dose-dependent increase in the
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)
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