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
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
| Molecular Formula | C17H12Cl2N4 |
| Molecular Weight | 343.21 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00897Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/017892s038lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00897
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/017892s038lbl.pdf
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 Triazolam is withdrawn in the United Kingdom due to risk of psychiatric adverse drug reactions.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 Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 0.8 nM [Ki] | |||
Target ID: CHEMBL2094130 |
0.59 nM [Ki] | ||
Target ID: CHEMBL2094121 |
0.8 nM [Ki] | ||
Target ID: CHEMBL2094120 |
1.43 nM [Ki] | ||
Target ID: CHEMBL2094122 |
1.54 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Halcion Approved UseHalcion is indicated for the short-term treatment of insomnia (generally 7–10 days). Use for more than 2–3 weeks requires complete reevaluation of the patient Launch Date4.06079996E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.75 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8275618/ |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAZOLAM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.39 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8275618/ |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAZOLAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
13.05 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8275618/ |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAZOLAM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
13.78 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8275618/ |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAZOLAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.07 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8275618/ |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAZOLAM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.27 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8275618/ |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAZOLAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
3 mg single, oral Highest studied dose |
unhealthy, 21 - 60 years n = 2 Health Status: unhealthy Condition: insomnia Age Group: 21 - 60 years Sex: M Population Size: 2 Sources: |
Disc. AE: Ataxia, Drowsiness... AEs leading to discontinuation/dose reduction: Ataxia (1 patient) Sources: Drowsiness (1 patient) |
0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
Disc. AE: Coordination abnormal, Drowsiness... AEs leading to discontinuation/dose reduction: Coordination abnormal Sources: Drowsiness Groggy Somnolence Depression Restlessness Dizziness Lightheadedness Headache Nausea Visual disturbance Nervousness Abdominal distress Bladder disorders NEC Aching in limb Backache Blepharitis |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Ataxia | 1 patient Disc. AE |
3 mg single, oral Highest studied dose |
unhealthy, 21 - 60 years n = 2 Health Status: unhealthy Condition: insomnia Age Group: 21 - 60 years Sex: M Population Size: 2 Sources: |
| Drowsiness | 1 patient Disc. AE |
3 mg single, oral Highest studied dose |
unhealthy, 21 - 60 years n = 2 Health Status: unhealthy Condition: insomnia Age Group: 21 - 60 years Sex: M Population Size: 2 Sources: |
| Abdominal distress | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Aching in limb | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Backache | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Bladder disorders NEC | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Blepharitis | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Coordination abnormal | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Depression | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Dizziness | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Drowsiness | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Groggy | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Headache | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Lightheadedness | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Nausea | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Nervousness | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Restlessness | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Somnolence | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
| Visual disturbance | Disc. AE | 0.25 mg 1 times / day steady, oral Recommended Dose: 0.25 mg, 1 times / day Route: oral Route: steady Dose: 0.25 mg, 1 times / day Sources: |
unhealthy n = 1003 Health Status: unhealthy Condition: insomnia Population Size: 1003 Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| yes | ||||
| yes | yes (co-administration study) Comment: contraindicated with strong CYP3A inhibitors such as ketoconazole, itraconazole, nefazodone, ritonavir, indinavir, nelfinavir, saquinavir, and lopinavir; from 2019 label: grapefruit juice increased maximum plasma concentration of triazolam by 25% and increased AUC by 48% Page: 7.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cytochrome P450 3A4 in vivo ketoconazole competitive inhibition: determination of Ki and dangers associated with high clearance drugs in general. | 1999 May-Aug |
|
| Pharmacophore/receptor models for GABA(A)/BzR subtypes (alpha1beta3gamma2, alpha5beta3gamma2, and alpha6beta3gamma2) via a comprehensive ligand-mapping approach. | 2000 Jan 13 |
|
| Topological alteration of the CYP3A4 active site by the divalent cation Mg(2+). | 2000 Oct |
|
| Triazolam substrate inhibition: evidence of competition for heme-bound reactive oxygen within the CYP3A4 active site. | 2001 |
|
| Brain glycine levels in triazolam-treated albino rats. | 2001 |
|
| Zolpidem, triazolam, and diazepam decrease distress vocalizations in mouse pups: differential antagonism by flumazenil and beta-Carboline-3-carboxylate-t-butyl ester (beta-CCt). | 2001 Apr |
|
| Triazolam substrate inhibition: evidence of competition for heme-bound reactive oxygen within the CYP3A4 active site. | 2001 Jan |
|
| Covalent alteration of the CYP3A4 active site: evidence for multiple substrate binding domains. | 2001 Jul 1 |
|
| Sleep inducing effects of propofol microinjection into the medial preoptic area are blocked by flumazenil. | 2001 Jul 27 |
|
| The hypnotic effect of propofol in the medial preoptic area of the rat. | 2001 Jul 6 |
|
| Benzodiazepines as a social problem: the case of halcion. | 2001 Jul-Aug |
|
| A double-blind, randomized and placebo-controlled study on the polysomnographic withdrawal effects of zopiclone, zolpidem and triazolam in healthy subjects. | 2001 Jun |
|
| Hypnotic action of melatonin during daytime administration and its comparison with triazolam. | 2001 Jun |
|
| Pharmacokinetics and clinical effects of sublingual triazolam in pediatric dental patients. | 2001 Jun |
|
| Behavioral effects of flunitrazepam: reinforcing and discriminative stimulus effects in rhesus monkeys and prevention of withdrawal signs in pentobarbital-dependent rats. | 2001 Jun 1 |
|
| Investigation of preference for nightly triazolam versus placebo in moderate social alcohol drinkers. | 2001 Mar |
|
| CYP3A inductive potential of the rifamycins, rifabutin and rifampin, in the rabbit. | 2001 May |
|
| Circadian phase shifting: Relationships between photic and nonphotic phase-response curves. | 2001 May |
|
| Functional pharmacology of GABA(A) receptors containing the chicken brain gamma 4 subunit. | 2001 May 4 |
|
| Isobolographic analysis of chlordiazepoxide and triazolam combinations in squirrel monkeys discriminating triazolam. | 2001 Nov |
|
| The hypnotic actions of the fatty acid amide, oleamide. | 2001 Nov |
|
| Effects of triazolam on brain activity during episodic memory encoding: a PET study. | 2001 Nov |
|
| Effect of methylprednisolone on CYP3A4-mediated drug metabolism in vivo. | 2001 Sep |
|
| Sensitive method for the detection of 22 benzodiazepines by gas chromatography-ion trap tandem mass spectrometry. | 2002 Apr 19 |
|
| [Pharmacological profile and clinical effect of zolpidem (Myslee tablets), a hypnotic agent]. | 2002 Feb |
|
| Distribution of triazolam and alpha-hydroxytriazolam in a fatal intoxication case. | 2002 Jan-Feb |
|
| Daily treatment with diazepam differentially modifies sensitivity to the effects of gamma-aminobutyric acid(A) modulators on schedule-controlled responding in rhesus monkeys. | 2002 Mar |
|
| Effects of endogenous steroids on CYP3A4-mediated drug metabolism by human liver microsomes. | 2002 May |
|
| Disposition of triazolam in the rat by brain microdialysis and semi-micro column high-performance liquid chromatography with UV absorbance detection. | 2002 May |
|
| Effects of triazolam, 8-OH-DPAT, and buspirone on repeated acquisition in squirrel monkeys. | 2002 Nov |
|
| Transnational industrial power, the medical profession and the regulatory state: adverse drug reactions and the crisis over the safety of Halcion in the Netherlands and the UK. | 2002 Nov |
|
| Interactions between recreational drugs and antiretroviral agents. | 2002 Oct |
|
| Comparison of the effects of zaleplon, zolpidem, and triazolam at various GABA(A) receptor subtypes. | 2002 Sep 13 |
|
| Melatonin microinjection into the medial preoptic area increases sleep in the rat. | 2002 Sep 13 |
|
| Pharmacokinetic interactions with rifampicin : clinical relevance. | 2003 |
|
| [Cytochrome P450 3A4 and Benzodiazepines]. | 2003 |
|
| Clinically important drug interactions with zopiclone, zolpidem and zaleplon. | 2003 |
|
| Clinical pharmacokinetic profile of modafinil. | 2003 |
|
| Discriminative-stimulus effects of triazolam in light and moderate drinkers. | 2003 Apr |
|
| A study into the rate of incorporation of eight benzodiazepines into rat hair. | 2003 Apr 23 |
|
| [Diagnostics and treatment of sleep disorders in elderly people]. | 2003 Apr-Jun |
|
| Semi-micro column HPLC of triazolam in rat plasma and brain microdialysate and its application to drug interaction study with itraconazole. | 2003 Jan 15 |
|
| Effects of short-acting hypnotics on sleep latency in rats placed on grid suspended over water. | 2003 Jan 24 |
|
| In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5. | 2003 Jul |
|
| Comparative abuse liability and pharmacological effects of meprobamate, triazolam, and butabarbital. | 2003 Jun |
|
| Selective effects of triazolam on memory for emotional, relative to neutral, stimuli: differential effects on gist versus detail. | 2003 Jun |
|
| Role of platelet activating factor in triazolobenzodiazepines-induced retrograde amnesia. | 2003 Jun 16 |
|
| Apparent mechanism-based inhibition of human CYP3A in-vitro by lopinavir. | 2003 Mar |
|
| Anxiolysis in general dental practice. | 2003 Mar |
|
| Triazolam-amphetamine interaction: dissociation of effects on memory versus arousal. | 2003 Mar |
Sample Use Guides
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:53:18 UTC 2023
by
admin
on
Wed Jul 05 22:53:18 UTC 2023
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| Record UNII |
1HM943223R
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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WHO-VATC |
QN05CD05
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NDF-RT |
N0000007542
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NCI_THESAURUS |
C1012
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NDF-RT |
N0000175694
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LIVERTOX |
NBK547843
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DEA NO. |
2887
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WHO-ATC |
N05CD05
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| Code System | Code | Type | Description | ||
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1HM943223R
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PRIMARY | |||
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6759
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2729
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DB00897
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DTXSID6046763
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M11035
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100000092518
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249-307-3
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TRIAZOLAM
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CHEMBL646
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5556
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28911-01-5
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3409
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D014229
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10767
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7313
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Triazolam
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1680506
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C29520
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9674
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SUB11258MIG
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1HM943223R
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BINDING
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