Rilmazafone

Rilmazafone
	Above: Rilmazafone molecular structure Below: 3D molecular representation
Clinical data
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
Legal status	Rx-only (JP);
Pharmacokinetic data
Elimination half-life	10.5 h
Excretion	Urine
Identifiers
	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 ;
PubChem CID	5069;
ChemSpider	4891 ;
UNII	CU3H37T766;
KEGG	D08481 ;
CompTox Dashboard (EPA)	DTXSID10244150 ;
Chemical and physical data
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) ; Key:KYHFRCPLIGODFH-UHFFFAOYSA-N ;
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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]

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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.

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[2]

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[6]

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Rilmazafone

See also

References

External links

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