Indiplon - CAS 325715-02-4
Catalog number:
325715-02-4
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C20H16N4O2S
Molecular Weight:
376.43
COA:
Inquire
Targets:
GABA Receptor
Description:
Indiplon acts as a high-affinity positive and orally active allosteric modulator of the GABAA receptor (Ki=1.2 nM in rat frontal cortex and Ki=1.7 nM and in cerebellum).
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Purity:
>99 %
Appearance:
Dark Yellow Solid
Synonyms:
INDIPLON;N-Methyl-N-[3-[3-(thien-2-ylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]acetamide;Acetamide, N-methyl-N-(3-(3-(2-thienylcarbonyl)pyrazolo(1,5-A)pyrimidin-7-yl)phenyl)-;NBI 34060;Unii-8bt63da42e
Solubility:
Soluble in DMSO
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -88℃ for long term (months to years).
MSDS:
Inquire
Application:
Sedative, hypnotic
Shelf Life:
2 years
Density:
1.35±0.1 g/cm3
InChIKey:
CBIAWPMZSFFRGN-UHFFFAOYSA-N
InChI:
1S/C20H16N4O2S/c1-13(25)23(2)15-6-3-5-14(11-15)17-8-9-21-20-16(12-22-24(17)20)19(26)18-7-4-10-27-18/h3-12H,1-2H3
Canonical SMILES:
CC(=O)N(C)C1=CC=CC(=C1)C2=CC=NC3=C(C=NN23)C(=O)C4=CC=CS4
1.[Role of Human Orphan Esterases in Drug-induced Toxicity].
Fukami T1. Yakugaku Zasshi. 2015;135(11):1235-44. doi: 10.1248/yakushi.15-00186.
Esterases hydrolyze compounds containing ester, amide, and thioester bonds, causing prodrug activation or detoxification. Among esterases, carboxylesterases have been studied in depth due to their ability to hydrolyze a variety of drugs. However, there are several drugs for which the involved esterase(s) is unknown. We found that flutamide, phenacetin, rifamycins (rifampicin, rifabutin, and rifapentine), and indiplon are hydrolyzed by arylacetamide deacetylase (AADAC), which is highly expressed in human liver and gastrointestinal tissues. Flutamide hydrolysis is considered associated with hepatotoxicity. Phenacetin, a prodrug of acetaminophen, was withdrawn due to side effects such as methemoglobinemia and renal failure. It was demonstrated in vitro and in vivo using mice that AADAC is responsible for phenacetin hydrolysis, which leads to methemoglobinemia. In addition, it was shown that AADAC-mediated hydrolysis attenuates the cytotoxicity of rifamycins.
2.Indiplon is hydrolyzed by arylacetamide deacetylase in human liver.
Shimizu M1, Fukami T, Ito Y, Kurokawa T, Kariya M, Nakajima M, Yokoi T. Drug Metab Dispos. 2014 Apr;42(4):751-8. doi: 10.1124/dmd.113.056184. Epub 2014 Jan 24.
Human arylacetamide deacetylase (AADAC) catalyzes the hydrolysis of some clinically used drugs, but the information available on its substrates is limited. To increase our knowledge of the AADAC substrates, we examined whether AADAC catalyzes the hydrolysis of indiplon, which was initially developed as a hypnotic sedative drug. It has been reported that approximately 30-40% of the administered indiplon was hydrolyzed to deacetylindiplon in humans, but the enzyme responsible for this hydrolysis had not been identified. We detected high levels of indiplon hydrolase activity in human liver microsomes (HLMs), but the levels found in human liver cytosol and plasma were scarcely detectable. Recombinant AADAC showed a high level of indiplon hydrolase activity, whereas recombinant carboxylesterase 1 (CES1) and 2 (CES2) showed marginal activity. The indiplon hydrolase activity of HLM was potently inhibited by vinblastine, a potent inhibitor of AADAC and CES2, but it was not inhibited by digitonin and telmisartan, inhibitors of CES1 and CES2, respectively.
3.Comparison of substrate specificity among human arylacetamide deacetylase and carboxylesterases.
Fukami T1, Kariya M2, Kurokawa T2, Iida A2, Nakajima M2. Eur J Pharm Sci. 2015 Oct 12;78:47-53. doi: 10.1016/j.ejps.2015.07.006. Epub 2015 Jul 8.
Human arylacetamide deacetylase (AADAC) is an esterase responsible for the hydrolysis of some drugs, including flutamide, indiplon, phenacetin, and rifamycins. AADAC is highly expressed in the human liver, where carboxylesterase (CES) enzymes, namely, CES1 and CES2, are also expressed. It is generally recognized that CES1 prefers compounds with a large acyl moiety and a small alcohol or amine moiety as substrates, whereas CES2 prefers compounds with a small acyl moiety and a large alcohol or amine moiety. In a comparison of the chemical structures of known AADAC substrates, AADAC most likely prefers compounds with the same characteristics as does CES2. However, the substrate specificity of human AADAC has not been fully clarified. To expand the knowledge of substrates of human AADAC, we measured its hydrolase activities toward 13 compounds, including known human CES1 and CES2 substrates, using recombinant enzymes expressed in Sf21 cells.
4.CB1 cannabinoid receptor stimulation during adolescence impairs the maturation of GABA function in the adult rat prefrontal cortex.
Cass DK1, Flores-Barrera E1, Thomases DR1, Vital WF1, Caballero A1, Tseng KY1. Mol Psychiatry. 2014 May;19(5):536-43. doi: 10.1038/mp.2014.14. Epub 2014 Mar 4.
Converging epidemiological studies indicate that cannabis abuse during adolescence increases the risk of developing psychosis and prefrontal cortex (PFC)-dependent cognitive impairments later in life. However, the mechanisms underlying the adolescent susceptibility to chronic cannabis exposure are poorly understood. Given that the psychoactive constituent of cannabis binds to the CB1 cannabinoid receptor, the present study was designed to determine the impact of a CB1 receptor agonist (WIN) during specific windows of adolescence on the functional maturation of the rat PFC. By means of local field potential recordings and ventral hippocampal stimulation in vivo, we found that a history of WIN exposure during early (postnatal days - P35-40) or mid-(P40-45) adolescence, but not in late adolescence (P50-55) or adulthood (P75-80), is sufficient to yield a state of frequency-dependent prefrontal disinhibition in adulthood comparable to that seen in the juvenile PFC.
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CAS 325715-02-4 Indiplon

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