Grundinformationen
- Standard-SMILES
Clc1ccc2c(c1)C(c1ccccc1)=NCc1nncn1-2- InChIKey
CDCHDCWJMGXXRH-UHFFFAOYSA-N- Summenformel
- C16H11ClN4
- Durchschnittliche Molmasse
- 294,74 g/mol
- Monoisotopische Masse
- 294,06722403
Überblick
Estazolam is 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. It has a role as an anxiolytic drug, an anticonvulsant and a GABA modulator. It is a triazolobenzodiazepine and a member of triazoles.
Namen und Bezeichner
- Bevorzugter Name
- Estazolam
- IUPAC
- 8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
- Lokaler Name
- Estazolam
- Englischer Name
- Estazolam
- Summenformel
- C16H11ClN4
- Molmasse
- 294.74
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
29975-16-4- PubChem CID
- 3261
- DTXSID
DTXSID5020572- ChEMBL
CHEMBL285674- ChEBI
CHEBI:4858- UNII
- 36S3EQV54C
- EC Number
- 249-982-4
- Nikkaji
- J9.280K
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,7
- Polarare Oberfläche (TPSA)
- 43,1 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 21
- Formalladung
- 0
- Komplexität
- 407
Experimentelle und physikochemische Eigenschaften
Drugs
DEA NFLIS-Drug Category -> Benzodiazepines
DEA Schedule IV Controlled Substance -> Depressants
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Pharmaceuticals -> Benzodiazepines
Pharmaceuticals -> Listed in ZINC15
Solubility
Practically insoluble (1.5 mg/L)
4.23e-02 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Benzodiazepines; Hypnotics and Sedatives
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Melting Point
228-229
228.5 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- 228 · 228-229°
- Siedepunkt
- 448.04 °C · 448.04°C (rough estimate)
- Dichte
- 1.2294 · 1.2294 (rough estimate)
- Brechungsindex
- 1.611 · 1.6110 (estimate)
- Flammpunkt
- 11 °C · 11 °C
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 30 mg/ml; · DMF: 30 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml; DMSO: 20 mg/ml; Ethanol: 10 mg/ml
- Aggregatzustand
- A crystalline solid
- pka
- 2.84 · pKa 2.84(H2O) (Uncertain)
- CAS Datenbank
- 29975 · 29975-16-4(CAS DataBase Reference)
- NIST chemische Informationen
- Estazolam(29975-16-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 2.3% (1 of 44) of reports.
Warning
H315 (93.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
DEA schedule IV controlled substance
4H-1,2,4Triazolo4,3-a1,4benzodiazepine, 8-chloro-6-phenyl-: Does not have an individual approval but may be used under an appropriate group standard
Toxikologische Informationen
Treatment
Gastric evacuation, either by the induction of emesis, lavage, or both, should be performed immediately. Maintenance of adequate ventilation is essential. General supportive care, including frequent monitoring of the vital signs and close observation of the patient, is indicated. Fluids should be administered intravenously to maintain blood pressure and encourage diuresis. The value of dialysis in treatment of benzodiazepine overdose has not been determined. The physician may wish to consider contacting a Poison Control Center for up-to-date information on the management of hypnotic drug product overdose. Flumazenil, a specific benzodiazepine receptor antagonist, is indicated for the complete or partial reversal of the sedative effects of benzodiazepines and may be used in situations when an overdose with a benzodiazepine is known or suspected. (L1712)
Hepatotoxicity
Estazolam, as with other benzodiazepines, is rarely associated with serum ALT elevations, and clinically apparent liver injury from estazolam is extremely rare, if it occurs at all. There have been no published case reports of symptomatic, acute liver injury from estazolam. Isolated cases of clinically apparent hepatitis have been reported with other benzodiazepines including alprazolam, chlordiazepoxide, clonazepam, diazepam, flurazepam, lorazepam, and triazolam. The clinical pattern of acute liver injury from benzodiazepines is typically cholestatic and mild-to-moderate in severity with a latency of 1 to 6 months and full recovery within 1 to 2 months. Fever and rash have not been described nor has autoantibody formation.
Exposure Routes
Tablets have been found to be equivalent in absorption to an orally administered solution of estazolam. In healthy subjects who received up to three times the recommended dose, peak estazolam plasma concentrations occurred within two hours after dosing (range 0.5 to 6.0 hours) and were proportional to the administered dose, suggesting linear pharmacokinetics over the dosage range tested.
Toxicity Summary
Benzodiazepines bind nonspecifically to benzodiazepine receptors, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABA<sub>A</sub>) receptors, this enhances the effects GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Carcinogen Classification
Estazolam
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 66: (1996) Some Pharmaceutical Drugs
1996
1996
3, not classifiable as to its carcinogenicity to humans. (L135)
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Estazolam
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
◈ What is estazolam?
Sicherheitsdaten
- wgk
- 3
- ridadr
- 3249
- hs_code
- 2933910000
- RTECS-Nr.
- XZ5473500
- risk_code
- 36/37/38-39/23/24/25-23/24/25-11
- Toxizität
- LD50 orally in male mice, rats and rabbits: 740, 3200, 300 mg/kg (Yokotani)
- hazard_code
- Xi,T,F
- safety_code
- 36/37/39-45-36/37-16-7
- hazard_class
- 6.1(b)
- packing_group
- III
Chemie und Industrie
Pharmakologische Informationen
ATC Code
N - Nervous system
QN - Nervous system
Mechanism of Action
Benzodiazepines bind nonspecifically to benzodiazepine receptors, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABA<sub>A</sub>) receptors, this enhances the effects GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Metabolism/Metabolites
Extensively metabolized in the liver. In vitro studies with human liver microsomes indicate that the biotransformation of estazolam to the major circulating metabolite 4-hydroxy-estazolam is mediated by cytochrome P450 3A (CYP3A).
Estazolam has known human metabolites that include 4-hydroxyestazolam.
Extensively metabolized in the liver. In vitro studies with human liver microsomes indicate that the biotransformation of estazolam to the major circulating metabolite 4-hydroxy-estazolam is mediated by cytochrome P450 3A (CYP3A). Route of Elimination: Estazolam is extensively metabolized. The elimination of the parent drug takes place via hepatic metabolism of estazolam to hydroxylated and other metabolites that are eliminated largely in the urine both free and conjugated. Less than 5% of a 2 mg dose of estazolam was excreted unchanged in the urine, with only 4% of the dose appearing in the feces. Radiolabel mass balance studies indicate that the main route of excretion is via the kidneys. After 5 days, 87% of the administered radioactivity was excreted in human urine. Less than 4% of the dose was excreted unchanged. Half Life: The range of estimates for the mean elimination half-life of estazolam varies from 10 to 24 hours.
FDA Pharmacological Classification
36S3EQV54C
ESTAZOLAM
Established Pharmacologic Class [EPC] - Benzodiazepine
Chemical Structure [CS] - Benzodiazepines
Estazolam is a Benzodiazepine.
ESTAZOLAM
MeSH Pharmacological Classification
Drugs used to prevent SEIZURES or reduce their severity.
Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.
Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here.
Absorption, Distribution and Excretion
Tablets have been found to be equivalent in absorption to an orally administered solution of estazolam. In healthy subjects who received up to three times the recommended dose, peak estazolam plasma concentrations occurred within two hours after dosing (range 0.5 to 6.0 hours) and were proportional to the administered dose, suggesting linear pharmacokinetics over the dosage range tested.
Estazolam is extensively metabolized. The elimination of the parent drug takes place via hepatic metabolism of estazolam to hydroxylated and other metabolites that are eliminated largely in the urine both free and conjugated. Less than 5% of a 2 mg dose of estazolam was excreted unchanged in the urine, with only 4% of the dose appearing in the feces. Radiolabel mass balance studies indicate that the main route of excretion is via the kidneys. After 5 days, 87% of the administered radioactivity was excreted in human urine. Less than 4% of the dose was excreted unchanged.
Verwendung und Herstellung
Anwendungen
VerwendenA benzodiazepine derivative possessing anxiolytic, anticonvulsant, and muscle relaxant properties. It is commonly prescribed to treat short-term insomnia. Controlled Substance.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Ergänzende Hinweise
DefinitionChEBI: 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 ma agement of insomnia.
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