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

Pyrithyldione - Wikipedia

From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Pyrithyldione Trade names Benedorm, Didropyridine, Dihydroprylone, Persedon, Presidon, Pyridion, Pyridione, Pyrithyldion, Pyrithyldione, Tetridin, Tetridine ATC code

N05CE03 (WHO)

IUPAC name

3,3-diethylpyridine-2,4(1H,3H)-dione

CAS Number

77-04-3^N

PubChem CID

4994

ChemSpider

4820^Y

UNII

8AB20823CK

KEGG

D07329^Y

ChEMBL

ChEMBL1722501^N

CompTox Dashboard (EPA)

DTXSID4045262

ECHA InfoCard 100.000.910 Formula C₉H₁₃NO₂ Molar mass 167.208 g·mol⁻¹ 3D model (JSmol)

Interactive image

SMILES

O=C1N/C=C\C(=O)C1(CC)CC

InChI

InChI=1S/C9H13NO2/c1-3-9(4-2)7(11)5-6-10-8(9)12/h5-6H,3-4H2,1-2H3,(H,10,12)
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Key:NZASCBIBXNPDMH-UHFFFAOYSA-N
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^NY (what is this?) (verify)

Pyrithyldione^[1] (Presidon, Persedon) is a psychoactive drug invented in 1949.^[2] An improved method of manufacture was patented by Roche in 1959.^[3] It was used as a hypnotic or sedative and presumed to be less toxic than barbiturates.^[4] Today, this substance is no longer used. Agranulocytosis was sometimes reported as adverse effect.^[5]^[6] Pyrithyldione is also a CYP2D6 inducer but is not as potent as glutethimide.^[7] In studies, it increased the O-demethylation of codeine by 20%.

^ US Patent 2090068 - 2,4-Dioxo-3,3-Dialkyl-Tetrahydropyridines and Process for the Manufacture of Same.
^ Becker EL, Fabing HD, Hawkins JR (April 1949). "Presidon; a new sedative-hypnotic". Christ Hospital Medical Bulletin. 2 (4): 80–4. PMID 18144514.
^ US patent 3019230, Hinderling R, Lutz AH, Schnider O, "Method for the preparation of 2,4-dioxo-tetrahydropyridines", issued 1962-01-30, assigned to Hoffmann-La Roche
^ Pribilla, O. (1956). "Zur Toxikologie des Persedons". Archiv für Toxikologie. 16 (1): 34–49. doi:10.1007/BF00577351. S2CID 38210598.
^ Ibáñez L, Ballarín E, Pérez E, Vidal X, Capellà D, Laporte JR (January 2000). "Agranulocytosis induced by pyrithyldione, a sedative hypnotic drug". European Journal of Clinical Pharmacology. 55 (10): 761–4. doi:10.1007/s002280050011. PMID 10663456. S2CID 25595314.
^ Covner AH, Halpern SL (January 1950). "Fatal agranulocytosis following therapy with presidon (3,3-diethyl-2,4-dioxotetrahydropyridine) a new sedative hypnotic agent". The New England Journal of Medicine. 242 (2): 49–52. doi:10.1056/NEJM195001122420203. PMID 15399031.
^ [Is pyrithyldione (Benedorm) an enzyme inducer (author's transl)] Pharmazie. 1982 Jan;37(1):69.