Compounds > 4-hydroxyalprazolam
Page last updated: 2024-12-08

4-hydroxyalprazolam

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-hydroxyalprazolam: alprazolam metabolite [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID182017
CHEMBL ID1313
CHEBI ID183714
SCHEMBL ID10891720
MeSH IDM0488424

Synonyms (20)

Synonym
4-hydroxyalprazolam
4-hydroxy-alprazolam(0.3%)
CHEMBL1313
CHEBI:183714
30896-57-2
8-chloro-1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-ol
unii-u0com4319x
rs-4-hydroxyalprazolam
4h-(1,2,4)triazolo(4,3-a)(1,4)benzodiazepin-4-ol, 8-chloro-1-methyl-6-phenyl-
u0com4319x ,
SCHEMBL10891720
8-chloro-1-methyl-6-phenyl-4h-(1,2,4)triazolo(4,3-a)(1,4)benzodiazepin-4-ol
(z)-8-chloro-1-methyl-6-phenyl-4h-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepin-4-ol
4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-ol, 8-chloro-1-methyl-6-phenyl-
DTXSID90932240
4-hydroxyalprazolam; rs-4-hydroxyalprazolam
4-hydroxy alprazolam
Q27290520
PD018226
4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-ol,8-chloro-1-methyl-6-phenyl-

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"(1) To determine the pharmacokinetic parameters of alprazolam and its two metabolites in plasma from healthy volunteers; (2) to identify a suitable single time point to take a plasma sample for CYP3A phenotyping."( Alprazolam as a probe for CYP3A using a single blood sample: pharmacokinetics of parent drug, and of alpha- and 4-hydroxy metabolites in healthy subjects.
Allqvist, A; Bertilsson, L; Gustafsson, LL; Mirghani, RA; Svensson, JO; Wennerholm, A, 2005)		0.33

Dosage Studied

ExcerptRelevanceReference
" If confirmed, this could have major implications for drug dosing in persistently inflamed patients."( Metabolism of alprazolam (a marker of CYP3A4) in hemodialysis patients with persistent inflammation.
Bertilsson, L; Carrero, JJ; Diczfalusy, U; Heimbürger, O; Lindholm, B; Molanaei, H; Odar-Cederlöf, I; Qureshi, AR; Stenvinkel, P, 2012)		0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
triazolobenzodiazepineAny organic heterotricyclic compound that is any benzodiazepine which is ortho-fused with a triazole.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID112344Evaluated for the pentylene induced clonic convulsions (P) in CF1 mice1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
8-Chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines with substituents at C-4.
AID1136387Effect on motor activity in ip dosed albino CF-1 mouse by traction test1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Pharmacology of some metabolites of triazolam, alprazolam, and diazepam prepared by a simple, one-step oxidation of benzodiazepines.
AID112334Evaluated for antagonistic activity on nicotine-induced tonic-extensor convulsions (TE) in CF1 mice1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
8-Chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines with substituents at C-4.
AID1136392Anticonvulsant activity in ip dosed albino CF-1 mouse assessed as inhibition of pentylenetetrazole-induced seizures1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Pharmacology of some metabolites of triazolam, alprazolam, and diazepam prepared by a simple, one-step oxidation of benzodiazepines.
AID113897Loss of traction (TR) was evaluated in CF1 mice1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
8-Chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines with substituents at C-4.
AID1136389Effect on motor activity in ip dosed albino CF-1 mouse by dish test1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Pharmacology of some metabolites of triazolam, alprazolam, and diazepam prepared by a simple, one-step oxidation of benzodiazepines.
AID1136394Anticonvulsant activity in ip dosed albino CF-1 mouse assessed as inhibition of strychnine-induced seizures1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Pharmacology of some metabolites of triazolam, alprazolam, and diazepam prepared by a simple, one-step oxidation of benzodiazepines.
AID1136388Effect on motor activity in ip dosed albino CF-1 mouse by chimney test1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Pharmacology of some metabolites of triazolam, alprazolam, and diazepam prepared by a simple, one-step oxidation of benzodiazepines.
AID113894Loss of righting reflex (LORR) was evaluated in CF1 mice1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
8-Chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines with substituents at C-4.
AID1136393Anticonvulsant activity in ip dosed albino CF-1 mouse assessed as inhibition of thiosemicarbazide-induced seizures1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Pharmacology of some metabolites of triazolam, alprazolam, and diazepam prepared by a simple, one-step oxidation of benzodiazepines.
AID1136395Anticonvulsant activity in ip dosed albino CF-1 mouse assessed as inhibition of maximal electric shock-induced seizures1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Pharmacology of some metabolites of triazolam, alprazolam, and diazepam prepared by a simple, one-step oxidation of benzodiazepines.
AID112343Evaluated for the antagonism of nicotine induced death (D) in CF1 mice1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
8-Chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines with substituents at C-4.
AID1136390Effect on motor activity in ip dosed albino CF-1 mouse by pedestal test1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Pharmacology of some metabolites of triazolam, alprazolam, and diazepam prepared by a simple, one-step oxidation of benzodiazepines.
AID1136397Anxiolytic activity in ip dosed albino CF-1 mouse under hypoxic stress1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Pharmacology of some metabolites of triazolam, alprazolam, and diazepam prepared by a simple, one-step oxidation of benzodiazepines.
AID1136396Antidepressant activity in ip dosed albino CF-1 mouse assessed as inhibition of ethanol-induced response1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Pharmacology of some metabolites of triazolam, alprazolam, and diazepam prepared by a simple, one-step oxidation of benzodiazepines.
AID1136391Anticonvulsant activity in ip dosed albino CF-1 mouse assessed as inhibition of nicotine-induced seizures1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Pharmacology of some metabolites of triazolam, alprazolam, and diazepam prepared by a simple, one-step oxidation of benzodiazepines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (28.57)18.7374
1990's0 (0.00)18.2507
2000's3 (42.86)29.6817
2010's1 (14.29)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.32

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.32 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.21 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.32)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (14.29%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
alpha-hydroxytriazolam
alpha-hydroxytriazolam: triazolam metabolite; structure in first source		1.9510triazolobenzodiazepine
alprazolam
Alprazolam: A triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of PANIC DISORDERS, with or without AGORAPHOBIA, and in generalized ANXIETY DISORDERS. (From AMA Drug Evaluations Annual, 1994, p238). alprazolam : A member of the class of triazolobenzodiazepines that is 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine carrying methyl, phenyl and chloro substituents at positions 1, 6 and 8 respectively. Alprazolam is only found in individuals that have taken this drug.		4.7871organochlorine compound;
triazolobenzodiazepine		anticonvulsant;
anxiolytic drug;
GABA agonist;
muscle relaxant;
sedative;
xenobiotic
nordazepam
Nordazepam: An intermediate in the metabolism of DIAZEPAM to OXAZEPAM. It may have actions similar to those of diazepam.. nordazepam : A 1,4-benzodiazepinone having phenyl and chloro substituents at positions 5 and 7 respectively; it has anticonvulsant, anxiolytic, muscle relaxant and sedative properties but is used primarily in the treatment of anxiety.		1.95101,4-benzodiazepinone;
organochlorine compound		anticonvulsant;
anxiolytic drug;
GABA modulator;
human metabolite;
sedative
diazepam
Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.		1.95101,4-benzodiazepinone;
organochlorine compound		anticonvulsant;
anxiolytic drug;
environmental contaminant;
sedative;
xenobiotic
estazolam
Estazolam: A benzodiazepine with anticonvulsant, hypnotic, and muscle relaxant properties. It has been shown in some cases to be more potent than DIAZEPAM or NITRAZEPAM.. estazolam : A triazolo[4,3-a][1,4]benzodiazepine having a phenyl group at position 6 and a chloro substituent at position 8. A short-acting benzodiazepine with general properties similar to diazepam, it is given by mouth as a hypnotic in the short-term management of insomnia.		2.2510triazoles;
triazolobenzodiazepine		anticonvulsant;
anxiolytic drug;
GABA modulator
ketoconazole
1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.		2.0310dichlorobenzene;
dioxolane;
ether;
imidazoles;
N-acylpiperazine;
N-arylpiperazine
oxazepam
Oxazepam: A benzodiazepine used in the treatment of anxiety, alcohol withdrawal, and insomnia.. oxazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a hydroxy group at position 3 and phenyl group at position 5.		1.95101,4-benzodiazepinone;
organochlorine compound		anxiolytic drug;
environmental contaminant;
xenobiotic
temazepam
Temazepam: A benzodiazepine that acts as a GAMMA-AMINOBUTYRIC ACID modulator and anti-anxiety agent.		1.9510benzodiazepine
triazolam
Triazolam: A short-acting benzodiazepine used 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.		2.420triazolobenzodiazepinesedative
adinazolam
adinazolam: structure in first source. adinazolam : A triazolo[4,3-a][1,4]benzodiazepine having a dimethylaminomethyl group at the 1-position, a phenyl group at the 6-position and a chloro substituent at the 8-position.		2.420triazolobenzodiazepineanticonvulsant;
antidepressant;
anxiolytic drug;
sedative
4-hydroxytriazolam
4-hydroxytriazolam: triazolam metabolite; structure in first source		1.9510triazolobenzodiazepine
alpha-hydroxyalprazolam
alpha-hydroxyalprazolam: alprazolam metabolite; structure in first source		4.4951triazolobenzodiazepine
quinidine
Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.		2.0310cinchona alkaloidalpha-adrenergic antagonist;
anti-arrhythmia drug;
antimalarial;
drug allergen;
EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor;
EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor;
muscarinic antagonist;
P450 inhibitor;
potassium channel blocker;
sodium channel blocker
3-hydroxyquinidine
3-hydroxyquinidine: RN given refers to (9S)-isomer		2.0310
ConditionIndicatedRelationship StrengthStudiesTrials
Chronic Kidney Diseases
[description not available]		02.0710
Renal Insufficiency, Chronic
Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)		02.0710