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Details

Stereochemistry ACHIRAL
Molecular Formula C17H12Cl2N4O
Molecular Weight 359.209
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-HYDROXYTRIAZOLAM

SMILES

OCC1=NN=C2CN=C(C3=CC=CC=C3Cl)C4=CC(Cl)=CC=C4N12

InChI

InChIKey=BHUYWUDMVCLHND-UHFFFAOYSA-N
InChI=1S/C17H12Cl2N4O/c18-10-5-6-14-12(7-10)17(11-3-1-2-4-13(11)19)20-8-15-21-22-16(9-24)23(14)15/h1-7,24H,8-9H2

HIDE SMILES / InChI

Molecular Formula C17H12Cl2N4O
Molecular Weight 359.209
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

a-Hydroxytriazolam is a major urinary and blood metabolite of the benzodiazepine, triazolam, a pharmaceutical used to treat severe insomnia. It is suitable for use in LC/MS or GC/MS applications for clinical toxicology, forensic analysis, urine drug testing, or pharmaceutical research. Triazolam is a triazolobenzodiazepine with hypnotic properties, advocated for use in acute or chronic insomnia, situational insomnia in hospitalised patients, and insomnia associated with other disease states. As triazolam has a relatively short half-life of about 2 to 3 hours in healthy subjects and has only 1 short acting active metabolite, alpha-hydroxytriazolam. a-Hydroxytriazolam is reported to have 50 to 100 % of the pharmacological activity of the parent compound. Triazolam (marketed in English-speaking countries under the brand names Apo-Triazo, Halcion, Hypam, and Trilam) is a benzodiazepine drug. It possesses pharmacological properties similar to that of other benzodiazepines, but it is generally only used as a sedative to treat severe insomnia. In addition to the hypnotic properties triazolam possesses, amnesic, anxiolytic, sedative, anticonvulsant and muscle relaxant properties are also present.

CNS Activity

Curator's Comment: a-Hydroxytriazolam is an active but short-lived metabolite of triazolam http://www.enzolifesciences.com/BML-J130/alpha-hydroxytriazolam/

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Halcion

Approved Use

Halcion 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 Date

1982
PubMed

PubMed

TitleDatePubMed
Urinary excretion of alpha-hydroxytriazolam following a single dose of halcion.
2005 Mar
Urinary excretion profiles of two major triazolam metabolites, alpha-hydroxytriazolam and 4-hydroxytriazolam.
2005 May-Jun
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: a-Hydroxytriazolam is an active metabolite of triazolam
Usual hypnotic doses of triazolam 0.25 or 0.5 mg per day
Route of Administration: Oral
The incubation mixture contained triazolam (substrate concentration: 0–250 nM; therapeutic level 6–60 nM, toxic level 120 nM, fatal level 200–300 nM) in a total volume of 0.5 ml. Incubations were carried out in microsomes from three pooled human livers t for 20 min in a shaking water-bath at 37 C.
Substance Class Chemical
Created
by admin
on Sat Dec 16 13:58:24 GMT 2023
Edited
by admin
on Sat Dec 16 13:58:24 GMT 2023
Record UNII
J53Y2M2SAH
Record Status Validated (UNII)
Record Version
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Name Type Language
.ALPHA.-HYDROXYTRIAZOLAM
Common Name English
1'-HYDROXYTRIAZOLAM
Common Name English
4H-(1,2,4)TRIAZOLO(4,3-A)(1,4)BENZODIAZEPINE-1-METHANOL, 8-CHLORO-6-(2-CHLOROPHENYL)-
Systematic Name English
8-CHLORO-6-(O-CHLOROPHENYL)-4H-S-TRIAZOLO(4,3-A)(1,4)BENZODIAZEPIN-1-METHANOL
Systematic Name English
Code System Code Type Description
PUBCHEM
1963
Created by admin on Sat Dec 16 13:58:24 GMT 2023 , Edited by admin on Sat Dec 16 13:58:24 GMT 2023
PRIMARY
CAS
37115-45-0
Created by admin on Sat Dec 16 13:58:24 GMT 2023 , Edited by admin on Sat Dec 16 13:58:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID50958284
Created by admin on Sat Dec 16 13:58:24 GMT 2023 , Edited by admin on Sat Dec 16 13:58:24 GMT 2023
PRIMARY
FDA UNII
J53Y2M2SAH
Created by admin on Sat Dec 16 13:58:24 GMT 2023 , Edited by admin on Sat Dec 16 13:58:24 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Major urine metabolite (50-100% active)
URINE