1-Hydroxymidazolam

Base Information

• Chemical Name: 1-Hydroxymidazolam
• CAS No.: 59468-90-5
• Molecular Formula: C18H13 Cl F N3 O
• Molecular Weight: 341.772
• UNII: E5142BN92Z
• DSSTox Substance ID: DTXSID50208175
• Nikkaji Number: J344.583F
• Wikidata: Q27276873
• ChEMBL ID: CHEMBL1188
• Mol file: 59468-90-5.mol

Synonyms:1'-hydroxymidazolam;1-hydroxymethylmidazolam;1-hydroxymidazolam;1-OH-MDZ;alpha-hydroxymidazolam

Chemical Property of 1-Hydroxymidazolam

Chemical Property:

• Appearance/Colour: white or off-white
• Vapor Pressure: 1.62E-12mmHg at 25°C
• Melting Point: 264-266oC
• Boiling Point: 540.6 °C at 760 mmHg
• PKA: 13.59±0.10(Predicted)
• Flash Point: 280.7 °C
• PSA: 50.41000
• Density: 1.43 g/cm³
• LogP: 2.94370
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 341.0731179
• Heavy Atom Count: 24
• Complexity: 491

Purity/Quality:

98%,99%, ^*data from raw suppliers

1′-Hydroxymidazolam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=CN=C(N2C3=C(C=C(C=C3)Cl)C(=N1)C4=CC=CC=C4F)CO
• Description: 1''-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.
• Uses: CYP3A4 metabolite of midazolam A metabolite of Midazolam (M343000).

Technology Process of 1-Hydroxymidazolam

There total 4 articles about 1-Hydroxymidazolam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

Midazolam (59467-70-8) → 1-hydroxymidazolam (59468-90-5)

Guidance literature:

With Beauveria bassiana ATCC₇₁₅₉;

DOI:10.1016/j.bmc.2012.06.052

Reference yield:

1-acetoxymethyl-8-chloro-(2-fluoro-phenyl)-4H-benzo[f]imidazo[1,5-a][1,4]diazepine (59468-89-2) → 1-hydroxymidazolam (59468-90-5)

Guidance literature:

With sodium methylate; In methanol;

Reference yield:

Midazolam (59467-70-8) → 4-hydroxymidazolam (59468-85-8) + 1-hydroxymidazolam (59468-90-5)

Guidance literature:

With intestinal microsoms from Wistar rat; isocitric dehydrogenase; NADP; NADPH; In phosphate buffer; at 37 ℃; for 0.266667h; pH=7.4; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1080/0049825021000012655

upstream raw materials:

Midazolam

1-acetoxymethyl-8-chloro-(2-fluoro-phenyl)-4H-benzo[f]imidazo[1,5-a][1,4]diazepine

Downstream raw materials:

8-chloro-6-(2-fluoro-phenyl)-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-1-carbaldehyde

1'-Hydroxymidazolam glucuronide

Refernces

• 1、 Feltrin, Clarissa,Farias, Ingrid Vicente,Sandjo, Louis Pergaud,Reginatto, Flávio Henrique,Sim?es, Cláudia Maria Oliveira. "Effects of Standardized Medicinal Plant Extracts on Drug Metabolism Mediated by CYP3A4 and CYP2D6 Enzymes". . p. 2408 - 2419. Retrieved 2020.
• 2、 Kumondai, Masaki,Rico, Evelyn Marie Gutiérrez,Hishinuma, Eiji,Ueda, Akiko,Saito, Sakae,Saigusa, Daisuke,Tadaka, Shu,Kinoshita, Kengo,Nakayoshi, Tomoki,Oda, Akifumi,Abe, Ai,Maekawa, Masamitsu,Mano, Nariyasu,Hirasawa, Noriyasu,Hiratsuka, Masahiro. "Functional characterization of 40 cyp3a4 variants by assessing midazolam 19-hydroxylation and testosterone 6b-hydroxylation". . p. 212 - 220. Retrieved 2021/03/14.
• 3、 Yang, Xin,Johnson, Nathaniel,Di, Li. "Evaluation of Cytochrome P450 Selectivity for Hydralazine as an Aldehyde Oxidase Inhibitor for Reaction Phenotyping". . p. 1627 - 1630. Retrieved 2019/01/16.