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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
Structure of 1′--HYDROXYMIDAZOLAM

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

HIDE SMILES / InChI

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Prolonged sedation due to accumulation of conjugated metabolites of midazolam.
1995 Jul 15
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.
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
1-HYDROXYMIDAZOLAM
Common Name English
RO-21-6347
Code English
Code System Code Type Description
FDA UNII
E5142BN92Z
Created by admin on Sat Dec 16 08:17:00 GMT 2023 , Edited by admin on Sat Dec 16 08:17:00 GMT 2023
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SMS_ID
100000176065
Created by admin on Sat Dec 16 08:17:00 GMT 2023 , Edited by admin on Sat Dec 16 08:17:00 GMT 2023
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CAS
59468-90-5
Created by admin on Sat Dec 16 08:17:00 GMT 2023 , Edited by admin on Sat Dec 16 08:17:00 GMT 2023
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PUBCHEM
107917
Created by admin on Sat Dec 16 08:17:00 GMT 2023 , Edited by admin on Sat Dec 16 08:17:00 GMT 2023
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EPA CompTox
DTXSID50208175
Created by admin on Sat Dec 16 08:17:00 GMT 2023 , Edited by admin on Sat Dec 16 08:17:00 GMT 2023
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