Adinazolam

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Adinazolam
Adinazolam.svg
Adinazolam3d.png
Systematic (IUPAC) name
1-(8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,5-a]
[1,4]benzodiazepin-1-yl)-N,N-dimethylmethanamine
Clinical data
Pregnancy cat. ?
Legal status Schedule IV(US)
Routes Oral
Pharmacokinetic data
Bioavailability ?
Metabolism Hepatic
Half-life < 3 hours
Excretion Renal
Identifiers
CAS number 37115-32-5 YesY
ATC code N05BA07
PubChem CID 37632
DrugBank DB00546
ChemSpider 34519 YesY
UNII KN08449444 YesY
KEGG D02770 YesY
ChEBI CHEBI:251412 YesY
ChEMBL CHEMBL328250 YesY
Chemical data
Formula C19H18ClN5 
Mol. mass 351.8
 YesY (what is this?)  (verify)

Adinazolam[1] (marketed under the brand name Deracyn) is a benzodiazepine derivative, and more specifically, a triazolobenzodiazepine (TBZD). It possesses anxiolytic, anticonvulsant, sedative, and antidepressant[2] properties. Adinazolam was developed by Dr. Jackson B. Hester, who was seeking to enhance the antidepressant properties of alprazolam, which he also developed.[3] Adinazolam was never FDA approved and never made available to the public market.

Indications[edit]

Adinazolam is indicated as a treatment for depression and anxiety.

Pharmacodynamics and pharmacokinetics[edit]

Adinazolam binds to peripheral-type benzodiazepine receptors that interact allosterically with GABA receptors as an agonist to produce inhibitory effects.

Metabolism[edit]

Adinazolam was reported to have active metabolites in the August 1984 issue of The Journal of Pharmacy and Pharmacology.[4] The main metabolite is N-desmethyladinazolam.[5] NDMAD has an approximately 25-fold high affinity for benzodiazepine receptors as compared to its precursor, accounting for the benzodiazepine-like effects after oral administration. (REF1) Multiple N-dealkylations lead to the removal dimethyl-aminoethyl side chain, leading to the difference in its potency. (REF5) The other two metabolites are alpha-hydroxyalprazolam and estazolam.[6] In the August 1986 issue of that same journal, Sethy, Francis and Day reported that proadifen inhibited the formation of N-desmethyladinazolam.[7]

Chemistry[edit]

Adinazolam Rx.png

Hester, J. B.; Rudzik, A. D.; Von Voigtlander, P. F.; J. Med. Chem. 1980, 23, 392.

http://dx.doi.org/10.1021/jm00178a009

See also[edit]

Alprazolam

References[edit]

  1. ^ FR Patent 2248050
  2. ^ Lahti, Robert A.; Vimala H. Sethy; Craig Barsuhn; Jackson B. Hester (November 1983). "Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine.". Neuropharmacology 22 (11): 1277–82. doi:10.1016/0028-3908(83)90200-9. PMID 6320036. 
  3. ^ "Discovers Award 2004" (PDF). Special Publications. Pharmaceutical Research and Manufacturers of America. April 2004. p. 39. Archived from the original on August 24, 2006. Retrieved August 18, 2006. 
  4. ^ Sethy, Vimala H.; R. J. Collins; E. G. Daniels (August 1984). "Determination of biological activity of adinazolam and its metabolites.". Journal of Pharmacy and Pharmacology 36 (8): 546–8. doi:10.1111/j.2042-7158.1984.tb04449.x. PMID 6148400. 
  5. ^ Peng, G. W. (August 1984). "Assay of adinazolam in plasma by liquid chromatography". Journal of Pharmaceutical Sciences 73 (8): 1173–5. doi:10.1002/jps.2600730840. PMID 6491930. 
  6. ^ Fraser, A. D.; A. F. Isner; W. Bryan (November–December 1993). "Urinary screening for adinazolam and its major metabolites by the Emit d.a.u. and FPIA benzodiazepine assays with confirmation by HPLC". Journal of Analytical Toxicology 17 (7): 427–31. PMID 8309217. 
  7. ^ Sethy, Vimala H.; Jonathan W. Francis; J. S. Day (August 1986). "The effect of proadifen on the metabolism of adinazolam". Journal of Pharmacy and Pharmacology 38 (8): 631–2. doi:10.1111/j.2042-7158.1986.tb03099.x. PMID 2876087.