Identification

Name
Etizolam
Accession Number
DB09166
Type
Small Molecule
Groups
Approved
Description

Etizolam is a thienodiazepine which is chemically related to benzodiazepine (BDZ) drug class; it differs from BDZs in having a benzene ring replaced with a thiophene ring. It is an agonist at GABA-A receptors and possesses amnesic, anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties. Initially introduced in 1983 in Japan as treatment for neurological conditions such as anxiety and sleep disorders, etizolam is marketed in Japan, Italy and India. It is not approved for use by FDA in the US; however it remains unscheduled in several states and is legal for research purposes.

Structure
Thumb
Synonyms
  • 4-(o-Chlorophenyl)-2-ethyl-9-methyl-6H-thieno(3,2-f)-s-triazolo(4,3-a)(1,4)diazepine
International/Other Brands
Arophalm (Nichi-Iko Pharmaceutical) / Capsafe (Ohara Yakuhin) / Dezolam (Taisho Yakuhin) / E1 (Aarpik) / Eticalm (Towa Yakuhin) / Etisedan (Kyowa Yakuhin) / Etizolan (Kobayashi Kako) / Mozun (Tatsumi Kagaku) / New Zomnia (Molekule) / Nonnerv (Nisshin Pharmaceutical) / Palgin (Fujinaga Seiyaku) / Sylkam (Dr. Reddy's)
Categories
UNII
A76XI0HL37
CAS number
40054-69-1
Weight
Average: 342.846
Monoisotopic: 342.070594897
Chemical Formula
C17H15ClN4S
InChI Key
VMZUTJCNQWMAGF-UHFFFAOYSA-N
InChI
InChI=1S/C17H15ClN4S/c1-3-11-8-13-16(12-6-4-5-7-14(12)18)19-9-15-21-20-10(2)22(15)17(13)23-11/h4-8H,3,9H2,1-2H3
IUPAC Name
7-(2-chlorophenyl)-4-ethyl-13-methyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0²,⁶]trideca-2(6),4,7,10,12-pentaene
SMILES
CCC1=CC2=C(S1)N1C(C)=NN=C1CN=C2C1=CC=CC=C1Cl

Pharmacology

Indication

Indicated for the treatment of generalized anxiety disorder with depression, panic disorder and insomnia.

Structured Indications
Not Available
Pharmacodynamics

Etizolam is a CNS depressant with anxiolytic, anticonvulsant, sedative-hypnotic and muscle relaxant effects. It acts on the benzodiazepine site of the GABA-A receptor as an agonist to increase inhibitory GABAergic transmission throughout the central nervous system. Studies indicate that etizolam mediates its pharmacological actions with 6 to 10 times more potency than that of diazepam. Clinical human studies performed in Italy showed clinical effectiveness of etizolam in relieving symptoms in patients with generalized anxiety disorders with depressive symptoms [2, 3, 4]. Etizolam also mediates imipramine-like neuropharmacological and behavioral effects, as well as minor effects on cognitive functioning. It is shown to substitute the actions of a short-acting barbiturate, pentobarbitol, in a drug discrimination study [8]. Etizolam is an antagonist at platelet-activating-factor (PAF) receptor and attenuates the recurrence of chronic subdural hematoma after neurosurgery in clinical studies [9]. It is shown to inhibit PAF-induced bronchoconstriction and hypotension [5].

Mechanism of action

Etizolam is selectively a full agonist at GABA-A receptors to increase GABAergic transmission and enhance GABA-induced Cl- currents [1]. It is reported to bind to the benzodiazepine binding site which is located across the interface between the alpha and gamma subunits. Benzodiazapines are reported to only bind to receptors that contain gamma 2 and alpha 1/2/3/5 subunits [7]. Alpha-1-containing receptors mediate the sedative effects of etizolam whereas alpha-2 and alpha-3 subunit-containing receptors mediate the anxiolytic effect [7]. Etizolam shows high potency and affinity towards GABA-A receptor with alpha 1 beta 2 gamma 2S subunit combination [1]. By binding to the regulatory site of the receptor, etizolam potentiates GABA transmission by facilitating the opening of GABA-induced chloride channels [7]. Etizolam is a specific antagonist at PAFR. It inhibits PAF-induced platelet aggregation by inhibiting PAF binding to the receptors located on the surface of platelets with an IC50 of 22nM [5].

TargetActionsOrganism
AGamma-aminobutyric acid receptor subunit alpha-1
agonist
Human
AGamma-aminobutyric acid receptor subunit alpha-2
agonist
Human
AGamma-aminobutyric acid receptor subunit alpha-3
agonist
Human
AGamma-aminobutyric acid receptor subunit gamma-2
agonist
Human
UPlatelet-activating factor receptor
antagonist
Human
Absorption

Etizolam is well absorbed from the intestines with a biological bioavailability of 93% following oral administration. After a single oral dosing of 0.5mg etizolam, it takes approximately 0.9 hours to reach the peak plasma concentration of 8.3 ng/mL [9].

Volume of distribution

Apparent distribution volume was 0.9 ± 0.2 L/kg following a single oral doing of 0.5mg etizolam [9].

Protein binding
Not Available
Metabolism

Biotransformation of etizolam is extensive and involves hydroxylation and conjugation [9]. The main metabolite formed via 1'-hydroxylation is α-hydroxyetizolam which retains pharmacological activity comparable to that of the parent drug, indicating that the action of metabolites may contribute to the clinical effects of etizolam [6]. CYP3A4 is predicted to be the main CYP enzyme responsible for mediating etizolam metabolism. CYP2C18 and CYP2C19 are also involved in the metabolic pathways [9, 5].

Route of elimination

In a rat study, the amounts of etizolam excreted was 30% in urine was 70% in feces, while the values in a mouse study were 40% in urine and 60% in feces [9].

Half life

The average elimination half life of etizolam following a single oral dose of 0.5mg is 3.4 hours but may be increased up to 17 hours depending on the rate of metabolism [9]. The main metabolite α-hydroxyetizolam displays a longer elimination half life of 8.2 hours [6].

Clearance
Not Available
Toxicity

Major adverse effects include drowsiness, sedation, muscle weakness and incoordination, fainting, headache, confusion, depression, slurred speech, visual disturbances and changes in libido and tremor [8]. Flumazenil is a competitive antagonist of GABA-A receptors and can be also used to reverse the effect of etizolam overdosage. Etizolam demonstrates no effects on fertility, development and teratogenicity [9]. LD50 values of etizolam when delivered orally, intraperitoneally, and subcutaneously are 3509mg/kg, 825mg/kg, and >5000mg/kg in rats, respectively, and 3070mg/kg, 783mg/kg and 5000mg/kg in mice, respectively [MSDS].

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Etizolam.Experimental
AbirateroneThe metabolism of Etizolam can be decreased when combined with Abiraterone.Approved
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Etizolam.Approved, Vet Approved
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Etizolam.Approved
AdipiplonThe risk or severity of adverse effects can be increased when Adipiplon is combined with Etizolam.Investigational
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Etizolam.Approved, Investigational
AlaproclateThe risk or severity of adverse effects can be increased when Etizolam is combined with Alaproclate.Experimental
AlfaxaloneThe risk or severity of adverse effects can be increased when Etizolam is combined with Alfaxalone.Vet Approved
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Etizolam.Approved, Illicit
AllopregnanoloneThe risk or severity of adverse effects can be increased when Etizolam is combined with Allopregnanolone.Investigational
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Etizolam.Experimental, Illicit
AlphaprodineThe risk or severity of adverse effects can be increased when Etizolam is combined with Alphaprodine.Illicit
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Etizolam.Approved, Illicit, Investigational
Ambroxol acefyllinateThe therapeutic efficacy of Etizolam can be decreased when used in combination with Ambroxol acefyllinate.Experimental
AminophyllineThe therapeutic efficacy of Etizolam can be decreased when used in combination with Aminophylline.Approved
AmiodaroneThe serum concentration of Etizolam can be increased when it is combined with Amiodarone.Approved, Investigational
AmisulprideThe risk or severity of adverse effects can be increased when Amisulpride is combined with Etizolam.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Etizolam is combined with Amitriptyline.Approved
AmobarbitalThe risk or severity of adverse effects can be increased when Amobarbital is combined with Etizolam.Approved, Illicit
AmoxapineThe risk or severity of adverse effects can be increased when Etizolam is combined with Amoxapine.Approved
AmperozideThe risk or severity of adverse effects can be increased when Amperozide is combined with Etizolam.Experimental
AprepitantThe serum concentration of Etizolam can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe risk or severity of adverse effects can be increased when Aripiprazole is combined with Etizolam.Approved, Investigational
ArmodafinilThe metabolism of Etizolam can be decreased when combined with Armodafinil.Approved, Investigational
ArticaineThe risk or severity of adverse effects can be increased when Articaine is combined with Etizolam.Approved
AsenapineThe risk or severity of adverse effects can be increased when Asenapine is combined with Etizolam.Approved
AtazanavirThe serum concentration of Etizolam can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Etizolam can be decreased when combined with Atomoxetine.Approved
AzaperoneThe risk or severity of adverse effects can be increased when Etizolam is combined with Azaperone.Vet Approved
AzelastineEtizolam may increase the central nervous system depressant (CNS depressant) activities of Azelastine.Approved
BaclofenThe risk or severity of adverse effects can be increased when Etizolam is combined with Baclofen.Approved
BarbitalThe risk or severity of adverse effects can be increased when Barbital is combined with Etizolam.Illicit
BenperidolThe risk or severity of adverse effects can be increased when Etizolam is combined with Benperidol.Investigational
BenzocaineThe risk or severity of adverse effects can be increased when Benzocaine is combined with Etizolam.Approved
Benzyl alcoholThe risk or severity of adverse effects can be increased when Benzyl alcohol is combined with Etizolam.Approved
BoceprevirThe serum concentration of Etizolam can be increased when it is combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Etizolam can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Etizolam can be decreased when it is combined with Bosentan.Approved, Investigational
BrexpiprazoleThe risk or severity of adverse effects can be increased when Etizolam is combined with Brexpiprazole.Approved
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Etizolam.Approved
BromazepamThe risk or severity of adverse effects can be increased when Bromazepam is combined with Etizolam.Approved, Illicit
BromisovalThe risk or severity of adverse effects can be increased when Etizolam is combined with Bromisoval.Experimental
BromperidolThe risk or severity of adverse effects can be increased when Etizolam is combined with Bromperidol.Investigational
BrompheniramineThe risk or severity of adverse effects can be increased when Etizolam is combined with Brompheniramine.Approved
BrotizolamThe risk or severity of adverse effects can be increased when Brotizolam is combined with Etizolam.Approved, Withdrawn
BupivacaineThe risk or severity of adverse effects can be increased when Bupivacaine is combined with Etizolam.Approved, Investigational
BuprenorphineEtizolam may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Etizolam.Approved, Investigational
ButabarbitalThe risk or severity of adverse effects can be increased when Butabarbital is combined with Etizolam.Approved, Illicit
ButacaineThe risk or severity of adverse effects can be increased when Etizolam is combined with Butacaine.Vet Approved
ButalbitalThe risk or severity of adverse effects can be increased when Etizolam is combined with Butalbital.Approved, Illicit
ButambenThe risk or severity of adverse effects can be increased when Etizolam is combined with Butamben.Approved
ButethalThe risk or severity of adverse effects can be increased when Butethal is combined with Etizolam.Approved, Illicit
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Etizolam.Approved, Illicit, Vet Approved
CanertinibThe risk or severity of adverse effects can be increased when Canertinib is combined with Etizolam.Investigational
CarbamazepineThe metabolism of Etizolam can be increased when combined with Carbamazepine.Approved, Investigational
CarbinoxamineThe risk or severity of adverse effects can be increased when Etizolam is combined with Carbinoxamine.Approved
CarfentanilThe risk or severity of adverse effects can be increased when Carfentanil is combined with Etizolam.Illicit, Vet Approved
CarisoprodolThe risk or severity of adverse effects can be increased when Etizolam is combined with Carisoprodol.Approved
CeritinibThe serum concentration of Etizolam can be increased when it is combined with Ceritinib.Approved
CetirizineThe risk or severity of adverse effects can be increased when Etizolam is combined with Cetirizine.Approved
Chloral hydrateThe risk or severity of adverse effects can be increased when Chloral hydrate is combined with Etizolam.Approved, Illicit, Vet Approved
ChloramphenicolThe metabolism of Etizolam can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChlordiazepoxideThe risk or severity of adverse effects can be increased when Chlordiazepoxide is combined with Etizolam.Approved, Illicit
ChlormezanoneThe risk or severity of adverse effects can be increased when Chlormezanone is combined with Etizolam.Approved, Withdrawn
ChloroprocaineThe risk or severity of adverse effects can be increased when Chloroprocaine is combined with Etizolam.Approved
ChlorphenamineThe risk or severity of adverse effects can be increased when Etizolam is combined with Chlorphenamine.Approved
ChlorpromazineThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Etizolam.Approved, Vet Approved
ChlorprothixeneThe risk or severity of adverse effects can be increased when Chlorprothixene is combined with Etizolam.Approved, Withdrawn
ChlorzoxazoneThe risk or severity of adverse effects can be increased when Etizolam is combined with Chlorzoxazone.Approved
CholecalciferolThe metabolism of Etizolam can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Etizolam can be decreased when combined with Cimetidine.Approved
CinchocaineThe risk or severity of adverse effects can be increased when Cinchocaine is combined with Etizolam.Approved, Vet Approved
CitalopramThe risk or severity of adverse effects can be increased when Etizolam is combined with Citalopram.Approved
ClarithromycinThe serum concentration of Etizolam can be increased when it is combined with Clarithromycin.Approved
ClemastineThe risk or severity of adverse effects can be increased when Etizolam is combined with Clemastine.Approved
ClidiniumThe risk or severity of adverse effects can be increased when Etizolam is combined with Clidinium.Approved
ClobazamThe risk or severity of adverse effects can be increased when Etizolam is combined with Clobazam.Approved, Illicit
clomethiazoleThe risk or severity of adverse effects can be increased when clomethiazole is combined with Etizolam.Investigational
ClomipramineThe risk or severity of adverse effects can be increased when Etizolam is combined with Clomipramine.Approved, Vet Approved
ClonazepamThe risk or severity of adverse effects can be increased when Etizolam is combined with Clonazepam.Approved, Illicit
ClonidineThe risk or severity of adverse effects can be increased when Etizolam is combined with Clonidine.Approved
ClopenthixolThe risk or severity of adverse effects can be increased when Etizolam is combined with Clopenthixol.Experimental
ClorazepateThe risk or severity of adverse effects can be increased when Clorazepate is combined with Etizolam.Approved, Illicit
ClothiapineThe risk or severity of adverse effects can be increased when Etizolam is combined with Clothiapine.Experimental
ClotrimazoleThe metabolism of Etizolam can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Etizolam is combined with Clozapine.Approved
CobicistatThe serum concentration of Etizolam can be increased when it is combined with Cobicistat.Approved
CocaineThe risk or severity of adverse effects can be increased when Cocaine is combined with Etizolam.Approved, Illicit
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Etizolam.Approved, Illicit
ConivaptanThe serum concentration of Etizolam can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Etizolam can be decreased when combined with Crizotinib.Approved
CyclizineThe risk or severity of adverse effects can be increased when Etizolam is combined with Cyclizine.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Etizolam.Approved
CyclosporineThe metabolism of Etizolam can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CyproheptadineThe risk or severity of adverse effects can be increased when Etizolam is combined with Cyproheptadine.Approved
DabrafenibThe serum concentration of Etizolam can be decreased when it is combined with Dabrafenib.Approved
DantroleneThe risk or severity of adverse effects can be increased when Etizolam is combined with Dantrolene.Approved
DapiprazoleThe risk or severity of adverse effects can be increased when Dapiprazole is combined with Etizolam.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Etizolam is combined with Dapoxetine.Investigational
DarunavirThe serum concentration of Etizolam can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Etizolam can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Etizolam can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Etizolam can be decreased when combined with Delavirdine.Approved
DeramciclaneThe risk or severity of adverse effects can be increased when Deramciclane is combined with Etizolam.Investigational
DesfluraneThe risk or severity of adverse effects can be increased when Desflurane is combined with Etizolam.Approved
DesipramineThe risk or severity of adverse effects can be increased when Etizolam is combined with Desipramine.Approved
DesloratadineThe risk or severity of adverse effects can be increased when Etizolam is combined with Desloratadine.Approved, Investigational
DesvenlafaxineThe risk or severity of adverse effects can be increased when Etizolam is combined with Desvenlafaxine.Approved
DetomidineThe risk or severity of adverse effects can be increased when Etizolam is combined with Detomidine.Vet Approved
DexbrompheniramineThe risk or severity of adverse effects can be increased when Etizolam is combined with Dexbrompheniramine.Approved
DexmedetomidineThe risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Etizolam.Approved, Vet Approved
DextromoramideThe risk or severity of adverse effects can be increased when Dextromoramide is combined with Etizolam.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Etizolam.Approved, Illicit, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Dezocine is combined with Etizolam.Approved
DiazepamThe risk or severity of adverse effects can be increased when Diazepam is combined with Etizolam.Approved, Illicit, Vet Approved
Diethyl etherThe risk or severity of adverse effects can be increased when Etizolam is combined with Diethyl ether.Experimental
DifenoxinThe risk or severity of adverse effects can be increased when Etizolam is combined with Difenoxin.Approved, Illicit
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Etizolam.Approved, Illicit
DihydroergotamineThe metabolism of Etizolam can be decreased when combined with Dihydroergotamine.Approved
DihydroetorphineThe risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Etizolam.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Dihydromorphine is combined with Etizolam.Experimental, Illicit
DiltiazemThe metabolism of Etizolam can be decreased when combined with Diltiazem.Approved
DimenhydrinateThe risk or severity of adverse effects can be increased when Etizolam is combined with Dimenhydrinate.Approved
DiphenhydramineThe risk or severity of adverse effects can be increased when Diphenhydramine is combined with Etizolam.Approved
DiphenoxylateThe risk or severity of adverse effects can be increased when Diphenoxylate is combined with Etizolam.Approved, Illicit
DixyrazineThe risk or severity of adverse effects can be increased when Etizolam is combined with Dixyrazine.Experimental
DoramectinThe risk or severity of adverse effects can be increased when Etizolam is combined with Doramectin.Vet Approved
DoxepinThe risk or severity of adverse effects can be increased when Etizolam is combined with Doxepin.Approved
DoxycyclineThe metabolism of Etizolam can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Etizolam.Approved, Vet Approved
DPDPEThe risk or severity of adverse effects can be increased when DPDPE is combined with Etizolam.Investigational
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Etizolam.Approved, Illicit
DronedaroneThe metabolism of Etizolam can be decreased when combined with Dronedarone.Approved
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Etizolam.Approved, Vet Approved
DrotebanolThe risk or severity of adverse effects can be increased when Drotebanol is combined with Etizolam.Experimental, Illicit
DuloxetineThe risk or severity of adverse effects can be increased when Etizolam is combined with Duloxetine.Approved
DyclonineThe risk or severity of adverse effects can be increased when Dyclonine is combined with Etizolam.Approved
DyphyllineThe therapeutic efficacy of Etizolam can be decreased when used in combination with Dyphylline.Approved
EcgonineThe risk or severity of adverse effects can be increased when Ecgonine is combined with Etizolam.Experimental, Illicit
EcopipamThe risk or severity of adverse effects can be increased when Etizolam is combined with Ecopipam.Investigational
EfavirenzThe risk or severity of adverse effects can be increased when Etizolam is combined with Efavirenz.Approved, Investigational
EltanoloneThe risk or severity of adverse effects can be increased when Etizolam is combined with Eltanolone.Investigational
EnfluraneThe risk or severity of adverse effects can be increased when Enflurane is combined with Etizolam.Approved, Vet Approved
EntacaponeThe risk or severity of adverse effects can be increased when Etizolam is combined with Entacapone.Approved, Investigational
EnzalutamideThe serum concentration of Etizolam can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Etizolam can be decreased when combined with Erythromycin.Approved, Vet Approved
EscitalopramThe risk or severity of adverse effects can be increased when Etizolam is combined with Escitalopram.Approved, Investigational
Eslicarbazepine acetateThe metabolism of Etizolam can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Etizolam can be decreased when combined with Esomeprazole.Approved, Investigational
EstazolamThe risk or severity of adverse effects can be increased when Estazolam is combined with Etizolam.Approved, Illicit
EszopicloneThe risk or severity of adverse effects can be increased when Eszopiclone is combined with Etizolam.Approved
EthanolEtizolam may increase the central nervous system depressant (CNS depressant) activities of Ethanol.Approved
EthchlorvynolThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Etizolam.Approved, Illicit, Withdrawn
EthosuximideThe risk or severity of adverse effects can be increased when Etizolam is combined with Ethosuximide.Approved
EthotoinThe risk or severity of adverse effects can be increased when Etizolam is combined with Ethotoin.Approved
Ethyl carbamateThe risk or severity of adverse effects can be increased when Ethyl carbamate is combined with Etizolam.Withdrawn
Ethyl chlorideThe risk or severity of adverse effects can be increased when Etizolam is combined with Ethyl chloride.Experimental
Ethyl loflazepateThe risk or severity of adverse effects can be increased when Ethyl loflazepate is combined with Etizolam.Approved, Illicit
EthylmorphineThe risk or severity of adverse effects can be increased when Ethylmorphine is combined with Etizolam.Approved, Illicit
EtidocaineThe risk or severity of adverse effects can be increased when Etidocaine is combined with Etizolam.Approved
EtifoxineThe risk or severity of adverse effects can be increased when Etifoxine is combined with Etizolam.Withdrawn
EtomidateThe risk or severity of adverse effects can be increased when Etomidate is combined with Etizolam.Approved
EtoperidoneThe risk or severity of adverse effects can be increased when Etizolam is combined with Etoperidone.Approved
EtorphineThe risk or severity of adverse effects can be increased when Etorphine is combined with Etizolam.Illicit, Vet Approved
EtravirineThe metabolism of Etizolam can be decreased when combined with Etravirine.Approved
EzogabineThe risk or severity of adverse effects can be increased when Etizolam is combined with Ezogabine.Approved
FelbamateThe risk or severity of adverse effects can be increased when Etizolam is combined with Felbamate.Approved
FencamfamineThe risk or severity of adverse effects can be increased when Fencamfamine is combined with Etizolam.Approved, Illicit, Withdrawn
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Etizolam.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe risk or severity of adverse effects can be increased when Etizolam is combined with Fexofenadine.Approved
FlibanserinThe risk or severity of adverse effects can be increased when Etizolam is combined with Flibanserin.Approved
FluanisoneThe risk or severity of adverse effects can be increased when Etizolam is combined with Fluanisone.Experimental
FluconazoleThe metabolism of Etizolam can be decreased when combined with Fluconazole.Approved
FludiazepamThe risk or severity of adverse effects can be increased when Fludiazepam is combined with Etizolam.Approved, Illicit
FlunarizineThe risk or severity of adverse effects can be increased when Etizolam is combined with Flunarizine.Approved
FlunitrazepamThe risk or severity of adverse effects can be increased when Flunitrazepam is combined with Etizolam.Approved, Illicit
FluoxetineThe risk or severity of adverse effects can be increased when Etizolam is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe risk or severity of adverse effects can be increased when Flupentixol is combined with Etizolam.Approved, Withdrawn
FluphenazineThe risk or severity of adverse effects can be increased when Fluphenazine is combined with Etizolam.Approved
FlurazepamThe risk or severity of adverse effects can be increased when Flurazepam is combined with Etizolam.Approved, Illicit
FluspirileneThe risk or severity of adverse effects can be increased when Fluspirilene is combined with Etizolam.Approved
Fluticasone propionateThe risk or severity of adverse effects can be increased when Etizolam is combined with Fluticasone propionate.Approved
FluvoxamineThe serum concentration of Etizolam can be increased when it is combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Etizolam can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Etizolam can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Etizolam.Approved
FospropofolThe risk or severity of adverse effects can be increased when Fospropofol is combined with Etizolam.Approved, Illicit
Fusidic AcidThe serum concentration of Etizolam can be increased when it is combined with Fusidic Acid.Approved
GabapentinThe risk or severity of adverse effects can be increased when Gabapentin is combined with Etizolam.Approved, Investigational
Gabapentin EnacarbilThe risk or severity of adverse effects can be increased when Etizolam is combined with Gabapentin Enacarbil.Approved
Gamma Hydroxybutyric AcidThe risk or severity of adverse effects can be increased when Gamma Hydroxybutyric Acid is combined with Etizolam.Approved, Illicit
GemfibrozilThe metabolism of Etizolam can be decreased when combined with Gemfibrozil.Approved
GepironeThe risk or severity of adverse effects can be increased when Etizolam is combined with Gepirone.Investigational
GlutethimideThe risk or severity of adverse effects can be increased when Glutethimide is combined with Etizolam.Approved, Illicit
GuanfacineThe risk or severity of adverse effects can be increased when Etizolam is combined with Guanfacine.Approved, Investigational
HalazepamThe risk or severity of adverse effects can be increased when Halazepam is combined with Etizolam.Approved, Illicit, Withdrawn
HaloperidolThe risk or severity of adverse effects can be increased when Haloperidol is combined with Etizolam.Approved
HalothaneThe risk or severity of adverse effects can be increased when Halothane is combined with Etizolam.Approved, Vet Approved
HeroinThe risk or severity of adverse effects can be increased when Heroin is combined with Etizolam.Approved, Illicit
HexobarbitalThe risk or severity of adverse effects can be increased when Hexobarbital is combined with Etizolam.Approved
HyaluronidaseThe therapeutic efficacy of Etizolam can be decreased when used in combination with Hyaluronidase.Approved, Investigational
HydrocodoneEtizolam may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.Approved, Illicit
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Etizolam.Approved, Illicit
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Etizolam.Approved
IdelalisibThe serum concentration of Etizolam can be increased when it is combined with Idelalisib.Approved
IloperidoneThe risk or severity of adverse effects can be increased when Etizolam is combined with Iloperidone.Approved
ImatinibThe metabolism of Etizolam can be decreased when combined with Imatinib.Approved
ImipramineThe risk or severity of adverse effects can be increased when Etizolam is combined with Imipramine.Approved
IndalpineThe risk or severity of adverse effects can be increased when Etizolam is combined with Indalpine.Investigational, Withdrawn
IndinavirThe serum concentration of Etizolam can be increased when it is combined with Indinavir.Approved
IndiplonThe risk or severity of adverse effects can be increased when Etizolam is combined with Indiplon.Investigational
IsavuconazoniumThe metabolism of Etizolam can be decreased when combined with Isavuconazonium.Approved, Investigational
IsofluraneThe risk or severity of adverse effects can be increased when Isoflurane is combined with Etizolam.Approved, Vet Approved
IsoniazidThe metabolism of Etizolam can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Etizolam can be decreased when combined with Isradipine.Approved
ItraconazoleThe serum concentration of Etizolam can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Etizolam can be increased when it is combined with Ivacaftor.Approved
KetamineThe risk or severity of adverse effects can be increased when Ketamine is combined with Etizolam.Approved, Vet Approved
KetazolamThe risk or severity of adverse effects can be increased when Ketazolam is combined with Etizolam.Approved
KetobemidoneThe risk or severity of adverse effects can be increased when Ketobemidone is combined with Etizolam.Approved
KetoconazoleThe serum concentration of Etizolam can be increased when it is combined with Ketoconazole.Approved, Investigational
LamotrigineThe risk or severity of adverse effects can be increased when Etizolam is combined with Lamotrigine.Approved, Investigational
LevetiracetamThe risk or severity of adverse effects can be increased when Etizolam is combined with Levetiracetam.Approved, Investigational
LevobupivacaineThe risk or severity of adverse effects can be increased when Levobupivacaine is combined with Etizolam.Approved
LevocabastineThe risk or severity of adverse effects can be increased when Etizolam is combined with Levocabastine.Approved
LevocetirizineThe risk or severity of adverse effects can be increased when Etizolam is combined with Levocetirizine.Approved
LevodopaThe risk or severity of adverse effects can be increased when Etizolam is combined with Levodopa.Approved
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Etizolam.Approved
LevomilnacipranThe risk or severity of adverse effects can be increased when Etizolam is combined with Levomilnacipran.Approved
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Etizolam.Approved
LidocaineThe risk or severity of adverse effects can be increased when Lidocaine is combined with Etizolam.Approved, Vet Approved
LithiumThe risk or severity of adverse effects can be increased when Lithium is combined with Etizolam.Approved
LobeglitazoneThe metabolism of Etizolam can be decreased when combined with Lobeglitazone.Approved
LofentanilThe risk or severity of adverse effects can be increased when Etizolam is combined with Lofentanil.Illicit
LopinavirThe serum concentration of Etizolam can be increased when it is combined with Lopinavir.Approved
LoprazolamThe risk or severity of adverse effects can be increased when Etizolam is combined with Loprazolam.Experimental
LoratadineThe risk or severity of adverse effects can be increased when Etizolam is combined with Loratadine.Approved
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Etizolam.Approved
LormetazepamThe risk or severity of adverse effects can be increased when Etizolam is combined with Lormetazepam.Approved
LovastatinThe metabolism of Etizolam can be decreased when combined with Lovastatin.Approved, Investigational
LoxapineThe risk or severity of adverse effects can be increased when Loxapine is combined with Etizolam.Approved
LuliconazoleThe serum concentration of Etizolam can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Etizolam can be decreased when it is combined with Lumacaftor.Approved
LurasidoneThe risk or severity of adverse effects can be increased when Lurasidone is combined with Etizolam.Approved
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Etizolam.Approved, Vet Approved
MaprotilineThe risk or severity of adverse effects can be increased when Etizolam is combined with Maprotiline.Approved
MebicarThe risk or severity of adverse effects can be increased when Etizolam is combined with Mebicar.Experimental
MeclizineThe risk or severity of adverse effects can be increased when Etizolam is combined with Meclizine.Approved
MedazepamThe risk or severity of adverse effects can be increased when Etizolam is combined with Medazepam.Experimental
MedetomidineThe risk or severity of adverse effects can be increased when Etizolam is combined with Medetomidine.Vet Approved
MelatoninThe risk or severity of adverse effects can be increased when Melatonin is combined with Etizolam.Approved, Nutraceutical, Vet Approved
MelperoneThe risk or severity of adverse effects can be increased when Etizolam is combined with Melperone.Approved
MepivacaineThe risk or severity of adverse effects can be increased when Mepivacaine is combined with Etizolam.Approved, Vet Approved
MeprobamateThe risk or severity of adverse effects can be increased when Meprobamate is combined with Etizolam.Approved, Illicit
MeptazinolThe risk or severity of adverse effects can be increased when Etizolam is combined with Meptazinol.Experimental
MesoridazineThe risk or severity of adverse effects can be increased when Mesoridazine is combined with Etizolam.Approved
MetaxaloneThe risk or severity of adverse effects can be increased when Etizolam is combined with Metaxalone.Approved
MethadoneEtizolam may increase the central nervous system depressant (CNS depressant) activities of Methadone.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Etizolam.Approved, Illicit
MethapyrileneThe risk or severity of adverse effects can be increased when Methapyrilene is combined with Etizolam.Withdrawn
MethaqualoneThe risk or severity of adverse effects can be increased when Methaqualone is combined with Etizolam.Illicit, Withdrawn
MethocarbamolThe risk or severity of adverse effects can be increased when Etizolam is combined with Methocarbamol.Approved, Vet Approved
MethohexitalThe risk or severity of adverse effects can be increased when Methohexital is combined with Etizolam.Approved
MethotrimeprazineEtizolam may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.Approved
MethoxyfluraneThe risk or severity of adverse effects can be increased when Methoxyflurane is combined with Etizolam.Approved, Vet Approved
MethsuximideThe risk or severity of adverse effects can be increased when Etizolam is combined with Methsuximide.Approved
MethylecgonineThe risk or severity of adverse effects can be increased when Methylecgonine is combined with Etizolam.Experimental
MethylphenobarbitalThe risk or severity of adverse effects can be increased when Methylphenobarbital is combined with Etizolam.Approved
MetyrosineEtizolam may increase the sedative activities of Metyrosine.Approved
MidazolamThe risk or severity of adverse effects can be increased when Midazolam is combined with Etizolam.Approved, Illicit
MifepristoneThe serum concentration of Etizolam can be increased when it is combined with Mifepristone.Approved, Investigational
MilnacipranThe risk or severity of adverse effects can be increased when Etizolam is combined with Milnacipran.Approved
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Etizolam.Approved, Investigational
MirtazapineEtizolam may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.Approved
MitotaneThe serum concentration of Etizolam can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Etizolam can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Etizolam can be decreased when combined with Modafinil.Approved, Investigational
MolindoneThe risk or severity of adverse effects can be increased when Molindone is combined with Etizolam.Approved
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Etizolam.Approved, Investigational
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Etizolam.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Etizolam.Approved
NefazodoneThe serum concentration of Etizolam can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Etizolam can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Etizolam can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Etizolam can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Etizolam can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Etizolam can be decreased when combined with Nilotinib.Approved, Investigational
NitrazepamThe risk or severity of adverse effects can be increased when Nitrazepam is combined with Etizolam.Approved
Nitrous oxideThe risk or severity of adverse effects can be increased when Nitrous oxide is combined with Etizolam.Approved, Vet Approved
NorfluraneThe risk or severity of adverse effects can be increased when Etizolam is combined with Norflurane.Investigational
NormethadoneThe risk or severity of adverse effects can be increased when Etizolam is combined with Normethadone.Approved, Illicit
NortriptylineThe risk or severity of adverse effects can be increased when Etizolam is combined with Nortriptyline.Approved
OlanzapineThe risk or severity of adverse effects can be increased when Olanzapine is combined with Etizolam.Approved, Investigational
OlaparibThe metabolism of Etizolam can be decreased when combined with Olaparib.Approved
OlopatadineThe risk or severity of adverse effects can be increased when Etizolam is combined with Olopatadine.Approved
OmeprazoleThe metabolism of Etizolam can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OndansetronThe risk or severity of adverse effects can be increased when Ondansetron is combined with Etizolam.Approved
OpiumThe risk or severity of adverse effects can be increased when Etizolam is combined with Opium.Approved, Illicit
OrphenadrineEtizolam may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.Approved
OsanetantThe risk or severity of adverse effects can be increased when Osanetant is combined with Etizolam.Investigational
OsimertinibThe serum concentration of Etizolam can be increased when it is combined with Osimertinib.Approved
OxazepamThe risk or severity of adverse effects can be increased when Oxazepam is combined with Etizolam.Approved
OxethazaineThe risk or severity of adverse effects can be increased when Etizolam is combined with Oxethazaine.Investigational
OxprenololThe risk or severity of adverse effects can be increased when Oxprenolol is combined with Etizolam.Approved
OxybuprocaineThe risk or severity of adverse effects can be increased when Oxybuprocaine is combined with Etizolam.Approved
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Etizolam.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Etizolam.Approved, Investigational, Vet Approved
PalbociclibThe serum concentration of Etizolam can be increased when it is combined with Palbociclib.Approved
PaliperidoneThe risk or severity of adverse effects can be increased when Paliperidone is combined with Etizolam.Approved
PantoprazoleThe metabolism of Etizolam can be decreased when combined with Pantoprazole.Approved
ParaldehydeEtizolam may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Etizolam is combined with Paroxetine.Approved, Investigational
PenfluridolThe risk or severity of adverse effects can be increased when Etizolam is combined with Penfluridol.Experimental
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Etizolam.Approved, Vet Approved
PentobarbitalThe metabolism of Etizolam can be increased when combined with Pentobarbital.Approved, Vet Approved
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Etizolam.Approved
PerazineThe risk or severity of adverse effects can be increased when Etizolam is combined with Perazine.Investigational
PerospironeThe risk or severity of adverse effects can be increased when Perospirone is combined with Etizolam.Approved
PerphenazineThe risk or severity of adverse effects can be increased when Perphenazine is combined with Etizolam.Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Etizolam.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Etizolam is combined with Phenazocine.Experimental
PhenibutThe risk or severity of adverse effects can be increased when Etizolam is combined with Phenibut.Experimental
PhenobarbitalThe metabolism of Etizolam can be increased when combined with Phenobarbital.Approved
PhenoperidineThe risk or severity of adverse effects can be increased when Etizolam is combined with Phenoperidine.Experimental
PhenoxyethanolThe risk or severity of adverse effects can be increased when Etizolam is combined with Phenoxyethanol.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Etizolam.Approved, Vet Approved
PimozideThe risk or severity of adverse effects can be increased when Pimozide is combined with Etizolam.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Etizolam is combined with Pipamperone.Approved
PipotiazineThe risk or severity of adverse effects can be increased when Etizolam is combined with Pipotiazine.Approved
PiritramideThe risk or severity of adverse effects can be increased when Etizolam is combined with Piritramide.Investigational
PizotifenThe risk or severity of adverse effects can be increased when Etizolam is combined with Pizotifen.Approved
PomalidomideThe risk or severity of adverse effects can be increased when Etizolam is combined with Pomalidomide.Approved
PosaconazoleThe serum concentration of Etizolam can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PramipexoleEtizolam may increase the sedative activities of Pramipexole.Approved, Investigational
PramocaineThe risk or severity of adverse effects can be increased when Etizolam is combined with Pramocaine.Approved
PrazepamThe risk or severity of adverse effects can be increased when Prazepam is combined with Etizolam.Approved, Illicit
PregabalinThe risk or severity of adverse effects can be increased when Pregabalin is combined with Etizolam.Approved, Illicit, Investigational
PrilocaineThe risk or severity of adverse effects can be increased when Prilocaine is combined with Etizolam.Approved
PrimidoneThe metabolism of Etizolam can be increased when combined with Primidone.Approved, Vet Approved
ProcaineThe risk or severity of adverse effects can be increased when Procaine is combined with Etizolam.Approved, Investigational, Vet Approved
ProchlorperazineThe risk or severity of adverse effects can be increased when Prochlorperazine is combined with Etizolam.Approved, Vet Approved
PromazineThe risk or severity of adverse effects can be increased when Promazine is combined with Etizolam.Approved, Vet Approved
PromethazineThe risk or severity of adverse effects can be increased when Etizolam is combined with Promethazine.Approved
PropanididThe risk or severity of adverse effects can be increased when Etizolam is combined with Propanidid.Experimental
ProparacaineThe risk or severity of adverse effects can be increased when Proparacaine is combined with Etizolam.Approved, Vet Approved
PropofolThe risk or severity of adverse effects can be increased when Propofol is combined with Etizolam.Approved, Investigational, Vet Approved
PropoxycaineThe risk or severity of adverse effects can be increased when Etizolam is combined with Propoxycaine.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Etizolam is combined with Protriptyline.Approved
ProxibarbalThe risk or severity of adverse effects can be increased when Etizolam is combined with Proxibarbal.Experimental
PSD502The risk or severity of adverse effects can be increased when PSD502 is combined with Etizolam.Investigational
QuazepamThe risk or severity of adverse effects can be increased when Quazepam is combined with Etizolam.Approved, Illicit
QuetiapineThe risk or severity of adverse effects can be increased when Quetiapine is combined with Etizolam.Approved
QuinisocaineThe risk or severity of adverse effects can be increased when Etizolam is combined with Quinisocaine.Experimental
RacloprideThe risk or severity of adverse effects can be increased when Etizolam is combined with Raclopride.Investigational
RamelteonThe risk or severity of adverse effects can be increased when Etizolam is combined with Ramelteon.Approved, Investigational
RanolazineThe metabolism of Etizolam can be decreased when combined with Ranolazine.Approved, Investigational
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Etizolam.Approved
RemoxiprideThe risk or severity of adverse effects can be increased when Remoxipride is combined with Etizolam.Approved, Withdrawn
ReserpineThe risk or severity of adverse effects can be increased when Reserpine is combined with Etizolam.Approved
RifabutinThe metabolism of Etizolam can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Etizolam can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Etizolam can be increased when combined with Rifapentine.Approved
RisperidoneThe risk or severity of adverse effects can be increased when Risperidone is combined with Etizolam.Approved, Investigational
RitanserinThe risk or severity of adverse effects can be increased when Etizolam is combined with Ritanserin.Investigational
RitonavirThe serum concentration of Etizolam can be increased when it is combined with Ritonavir.Approved, Investigational
RomifidineThe risk or severity of adverse effects can be increased when Etizolam is combined with Romifidine.Vet Approved
RopiniroleEtizolam may increase the sedative activities of Ropinirole.Approved, Investigational
RopivacaineThe risk or severity of adverse effects can be increased when Ropivacaine is combined with Etizolam.Approved
RotigotineEtizolam may increase the sedative activities of Rotigotine.Approved
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Etizolam.Approved
SaquinavirThe serum concentration of Etizolam can be increased when it is combined with Saquinavir.Approved, Investigational
ScopolamineThe risk or severity of adverse effects can be increased when Etizolam is combined with Scopolamine.Approved
SecobarbitalThe risk or severity of adverse effects can be increased when Secobarbital is combined with Etizolam.Approved, Vet Approved
SepranoloneThe risk or severity of adverse effects can be increased when Etizolam is combined with Sepranolone.Investigational
SertindoleThe risk or severity of adverse effects can be increased when Sertindole is combined with Etizolam.Approved, Withdrawn
SertralineThe risk or severity of adverse effects can be increased when Etizolam is combined with Sertraline.Approved
SevofluraneThe risk or severity of adverse effects can be increased when Sevoflurane is combined with Etizolam.Approved, Vet Approved
SildenafilThe metabolism of Etizolam can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Etizolam can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Etizolam can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Etizolam can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Etizolam can be increased when it is combined with Stiripentol.Approved
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Etizolam.Approved, Investigational
SulfisoxazoleThe metabolism of Etizolam can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulpirideThe risk or severity of adverse effects can be increased when Sulpiride is combined with Etizolam.Approved
SultoprideThe risk or severity of adverse effects can be increased when Etizolam is combined with Sultopride.Experimental
SuvorexantEtizolam may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.Approved
TandospironeThe risk or severity of adverse effects can be increased when Etizolam is combined with Tandospirone.Investigational
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Etizolam.Approved
TasimelteonThe risk or severity of adverse effects can be increased when Etizolam is combined with Tasimelteon.Approved
TeduglutideThe serum concentration of Etizolam can be increased when it is combined with Teduglutide.Approved
TelaprevirThe serum concentration of Etizolam can be increased when it is combined with Telaprevir.Withdrawn
TelithromycinThe serum concentration of Etizolam can be increased when it is combined with Telithromycin.Approved
TemazepamThe risk or severity of adverse effects can be increased when Temazepam is combined with Etizolam.Approved
TetrabenazineThe risk or severity of adverse effects can be increased when Etizolam is combined with Tetrabenazine.Approved
TetracaineThe risk or severity of adverse effects can be increased when Tetracaine is combined with Etizolam.Approved, Vet Approved
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Etizolam is combined with Tetrahydropalmatine.Investigational
TetrodotoxinThe risk or severity of adverse effects can be increased when Tetrodotoxin is combined with Etizolam.Investigational
ThalidomideEtizolam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.Approved, Investigational, Withdrawn
TheophyllineThe therapeutic efficacy of Etizolam can be decreased when used in combination with Theophylline.Approved
ThiamylalThe risk or severity of adverse effects can be increased when Thiamylal is combined with Etizolam.Approved, Vet Approved
ThiopentalThe risk or severity of adverse effects can be increased when Thiopental is combined with Etizolam.Approved, Vet Approved
ThioridazineThe risk or severity of adverse effects can be increased when Thioridazine is combined with Etizolam.Withdrawn
ThiothixeneThe risk or severity of adverse effects can be increased when Thiothixene is combined with Etizolam.Approved
TiagabineThe risk or severity of adverse effects can be increased when Etizolam is combined with Tiagabine.Approved
TiaprideThe risk or severity of adverse effects can be increased when Etizolam is combined with Tiapride.Approved, Investigational
TiclopidineThe metabolism of Etizolam can be decreased when combined with Ticlopidine.Approved
TiletamineThe risk or severity of adverse effects can be increased when Etizolam is combined with Tiletamine.Vet Approved
TilidineThe risk or severity of adverse effects can be increased when Etizolam is combined with Tilidine.Experimental
TizanidineThe risk or severity of adverse effects can be increased when Etizolam is combined with Tizanidine.Approved
TocilizumabThe serum concentration of Etizolam can be decreased when it is combined with Tocilizumab.Approved
TolcaponeThe risk or severity of adverse effects can be increased when Etizolam is combined with Tolcapone.Approved, Withdrawn
TopiramateThe risk or severity of adverse effects can be increased when Etizolam is combined with Topiramate.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Etizolam.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Etizolam.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Etizolam.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Etizolam.Approved, Investigational
TriazolamThe risk or severity of adverse effects can be increased when Triazolam is combined with Etizolam.Approved
Tricaine methanesulfonateThe risk or severity of adverse effects can be increased when Etizolam is combined with Tricaine methanesulfonate.Vet Approved
TrichloroethyleneThe risk or severity of adverse effects can be increased when Etizolam is combined with Trichloroethylene.Experimental
TrifluoperazineThe risk or severity of adverse effects can be increased when Trifluoperazine is combined with Etizolam.Approved
TrifluperidolThe risk or severity of adverse effects can be increased when Etizolam is combined with Trifluperidol.Experimental
TriflupromazineThe risk or severity of adverse effects can be increased when Triflupromazine is combined with Etizolam.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Etizolam is combined with Trimipramine.Approved
TriprolidineThe risk or severity of adverse effects can be increased when Etizolam is combined with Triprolidine.Approved
Valproic AcidThe risk or severity of adverse effects can be increased when Valproic Acid is combined with Etizolam.Approved, Investigational
VenlafaxineThe risk or severity of adverse effects can be increased when Etizolam is combined with Venlafaxine.Approved
VeraliprideThe risk or severity of adverse effects can be increased when Etizolam is combined with Veralipride.Experimental
VerapamilThe metabolism of Etizolam can be decreased when combined with Verapamil.Approved
VigabatrinThe risk or severity of adverse effects can be increased when Etizolam is combined with Vigabatrin.Approved
Vinyl etherThe risk or severity of adverse effects can be increased when Etizolam is combined with Vinyl ether.Experimental
VoriconazoleThe serum concentration of Etizolam can be increased when it is combined with Voriconazole.Approved, Investigational
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Etizolam.Approved
XenonThe risk or severity of adverse effects can be increased when Etizolam is combined with Xenon.Experimental
XylazineThe risk or severity of adverse effects can be increased when Etizolam is combined with Xylazine.Vet Approved
YohimbineThe therapeutic efficacy of Etizolam can be decreased when used in combination with Yohimbine.Approved, Vet Approved
ZaleplonThe risk or severity of adverse effects can be increased when Zaleplon is combined with Etizolam.Approved, Illicit, Investigational
ZiconotideThe risk or severity of adverse effects can be increased when Etizolam is combined with Ziconotide.Approved
ZimelidineThe risk or severity of adverse effects can be increased when Etizolam is combined with Zimelidine.Withdrawn
ZiprasidoneThe risk or severity of adverse effects can be increased when Ziprasidone is combined with Etizolam.Approved
ZolazepamThe risk or severity of adverse effects can be increased when Etizolam is combined with Zolazepam.Vet Approved
ZolpidemEtizolam may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.Approved
ZonisamideThe risk or severity of adverse effects can be increased when Etizolam is combined with Zonisamide.Approved, Investigational
ZopicloneThe risk or severity of adverse effects can be increased when Zopiclone is combined with Etizolam.Approved
ZotepineThe risk or severity of adverse effects can be increased when Etizolam is combined with Zotepine.Approved
ZucapsaicinThe metabolism of Etizolam can be decreased when combined with Zucapsaicin.Approved
ZuclopenthixolThe risk or severity of adverse effects can be increased when Zuclopenthixol is combined with Etizolam.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Tahara T, Araki K, Shiroki M, Matsuo H, Munakata T. Syntheses and structure-activity relationships of 6-aryl-4H-s-triazolo[3,4-c]thieno[2,3-e] [1,4]diazepines. Arzneimittelforschung. 1978;28(7):1153-8.

General References
  1. Sanna E, Pau D, Tuveri F, Massa F, Maciocco E, Acquas C, Floris C, Fontana SN, Maira G, Biggio G: Molecular and neurochemical evaluation of the effects of etizolam on GABAA receptors under normal and stress conditions. Arzneimittelforschung. 1999 Feb;49(2):88-95. [PubMed:10083975]
  2. Casacchia M, Bolino F, Ecari U: Etizolam in the treatment of generalized anxiety disorder: a double-blind study versus placebo. Curr Med Res Opin. 1990;12(4):215-23. [PubMed:1981698]
  3. Bertolino A, Mastucci E, Porro V, Corfiati L, Palermo M, Ecari U, Ceccarelli G: Etizolam in the treatment of generalized anxiety disorder: a controlled clinical trial. J Int Med Res. 1989 Sep-Oct;17(5):455-60. [PubMed:2572494]
  4. Pariante F, Caddeo S, Ecari U: Etizolam in the treatment of generalized anxiety disorder associated with depressive symptoms. Curr Med Res Opin. 1989;11(9):543-9. [PubMed:2692969]
  5. Mikashima H, Takehara S, Muramoto Y, Khomaru T, Terasawa M, Tahara T, Maruyama Y: An antagonistic activity of etizolam on platelet-activating factor (PAF). In vitro effects on platelet aggregation and PAF receptor binding. Jpn J Pharmacol. 1987 Aug;44(4):387-91. [PubMed:2890779]
  6. Fracasso C, Confalonieri S, Garattini S, Caccia S: Single and multiple dose pharmacokinetics of etizolam in healthy subjects. Eur J Clin Pharmacol. 1991;40(2):181-5. [PubMed:2065698]
  7. 43. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 533-538). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  8. US Drug Enforcement Administration: ETIZOLAM Drug information [Link]
  9. World Health Organization: Etizolam (INN) Pre-Review Report [Link]
External Links
Human Metabolome Database
HMDB41890
KEGG Drug
D01514
ChemSpider
3191
ChEBI
31583
ChEMBL
CHEMBL1289779
Wikipedia
Etizolam
ATC Codes
N05BA19 — Etizolam
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Download (31.4 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)147-148World Health Organization: Etizolam (INN) Pre-Review Report
water solubilityPractically insolubleWorld Health Organization: Etizolam (INN) Pre-Review Report
Predicted Properties
PropertyValueSource
Water Solubility0.0425 mg/mLALOGPS
logP2.98ALOGPS
logP2.98ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)18.28ChemAxon
pKa (Strongest Basic)4.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.07 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity104.72 m3·mol-1ChemAxon
Polarizability35.64 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as thienodiazepines. These are heteropolycyclic containing a thiophene ring fused to a diazepine ring. Thiophene is 5-membered ring consisting of four carbon and one sulfur atoms. Diazepine is a 7-membered ring consisting of five carbon and two nitrogen atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thienodiazepines
Sub Class
Not Available
Direct Parent
Thienodiazepines
Alternative Parents
2,3,5-trisubstituted thiophenes / Chlorobenzenes / 1,4-diazepines / Aryl chlorides / Triazoles / Heteroaromatic compounds / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents
Thieno-para-diazepine / 2,3,5-trisubstituted thiophene / Para-diazepine / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Heteroaromatic compound
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRA1
Uniprot ID
P14867
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight
51801.395 Da
References
  1. Sanna E, Pau D, Tuveri F, Massa F, Maciocco E, Acquas C, Floris C, Fontana SN, Maira G, Biggio G: Molecular and neurochemical evaluation of the effects of etizolam on GABAA receptors under normal and stress conditions. Arzneimittelforschung. 1999 Feb;49(2):88-95. [PubMed:10083975]
  2. 43. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 534). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA2
Uniprot ID
P47869
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-2
Molecular Weight
51325.85 Da
References
  1. Sanna E, Pau D, Tuveri F, Massa F, Maciocco E, Acquas C, Floris C, Fontana SN, Maira G, Biggio G: Molecular and neurochemical evaluation of the effects of etizolam on GABAA receptors under normal and stress conditions. Arzneimittelforschung. 1999 Feb;49(2):88-95. [PubMed:10083975]
  2. 43. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 534). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA3
Uniprot ID
P34903
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-3
Molecular Weight
55164.055 Da
References
  1. Sanna E, Pau D, Tuveri F, Massa F, Maciocco E, Acquas C, Floris C, Fontana SN, Maira G, Biggio G: Molecular and neurochemical evaluation of the effects of etizolam on GABAA receptors under normal and stress conditions. Arzneimittelforschung. 1999 Feb;49(2):88-95. [PubMed:10083975]
  2. 43. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 534). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRG2
Uniprot ID
P18507
Uniprot Name
Gamma-aminobutyric acid receptor subunit gamma-2
Molecular Weight
54161.78 Da
References
  1. Sanna E, Pau D, Tuveri F, Massa F, Maciocco E, Acquas C, Floris C, Fontana SN, Maira G, Biggio G: Molecular and neurochemical evaluation of the effects of etizolam on GABAA receptors under normal and stress conditions. Arzneimittelforschung. 1999 Feb;49(2):88-95. [PubMed:10083975]
  2. 43. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 534). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Platelet activating factor receptor activity
Specific Function
Receptor for platelet activating factor, a chemotactic phospholipid mediator that possesses potent inflammatory, smooth-muscle contractile and hypotensive activity. Seems to mediate its action via ...
Gene Name
PTAFR
Uniprot ID
P25105
Uniprot Name
Platelet-activating factor receptor
Molecular Weight
39203.075 Da
References
  1. Mikashima H, Takehara S, Muramoto Y, Khomaru T, Terasawa M, Tahara T, Maruyama Y: An antagonistic activity of etizolam on platelet-activating factor (PAF). In vitro effects on platelet aggregation and PAF receptor binding. Jpn J Pharmacol. 1987 Aug;44(4):387-91. [PubMed:2890779]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Araki K, Yasui-Furukori N, Fukasawa T, Aoshima T, Suzuki A, Inoue Y, Tateishi T, Otani K: Inhibition of the metabolism of etizolam by itraconazole in humans: evidence for the involvement of CYP3A4 in etizolam metabolism. Eur J Clin Pharmacol. 2004 Aug;60(6):427-30. Epub 2004 Jul 1. [PubMed:15232663]
  2. World Health Organization: Etizolam (INN) Pre-Review Report [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
References
  1. World Health Organization: Etizolam (INN) Pre-Review Report [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Fukasawa T, Yasui-Furukori N, Suzuki A, Inoue Y, Tateishi T, Otani K: Pharmacokinetics and pharmacodynamics of etizolam are influenced by polymorphic CYP2C19 activity. Eur J Clin Pharmacol. 2005 Dec;61(11):791-5. Epub 2005 Nov 1. [PubMed:16261363]
  2. World Health Organization: Etizolam (INN) Pre-Review Report [Link]

Drug created on October 13, 2015 17:46 / Updated on October 02, 2017 06:13