Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H13ClFN3O |
| Molecular Weight | 341.767 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OCC1=NC=C2CN=C(C3=C(F)C=CC=C3)C4=C(C=CC(Cl)=C4)N12
InChI
InChIKey=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
| Molecular Formula | C18H13ClFN3O |
| Molecular Weight | 341.767 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17998299 | https://www.ncbi.nlm.nih.gov/pubmed/10606840 | https://www.ncbi.nlm.nih.gov/pubmed/16220317
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17998299 | https://www.ncbi.nlm.nih.gov/pubmed/10606840 | https://www.ncbi.nlm.nih.gov/pubmed/16220317
1-Hydroxymidazolam (Alpha-hydroxy-midazolam) is pharmacologically active midazolam metabolite, which is, like the parent drug midazolam a neuronal depressant drug. There are numerous studies in which the statements concerning the contribution of 1-Hydroxymidazolam to the clinical actions of midazolam range from “almost equipotent” to “no major contributing factor”. In humans, Hydroxymidazolam is subject to further glucuronidation, followed by renal excretion. In humans, urinary recovery of 1-Hydroxymidazolam glucuronide accounted for 60 to 70% of an administered dose of [14C]midazolam. 1-Hydroxymidazolam and it’s glucuronide were found in patients with renal failure after administration of midazolam and may account for the prolonged sedation observed in those patients.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Prolonged sedation due to accumulation of conjugated metabolites of midazolam. | 1995 Jul 15 |
|
| Monolithic silica rod liquid chromatography with ultraviolet or fluorescence detection for metabolite analysis of cytochrome P450 marker reactions. | 2002 Nov 25 |
|
| Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes. | 2008 Mar 15 |
|
| Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. | 2010 Dec 20 |
|
| Interactions of sesquiterpenes zederone and germacrone with the human cytochrome P450 system. | 2013 Sep |
Sample Use Guides
short i. v. injection of 0.15 mg/kg-1 alpha-hydroxy-midazolam
Route of Administration:
Intravenous
The reaction mixture consisted of 1’-hydroxymidazolam (5–200 _M), 100 mM potassium phosphate buffer (pH 7.5) with 2 mM MgCl2, and human/rat liver microsomes (0.5 mg of protein/ml) or recombinant UGTs (1 mg of protein/ml) treated with alamethicin at 50 mkg/mg of microsomal protein. The reactions were initiated by the addition of UDPGA (2 mM), incubated at 37°C, and terminated with ice-cold acetonitrile containing 0.2% formic acid and phenolphthalein-beta-D-glucuronide as the internal standard. Samples were centrifuged at 3220g for 15 min, and supernatants were subjected to LC-MS/MS analysis.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:16:59 UTC 2023
by
admin
on
Sat Dec 16 08:16:59 UTC 2023
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| Record UNII |
E5142BN92Z
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| Record Status |
Validated (UNII)
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| Record Version |
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BINDER->LIGAND |
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PARENT -> METABOLITE ACTIVE |
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