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Alprazolam triazolobenzophenone

From Wikipedia, the free encyclopedia
Alprazolam prodrug
Pharmaceutical compound
Alprazolam triazolobenzophenone
Identifiers
  • {2-[3-(Aminomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-5-chlorophenyl}(phenyl)methanone
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC17H15ClN4O
Molar mass326.78 g·mol−1
3D model (JSmol)
  • CC1=NN=C(N1C2=C(C=C(C=C2)Cl)C(=O)C3=CC=CC=C3)CN
  • InChI=1S/C17H15ClN4O/c1-11-20-21-16(10-19)22(11)15-8-7-13(18)9-14(15)17(23)12-5-3-2-4-6-12/h2-9H,10,19H2,1H3
  • Key:WWADXOXMCNJJKR-UHFFFAOYSA-N

Alprazolam triazolobenzophenone is a chemical compound that is aprodrug for thebenzodiazepine derivativealprazolam. At neutral pH it readily cyclizes to alprazolam, while in acidic conditions alprazolam undergoes a ring-opening reaction back to the ketone. A series of relatedacyl derivatives was researched in the 1980s as injectable water-soluble prodrugs of alprazolam,[1] but were never developed for medical use. Subsequently, this compound has been detected as adesigner drug, first being identified from a seizure in Spain in March 2014.[2]

See also

[edit]

References

[edit]
  1. ^Cho MJ, Sethy VH, Haynes LC (August 1986). "Sequentially labile water-soluble prodrugs of alprazolam".Journal of Medicinal Chemistry.29 (8):1346–50.doi:10.1021/jm00158a004.PMID 3016261.
  2. ^"Novel Benzodiazepines. A review of the evidence of use and harms of Novel Benzodiazepines"(PDF). Advisory Council on the Misuse of Drugs. April 2020.
1,4-Benzodiazepines
1,5-Benzodiazepines
2,3-Benzodiazepines*
Triazolobenzodiazepines
Imidazobenzodiazepines
Oxazolobenzodiazepines
Thienodiazepines
Thienotriazolodiazepines
Thienobenzodiazepines*
Pyridodiazepines
Pyridotriazolodiazepines
Pyrazolodiazepines
Pyrrolodiazepines
Tetrahydroisoquinobenzodiazepines
Pyrrolobenzodiazepines*
Benzodiazepine prodrugs
* atypical activity profile (notGABAA receptor ligands)
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