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Details

Stereochemistry ACHIRAL
Molecular Formula C18H13ClFN3O
Molecular Weight 341.7673
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1-HYDROXYMIDAZOLAM

SMILES

c1ccc(c(c1)C2=NCc3cnc(CO)n3-c4ccc(cc42)Cl)F

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

HIDE SMILES / InChI

Molecular Formula C18H13ClFN3O
Molecular Weight 341.7673
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: 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.

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Patents

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 Sat Jun 26 05:01:24 UTC 2021
Edited
by admin
on Sat Jun 26 05:01:24 UTC 2021
Record UNII
E5142BN92Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1-HYDROXYMIDAZOLAM
Common Name English
4H-IMIDAZO(1,5-A)(1,4)BENZODIAZEPINE-1-METHANOL, 8-CHLORO-6-(2-FLUOROPHENYL)-
Systematic Name English
.ALPHA.-HYDROXYMIDAZOLAM
Common Name English
RO-21-6347
Code English
Code System Code Type Description
FDA UNII
E5142BN92Z
Created by admin on Sat Jun 26 05:01:24 UTC 2021 , Edited by admin on Sat Jun 26 05:01:24 UTC 2021
PRIMARY
CAS
59468-90-5
Created by admin on Sat Jun 26 05:01:24 UTC 2021 , Edited by admin on Sat Jun 26 05:01:24 UTC 2021
PRIMARY
PUBCHEM
107917
Created by admin on Sat Jun 26 05:01:24 UTC 2021 , Edited by admin on Sat Jun 26 05:01:24 UTC 2021
PRIMARY
EPA CompTox
59468-90-5
Created by admin on Sat Jun 26 05:01:24 UTC 2021 , Edited by admin on Sat Jun 26 05:01:24 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
Related Record Type Details
PARENT -> METABOLITE ACTIVE