Naloxon

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H302：Gesundheitsschädlich bei Verschlucken.

• Sicherheit

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P270：Bei Gebrauch nicht essen, trinken oder rauchen.

  P301+P312：BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

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

Naloxone Chemische Eigenschaften,Einsatz,Produktion Methoden

• Beschreibung

  It is worth mentioning that N-allylic substitution in a number of morphine derivatives, as a rule, leads to antagonistic properties. Naloxone is a few times stronger than nalorphine as an antagonist. It blocks opiate receptors. It eliminates central and peripheral action of opioids, including respiratory depression. Naloxone is used upon overdose of narcotic analgesics.

• Originator

  Narcan,Du Pont,US,1971

• Verwenden

  Naloxone is a specific opioid antagonist. Narcotic antagonist.

• Verwenden

  antineoplastic

• Definition

  ChEBI: A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an all l group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.

• Manufacturing Process

  10 grams of 14-hydroxydihydromorphinone (oxymorphone) was converted into its diacetate by warming it on the steam bath with 80 cc of acetic anhydride for about 2 hours. The acetic anhydride was removed on the water bath under a vacuum of about 30 mm absolute pressure. The melting point of the residue was 220°C. The residue was taken up in 100 cc of chloroform. An equal amount by weight of cyanogen bromide was added and the mixture was refluxed at about 60°C for about 5 hours. After refluxing, the mixture was washed with 100 cc of a 5% aqueous hydrochloric acid solution, dried over sodium sulfate and the chloroform removed by evaporation under a vacuum of about 30 mm. The residue had a melting point of 240°C.
  The residue was then heated at about 90°C for 16 hours on a steam bath with 300 cc of 20% aqueous hydrochloric acid solution, and treated with a small amount, e.g., 1 gram of charcoal. The hydrochloric acid was then removed under a vacuum of 15 mm, the residue dissolved in 30 cc of water and precipitated by the addition of 2.4 cc of concentrated aqueous ammonia. The precipitate was filtered off and dried. It consists of 14- hydroxydihydronormorphinone. It is soluble in ethanol.
  The 14-hydroxydihydronormorphinone was suspended in 200 cc of pure ethyl alcohol, half its weight of sodium bicarbonate and half its weight of allyl bromide added and the resulting mixture was refluxed at about 75°C for 48 hours. The solution was cooled, e.g., to 10°C and filtered and the alcohol removed under a vacuum of 30 mm. The residue was dissolved in chloroform and filtered. The chloroform was removed under a vacuum of 30 mm and the residue was crystallized from ethylacetate. The crystallized product, N-allyl- 1,4-hydroxydihydronormorphinone, has a melting point of 184°C, is soluble in chloroform and insoluble in petroleum ether. The yield amounts to 20% based on the weight of the reacted 14-hydroxydihydromorphinone.

• Trademarks

  Narcan (Bristol-Myers Squibb); Narcan (Endo).

• Therapeutic Function

  Narcotic antagonist

• Biologische Funktion

  Because of its fast onset (minutes), naloxone (Narcan) administered IV is used most frequently for the reversal of opioid overdose. However, it fails to block some side effects of the opioids that are mediated by the δ- receptor, such as hallucinations. The rapid offset of naloxone makes it necessary to administer the drug repeatedly until the opioid agonist has cleared the system to prevent relapse into overdose. The half-life of naloxone in plasma is 1 hour. It is rapidly metabolized via glucuronidation in the liver and cleared by the kidney. Naloxone given orally has a large first-pass effect, which reduces its potency significantly. Often an overshoot will follow the administration of naloxone for overdose. The heart rate and blood pressure of the patient may rise significantly. The overshoot is thought to be due to precipitation of acute withdrawal signs by naloxone. Given alone to nonaddicts, naloxone produces no pharmacological effects.
  Naloxone is approved for use in neonates to reverse respiratory depression induced by maternal opioid use. In addition, naloxone has been used to improve circulation in patients in shock, an effect related to blockade of endogenous opioids. Other experimental and less well documented uses for naloxone include reversal of coma in alcohol overdose, appetite suppression, and alleviation of dementia from schizophrenia. Side effects of naloxone are minor.

• Allgemeine Beschreibung

  Naloxone (Narcan) is a pure antagonist at allopioid receptor subtypes. Structurally, it resembles oxymorphoneexcept that the methyl group on the nitrogen isreplaced by an allyl group. This minor structural change retains high binding affinity to the receptor, but no intrinsicactivity. It is used to reverse the respiratory depressant effectsof opioid overdoses.
  Naloxone is administered intravenously with an onset ofaction within 2 minutes. Because it is competing with theopioid for the receptor sites, the dose and frequency of administrationwill depend on the amount and type of narcoticbeing antagonized. Overdoses of long-acting opioids(methadone) may require multiple IV doses of naloxone orcontinuous infusions. Neonates born to opioid-exposedmothers may be given IV naloxone at birth to reverse the effectsof opiates.
  Very few metabolism studies on naloxone have beenconducted, although the major metabolite found in the urineis naloxone-3-glucuronide.

• Clinical Use

  Naloxone has no analgesic activity. The compound is the standard antidote to treat opioid adverse reactions, opioid overdoses, or to stop an intended use of an opioid compound. Typical indications are inhibition of opioid-induced respiratory depression, termination of opioid anesthesia or protection of neonates following opioid treatment during labor. Naloxone has a short duration of action and repetitive administration may be necessary to antagonize longer acting agonists. To avoid parenteral misuse of nonscheduled oral opioid formulations (tilidine, pentazcocine), a small amount of naloxone is added which is orally inactivated, but is fully active after parenteral administration.
  Naloxone is orally inactive and is only used parenterally in single or repetitive doses of 0.4– 2 mg up to a total dose of 10 mg, as an intravenous bolus injection or by infusion. The compound is more potent against pure opioid agonists than against mixed agonist – antagonists. Caution should be used in opioid-dependent persons or in persons under high-dose opioid treatment, as naloxone may precipitate an acute withdrawal reaction. Naloxone is relatively free of side effects. Nausea, vomiting, and convulsions have occasionally been reported.

• Synthese

  Naloxone, (-)-17-(allyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one (3.1.92), is synthesized by the alkylation of 14-hydroxydihydronormorphinane (3.1.82) by allylbromide [55¨C58].

  

Naloxone Upstream-Materialien And Downstream Produkte

Naloxon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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