Basic information
- CAS
59468-90-5- Standard SMILES
OCc1ncc2n1-c1ccc(Cl)cc1C(c1ccccc1F)=NC2- InChIKey
QHSMEGADRFZVNE-UHFFFAOYSA-N- Molecular formula
- C18H13ClFN3O
- Average molar mass
- 341.8 g/mol
- Monoisotopic mass
- 341.0731179
Overview
1-hydroxymidazolam is an imidazobenzodiazepine that is midazolam in which one of the hydrogens of the methyl group is substituted by a hydroxy group. It is the major metabolite of the anesthetic, midazolam. It has a role as a drug metabolite, a human urinary metabolite and a human blood serum metabolite. It is an imidazobenzodiazepine, an aromatic primary alcohol, an organochlorine compound and a member of monofluorobenzenes. It is functionally related to a midazolam.
Names & identifiers
- Preferred name
- 1'-Hydroxymidazolam
- IUPAC
- [8-chloro-6-(2-fluorophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepin-1-yl]methanol
- English name
- 1'-HYDROXYMIDAZOLAM
- Molecular formula
- C18H13ClFN3O
- Molecular weight
- 341.77
Names & synonyms
1'-hydroxymidazolam1-Hydroxymidazolam59468-90-5alpha-Hydroxymidazolam1-Hydroxymethylmidazolam1-OH-MdzDTXSID50208175E5142BN92Z1'--HYDROXYMIDAZOLAM8-Chloro-6-(2-fluorophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine-1-methanolCHEBI:145330RO-21-6347
Show more names
α-HydroxymidazolamA-HYDROXYMIDAZOLAM1Hydroxymidazolame1-HYDROXY MIDAZOLAMMidazolam Impurity 1Midazolam Impurity 12
8-Chloro-6-(2-fluorophenyl)-4H-imidazo(1,5-a)(1,4)benzodiazepine-1-methanol4H-Imidazo(1,5-a)(1,4)benzodiazepine-1-methanol, 8-chloro-6-(2-fluorophenyl)-RefChem:433186DTXCID701306661'-Hydroxy Midazolam[8-chloro-6-(2-fluorophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepin-1-yl]methanolALPHA-HYDROXY-MIDAZOLAMRo 21-6347
Database identifiers
- CAS
59468-90-5- PubChem CID
- 107917
- DTXSID
DTXSID50208175
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 50.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 491
Physicochemical properties
- Melting point
- 264 · 264-266oC
- Boiling point
- 540.6 · 540.6±60.0 °C(Predicted)
- Density
- 1.43 · 1.43±0.1 g/cm3(Predicted)
- Flash point
- 9 ℃ · 9℃
- storage temp.
- 2 · 2-8°C
- solubility
- 2 mg/ml; · DMF: 2 mg/ml; DMSO: 1 mg/ml
- form
- A crystalline solid
- pka
- 13.59 · 13.59±0.10(Predicted)
- color
- white or off-white
- Major Application
- clinical testing
- 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
- InChIKey
- QHSMEGADRFZVNE-UHFFFAOYSA-N
- SMILES
- OCc1ncc2CN=C(c3ccccc3F)c4cc(Cl)ccc4-n12
- FDA UNII
- 5142 BN92Z · E5142BN92Z
- UNSPSC Code
- 41116107 · 41116107
- NACRES
Safety & regulation
Hazard information
Regulatory Information4H-Imidazo1,5-a1,4benzodiazepine-1-methanol, 8-chloro-6-(2-fluorophenyl)-: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- wgk
- 3
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- risk_code
- 11-23/24/25-39/23/24/25
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06,GHS08
- hazard_code
- F,T
- safety_code
- 7-16-36/37-45
- Storage Class
- 3 - Flammable liquids
- target organs
- Eyes
- Hazard statements
- H225-H301+H311+H331-H370
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- Precautionary statements
- P210-P260-P280-P301+P310-P311
Chemistry & industry
Pharmacology
Metabolism/Metabolites1'-Hydroxymidazolam is a known human metabolite of midazolam.
Tissue LocationsKidney
Cellular LocationsCytoplasm
Applications
Description1''-hydroxy Midazolam is the major metabolite of the anesthetic, midazolam. It is produced rapidly by the actions of hepatic cytochrome P450 3A and has been shown to be equipotent to midazolam.
UsesCYP3A4 metabolite of midazolam
UsesA metabolite of Midazolam (M343000).
Additional notes
DefinitionChEBI: 1-hydroxymidazolam is an imidazobenzodiazepine that is midazolam in which one of the hydrogens of the methyl group is substituted by a hydroxy group. It is the major metabolite of the anesthetic, midazolam. It has a role as a drug metabolite, a human blood serum metabolite and a human urinary metabolite. It is an imidazobenzodiazepine, an organochlorine compound, a member of monofluorobenzenes and an aromatic primary alcohol. It is functionally related to a midazolam.
Related reactions
2 records
Compound notes
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