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Merck
CN

UC431

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
UNSPSC Code:
12161501
PubChem Substance ID:
24724656
NACRES:
NA.77
MDL number:
MFCD00871459

Key Documents

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Product Name

4-Hydroxymidazolam,

form

solid

SMILES string

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

InChI key

ZYISITHKPKHPKG-UHFFFAOYSA-N

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

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

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

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK9080
BCCH1232
BCCF9039
BCCF4396
BCCC6509

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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
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
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
J C Gorski et al.
Biochemical pharmacology, 47(9), 1643-1653 (1994-04-29)
The capabilities of cytochrome P4503A4 (CYP3A4), CYP3A5, and fetal hepatic microsomes containing CYP3A7 to metabolize midazolam were investigated using human hepatic microsomes and purified CYP3A4 and CYP3A5. Under initial rate conditions and high substrate concentration (400 microM midazolam), variability among
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