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UC431

Sigma-Aldrich

4-Hydroxymidazolam

≥97% (HPLC), solid

Synonym(s):

8-Chloro-6-(2-fluorophenyl)-4-hydroxy-4H-imidazo[1,5a][1,4]bezodiazepine

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About This Item

Empirical Formula (Hill Notation):
C18H13ClFN3O
CAS Number:
59468-85-8
Molecular Weight:
341.77
MDL number:
MFCD00871459
UNSPSC Code:
12161501
PubChem Substance ID:
24724656
NACRES:
NA.77

product name

4-Hydroxymidazolam,

form

solid

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

white to off-white

mp

186-187 °C

storage temp.

2-8°C

SMILES string

FC(C=CC=C1)=C1C2=NC(O)C3=CN=C(C)N3C4=C2C=C(Cl)C=C4

InChI

1S/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

InChI key

ZYISITHKPKHPKG-UHFFFAOYSA-N

Application

4′-Hydroxymidazolam can be used in cell biology studies. It can also be used for studying cell signaling and neuroscience.

Biochem/physiol Actions

4′-Hydroxymidazolam is the minor hydroxylated metabolite of Midazolam (MDZ). The product contributes in the pharmacological impact of MDZ.
CYP3A4 metabolite of midazolam.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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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A Ghosal et al.
Drug metabolism and disposition: the biological fate of chemicals, 24(9), 940-947 (1996-09-01)
Midazolam (MDZ) is metabolized in human liver microsomes by the cytochrome P450 (CYP) 3A subfamily to 1'-hydroxy (1'-OH) and 4-hydroxy (4-OH) metabolites. MDZ is metabolized in the rat primarily to 4-OH MDZ, 1'-OH MDZ, and 1',4-dihydroxy (1',4-diOH) MDZ. The kinetics
Valérie Wauthier et al.
Experimental gerontology, 41(9), 846-854 (2006-08-08)
The effect of ageing on CYP3A2, a male specific isoform, was examined in adult (9 months) and senescent (24 months) male rats. A significant decrease (65%) of CYP3A2-related activity (midazolam oxidation) was observed in all senescent rats. Half of these
Shotaro Uehara et al.
Drug metabolism and disposition: the biological fate of chemicals, 45(5), 457-467 (2017-02-16)
Common marmosets (
M P Gascon et al.
European journal of clinical pharmacology, 41(6), 573-578 (1991-01-01)
The biotransformation of midazolam is mediated by a cytochrome P-450 isozyme (P-450 IIIA) whose activity is highly variable. The kinetics of the 1'- and 4-hydroxylation of midazolam, the major routes of midazolam oxidation, by human liver microsomes have been examined
V Mastey et al.
Journal of chromatography. B, Biomedical applications, 655(2), 305-310 (1994-05-13)
A high-performance liquid chromatographic assay coupled with UV detection (254 nm) has been developed for the determination of midazolam and two of its hydroxylated metabolites, 1-hydroxymidazolam (1-OH) and 4-hydroxymidazolam (4-OH), in human plasma. Following a novel solid-phase extraction procedure, midazolam
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