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Identification
NameAdinazolam
Accession NumberDB00546  (APRD00724)
TypeSmall Molecule
GroupsApproved
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. Adinazolam was never FDA approved and was never available to the public.

Structure
Thumb
Synonyms
SynonymLanguageCode
8-Chloro-1-((dimethylamino)methyl)-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepineNot AvailableNot Available
AdinazolamumLatinINN
SaltsNot Available
Brand names
NameCompany
DeracynUpjohn
Brand mixturesNot Available
Categories
CAS number37115-32-5
WeightAverage: 351.833
Monoisotopic: 351.125073308
Chemical FormulaC19H18ClN5
InChI KeyGJSLOMWRLALDCT-UHFFFAOYSA-N
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
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
SMILES
CN(C)CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzodiazepines
SubclassNot Available
Direct parentBenzodiazepines
Alternative parentsChlorobenzenes; Aryl Chlorides; Triazoles; Tertiary Amines; Polyamines; Organochlorides
Substituentschlorobenzene; aryl halide; aryl chloride; benzene; azole; 1,2,4-triazole; tertiary amine; polyamine; organochloride; organohalogen; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms).
Pharmacology
IndicationFor the treatment of anxiety and status epilepticus.
PharmacodynamicsAdinazolam 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.
Mechanism of actionAdinazolam binds to peripheral-type benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic. The main metabolite is N-desmethyladinazolam. The other two metabolites are alpha-hydroxyalprazolam and estazolam.

SubstrateEnzymesProduct
Adinazolam
desmethyladinazolamDetails
Adinazolam
Not Available
EstazolamDetails
Adinazolam
Not Available
alpha-HydroxyalprazolamDetails
Route of eliminationNot Available
Half lifeLess than 3 hours.
ClearanceNot Available
ToxicitySigns 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9382
Caco-2 permeable + 0.6532
P-glycoprotein substrate Substrate 0.666
P-glycoprotein inhibitor I Inhibitor 0.5
P-glycoprotein inhibitor II Inhibitor 0.942
Renal organic cation transporter Inhibitor 0.8284
CYP450 2C9 substrate Non-substrate 0.8375
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Substrate 0.7407
CYP450 1A2 substrate Inhibitor 0.6707
CYP450 2C9 substrate Inhibitor 0.5
CYP450 2D6 substrate Non-inhibitor 0.7089
CYP450 2C19 substrate Non-inhibitor 0.6787
CYP450 3A4 substrate Non-inhibitor 0.7326
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7718
Ames test Non AMES toxic 0.8085
Carcinogenicity Non-carcinogens 0.6543
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.6288 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9259
hERG inhibition (predictor II) Non-inhibitor 0.6971
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP4.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0672ALOGPS
logP2.57ALOGPS
logP2.24ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)6.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.31 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity112.31 m3·mol-1ChemAxon
Polarizability37.15 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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
  3. 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
ResourceLink
KEGG DrugD02770
PubChem Compound37632
PubChem Substance46509054
ChemSpider34519
ChEBI251412
ChEMBLCHEMBL328250
Therapeutic Targets DatabaseDAP001251
PharmGKBPA164783813
WikipediaAdinazolam
ATC CodesN05BA07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Gamma-aminobutyric acid receptor subunit alpha-1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-1 P14867 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

2. Gamma-aminobutyric acid receptor subunit alpha-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-2 P47869 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

3. Gamma-aminobutyric acid receptor subunit alpha-3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-3 P34903 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

4. Gamma-aminobutyric acid receptor subunit alpha-5

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-5 P31644 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

5. Gamma-aminobutyric acid receptor subunit gamma-1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit gamma-1 Q8N1C3 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

6. Gamma-aminobutyric acid receptor subunit gamma-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit gamma-2 P18507 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

7. Gamma-aminobutyric acid receptor subunit gamma-3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit gamma-3 Q99928 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

8. Gamma-aminobutyric acid receptor subunit beta-1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit beta-1 P18505 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

9. Gamma-aminobutyric acid receptor subunit beta-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit beta-2 P47870 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

10. Gamma-aminobutyric acid receptor subunit beta-3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit beta-3 P28472 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

11. Gamma-aminobutyric acid receptor subunit delta

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit delta O14764 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

12. Gamma-aminobutyric acid receptor subunit epsilon

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit epsilon P78334 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

13. Gamma-aminobutyric acid receptor subunit pi

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit pi O00591 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

14. Gamma-aminobutyric acid receptor subunit rho-1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit rho-1 P24046 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

15. Gamma-aminobutyric acid receptor subunit rho-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit rho-2 P28476 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

16. Gamma-aminobutyric acid receptor subunit rho-3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit rho-3 A8MPY1 Details

References:

  1. Lahti RA, Sethy VH, Barsuhn C, Hester JB: Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. Neuropharmacology. 1983 Nov;22(11):1277-82. Pubmed
  2. 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

Enzymes

1. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Application available online: The P450 Program
  2. Venkatakrishnan K, von Moltke LL, Duan SX, Fleishaker JC, Shader RI, Greenblatt DJ: Kinetic characterization and identification of the enzymes responsible for the hepatic biotransformation of adinazolam and N-desmethyladinazolam in man. J Pharm Pharmacol. 1998 Mar;50(3):265-74. Pubmed
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Venkatakrishnan K, von Moltke LL, Duan SX, Fleishaker JC, Shader RI, Greenblatt DJ: Kinetic characterization and identification of the enzymes responsible for the hepatic biotransformation of adinazolam and N-desmethyladinazolam in man. J Pharm Pharmacol. 1998 Mar;50(3):265-74. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on May 20, 2014 16:50