Pyrithyldione

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%.

Pyrithyldione
Clinical data
Trade namesBenedorm, Didropyridine, Dihydroprylone, Persedon, Presidon, Pyridion, Pyridione, Pyrithyldion, Pyrithyldione, Tetridin, Tetridine
ATC code
Identifiers
IUPAC name
  • 3,3-diethylpyridine-2,4(1H,3H)-dione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.910
Chemical and physical data
FormulaC9H13NO2
Molar mass167.208 g·mol−1
3D model (JSmol)
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) Y
  • Key:NZASCBIBXNPDMH-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

See also

References
  1. US Patent 2090068 - 2,4-Dioxo-3,3-Dialkyl-Tetrahydropyridines and Process for the Manufacture of Same.
  2. Becker EL, Fabing HD, Hawkins JR (April 1949). "Presidon; a new sedative-hypnotic". Christ Hospital Medical Bulletin. 2 (4): 80–4. PMID 18144514.
  3. 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
  4. Pribilla, O. (1956). "Zur Toxikologie des Persedons". Archiv für Toxikologie. 16 (1): 34–49. doi:10.1007/BF00577351. S2CID 38210598.
  5. 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.
  6. 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.
  7. [Is pyrithyldione (Benedorm) an enzyme inducer (author's transl)] Pharmazie. 1982 Jan;37(1):69.
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