Adinazolam
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| Systematic (IUPAC) name | |
| 1-(8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,5-a] [1,4]benzodiazepin-1-yl)-N,N-dimethylmethanamine |
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| 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  |
| ATC code | N05BA07 |
| PubChem | CID 37632 |
| DrugBank | DB00546 |
| ChemSpider | 34519 |
| UNII | KN08449444 |
| KEGG | D02770 |
| ChEBI | CHEBI:251412 |
| ChEMBL | CHEMBL328250 |
| Chemical data | |
| Formula | C19H18ClN5 |
| Mol. mass | 351.8 |
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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.
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Indications [edit]
Adinazolam is indicated as a treatment for anti-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]
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]
References [edit]
- ^ FR Patent 2248050
- ^ 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.
- ^ "Discovers Award 2004" (PDF). Special Publications. Pharmaceutical Research and Manufactureres of America. April 2004. p. 39. Archived from the original on August 24, 2006. Retrieved August 18, 2006.
- ^ Sethy, Vimala H.; R. J. Collins and 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.
- ^ 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.
- ^ Fraser, A. D.; A. F. Isner and 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.
- ^ Sethy, Vimala H.; Jonathan W. Francis and 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.
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