99593-25-6 Usage
Description
Rilmazafone, one of the 'Japanese benzos,' is a substituted heterocyclic 1,2,4 triazole of the class triazolyl benzophenones. It is a benzodiazepine pro-drug, primarily used for the short-term treatment of insomnia in Japan. Although it is not a benzodiazepine itself, it exhibits sedative and hypnotic neuropsychiatric properties.
Uses
Used in Pharmaceutical Industry:
Rilmazafone is used as a water-soluble benzodiazepine prodrug for its sedative and hypnotic neuropsychiatric effects.
Used in Sleep Aid Applications:
Rilmazafone is used as a short-term treatment for insomnia, helping individuals achieve better sleep quality.
Used in Research:
Rilmazafone is used as a subject in research studies to examine the anxiolytic effects of short-acting benzodiazepine hypnotics. Nishino et al (2008) found that rilmazafone was more potent than diazepam at smaller doses when tested in mice using an elevated plus-maze.
Used in Equine Athlete Performance:
Rilmazafone has been considered to have a high potential to influence performance in equine athletes, as noted by the Kentucky Horse Racing Commission in 2015.
Pharmacology
Rilmafazone belongs to a group of open-ring benzodiazepinone analogs called peptide aminobenzophenones.It appears to be a precursor of the triazolobenzodiazepinones.It has both sedative and antianxiety effects.
Synthesis
Rilmafazone is prepared from 2,5-dichloro-2-aminobenzophenone as described in below:
Metabolism
Rilmazafone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives.Rilmazafone, were suggested to have more beneficial pharmacolog-ical properties in comparison to standard benzodiazepines.Rilmazafone is a ring-opened derivative of 1,4-benzodiazepine (Scheme 12.28) and was developed inJapan as an orally active sleep inducer.Rilmazafone is exclusively metabolized byaminopeptidases in the small intestine to the labile desglycylated metabolite 173and then to its cyclic form 174.The concentration of 174 in the systemic plasma (i.e., bioavailability) after oral administration of rilmazafone has been reported to behigher than that observed after administration of 174 due to the lower hepatic extrac-tion of 173 than 174.
Check Digit Verification of cas no
The CAS Registry Mumber 99593-25-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,9,5,9 and 3 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 99593-25:
(7*9)+(6*9)+(5*5)+(4*9)+(3*3)+(2*2)+(1*5)=196
196 % 10 = 6
So 99593-25-6 is a valid CAS Registry Number.
InChI:InChI=1/C21H20Cl2N6O3/c1-28(2)21(32)20-26-17(11-25-18(30)10-24)29(27-20)16-8-7-12(22)9-14(16)19(31)13-5-3-4-6-15(13)23/h3-9H,10-11,24H2,1-2H3,(H,25,30)
99593-25-6Relevant articles and documents
Synthesis and biological activity of (3,5-disubstituted-1H-1,2,4-triazol-1-yl)benzophenone derivatives (1)
Hirai,Sugimoto,Ishiba,et al.
, p. 1363 - 1369 (2007/10/02)
The synthesis of (5-acylaminomethyl-3-carbamoyl-1H-1,2,4-triazol-1-yl)benzophenone derivatives is described. Acylation of the key intermediate, 1-benzoylphenylazo-1-aminoacetamide followed by cyclization in the presence of acid afforded 1H-1,2,4-triazole derivates. These compounds were evaluated for their central nervous system (CNS) activity. Some of these compounds exhibited high activities in anti-pentylene tetrazole and rotarod test in mice orally administered.
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