({12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl}methyl)dimethylamine

• ChemBase ID: 428
• Molecular Formular: C19H18ClN5
• Molecular Mass: 351.83272
• Monoisotopic Mass: 351.12507328
• SMILES: Clc1cc2c(n3c(nnc3CN=C2c2ccccc2)CN(C)C)cc1
• Canonical SMILES: CN(Cc1nnc2n1c1ccc(cc1C(=NC2)c1ccccc1)Cl)C
• InChI: InChI=1S/C19H18ClN5/c1-24(2)12-18-23-22-17-11-21-19(13-6-4-3-5-7-13)15-10-14(20)8-9-16(15)25(17)18/h3-10H,11-12H2,1-2H3
• InChIKey: GJSLOMWRLALDCT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl}methyl)dimethylamine
• IUPAC Traditional name: deracyn
• Brand Name: Deracyn
• Synonyms: Adinazolamum [INN-Latin]; Adinazolam

Database IDs

• CAS Number: 37115-32-5
• PubChem SID: 46509054; 160963891
• PubChem CID: 37632

CALCULATED PROPERTIES

ALOGPS 2.1

• LOG S: -3.72
• Solubility (Water): 6.72e-02 g/l
• Log P: 2.57

JChem

• Molar Refractivity: 112.308 cm^3
• Polarizability: 38.688606 Å^3
• Polar Surface Area: 46.31 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 18.384146
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.3425525
• LogD (pH = 7.4): 1.3221885
• Log P: 2.2407

PROPERTIES

Physical Property

• Hydrophobicity(logP): 4.4

DETAILS

DrugBank - DB00546

• Drug Groups: approved
• Description: Adinazolam (Deracyn?) is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative, and antidepressant properties. Adinazolam was developed by Dr. Jackson B. Hester, who was seeking to enhance the antidepressant properties of alprazolam, which he also developed.
• Indication: For the treatment of anxiety and status epilepticus.
• Pharmacology: Adinazolam is a benzodiazepine derivative used to treat anxiety, status epilepticus, and for sedation induction and anterograde amnesia. Adinazolam binds with high affinity to the GABA benzodiazepine receptor complex. Considerable evidence suggest that the central pharmacologic/therapeutic actions of alprazolam are mediated via interaction with this receptor complex.
• Toxicity: Signs of overdose may include muscle weakness, ataxia, dysarthria and particularly in children paradoxical excitement. In more severe cases diminished reflexes, confusion, and coma may ensue.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. The main metabolite is N-desmethyladinazolam. The other two metabolites are alpha-hydroxyalprazolam and estazolam.
• Half Life: Less than 3 hours.
• References: Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. [Pubmed] ; Sethy VH, Collins RJ, Daniels EG: Determination of biological activity of adinazolam and its metabolites. J Pharm Pharmacol. 1984 Aug;36(8):546-8. [Pubmed] ; File SE, Pellow S: Triazolobenzodiazepines antagonize the effects of anxiogenic drugs mediated at three different central nervous system sites. Neurosci Lett. 1985 Oct 24;61(1-2):115-9. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
• Sethy VH, Collins RJ, Daniels EG: Determination of biological activity of adinazolam and its metabolites. J Pharm Pharmacol. 1984 Aug;36(8):546-8. Pubmed
• File SE, Pellow S: Triazolobenzodiazepines antagonize the effects of anxiogenic drugs mediated at three different central nervous system sites. Neurosci Lett. 1985 Oct 24;61(1-2):115-9. Pubmed