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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.[1]
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_germany

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
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
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
Shotaro Uehara et al.
Drug metabolism and disposition: the biological fate of chemicals, 45(5), 457-467 (2017-02-16)
Common marmosets (
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
C B Eap et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 802(2), 339-345 (2004-03-17)
Midazolam is a widely accepted probe for phenotyping cytochrome P4503A. A gas chromatography-mass spectrometry (GC-MS)-negative chemical ionization method is presented which allows measuring very low levels of midazolam (MID), 1-OH midazolam (1OHMID) and 4-OH midazolam (4OHMID), in plasma, after derivatization
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