Grundinformationen
- Standard-SMILES
O=C1CN=C(c2ccccc2)c2cc(Cl)ccc2N1CC1CC1- InChIKey
MWQCHHACWWAQLJ-UHFFFAOYSA-N- Summenformel
- C19H17ClN2O
- Durchschnittliche Molmasse
- 324,8 g/mol
- Monoisotopische Masse
- 324,1029409
Namen und Bezeichner
- Bevorzugter Name
- Prazepam
- IUPAC
- 7-chloro-1-(cyclopropylmethyl)-5-phenyl-3H-1,4-benzodiazepin-2-one
- Lokaler Name
- Prazepam
- Englischer Name
- PRAZEPAM
- Summenformel
- C19H17ClN2O
- Molmasse
- 324.8
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
2955-38-6- PubChem CID
- 4890
- DTXSID
DTXSID4021181- ChEMBL
CHEMBL969- ChEBI
CHEBI:8362- UNII
- Q30VCC064M
- EC Number
- 220-975-8
- Nikkaji
- J3.397I
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,6
- Polarare Oberfläche (TPSA)
- 32,7 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 482
Experimentelle und physikochemische Eigenschaften
LogP
3.73
3.73
Melting Point
145-146 °C
145 - 146 °C
Kovats Retention Index
2648;2651;2624;2624;2630;2652;2652;2676;2679;2694;2638;2610;2655;2641;2676;2650.1;2620;2619;2656;2641
2746.9;2646.3;2633.2;2676;2660.5;2660.5;2685
Physikochemische Eigenschaften
- Schmelzpunkt
- 145 · 145-146°
- Siedepunkt
- 538.5 · 538.5±50.0 °C(Predicted)
- Dichte
- 1.166 · 1.1660 (rough estimate)
- Brechungsindex
- 1.579 · 1.5790 (estimate)
- Flammpunkt
- 11 °C · 11 °C
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 0.25 g · Dissolve 0.25 g in alcohol R and dilute to 10 mL with the same solvent. The solution is clear (2.2.1) and colourless (2.2.2, Method II).
- Aggregatzustand
- Solid
- pka
- 2.94 · pKa 2.94 (Uncertain)
- Farbe
- White to Off-White
- Wasserlöslichkeit
- 9.095 mg/L · 9.095mg/L(25 ºC)
- Major Application
- pharmaceutical (small molecule)
- InChI
- 1S/C19H17ClN2O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)21-11-18(23)22(17)12-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2
- InChIKey
- MWQCHHACWWAQLJ-UHFFFAOYSA-N
- SMILES
- Clc1ccc2N(CC3CC3)C(=O)CN=C(c4ccccc4)c2c1
- EPA chemische Informationen
- 2 H-1,4-Benzodiazepin-2-one, · 2H-1,4-Benzodiazepin-2-one, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl- (2955-38-6)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
Warning
H336 (66.7%): May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure; Narcotic effects];H361 (66.7%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity];H362 (33.3%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]
P203, P260, P261, P263, P264, P270, P271, P280, P304+P340, P318, P319, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 3 reports by companies.;There are 2 notifications provided by 2 of 3 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Regulatory Information
DEA schedule IV controlled substance
2H-1,4-Benzodiazepin-2-one, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety Information
IMAP assessments - 2H-1,4-Benzodiazepin-2-one, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-: Human health tier I assessment;IMAP assessments - 2H-1,4-Benzodiazepin-2-one, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-: Environment tier I assessment
Toxikologische Informationen
Treatment
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.
Toxicity Summary
Prazepam is believed to stimulate GABA receptors in the ascending reticular activating system. Since GABA is inhibitory, receptor stimulation increases inhibition and blocks both cortical and limbic arousal following stimulation of the brain stem reticular formation.
Carcinogen Classification
Prazepam
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 Severity and Toxicity (DILIst)
Prazepam
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Regulatorische Informationen
Regulatory Information
DEA schedule IV controlled substance
2H-1,4-Benzodiazepin-2-one, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Sicherheitsdaten
- wgk
- 2
- ridadr
- 3249
- hs_code
- 2933910000
- RTECS-Nr.
- DF2368000
- risk_code
- 11-23/24/25-39/23/24/25
- hazard_code
- F,T
- safety_code
- 22-24/25-45-36/37-16-7
- hazard_class
- 6.1(b)
- packing_group
- III
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
ATC Code
N05BA11
N - Nervous system;N05 - Psycholeptics;N05B - Anxiolytics;N05BA - Benzodiazepine derivatives;N05BA11 - Prazepam
QN - Nervous system;QN05 - Psycholeptics;QN05B - Anxiolytics;QN05BA - Benzodiazepine derivatives;QN05BA11 - Prazepam
Pharmacodynamics
Prazepam is a benzodiazepine derivative with anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant activity. Benzodiazepines may be habit-forming (causing mental or physical dependence), especially when taken for a long time or in high doses.
Mechanism of Action
Prazepam is believed to stimulate GABA receptors in the ascending reticular activating system. Since GABA is inhibitory, receptor stimulation increases inhibition and blocks both cortical and limbic arousal following stimulation of the brain stem reticular formation.
Metabolism/Metabolites
Hepatic.
Hepatic. Prazepam is metabolised into descyclopropylmethylprazepam (also known as desmethyldiazepam) and 3-hydroxyprazepam which is further metabolised into oxazepam. [Wikipedia] Half Life: 36-200 hours
MeSH Pharmacological Classification
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.
Verwendung und Herstellung
Uses
Use (kg; approx.) in Germany (2009): >25;Use (kg) in France (2004): 2166;Consumption (g per capita; approx.) in Germany (2009): 0.000305;Consumption (g per capita) in France (2004): 0.0358;Calculated removal (%): 33.7
For the treatment of anxiety disorders.
Anwendungen
BeschreibungPrazepam (Item No. 18358) is an analytical reference material categorized as a benzodiazepine. Prazepam is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.
VerwendenSedative-hypnotic.
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