5-Ethyl-5-phenyl-barbitursäure

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H317：Kann allergische Hautreaktionen verursachen.

  H351：Kann vermutlich Krebs verursachen.

• Sicherheit

  P201：Vor Gebrauch besondere Anweisungen einholen.

  P202：Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.

  P261：Einatmen von Staub vermeiden.

  P272：Kontaminierte Arbeitskleidung nicht außerhalb des Arbeitsplatzes tragen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P281：Vorgeschriebene persönliche Schutzausrüstung verwenden.

  P302+P352：BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

  P308+P313：BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

  P321：Besondere Behandlung

  P333+P313：Bei Hautreizung oder -ausschlag: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

  P363：Kontaminierte Kleidung vor erneutem Tragen waschen.

  P405：Unter Verschluss aufbewahren.

  P501：Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Phenobarbital Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R61:Kann das Kind im Mutterleib schädigen.
  R25:Giftig beim Verschlucken.
  R40:Verdacht auf krebserzeugende Wirkung.
  R43:Sensibilisierung durch Hautkontakt möglich.
  R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
  R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
  R11:Leichtentzündlich.

• S-Sätze Betriebsanweisung:

  S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
  S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
  S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).

• Beschreibung

  Phenobarbital (Item No. 9001494) is an analytical reference material categorized as a barbiturate. Phenobarbital is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.

• Chemische Eigenschaften

  Crystalline Solid

• Originator

  Phenobarbital ,Inter-Chemical Ltd.

• Verwenden

  Phenobarbital exhibits relaxant, soporific, and anticonvulsant activities. It is widely used in treating epilepsy, chorea, and spastic paralysis, and is used as a component of a large number of combined drugs, valocordin and corvalol in particular.

• Verwenden

  This is a controlled substance (depressant). Anticonvulsant; sedative; hypnotic

• Indications

  Phenobarbital can reduce cholestatic pruritus, possibly by enhancing hepatic microsomal function. Phenobarbital is sedating and may interfere with the metabolism of many drugs.

• Definition

  ChEBI: A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.

• Manufacturing Process

  528 g phenylethyl malonic diethyl ester is dissolved in 500 ml of absolute alcohol. There is then added 140 g urea to the mixture. To this mixture is then added a solution of 57.5 g sodium in 1000 ml absolute alcohol, at such rate that one-half the solution is added during the first hour, a quarter the second hour; an eighth the third hour, and the final eighth during the 4 hours. Then the alcohol is distilled from the reaction mixture. When the alcohol has all been removed, 250 ml xylol is added to the mixture. The reaction mixture is cooled to room temperature and 3 L of water added. The xylene layer was separated and the water solution washed with another 200 ml portion of xylene There is then added to the water solution a 10% excess of a 50% by weight solution of sulfuric acid. The phenobarbital is precipitated as nearly white fluffy crystals, which are filtered off. When dried, they showed 100% phenobarbital by titration. This product may be purified by recrystallization. The unreacted ester in the xylene solution was recovered by distilling off the xylene, and then the phenylethyl malonic ester.

• Trademarks

  Luminal Sodium (Sterling Winthrop);3p spas;Aaciasthma;Adocor;Allergasthmin;Anaspaz;Anti-spas;Asmo fedrilum;Asthmatussin;Bakersed;Barbellen;Barberine;Barbilletae;Barcole;Barophen;Bay-ase;Bebtoyl;Bediphen;Belergamin;Bellademal s;Belladenal;Bellasectal;Bellastal;Bellergal s;Belllumal;Bergofen;Bock-ase;Bonexyl;Broncosmin;C 147;Ce 10010;Ceepa;Cemealonal;Clemodril;Coffecodin;Cor-asthmolyticum;Cortasmyl;Corverum;Dafodil;Digi-pulsnorma;Dithene-r;Dolo-eupaco;Donibin;Donna-lix;Donnaplex;Eeskabarb span;Elibese;Elmigrin;Ephedrobarbital-t;Ephestmin;Epidormb;Ergojuvan;Espafren;Extrovent;Fasconal;Fedrinal;Fenalgin;Fenilcal;Fenosed bitabs;Gardenale;Gastrop;Giolate;Glyanphen;Glyuferal;Gourmase;Gratusminal;Hasp;Hyonol;Ila-med;Irs 109a;Kenedes;Koronar;Lagaspasm;Lardet;Legatin;Lircapil;Lumcalcio;Lunadon;Lysadestal;Mazur-a;Md 1020;Mediphen;Meprobit;Mepropon;Metrojen;Mialgone;Migrane-dolviran;Modirit;Neo-nervostat;Nilspasm;Novodon;Oxabar;Oxoids;Pavadel;Peba;Pen-nitate;Phen bar;Phen-bel;Phenogen;Pheno-gesic;Phental;Phentral cratecil;Piraminal;Plivalgin;Preminal;Prenoxan;Pribetal;Purphen;Quad-sed;Rau-fridetten;Resirol;Respisane;S 611-3;Salviton;Sapos;Scotatal;Secophen-c;Sedacoral;Seda-intestain;Seda-ko;Sedalgin;Sedapar;Sedo corodil;Sedopsic;Sedragesic;Solofoton;Soniphen;Spascol;Spasdel;Spasmalones;Spasmo-compragyl;Spasmogentarol;Spasmotal;Spasmo-van;Spasmoveragin;Spastyl;Spondyneuron;Stollerine;Supamidal;Susano;Syntospon;Tedralan;Teofedrin;Thefedral;Theodrine;Theotabs;Vanital;Zirkonorm.

• Therapeutic Function

  Anticonvulsant, Antiepileptic, Hypnotic, Sedative

• Weltgesundheitsorganisation (WHO)

  Phenobarbital is a long-acting barbiturate which is controlled under Schedule IV of the 1971 Convention on Psychotropic Substances. Phenobarbital is of value in the treatment of epilepsy and preparations for such use are included in the WHO Model List of Essential Drugs. See also WHO comment for barbiturates. (Reference: (UNCPS4) United Nations Convention on Psychotropic Substances (IV), , , 1971)

• Allgemeine Beschreibung

  Phenobarbital, 5-ethyl-5-phenylbarbituricacid (Luminal), is a long-acting sedative and hypnotic.It is also a valuable anticonvulsant, especially in generalizedtonic–clonic and partial seizures (see the discussionon anticonvulsants). Metabolism to the p-hydroxylphenylcompound followed by glucuronidation accounts for about90% of a dose.

• Allgemeine Beschreibung

  Odorless white crystalline powder or colorless crystals. A saturated aqueous solution is acid to litmus (approximately pH 5). Slightly bitter taste.

• Air & Water Reaktionen

  Sensitive to hydrolysis. Alkaline solutions react more rapidly than acidic solutions. At pH 7 and 176°F, has a half life of 74 hours. Insoluble in water.

• Reaktivität anzeigen

  Phenobarbital is also sensitive to prolonged exposure to light. Incompatible with strong oxidizing agents. Forms a complex of reduced solubility with macrogol 4000. Able to form metal derivatives .

• Brandgefahr

  Phenobarbital is combustible.

• Clinical Use

  Antiepileptic

• Sicherheitsprofil

  Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. A human poison by ingestion. An experimental poison by ingestion, intraperitoneal, subcutaneous, intravenous, and rectal routes. Human systemic effects by ingestion: somnolence, motor activity changes, pulmonary changes, allergc dermatitis, and fever. Human reproductive effects by ingestion: drug dependence and other postnatal measures or effects. Human teratogenic effects include developmental abnormalities of the central nervous system, body wall, musculoskeletal, respiratory, gastrointestinal, and urogenital systems. Experimental reproductive effects. Human mutation data reported. Used as a drug in the treatment of epilepsy, and as a hypnotic and sedative. When heated to decomposition it emits toxic fumes of NOx.See also BARBITURATES.

• Synthese

  Phenobarbital, 5-ethyl-5-phenylbarbituric acid or 5-ethyl-5-phenylhexahydropyrimindin-2,4,6-trione (4.1.4), has been synthesized in several different ways [1¨C4]. There is no major difference between them. The first method consists of ethanolysis of benzyl cyanide in the presence of acid, giving phenylacetic acid ethyl ether, the methylene group of which undergoes acylation using the diethyloxalate, giving diethyl ester of phenyloxobutandioic acid (4.1.1), which upon heating easily loses carbon oxide and turns into phenylmalonic ester (4.1.2). Alkylation of the obtained product using ethylbromide in the presence of sodium ethoxide leads to the formation of |á-phenyl-|á- ethylmalonic ester (4.1.3), the condensation of which with urea gives phenobarbital (4.1.4) [1].

  

  
  Another method of phenobarbital synthesis starts with condensation of benzyl cyanide with diethylcarbonate in the presence of sodium ethoxide to give |á-phenylcyanoacetic ester (4.1.5). Alkylation of the ester (4.1.5) using ethylbromide gives |á-phenyl-|á-ethylcyanoacetic ester (4.1.6), which is further converted into the 4-iminoderivative (4.1.7). Acidic hydrolysis of the resulting product gives phenobarbital (4.1.4) [2].

  

• Arzneimittelwechselwirkung

  Potentially hazardous interactions with other drugs
  Aminophylline and theophylline: metabolism of aminophylline and theophylline increased, reduced effect.
  Anthelmintics: concentration of albendazole and praziquantel reduced.
  Anti-arrhythmics: reduced concentration of disopyramide; possibly reduced concentration of dronedarone - avoid; possibly increases metabolism of propafenone.
  Antibacterials: reduced concentration of chloramphenicol, doxycycline, metronidazole, telithromycin and rifampicin - avoid with telithromycin.
  Anticoagulants: increased metabolism of coumarins (reduced effect); concentration of apixaban, edoxaban and rivaroxaban reduced.
  Antidepressants: antagonise anticonvulsant effect; reduces concentration of paroxetine, reboxetine, mianserin and tricyclics; concentration reduced by St John’s wort - avoid.
  Antiepileptics: concentration increased by oxcarbazepine, phenytoin, stripentol and valproate and possibly carbamazepine, also active metabolite of oxcarbazepine reduced and valproate concentration reduced, concentration of fosphenytoin and phenytoin usually reduced but can also be increased; concentration of ethosuximide, rufinamide and topiramate possibly reduced; concentration of lamotrigine, tiagabine and zonisamide reduced.
  Antifungals: possibly reduced concentration of itraconazole, isavuconazole, posaconazole and voriconazole - avoid with voriconazole; reduced absorption of griseofulvin (reduced effect).
  Antimalarials: avoid with piperaquine with artenimol; anticonvulsant effect antagonised by mefloquine.
  Antimuscarinics: possibly reduces active metabolite of fesoterodine - avoid.
  Antipsychotics: antagonise anticonvulsant effect; metabolism of haloperidol increased; possibly reduces aripiprazole concentration - increase aripiprazole dose; concentration of both drugs reduced with chlorpromazine; possibly reduces clozapine concentration; possibly reduces lurasidone concentration - avoid.
  Antivirals: concentration of abacavir, boceprevir, darunavir, fosamprenavir, indinavir, lopinavir, rilpivirine and saquinavir possibly reduced; avoid with boceprevir and rilpivirine; possibly reduces daclatasvir, dasabuvir, ombitasvir, paritaprevir and simeprevir concentration - avoid; avoid with elvitegravir, etravirine, ledipasvir, sofosbuvir and telaprevir; possibly reduces concentration of dolutegravir.
  Apremilast: possibly reduces concentration of apremilast - avoid.
  Bile acids: avoid with cholic acid.
  Calcium-channel blockers: effects of calcium-channel blockers probably reduced - avoid with isradipine and nimodipine.
  Cannabis extract: possibly reduces concentration of cannabis extract - avoid.
  Ciclosporin: reduced ciclosporin levels.
  Cobicistat: possibly reduces concentration of cobicistat - avoid.
  Corticosteroids: metabolism of corticosteroids accelerated, reduced effect.
  Cytotoxics: possibly reduced concentration of axitinib, increase axitinib dose; possibly reduced concentration of bortezomib, bosutinib, cabozantinib, ceritinib, crizotinib, dasatinib, ponatinib and vandetanib - avoid; avoid with cabazitaxel, ceritinib, dabrafenib, gefitinib, olaparib and panobinostat; concentration of irinotecan and its active metabolite and possibly etoposide reduced; possible increased hypersensitivity reactions with procarbazine.
  Diuretics: concentration of eplerenone reduced - avoid; increased risk of osteomalacia with carbonic anhydrase inhibitors.
  Guanfacine: concentration of guanfacine possibly reduced - increase dose of guanfacine.
  Hormone antagonists: possibly reduced concentration of abiraterone - avoid; metabolism of toremifene accelerated.
  Ivacaftor: possibly reduced concentration of ivacaftor - avoid.
  Oestrogens and progestogens: metabolism accelerated, reduced contraceptive effect.
  Orlistat: possibly inc

• Stoffwechsel

  Partly metabolised in the liver.
  25% of a dose is excreted in the urine unchanged at normal urinary pH.

Phenobarbital Upstream-Materialien And Downstream Produkte

50-06-6, Phenobarbital Verwandte Suche: