TRIAZOLAM

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC N05CD05
UNII 1HM943223R
EPA CompTox DTXSID6046763

Structure

InChI Key JOFWLTCLBGQGBO-UHFFFAOYSA-N
Smiles Cc1nnc2n1-c1ccc(Cl)cc1C(c1ccccc1Cl)=NC2
InChI
InChI=1S/C17H12Cl2N4/c1-10-21-22-16-9-20-17(12-4-2-3-5-14(12)19)13-8-11(18)6-7-15(13)23(10)16/h2-8H,9H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H12Cl2N4
Molecular Weight 343.22
AlogP 4.23
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 1.0
Polar Surface Area 43.07
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 23.0

Bioactivity

Mechanism of Action Action Reference
GABA-A receptor; anion channel positive allosteric modulator POSITIVE ALLOSTERIC MODULATOR FDA ISBN
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit pi
Organism : Homo sapiens
O00591 ENSG00000094755
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit delta
Organism : Homo sapiens
O14764 ENSG00000187730
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-1
Organism : Homo sapiens
P14867 ENSG00000022355
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-1
Organism : Homo sapiens
P18505 ENSG00000163288
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-2
Organism : Homo sapiens
P18507 ENSG00000113327
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-3
Organism : Homo sapiens
P28472 ENSG00000166206
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-5
Organism : Homo sapiens
P31644 ENSG00000186297
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-3
Organism : Homo sapiens
P34903 ENSG00000011677
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-2
Organism : Homo sapiens
P47869 ENSG00000151834
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-2
Organism : Homo sapiens
P47870 ENSG00000145864
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-4
Organism : Homo sapiens
P48169 ENSG00000109158
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit epsilon
Organism : Homo sapiens
P78334 ENSG00000102287
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-6
Organism : Homo sapiens
Q16445 ENSG00000145863
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-1
Organism : Homo sapiens
Q8N1C3 ENSG00000163285
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-3
Organism : Homo sapiens
Q99928 ENSG00000182256
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit theta
Organism : Homo sapiens
Q9UN88 ENSG00000268089
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Ligand-gated ion channel GABA-A receptor
- - 1 1-2086 -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Cholecystokinin receptor
- 39000 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) PAF receptor
- 11100 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - -
Assay Description Organism Bioactivity Reference
Binding affinity for Diazepam sensitive (DS) isoform of the benzodiazepine (Bz) binding site on GABAA receptors None 0.8 nM
Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-1-beta-3-gamma-2 None 0.8 nM
Binding affinity to human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-2-beta-3-gamma-2 None 0.59 nM
Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-3-beta-3-gamma-2 None 1.43 nM
Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-5-beta-3-gamma-2 None 1.54 nM
Binding affinity to GABAA alpha-1-beta-2-gamma-2 receptor None 1.0 nM
Binding affinity to GABAA alpha-5-beta-2-gamma-2 receptor None 4.0 nM
Displacement of [3H]flunitrazepam from GABAA benzodiazepine receptor in rat brain membrane Rattus norvegicus 1.54 nM
Inhibition of CYP3A activity in orally dosed human Homo sapiens 95.0 %
Allosteric modulation of gamma-aminobutyric acid receptor A alpha1beta2gamma2S expressed in Xenopus oocytes assessed as potentiation of GABA-mediated chloride current by voltage clamp analysis None 22.0 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 45.7 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 18.7 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens -20.5 %

Related Entries

Cross References

Resources Reference
ChEBI 9674
ChEMBL CHEMBL646
DrugBank DB00897
DrugCentral 2729
FDA SRS 1HM943223R
Human Metabolome Database HMDB0015034
Guide to Pharmacology 7313
KEGG D00387
PharmGKB PA451753
PubChem 5556
SureChEMBL SCHEMBL29228
ZINC ZINC000000002212
CONTENTS