Amantadin

Amantadine Struktur
768-94-5
CAS-Nr.
768-94-5
Bezeichnung:
Amantadin
Englisch Name:
Amantadine
Synonyma:
1-ADAMANTYLAMINE;Adamantylamine;1-ADAMANTANAMINE;Adamantamine;adamantan-1-amine;1-AMINOADAMANTANE;(3s,5s,7s)-adaMantan-1-aMine;Amantidine;ADAMANTANAMINE;Amanta
CBNumber:
CB3259991
Summenformel:
C10H17N
Molgewicht:
151.25
MOL-Datei:
768-94-5.mol

Amantadin Eigenschaften

Schmelzpunkt:
206-208 °C(lit.)
Siedepunkt:
263.29°C (rough estimate)
Dichte
0.9510 (rough estimate)
Brechungsindex
1.5220 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
1 M HCl: soluble5%, clear to hazy, colorless to faint yellow or tan
Aggregatzustand
Powder
pka
10.1(at 25℃)
Farbe
White to cream
Wasserlöslichkeit
Soluble in organic solvents. Insoluble in water.
Merck 
14,374
BRN 
2204333
InChIKey
DKNWSYNQZKUICI-UHFFFAOYSA-N
CAS Datenbank
768-94-5(CAS DataBase Reference)
NIST chemische Informationen
Tricyclo[3.3.1.13,7]decane-1-amine(768-94-5)
EPA chemische Informationen
Tricyclo[3.3.1.13,7]decan-1-amine (768-94-5)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,Xi
R-Sätze: 22-36/37/38
S-Sätze: 26-36
WGK Germany  3
RTECS-Nr. YD1925000
10-34
HS Code  29213000
Giftige Stoffe Daten 768-94-5(Hazardous Substances Data)
Toxizität LD50 oral in rat: 900mg/kg
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung P264, P270, P301+P312, P330, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung
Sicherheit
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.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Amantadin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-Sätze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Beschreibung

Amantadine is an agent that raises the concentration of dopamine in the synaptic cleft by releasing it from neurons and suppressing the process of reuptake.

Chemische Eigenschaften

White to cream powder

Verwenden

Amantadine is a primary amine derivative of adamantane. It has an effect on mycoviruses, which are RNA-containing viruses. It has a very narrow spectrum of action and is used only for treating and preventing influenza A. It is also used for treating Parkinsonism. The exact mechanism of antiviral action of amantadine is not completely understood. It is believed that it is an ion channel blocker. It has also been suggested that amantadine inhibits absorption of viral particles into the host cell, which is expressed in the breakdown of diffusion of the virus into the cell, or inhibition of the “stripping process” of the virus. The main use is for the prevention of type A2 influenza. Synonyms of this drug are simmetrel, viregit, mantadan, and others.

Definition

ChEBI: A member of the class of adamantanes that is used as an antiviral and antiparkinson drug.

Biologische Funktion

Amantadine was originally introduced as an antiviral compound, but it is modestly effective in treating symptoms of parkinsonism. It is useful in the early stages of parkinsonism or as an adjunct to levodopa therapy. Its mechanism of action in parkinsonism is not clear, but amantadine may affect dopamine release and reuptake. Additional sites of action may include antagonism at muscarinic and N-methyl-Daspartate (NMDA) receptors. Adverse effects include nausea, dizziness, insomnia, confusion, hallucinations, ankle edema, and livedo reticularis. Amantadine and the anticholinergics may exert additive effects on mental functioning

Antimicrobial activity

It inhibits influenza A virus replication at concentrations of 0.2– 0.6 mg/L, but has little or no activity against influenza B or C.

Acquired resistance

Resistance is the consequence of mutations in amino acid positions 27, 30 and 31 in the M2 transmembrane sequence. Cross-resistance between amantadine and rimantadine is universal. Influenza H3N2 strains worldwide are now resistant, but seasonal H1N1 strains remain susceptible. Postexposure family prophylaxis results in the prompt emergence of drug resistance after onset of treatment.

Allgemeine Beschreibung

Amantadine has been used for years as a treatment for Parkinson disease. The adamantanamines have twomechanisms in common:they inhibit an early step in viralreplication, most likely viral uncoating,and in somestrains, they affect a later step that probably involves viral assembly,possibly by interfering with hemagglutinin processing.The main biochemical locus of action is the influenzatype A virus M2 protein, which is an integral membrane proteinthat functions as an ion channel. The M2 channel is a protontransport system. By interfering with the function of theM2 protein, the adamantanamines inhibit acid-mediated dissociationof the ribonucleoprotein complex early in replication.They also interfere with transmembrane proton pumping,maintaining a high intracellular proton concentrationrelative to the extracellular concentration and enhancingacidic pH-induced conformational changes in the hemagglutininduring its intracellular transport at a later stage. The conformationalchanges in hemagglutinin prevent transfer of thenascent virus particles to the cell membrane for exocytosis.

Pharmazeutische Anwendungen

A symmetrical synthetic C-10 tricyclic amine with an unusual cage-like structure, supplied as the hydrochloride for oral administration.

Mechanism of action

Amantadine hydrochloride (1-adamantanamine hydrochloride) is a symmetric, tricyclic, primary amine that inhibits penetration of RNA viral particles into the host cell. It also inhibits the early stages of viral replication by blocking the uncoating of the viral genome and the transfer of nucleic acid into the host cell.

Pharmakokinetik

Oral absorption: >90%
Cmax 200 mg oral per day: 0.4–0.9 mg/L after c. 4–6 h
Plasma half-life: 9.7–14.5 h
Volume of distribution: 10.4 L/kg
Plasma protein binding: 65%
Absorption and distribution
Absorption after oral administration is almost complete. Levels in secretions approach plasma concentrations.
Metabolism and excretion
About 56% of a single oral dose is excreted unchanged within 24 h by the kidney. Altogether 90% of an oral dose is excreted in the urine with a mean elimination half-life of 11.8 h in subjects with normal renal function. In elderly men, the half-life is 28.9 h and in patients with renal insufficiency half-lives of 18.5 h to 33.8 days have been observed. The renal clearance is around 398 mL/min (range 112–772 mL/min), indicating active secretion as well as glomerular filtration. Less than 5% of a dose is removed during hemodialysis and average half-lives of 8.3 and 13 days have been reported in patients on chronic hemodialysis. Extreme care must be taken to ensure that drug does not accumulate to toxic levels.

Clinical Use

Amantadine is used for the treatment of diseases caused by influenza A strains.

Nebenwirkungen

Embryotoxicity and teratogenicity have been observed in rats receiving 50 mg/kg per day, about 15 times the usual human dose. Neurological side effects include drowsiness, insomnia, light-headedness, difficulty in concentration, nervousness, dizziness and headache in up to 20% of individuals. Other side effects include anorexia, nausea, vomiting, dry mouth, constipation and urinary retention. All develop during the first 3–4 days of therapy and are reversible by discontinuing the drug. An exception to rapid onset of adverse reactions is livedo reticularis. Convulsions, hallucinations and confusion are dose related, usually occurring at levels in excess of 1.5 mg/L; convulsions may occur at a lower threshold in patients with a history of epilepsy and the drug is best avoided in such patients.

Sicherheitsprofil

Poison by intraperitoneal route.Moderately toxic by ingestion. Mutation data reported.When heated to decomposition it emits toxic fumes ofNOx. Used as an antiviral agent.

läuterung methode

Dissolve the amine in Et2O, dry it over KOH, evaporate and sublime it in vacuo. [Stetter et al. Chem Ber 93 226 1960.]

Amantadin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Amantadin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 436)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Huzhou Chenxi Environmental Protection Technology Co. , Ltd.
+8616762203950
1034385273@qq.com China 27 58
Hebei Dangtong Import and export Co LTD
+8615632927689
admin@hbdangtong.com China 998 58
Anhui Ruihan Technology Co., Ltd
+8617756083858
daisy@anhuiruihan.com China 994 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806
sales@capotchem.com China 29797 60
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21700 55
Shanghai Time Chemicals CO., Ltd.
+86-021-57951555 +8617317452075
jack.li@time-chemicals.com China 1807 55
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714
fandachem@gmail.com China 9354 55
career henan chemical co
+86-0371-86658258
sales@coreychem.com China 29914 58
Zhejiang ZETian Fine Chemicals Co. LTD
18957127338
stella@zetchem.com China 2141 58
Hubei Jusheng Technology Co.,Ltd.
18871490254
linda@hubeijusheng.com CHINA 28180 58

768-94-5(Amantadin)Verwandte Suche:


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  • 1-Amantadine
  • 1-Aminoadamatane
  • 1-aminodiamantane
  • 1-aminotricyclo(3.3.1.1(sup3,7))decane
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  • tricyclo(3.3.1.1(sup3.7))decan-1-amine
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  • Adamantan-1-amine, Tricyclo[3.3.1.1~3,7~]decan-1-amine
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  • 1-ADAMANTAMINE (1-AMINOADAMANTANE)
  • C06818
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  • 1-AMINOADAMANTANE
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  • Amantidine
  • Aminoadamantane
  • ADAMANTANAMINE
  • tricyclo[3.3.1.13,7]decan-1-amine
  • Symadine
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  • (3s,5s,7s)-adaMantan-1-aMine
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  • 1-Adamantanamine (AS)
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