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Details

Stereochemistry ACHIRAL
Molecular Formula C17H12Cl2N4
Molecular Weight 343.21
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIAZOLAM

SMILES

CC1=NN=C2CN=C(C3=C(Cl)C=CC=C3)C4=C(C=CC(Cl)=C4)N12

InChI

InChIKey=JOFWLTCLBGQGBO-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C17H12Cl2N4
Molecular Weight 343.21
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Triazolam is a short-acting benzodiazepine used as a hypnotic agent in the treatment of insomnia. Some countries temporarily withdrew triazolam from the market because of concerns about adverse reactions, mostly psychological, associated with higher dose ranges. Its use at lower doses with appropriate care and labeling has been reaffirmed by the FDA and most other countries. Triazolam has a shorter half-life than chlordiazepoxide, flurazepam, and prazepam and does not generate active metabolites. Benzodiazepines bind nonspecifically to bezodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell. Triazolam is used for the short-term treatment of insomnia. Triazolam`s original brand name is Halcion. Triazolam is withdrawn in the United Kingdom due to risk of psychiatric adverse drug reactions. This drug continues to be available in the U.S. Internationally, triazolam is a Schedule IV drug under the Convention on Psychotropic Substances.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.8 nM [Ki]
0.59 nM [Ki]
0.8 nM [Ki]
1.43 nM [Ki]
1.54 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Halcion

Cmax

ValueDoseCo-administeredAnalytePopulation
3.75 ng/mL
0.25 mg single, oral
TRIAZOLAM plasma
Homo sapiens
4.39 ng/mL
0.25 mg single, oral
TRIAZOLAM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
13.05 ng × h/mL
0.25 mg single, oral
TRIAZOLAM plasma
Homo sapiens
13.78 ng × h/mL
0.25 mg single, oral
TRIAZOLAM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4.07 h
0.25 mg single, oral
TRIAZOLAM plasma
Homo sapiens
2.27 h
0.25 mg single, oral
TRIAZOLAM plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended dose for most adults is 0.25 mg before retiring. A dose of 0.125 mg may be found to be sufficient for some patients (e.g., low body weight). A dose of 0.5 mg should be used only for exceptional patients who do not respond adequately to a trial of a lower dose since the risk of several adverse reactions increases with the size of the dose administered. A dose of 0.5 mg should not be exceeded.
Route of Administration: Oral
In Vitro Use Guide
Triazolam inhibited [3H]flunitrazepam binding with an IC50 value of 0.85 nM and a Ki value of 0.50 nM in mice.
Substance Class Chemical
Record UNII
1HM943223R
Record Status Validated (UNII)
Record Version