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Camazepam

HCID 37367
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
36104-80-0
Standard-SMILES
CN(C)C(=O)OC1N=C(c2ccccc2)c2cc(Cl)ccc2N(C)C1=O
InChIKey
PXBVEXGRHZFEOF-UHFFFAOYSA-N
Summenformel
C19H18ClN3O3
Durchschnittliche Molmasse
371,8 g/mol
Monoisotopische Masse
371,1036691

Überblick

Camazepam is a benzodiazepine.

Namen und Bezeichner

Bevorzugter Name
Camazepam
IUPAC
(7-chloro-1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepin-3-yl) N,N-dimethylcarbamate
Lokaler Name
Camazepam
Englischer Name
camazepam
Summenformel
C19H18ClN3O3
Molmasse
371.82

Namen und Synonyme

CamazepamAlbegoPaxorLimpidonCamazepamumPanevrilNebolan36104-80-0SB 5833HZ3XRH03C3Carbamic acid, dimethyl-, 7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl ester3-N,N-Dimethylcarbamoyloxy-7-chloro-5-phenyl-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
Weitere Namen anzeigen
B-5333SB-5833KTH-497dl-CaMazepaMRaceMic CaMazepaMcamazepam USP/EP/BPPXBVEXGRHZFEOF-UHFFFAOYSA-NDimethylcarbamic acid 7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl ester
DTXSID50865803(+-)-CamazepamRefChem:573665DTXCID10814170N05BA157-chloro-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl N,N-dimethylcarbamateB-5833S-58-33

Datenbank-Bezeichner

CAS
36104-80-0

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,8
Polarare Oberfläche (TPSA)
62,2 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
3
Schwere Atome
26
Formalladung
0
Komplexität
574

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Human DrugsPharmaceuticals
Melting Point173-174

Physikochemische Eigenschaften

Schmelzpunkt
173 · 173-174°
Siedepunkt
568.3 · 568.3±50.0 °C(Predicted)
Dichte
1.2902 · 1.2902 (rough estimate)
Brechungsindex
1.647 · 1.6470 (estimate)
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
pka
2.21 · 2.21±0.50(Predicted)
Farbe
White to Off-White
Stabilität
Light Sensitive

Sicherheit und Regulatorisches

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

Gefahrenhinweise

Regulatory InformationDEA schedule IV controlled substance

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.

Exposure RoutesAlmost completely absorbed into the bloodstream after oral administration. 90% bioavailability can be achieved in humans.
Toxicity Summary · 1 Eintrag

Camazepam has been shown to bind competitively to benzodiazepine receptors in the brain with a relatively low affinity in animal models. This binding of benzodiazepine receptors by camazepam and its active metabolites is responsible for its anticonvulsant effects. Notably, only three metabolites were shown to exert anticonvulsant activity, temazepam, oxazepam, and hydroxy camazepam. The anxiolytic properties of camazepam are also attributed to their ability to bind benzodiazepine receptors, also known as GABA receptors. When benzodiazepines bind to GABA receptors they increase the efficiency with which the inhibitory neurotransmitter GABA binds.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

N - Nervous system

QN - Nervous system

Mechanism of Action · 1 Eintrag

Camazepam has been shown to bind competitively to benzodiazepine receptors in the brain with a relatively low affinity in animal models. This binding of benzodiazepine receptors by camazepam and its active metabolites is responsible for its anticonvulsant effects. Notably, only three metabolites were shown to exert anticonvulsant activity, temazepam, oxazepam, and hydroxy camazepam. The anxiolytic properties of camazepam are also attributed to their ability to bind benzodiazepine receptors, also known as GABA receptors. When benzodiazepines bind to GABA receptors they increase the efficiency with which the inhibitory neurotransmitter GABA binds.

Metabolism/Metabolites · 2 Einträge

Metabolized by the liver into more than 10 metabolites, some of which are also active and posses anticonvulsant properties. [3] One active metabolite of note is temazepam which has roughly equal in effectiveness as an anxiolytic, but is less anticonvulsant, sedating, and motor-impairing. Camazepam undergoes enantioselective metabolism by human liver microsomes. [1]

Metabolized by the liver into more than 10 metabolites, some of which are also active and posses anticonvulsant properties. [3] One active metabolite of note is temazepam which has roughly equal in effectiveness as an anxiolytic, but is less anticonvulsant, sedating, and motor-impairing. Camazepam undergoes enantioselective metabolism by human liver microsomes. [1] Route of Elimination: Renally eliminated.

Absorption, Distribution and Excretion · 2 Einträge

Almost completely absorbed into the bloodstream after oral administration. 90% bioavailability can be achieved in humans.

Renally eliminated.

Verwendung und Herstellung

UsesCamazepam has been used in placebo controlled studies for the treatment of patients suffering from anxiety and depression.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
PubChem CID
37367
DTXSID
DTXSID50865803
ChEMBL
CHEMBL1095282
ChEBI
CHEBI:135570
UNII
HZ3XRH03C3
EC Number
252-866-6
Nikkaji
J19.779C
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

ridadr
3249
Toxizität
LD50 in mice, rats (mg/kg): 970, >4000 orally (Ferrini)
hazard_class
6.1(b)
packing_group
III
Use ClassificationPharmaceuticals

Anwendungen

VerwendenAnxiolytic. Controlled substance (depressant).

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

PhenylchlorformiatAzaN-Methylmethanamin, gasförmig4-Benzodiazepine-2-One