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MedKoo Cat#: 561610 | Name: Rilmazafone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rilmazafone is a water-soluble benzodiazepine prodrug that acts as a sedative and hypnotic neuropsychiatric agent. Rilmazafone itself is inactive but is metabolized in the body to yield active benzodiazepine derivatives, primarily desmethylrilmazolam, which act as positive allosteric modulators of GABA receptors. It is mainly prescribed in Japan for the short-term treatment of insomnia. In healthy volunteers, oral rilmazafone at doses of 1–2 mg produces dose-dependent sedative effects, with peak plasma levels of the active metabolites reached in about 1.5–2 hours. In clinical studies, rilmazafone has shown comparable hypnotic efficacy to flurazepam, with significant reductions in sleep latency and increases in total sleep time and sleep efficiency, but with fewer next-day residual effects due to its short elimination half-life (~10 hours for active metabolites).

Chemical Structure

Rilmazafone
Rilmazafone
CAS#99593-25-6 (free base)

Theoretical Analysis

MedKoo Cat#: 561610

Name: Rilmazafone

CAS#: 99593-25-6 (free base)

Chemical Formula: C21H20Cl2N6O3

Exact Mass: 474.0900

Molecular Weight: 475.33

Elemental Analysis: C, 53.06; H, 4.24; Cl, 14.92; N, 17.68; O, 10.10

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
85815-37-8 (HCl) 99593-25-6 (free base)
Synonym
Rilmazafone; 450191-S; 450191S;
IUPAC/Chemical Name
5-[[(2-Aminoacetyl)amino]methyl]-1-[4-chloro-2-(2-chlorobenzoyl)phenyl]-N,N-dimethyl-1,2,4-triazole-3-carboxamide
InChi Key
KYHFRCPLIGODFH-UHFFFAOYSA-N
InChi Code
InChI=1S/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)
SMILES Code
O=C(C1=NN(C2=CC=C(Cl)C=C2C(C3=CC=CC=C3Cl)=O)C(CNC(CN)=O)=N1)N(C)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 475.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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Hypnotic and sleep quality-enhancing properties of kavain in sleep-disturbed rats. J Pharmacol Sci. 2009 Nov;111(3):293-8. Epub 2009 Oct 31. PubMed PMID: 19881224. 5: Nishino T, Takeuchi T, Takechi K, Kamei C. Evaluation of anxiolytic-like effects of some short-acting benzodiazepine hypnotics in mice. J Pharmacol Sci. 2008 Jul;107(3):349-54. Epub 2008 Jul 5. PubMed PMID: 18603828. 6: Sugaya K, Nishijima S, Miyazato M, Kadekawa K, Ogawa Y. Effects of melatonin and rilmazafone on nocturia in the elderly. J Int Med Res. 2007 Sep-Oct;35(5):685-91. PubMed PMID: 17900408. 7: Takiguchi A, Masuoka T, Yamamoto Y, Mikami A, Kamei C. Potentiation of ethanol in spatial memory deficits induced by some benzodiazepines. J Pharmacol Sci. 2006 Aug;101(4):325-8. Epub 2006 Aug 5. PubMed PMID: 16891765. 8: Yasui M, Kato A, Kanemasa T, Murata S, Nishitomi K, Koike K, Tai N, Shinohara S, Tokomura M, Horiuchi M, Abe K. [Pharmacological profiles of benzodiazepinergic hypnotics and correlations with receptor subtypes]. Nihon Shinkei Seishin Yakurigaku Zasshi. 2005 Jun;25(3):143-51. Japanese. PubMed PMID: 16045197. 9: Matsubara T. Safety evaluation and drug development based on biological fate of drugs -efforts made to overcome drug interaction in drug development-. Drug Metab Pharmacokinet. 2002;17(5):379-94. PubMed PMID: 15618690. 10: Shimizu K, Matsubara K, Uezono T, Kimura K, Shiono H. Reduced dorsal hippocampal glutamate release significantly correlates with the spatial memory deficits produced by benzodiazepines and ethanol. Neuroscience. 1998 Apr;83(3):701-6. PubMed PMID: 9483554. 11: Muranushi N, Miyauchi S, Suzuki H, Sugiyama Y, Hanano M, Kinoshita H, Oguma T, Yamada H. Comparative hepatic transport of desglycylated and cyclic metabolites of rilmazafone in rats: analysis by multiple indicator dilution method. Biopharm Drug Dispos. 1993 May;14(4):279-90. PubMed PMID: 8499579. 12: Koike M, Futaguchi S, Takahashi S, Sugeno K. Biopharmaceutical characterization of 450191-S, a ring-opened derivative of 1,4-benzodiazepine. II. Evidence for reduced first-pass extraction by rat liver. Drug Metab Dispos. 1988 Jul-Aug;16(4):609-15. PubMed PMID: 2903031. 13: Koike M, Norikura R, Iwatani K, Sugeno K, Takahashi S, Nakagawa Y. Structure determination of metabolites of rilmazafone, a 1H-1,2,4-triazolyl benzophenone derivative in monkey urine. Xenobiotica. 1988 Mar;18(3):257-68. PubMed PMID: 3381539. 14: Ikenishi R, Kitagawa T. Analytical studies on 1-(2-o-chlorobenzoyl-4-chlorophenyl)-3-dimethylcarbamoyl-5-glycylam inomethyl- 1H-1,2,4-triazole hydrochloride dihydrate. III. High-performance liquid chromatographic method applicable to animal feed. Chem Pharm Bull (Tokyo). 1987 Nov;35(11):4544-51. PubMed PMID: 3442888. 15: Yamaguchi T, Nakanishi M, Yamashita M, Matsumoto H, Nakamura M, Kominami G, Iwatani K, Nakagawa Y, Kono M, Sugeno K, et al. [Pharmacology of a new sleep-inducer, a 1H-1,2,4-triazolyl benzophenone derivative, 450191-S (VIII). Examination and determination of metabolites in human plasma and urine]. Nihon Yakurigaku Zasshi. 1987 Oct;90(4):239-47. Japanese. PubMed PMID: 3428781. 16: Yamamoto K, Naito Y, Sawada T. [Pharmacological studies of a new sleep inducer, 1H-1,2,4-triazolyl benzophenone derivatives (450191-S, rilmazafone hydrochloride) (VII). Comparison of sleep-inducing activities between young and elderly rhesus monkeys]. Nihon Yakurigaku Zasshi. 1987 Sep;90(3):155-62. Japanese. PubMed PMID: 3428774. 17: Matsubara T, Touchi A, Yamada N. Effect of change of hepatic drug-metabolizing activity on plasma concentrations of major metabolites of the new sleep inducer 450191-S, a 1H-1,2,4-triazolyl benzophenone derivative. Jpn J Pharmacol. 1987 Aug;44(4):429-36. PubMed PMID: 3682408. 18: Kominami G, Matsumoto H, Nishimura R, Yamaguchi T, Konaka R, Sugeno K, Hirai K, Kono M. Combined high-performance liquid chromatography and enzyme immunoassay for active metabolites of a sleep inducer (rilmazafone), a ring-opened derivative of benzodiazepines, in human plasma. J Chromatogr. 1987 Jun 5;417(1):216-22. PubMed PMID: 3305535. 19: Koike M, Norikura R, Futaguchi S, Yamaguchi T, Sugeno K, Iwatani K, Ikenishi Y, Nakagawa Y. N-hydroxymethyl metabolites of 450191-S, a 1H-1,2,4,-triazolyl benzophenone derivative, in dog plasma. Drug Metab Dispos. 1987 May-Jun;15(3):426-8. PubMed PMID: 2886322. 20: Kominami G, Matsumoto H, Nakamura M, Kono M. An enzyme immunoassay for a metabolite of a new sleep inducer (450191-S), a ring-opened derivative of 1,4-benzodiazepine, in human serum. J Immunoassay. 1987;8(2-3):267-81. PubMed PMID: 3114326.