Estazolam

HCID 3261CAS 29975-16-4

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

estazolam29975-16-4EurodinProSomEsilganD 40TAEstazolamum8-Chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepineAbbott-47631Estazolam civDTXSID50205728-Chloro-6-phenyl-4H-s-triazolo(4,3-a)(1,4)benzodiazepine
Weitere Namen anzeigen
8-CHLORO-6-PHENYL-4H-[1,2,4]-TRIAZOLO[4,3-A][1,4]BENZODIAZEPINEu33737Cannocd-40taNemurelJulodin
NSC-29081836S3EQV54C4H-(1,2,4)Triazolo(4,3-a)(1,4)benzodiazepine, 8-chloro-6-phenyl-8-Chloro-6-phenyl-4H-(1,2,4)triazolo-(4,3-a)(1,4)benzodiazepineDTXCID50572CHEBI:48588-Chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepineNSC290818

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

Experimentelle und physikochemische Eigenschaften

Drugs · 5 Einträge

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Pharmaceuticals -> Benzodiazepines

Pharmaceuticals -> Listed in ZINC15

LogP4.7
Solubility · 2 Einträge

Practically insoluble (1.5 mg/L)

4.23e-02 g/L

Human Drugs · 4 Einträge

Breast Feeding; Lactation; Milk, Human; Benzodiazepines; Hypnotics and Sedatives

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Melting Point · 2 Einträge

228-229

228.5 °C

Physical DescriptionSolid

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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 · 2 Einträge

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

Hazard Classes and CategoriesSkin Irrit. 2 (93.2%)

Toxikologische Informationen

Treatment · 1 Eintrag

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)

Health EffectsMay cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
Hepatotoxicity · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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.

Signs and SymptomsSymptoms of overdose include confusion, depressed breathing, drowsiness and eventually coma, lack of coordination, and slurred speech.

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)

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

N - Nervous system

QN - Nervous system

Protein Binding93% protein bound, independant of concentration.
PharmacodynamicsEstazolam, a triazolobenzodiazepine derivative, is an oral hypnotic agent with anticonvulsant, hypnotic, and muscle relaxant properties. It has been shown in some cases to be more potent than diazepam or nitrazepam.
Mechanism of Action · 1 Eintrag

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.

Biological Half-LifeThe range of estimates for the mean elimination half-life of estazolam varies from 10 to 24 hours.
Metabolism/Metabolites · 3 Einträge

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.

Verwendung und Herstellung

UsesFor the short-term management of insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings, and/or early morning awakenings.
Use ClassificationPharmaceuticals

Anwendungen

VerwendenA benzodiazepine derivative possessing anxiolytic, anticonvulsant, and muscle relaxant properties. It is commonly prescribed to treat short-term insomnia. Controlled Substance.

Ergänzende Hinweise · 1 Eintrag

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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