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Loxoribin

Strukturformel
Struktur von Loxoribin
Allgemeines
Freiname Loxoribin[1]
Andere Namen
  • 7-Allyl-7,8-dihydro-8-oxoguanosin
  • 7-Allyl-2-amino-9-β-D-ribofuranosylpurin-6,8(1H,9H)-dion (WHO)
  • RWJ-21757
Summenformel C13H17N5O6
Externe Identifikatoren/Datenbanken
CAS-Nummer 121288-39-9
PubChem 60737
ChemSpider 54740
DrugBank DB17589
Wikidata Q27081526
Arzneistoffangaben
Wirkstoffklasse

Antimetabolit, Immunmodulator

Eigenschaften
Molare Masse 339,30 g·mol−1
Aggregatzustand

fest[2]

Sicherheitshinweise
GHS-Gefahrstoffkennzeichnung[2]
keine GHS-Piktogramme

H- und P-Sätze H: keine H-Sätze
P: keine P-Sätze[2]
Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa).

Loxoribin ist eine chemische Verbindung aus der Gruppe der Guanosin-Nukleoside, die Toll-like-Rezeptoren vom Typ 7 (TLR 7) aktiviert.

Eigenschaften

Loxoribin ist ein Agonist des TLR 7 und aktiviert die angeborene Immunantwort.[3] In Folge wird vermehrt IFN-alpha/beta, IFN-gamma, TNF-alpha, TNF-beta, IL-1, IL-6 und die 40 kDa-Kette von IL-12 gebildet.[4] Loxoribin induziert die Reifung von Monozyten-abgeleiteten dendritischen Zellen.[5] Alternative Agonisten des TLR 7 sind Imiquimod, Resiquimod und Bropirimin.

Einzelnachweise

  1. ↑ INN Recommended List 31, World Health Organisation (WHO), 9. September 1991.
  2. ↑ a b c Datenblatt 7-Allyl-7,8-dihydro-8-oxoguanosine, 95% bei Sigma-Aldrich, abgerufen am 19. Juni 2023 (PDF).
  3. ↑ S. Fasciano, L. Li: Intervention of Toll-like receptor-mediated human innate immunity and inflammation by synthetic compounds and naturally occurring products. In: Current medicinal chemistry. Band 13, Nummer 12, 2006, S. 1389–1395, doi:10.2174/092986706776872916, PMID 16719784.
  4. ↑ M. G. Goodman: A new approach to vaccine adjuvants. Immunopotentiation by intracellular T-helper-like signals transmitted by loxoribine. In: Pharmaceutical biotechnology. Band 6, 1995, S. 581–609, PMID 7551237.
  5. ↑ T. Dzopalic, A. Dragicevic, S. Vasilijic, D. Vucevic, I. Majstorovic, B. Bozic, B. Balint, M. Colic: Loxoribine, a selective Toll-like receptor 7 agonist, induces maturation of human monocyte-derived dendritic cells and stimulates their Th-1- and Th-17-polarizing capability. In: International Immunopharmacology. Band 10, Nummer 11, November 2010, S. 1428–1433, doi:10.1016/j.intimp.2010.08.010, PMID 20817120.

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