59469-03-3

Basic information

• Product Name: 8-chloro-6-(2-fluorophenyl)-1-hydroxy-methyl-4H-imidazo(1,5-a)(1,4)-benzodiazepine
• Synonyms: 8-chloro-6-(2-fluorophenyl)-1-hydroxy-methyl-4H-imidazo(1,5-a)(1,4)-benzodiazepine
• CAS NO: 59469-03-3
• Molecular Weight: 343.788
• Mol File: 59469-03-3.mol

Chemical Properties

• CAS DataBase Reference: 8-chloro-6-(2-fluorophenyl)-1-hydroxy-methyl-4H-imidazo(1,5-a)(1,4)-benzodiazepine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-chloro-6-(2-fluorophenyl)-1-hydroxy-methyl-4H-imidazo(1,5-a)(1,4)-benzodiazepine(59469-03-3)
• EPA Substance Registry System: 8-chloro-6-(2-fluorophenyl)-1-hydroxy-methyl-4H-imidazo(1,5-a)(1,4)-benzodiazepine(59469-03-3)

Safety Data

• Hazardous Substances Data: 59469-03-3(Hazardous Substances Data)

Upstream product

• 59468-83-6 8-Chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepine 5-oxide 
• 59467-70-8 Midazolam 

Downstream Products

• 59467-70-8 Midazolam 
• 59468-72-3 5-chloro-2'-fluoro-2-(5-hydroxymethyl-2-methyl-imidazol-1-yl)-benzophenone 
• 64740-65-4 8-chloro-6-(2-fluoro-phenyl)-1-methyl-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-4-carboxylic acid methyl ester 
• 59469-38-4 2-Chloro-13a-(2-fluorophenyl)-12,13a-dihydro-6-methyl-9H,11H-imidazo[1,5-a]oxazolo[3,2-d][1,4]benzodiazepine 
• 59468-92-7 3-bromo-8-chloro-6-(2-fluoro-phenyl)-1-methyl-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59469-01-1 8-chloro-6-(2-fluoro-phenyl)-1-methyl-5-(toluene-4-sulfonyl)-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59469-06-6 5-acetyl-8-chloro-6-(2-fluoro-phenyl)-1-methyl-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59469-02-2 8-chloro-6-(2-fluoro-phenyl)-1-methyl-5-nitroso-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59469-05-5 5-allyl-8-chloro-6-(2-fluoro-phenyl)-1-methyl-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59469-04-4 8-chloro-6-(2-fluoro-phenyl)-1,5-dimethyl-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine 
• 59468-07-4 8-chloro-6-(2-fluorophenyl)-5,6-dihydro-1-methyl-6H-imidazo<1,5-a><1,4>benzodiazepine 
• 59468-73-4 5-aminomethyl-1-[4-chloro-2-(2-fluorobenzoyl)phenyl]-2-methyl-imidazole dihydrochloride 

Relevant articles and documents

Metabolism of amiodarone (part III): Identification of rabbit cytochrome p450 isoforms involved in the hydroxylation of mono-N-desethylamiodarone

1. Amiodarone (AMI) is a potent anti-arrhythmic drug and mono-N-desethylamiodarone (MDEA) is its only known metabolite. It was found recently that in rabbit liver microsomes MDEA was biotransformed to n-3-hydroxybutyl-MDEA (3OH-MDEA). 2. In liver microsomes isolated from the untreated rabbit, the formation of 3OH-MDEA obeyed Michaelis-Menten enzyme kinetics with Km = 6.39 ± 1.07 μM and Vmax = 0.56 ± 0.21 nmol min-1 mg-1 protein. 3. Furthermore, (1) among chemicals usually used as inhibitors of cytochrome P450, only midazolam (MDZ), cyclosporin A and ketoconazole inhibited the MDEA hydroxylase activity significantly (> 60% inhibition), (2) MDZ, a substrate of CYP3A, inhibited the 3OH-MDEA formation competitively (Ki = 10 ± 5 μM), (3) the formation rates of 3OH-MDEA correlated positively with those of 1OH-MDZ (r = 0.81; n = 6), and (4) MDEA hydroxylase activity of microsomes isolated from rabbit rifampicin-induced cultured hepatocytes was 4-fold more active than the control. 4. Since CYP3A6 is mainly induced by rifampicin in rabbit-cultured hepatocytes, the data suggest that this isoform is involved in the biotransformation of MDEA to 3OH-MDEA. 5. Since α-naphthoflavone, cimetidine and quinidine also partially inhibited the MDEA hydroxylase activity, it is possible that other CYPs, such as 1A, 2C and 2D, may also be active in the metabolism of amiodarone.

Imidazodiazepines and processes therefor

Novel Imidazobenzodiazepines and their analogs are useful as anticonvulsants, muscle relaxant, anxiolytic and sedative agents. Preferred compounds of this class belong to the imidazo[1,5-a][1,4]diazepine series which may have a very wide variety of organic substituents. An especially preferred genus included within the purview of the invention encompasses a compound of the formula STR1 wherein R1 is hydrogen and lower alkyl preferably methyl; R3 and R5 are hydrogen; R4 is hydrogen, nitro and halogen, most preferably, chlorine, and in a most preferred embodiment when positioned on the fused benzo portion of the imidazobenzodiazepine is in the 8-position thereof, R6 is phenyl or halo, nitro, or lower alkyl-substituted phenyl, preferably, halo, with fluorine being the preferred halogen, the substituted fluoro being positioned in the 2-position of the phenyl moiety and R2 is hydrogen and lower alkyl.