HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
7-Chlor-1-(2-(diethylamino)ethyl)-5-(2-fluorphenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-on
D00329 · Felmane · Noctosom · dalmane-r · ro56901/3 · Ro 56901/3 · Stauroderm · FLURAZEPAM
Identifikatoren & physikalische Daten
| CAS No. | 17617-23-1 |
|---|---|
| Summenformel | C21H23ClFN3O |
| Durchschnittliche Molmasse | 387,9 g/mol |
| Monoisotopische Masse | 387,15136826 g/mol |
| SMILES | CCN(CC)CCN1C(=O)CN=C(c2ccccc2F)c2cc(Cl)ccc21 |
| InChIKey | SAADBVWGJQAEFS-UHFFFAOYSA-N |
| PubChem CID | 3393 |
| ChEMBL | CHEMBL968 |
| ChEBI | CHEBI:5128 |
| EC No. | 241-591-7 |
| DTXSID | DTXSID1023071 |
| Lokaler Name | 7-Chlor-1-(2-(diethylamino)ethyl)-5-(2-fluorphenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-on |
Chemische & physikalische Eigenschaften
| XLogP | 3 |
|---|---|
| Polarare Oberfläche (TPSA) | 35,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 27 |
| Formalladung | 0 |
| Komplexität | 540 |
| Arzneimittel | DEA NFLIS-Drug Category -> BenzodiazepinesDEA Schedule IV Controlled Substance -> DepressantsPharmaceuticalsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive CompoundsPharmaceuticals -> Nervous system -> Anxiolytics |
| LogP (Verteilungskoeffizient) | 3.8 |
| Color/Form | White rods from ether-petroleum ether |
| Löslichkeit | OFF-WHITE TO YELLOW, CRYSTALLINE POWDERSLIGHT ODOR TO ODORLESSMODERATELY HYGROSCOPICMELTS WITH DECOMPOSITION AT ABOUT 212 °CSOLUBILITY: 1 G IN 2 ML WATERFREELY SOL IN ALCOHOLSLIGHTLY SOL IN CHLOROFORM /FLURAZEPAM DIHYDROCHLORIDE/1.00e-02 g/L45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: <6 mg/mL |
| Human Drugs | Breast FeedingLactationMilk, HumanBenzodiazepinesHypnotics and SedativesPharmaceuticals |
| Schmelzpunkt | 190-22077-82 °CWHITE RODSPALE YELLOW CRYSTALS FROM METHANOL + ETHERMP: 190-220 °C /FLURAZEPAM DIHYDROCHLORIDE/79.5 °C77-82° |
| Physical Description | Solid |
| Stability/Shelf Life | Store in air tight containers. Protect from light. /Flurazepam hydrochloride/ |
| Dissociation Constants | pKa values 1.9 and 8.16 |
| Collision Cross Section | 185.3 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)] |
| Siedepunkt | 551.4±50.0 °C(Predicted) |
| Dichte | 1.2089 (estimate) |
| Flammpunkt | 9℃ |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | solid |
| pKa (Säurekonstante) | pKa 1.90±0.05(H2O) (Uncertain)8.16±0.05 (Uncertain) |
| Farbe | light yellow |
| EPA chemische Informationen | 2H-1,4-Benzodiazepin-2-one, 7-chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-1,3-dihydro- (17617-23-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 44 reports by companies from 3 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | DEA schedule IV controlled substanceStatus: Active Update: 05-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20551 |
| Weitere Sicherheitsinformationen | IMAP assessments - 2H-1,4-Benzodiazepin-2-one, 7-chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-1,3-dihydro-: Human health tier I assessment |
| FDA-Anforderungen | Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule IV includes flurazepam, DEA Code #2767. |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Lagerbedingungen | Store below 40 °C (104 °F), preferably between 15 and 30 °C (59 and 86 °F), unless otherwise specified by manufacturer. Store in a tight, light-resistant container. /Flurazepam hydrochloride/ |
| Treatment | General supportive measures should be employed, along with immediate gastric lavage. Intravenous fluids should be administered and an adequate airway maintained. Hypotension and CNS depression may be combated by judicious use of appropriate therapeutic agents. If excitation occurs in patients following Flurazepam overdosage, barbiturates should not be used. Flumazenil, a specific benzodiazepine-receptor antagonist, is indicated for the complete or partial reversal of the sedative effects of benzodiazepines and may be useful in situations when an overdose with a benzodiazepine is known or suspected. (L1712) |
| Wechselwirkungen | PATIENTS RECEIVING ... /AMITRIPTYLINE & FLURAZEPAM/ CONCURRENTLY SHOULD BE WARNED ABOUT POSSIBLE ENHANCED CNS DEPRESSION. ... TRICYCLIC ANTIDEPRESSANTS ... ARE STRUCTURALLY & PHARMACOLOGICALLY RELATED TO AMITRIPTYLINE ... .NEXT MORNING STUDIES OF THE EFFECTS OF ALCOHOL ON THE PERFORMANCE OF PSYCHOMOTOR SKILLS OF SUBJECTS WHO HAD ... FLURAZEPAM ... AS A HYPNOTIC THE NIGHT BEFORE SHOWED THAT A SIGNIFICANT & DETRIMENTAL "HANGOVER" INTERACTION TAKES PLACE.... BENZODIAZEPINES SUCH AS ... FLURAZEPAM ... MIGHT BE EXPECTED TO INTERACT SIMILARLY WITH GALLAMINE TRIETHIODIDE & OTHER NONDEPOLARIZING NEUROMUSCULAR BLOCKING AGENTS ... AS WELL AS DEPOLARIZING NEUROMUSCULAR BLOCKING AGENTS ... ./DRUG INTERACTIONS/ ... ARE INFREQUENT ... EXCEPT FOR AN ADDITIVE EFFECT WITH OTHER CNS DEPRESSANTS ... HEAVY CIGARETTE SMOKING MAY DECREASE THE EFFECTIVENESS OF USUAL DOSES ... . /BENZODIAZEPINES/For more Interactions (Complete) data for FLURAZEPAM (12 total), please visit the HSDB record page. |
| Gesundheitliche Auswirkungen | They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. |
| Hepatotoxicity | Flurazepam, as with other benzodiazepines, is rarely associated with serum ALT or alkaline phosphatase elevations, and clinically apparent liver injury is rare. Only a few case reports of acute liver injury from flurazepam have been published and mostly before 1980. The latency to onset of acute liver injury varied between 2 to 6 months and the pattern of liver enzyme elevations was cholestatic. The injury was usually mild-to-moderate in severity and self-limited in course. Fever and rash were not described nor autoantibody formation. Similar rare cases of self-limited, mild-to-moderate, cholestatic liver injury have been reported with other benzodiazepines including alprazolam, chlordiazepoxide, clonazepam, diazepam, lorazepam, and triazolam. |
| Expositionspfade | Oral. Flurazepam hydrochloride is rapidly (30 minutes) absorbed from the gastrointestinal tract |
| Toxizitätsübersicht | Benzodiazepines bind nonspecifically to bezodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell. |
| Signs and Symptoms | Coma, confusion, low blood pressure, sleepiness |
| Medical Surveillance | Liver and kidney function tests and blood counts should be performed regularly during long-term therapy. /Benzodiazepines/ |
| Human Toxicity Excerpts | ... FLURAZEPAM CAUSES AN IMPRESSIVE NUMBER OF SIDE EFFECTS. THE INCIDENCE APPEARS TO BE ABOUT 7%. EXCESSIVE DROWSINESS OCCURS IN ABOUT 2% OF CASESIN ELDERLY OR DEBILITATED PATIENTS, THIS IS MORE COMMON, & THERE MAY ALSO BE VERTIGO, ATAXIA, & FALLING. RARE INSTANCES OF FAINTING, SLURRED SPEECH, LETHARGY, DISORIENTATION, & ALSO COMA CAN OCCUR EVEN IN YOUNGER PATIENTS ... ELEVATED SERUM LEVELS OF THE TRANSAMINASES, ALKALINE PHOSPHATASE, & BILIRUBIN HAVE BEEN REPORTED ON OCCASION ... . /FLURAZEPAM CHLORIDE/OTHER REPORTED SIDE EFFECTS INCLUDE ... HEADACHE, HEARTBURN, UPSET STOMACH, NAUSEA, VOMITING, DIARRHEA, CONSTIPATION, GI PAIN, NERVOUSNESS, TALKATIVENESS, APPREHENSION, IRRITABILITY, WEAKNESS, PALPITATION, CHEST PAINS, BODY & JOINT PAIN, & GENITOURINARY COMPLAINTS. LESS FREQUENTLY SWEATING, FLUSHES, BLURRED VISION, DIFFICULTY IN FOCUSING, BURNING EYES, ... SHORTNESS OF BREATH, PRURITUS, SKIN RASH, ... BITTER TASTE, EXCESSIVE SALIVATION, ANOREXIA, ... DEPRESSION ... . /FLURAZEPAM DIHYDROCHLORIDE/... FLURAZEPAM OCCASIONALLY INCREASE/S/ THE INCIDENCE OF NIGHTMARES, ESPECIALLY DURING THE FIRST WK OF USE. FLURAZEPAM OCCASIONALLY CAUSES GARRULOUSNESS, ANXIETY, IRRITABILITY, TACHYCARDIA, & SWEATING. EUPHORIA, RESTLESSNESS, HALLUCINATIONS, & HYPOMANIC BEHAVIOR HAVE BEEN REPORTED TO OCCUR DURING USE OF VARIOUS BENZODIAZEPINES.... EQUALLY PARADOXICAL IS AN INCREASE IN ANXIETY ... BOTH PSYCHOSES & SUDDEN SUICIDAL IMPULSES HAVE OCCASIONALLY BEEN REPORTED IN PATIENTS RECEIVING HIGH DOSES ... IN GENERAL, THE CLINICAL TOXICITY ... IS LOW. /BENZODIAZEPINES/For more Human Toxicity Excerpts (Complete) data for FLURAZEPAM (16 total), please visit the HSDB record page. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)flurazepamDILI PositiveOralDOI:10.1016/j.drudis.2019.09.022 |
| Non-Human Toxicity Excerpts | IN DOSES UP TO 80 MG/KG DURING VARIOUS PERIODS OF GESTATION IN THE RAT, NEITHER TERATOGENIC NOR POSTNATAL CHANGES WERE PRODUCED IN THE OFFSPRING. IN THE RABBIT, DOSES OF 20 MG/KG/DAY FROM DAY 6 THROUGH 18 PRODUCED NO OBSERVABLE ADVERSE FETAL EFFECTS. |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | 3249 |
| RTECS-Nr. | DF0875000 |
| R-Sätze (R) | 22-33-39/23/24/25-23/24/25-11 |
| Gefahrensymbole | Xn,T,F |
| Sicherheitshinweise (S) | 1/2-22-36-45-36/37-16-7 |
| Gefahrenklasse | 6.1(b) |
| Verpackungsgruppe | III |
| Gefahrstoffdaten | 17617-23-1(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Flurazepam (CRM) (Item No. 18160) is a certified reference material that is structurally categorized as a benzodiazepine. It acts as a partial agonist of the benzodiazepine site on GABAA receptors, potentiating the action of GABA with an EC50 value of 930 nM in neuronal chick spinal cord cultures. Through this signaling mechanism, flurazepam produces anxiolytic and sedative properties that have been implemented clinically in the treatment of insomnia but also carry a potential for misuse. This product is intended for forensic and research purposes.
Verwenden
Anticonvulsant; relaxant (muscle); sedative-hypnotic Dalmane (Valeant.