Amantadiini

Amantadiini
Amantadiini
Amantadiini
Systemaattinen (IUPAC) nimi
Adamantan-1-amiini[1]
Tunnisteet
CAS-numero 768-94-5
ATC-koodi N04BB01
PubChem CID 2130
DrugBank APRD00787
Kemialliset tiedot
Kaava C10H17N 
Moolimassa 151,246 g/mol
SMILES Etsi tietokannasta: eMolecules, PubChem
Fysikaaliset tiedot
Sulamispiste 180 °C [2]
Liukoisuus veteen 6,290 [2](25 °C)
Farmakokineettiset tiedot
Hyötyosuus Hyvin imeytyvä
Proteiinisitoutuminen 67 %
Metabolia vähäinen
Puoliintumisaika 14–15 tuntia [3]
Ekskreetio renaalinen
Terapeuttiset näkökohdat
Raskauskategoria

C(AU) C(US)

Reseptiluokitus


Antotapa oraalinen

Amantadiini (C10H17N) on adamantaanin aminojohdannainen. Amantadiinia käytetään influenssavirus A:n ja Parkinsonin taudin hoitoon.[4] Aine haittaa virusten määrän lisääntymistä estämällä viruksen tunkeutumista solujen sisälle. Sen vaikutusmekanismit Parkinsonin taudin hoidossa eivät ole täysin tiedossa, mutta aine mahdollisesti lisää dopamiinin tuotantoa.[1] Lääkkeen kauppanimi on Atarin. Suomessa amantadiinia myydään valmistenimellä Amantadin-ratiopharm ja se vaatii erityisluvan.[5]

Synteesi

Amantadiinia valmistetaan käsittelemällä adamantiinia bromilla ja typpihapolla, jolloin saadaan esteri. Yhdisteen reaktio asetonitriilin kanssa muodostaa asetamidin, joka hydrolysoituu amantadiiniksi.[6]

Sivuvaikutukset

Amantadiini on yleensä hyvin siedetty lääkeaine. Sivuvaikutuksia voivat olla oireet keskushermostossa ja ruuansulatuskanavassa. Harvinaisia haittavaikutuksia ovat hallusinaatiot ja raajojen turpoaminen. Eläinkokeissa on ilmennyt, että aine voi mahdollisesti hankaloittaa sikiön kehitystä, minkä vuoksi ainetta ei suositella käytettäväksi raskauden aikana.[4]

Vuosina 2005 ja 2006 huomattiin, että eräät influenssatyypit H3N2 ja H1N1 olivat muuntuneet siten, että ne olivat tulleet amantadiinille vastustuskykyisiksi. [7]

Lähteet

  1. ↑ a b Amantadine - Substance Summary NCBI. Viitattu 2. tammikuuta 2009.
  2. ↑ a b Physical properties: Amantadine NLM Viitattu 2.1.2009
  3. ↑ Virustautien hoitoon tarkoitetut mikrobilääkkeet Medicina. Viitattu 3.10.2023.
  4. ↑ a b Amantadiini Lääkelaitos. Viitattu 2.1.2009.[vanhentunut linkki]
  5. ↑ Korvattavat määräaikaisella erityisluvalla toimitettavat lääkkeet Kela 3.10.2023.
  6. ↑ I. K. Moiseev, R. I. Doroshenko & V. I. Ivanova: Synthesis of amantadine via the nitrate of 1-adamantanol. Pharmaceutical Chemistry Journal, 4, April, 1976, 10. vsk. Springer New York. Artikkelin tiivistelmä. Viitattu 2.1.2009. (englanniksi)
  7. ↑ Bright R. A., Shay D. K., Shu B., Cox N. J., Klimov A. I.: Adamantane resistance among influenza A viruses isolated early during the 2005-2006 influenza season in the United States. JAMA. 2006 Feb 22;295(8):891-4. Epub 2006 Feb 2. PubMed. Viitattu 2.1.2009. (englanniksi)

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