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Cloxazolam

HCID 2816
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
24166-13-0
Standard-SMILES
O=C1CN2CCOC2(c2ccccc2Cl)c2cc(Cl)ccc2N1
InChIKey
ZIXNZOBDFKSQTC-UHFFFAOYSA-N
Summenformel
C17H14Cl2N2O2
Durchschnittliche Molmasse
349,2 g/mol
Monoisotopische Masse
348,0432331

Überblick

Cloxazolam is a hemiaminal ether and an oxazolobenzodiazepine.

Namen und Bezeichner

Bevorzugter Name
Cloxazolam
IUPAC
10-chloro-11b-(2-chlorophenyl)-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-one
Englischer Name
CLOXAZOLAM
Summenformel
C17H14Cl2N2O2
Molmasse
349.21

Namen und Synonyme

cloxazolamCloxazolazepamSepazonEnadelOlcadil24166-13-0CloxazolamumTolestanBetavelCloxamCS 370DTXSID0022854
Weitere Namen anzeigen
cs370Lubalixmt14-411Sepazone
MT 14-411GYL649Z0HY10-chloro-11b-(2-chlorophenyl)-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-oneDTXCID902854CHEBI:3142610-Chloro-11b-(o-chlorophenyl)-2,3,7,11b-tetrahydro-oxazolo(3,2-d) (1,4)benzodiazepin-6(5H)-one10-Chloro-2,3,5,6,7,11b-hexahydro-11b-(o-chlorophenyl)benzo(6,7)-1,4-diazepino-(5,4-b)-oxazol-6-one10-chloro-11b-(2-chlorophenyl)-2,3,5,7-tetrahydro-(1,3)oxazolo(3,2-d)(1,4)benzodiazepin-6-one

Datenbank-Bezeichner

CAS
24166-13-0
PubChem CID
2816
DTXSID
DTXSID0022854
ChEMBL
CHEMBL2107254
ChEBI
CHEBI:31426
UNII
GYL649Z0HY
EC Number
815-874-6
Nikkaji
J3.158E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,2
Polarare Oberfläche (TPSA)
41,6 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
1
Schwere Atome
23
Formalladung
0
Komplexität
478

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Melting Point202-204

Physikochemische Eigenschaften

Schmelzpunkt
202 · 202-204° (dec)
Siedepunkt
172 °C · 172°C (rough estimate)
Dichte
1.4125 · 1.4125 (rough estimate)
Brechungsindex
1.61 · 1.6100 (estimate)
pka
12.7 · 12.70±0.40(Predicted)
CAS Datenbank
24166 · 24166-13-0

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302+H312+H332 (50%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P319, P321, P330, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationDEA schedule IV controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (50%)

Toxikologische Informationen

Treatment · 1 Eintrag

General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

N05BA22

N - Nervous system

QN - Nervous system

Pharmacodynamics · 1 Eintrag

Studies have shown a superiority of 4mg/day of cloxazepam to 12mg/day of bromazepam in terms of anxiety, depressed mood, and sleep; an insignificant difference in terms of sedative effect; and less muscle relaxant effects. [3] Cloxazolam, administered as a single oral dose of 3mg, when compared to a single 5 mg dose of diazepam in one study, showed similar subjective measures; however, there cloxazolam caused more fatigue, and less mood improvement. Cloxazolam also induced a significant increase in heart rate in the control group of this study. [3]

Mechanism of ActionCloxazolam is a long acting benzodiazepine. It acts as a prodrug, with pharmacologically active metabolites, which bind to to the GABAa receptor, which other benzodiazepines bind to, to illicit a physiological response.
Biological Half-Life65 hours
Metabolism/Metabolites · 2 Einträge

Cloxazolam is metabolised by the liver into the active metabolite chlordesmethyldiazepam (delorazepam). [5]

Cloxazolam is metabolised by the liver into the active metabolite chlordesmethyldiazepam (delorazepam). [5] Route of Elimination: Renal elimination. Half Life: 65 hours

Absorption, Distribution and ExcretionRenal elimination.

Verwendung und Herstellung

UsesUsed primarily as an anti-anxiety agent. Typically used short term, and may be given as a single dose of up to 100mcg/kg to reduce anxiety and tension experienced prior to surgery.

Anwendungen

Zugehörige Reaktionen

6
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 305735
HRID 305735als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
Reaktionsgleichung von HRID 328481
HRID 328481als Eduktuspto-grants-1977_04
Reaktionsgleichung von HRID 328493
HRID 328493als Eduktuspto-grants-1977_04
Reaktionsgleichung von HRID 597627
HRID 597627als Eduktuspto-grants-1977_03
Reaktionsgleichung von HRID 1658604
HRID 1658604als Eduktuspto-grants-1976_06
Reaktionsgleichung von HRID 1973528
HRID 1973528als Eduktuspto-grants-1976_12

Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Toxicity SummaryCloxazolam is a long acting benzodiazepine. It acts as a prodrug, with pharmacologically active metabolites, which bind to to the GABAa receptor, which other benzodiazepines bind to, to illicit a physiological response.
Signs and Symptoms · 1 Eintrag

Drowsiness and ataxia are dose related. Central nervous system toxicity may result in respiratory depression and loss of consciousness. As such, pre-existing central nervous system depression and severe hepatic impairment are two particular contraindications for use.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

ridadr
3249
Toxizität
LD50 in mice (g/kg): 3.3 orally; >2.0 i.p. (Kamioka)
hazard_class
6.1(b)
packing_group
III

VerwendenCLOXAZOLAM is a benzodiazepine derivative with anxiolytic, hypnotic and antihypertensive properties used as an anti-anxiety drug. It is metabolized into the active metabolite Delorezepam (D230675). Controlled Subs tance.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2-Aminoethanol