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Showing content from https://en.wikipedia.org/wiki/Rilmazafone below:

Rilmazafone - Wikipedia

From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Rilmazafone

Above: Rilmazafone molecular structure Below: 3D molecular representation

Trade names Rhythmy Other names 5-([(2-aminoacetyl)amino]methyl)-1-[4-chloro-2-(2-chlorobenzoyl)phenyl]-N,N-dimethyl-1,2,4-triazole-3-carboxamide AHFS/Drugs.com International Drug Names Routes of
administration Oral (tablets) ATC code

none

Legal status

Rx-only (JP)

Elimination half-life 10.5 h Excretion Urine IUPAC name

1-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-[(glycylamino)methyl]-N,N-dimethyl-1H-1,2,4-triazole-3-carboxamide

CAS Number

99593-25-6^Y

PubChem CID

5069

ChemSpider

4891^Y

UNII

CU3H37T766

KEGG

D08481^Y

CompTox Dashboard (EPA)

DTXSID10244150

Formula C₂₁H₂₀Cl₂N₆O₃ Molar mass 475.33 g·mol⁻¹ 3D model (JSmol)

Interactive image

SMILES

ClC1=C(C(C2=CC(Cl)=CC=C2N3C(CNC(CN)=O)=NC(C(N(C)C)=O)=N3)=O)C=CC=C1

InChI

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)
^Y
Key:KYHFRCPLIGODFH-UHFFFAOYSA-N
^Y

(verify)

Rilmazafone^[1] (リスミー, Rhythmy, previously known as 450191-S) is a water-soluble prodrug developed in Japan.^[2] Inside the human body, rilmazafone is converted into several benzodiazepine metabolites that have sedative and hypnotic effects.^[3]^[4]^[5]

Rilmazafone is not a benzodiazepine, since there is no benzene ring fused with a diazepine ring in the compound; in fact, the parent drug has no diazepine ring. It is therefore not classified as a benzodiazepine in several countries, including the United States, where it is not designated a controlled substance. Rilmazafone has no effects on benzodiazepine receptors itself, nor does it produce any psychoactive effects prior to metabolism. However, once inside the body it is metabolized by aminopeptidase enzymes in the small intestine to form the principal active benzodiazepine rilmazolam (8-chloro-6-(2-chlorophenyl)-N,N-dimethyl-4H-1,2,4-triazolo [1,5-a][1,4]benzodiazepine-2-carboxamide).^[6]^[7] As can be seen in the molecular diagram below, the principal metabolite contains a benzodiazepine ring structure (i.e., a benzene ring fused with a diazepine ring), unlike the parent compound (rilmazafone), which has no diazepine ring.

Rilmazolam — an active metabolite

^ DE Patent 2725164
^ Yamamoto K, Hirose K, Matsushita A, Yoshimura K, Sawada T, Eigyo M, Jyoyama H, Fujita A, Matsubara K, Tsukinoki Y (July 1984). "[Pharmacological studies of a new sleep-inducer, 1H-1,2,4-triazolyl benzophenone derivatives (450191-S) (I). Behavioral analysis]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 84 (1): 109–54. doi:10.1254/fpj.84.109. PMID 6149174.
^ Yamamoto K, Matsushita A, Sawada T, Naito Y, Yoshimura K, Takesue H, Utsumi S, Kawasaki K, Hirono S, Koshida H (July 1984). "[Pharmacology of a new sleep inducer, 1H-1,2,4-triazolyl benzophenone derivative, 450191-S (II). Sleep-inducing activity and effect on the motor system]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 84 (1): 25–89. doi:10.1254/fpj.84.25. PMID 6149175.
^ Ibii N, Horiuchi M, Yamamoto K (August 1984). "[Pharmacology of a 1H-1, 2, 4-triazolyl benzophenone derivative (450191-S), a new sleep-inducer (III). Behavioral study on interactions of 450191-S and other drugs in mice]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 84 (2): 155–73. doi:10.1254/fpj.84.155. PMID 6149177.
^ Yasui M, Kato A, Kanemasa T, Murata S, Nishitomi K, Koike K, et al. (June 2005). "[Pharmacological profiles of benzodiazepinergic hypnotics and correlations with receptor subtypes]". Nihon Shinkei Seishin Yakurigaku Zasshi = Japanese Journal of Psychopharmacology. 25 (3): 143–51. PMID 16045197.
^ Koike M, Norikura R, Sugeno K (March 1986). "Intestinal activation of a new sleep inducer 450191-S, a 1H-1,2,4-triazolyl benzophenone derivative, in rats". Journal of Pharmacobio-Dynamics. 9 (3): 315–20. doi:10.1248/bpb1978.9.315. PMID 3454653.
^ Muranushi N, Miyauchi S, Suzuki H, Sugiyama Y, Hanano M, Kinoshita H, Oguma T, Yamada H (May 1993). "Comparative hepatic transport of desglycylated and cyclic metabolites of rilmazafone in rats: analysis by multiple indicator dilution method". Biopharmaceutics & Drug Disposition. 14 (4): 279–90. doi:10.1002/bdd.2510140402. PMID 8499579. S2CID 24923818.