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Loxoribine

Loxoribine structure

Loxoribine 

structure
  • CAS No:

    121288-39-9

  • Formula:

    C13H17N5O6

  • Chemical Name:

    Loxoribine

  • Synonyms:

    Guanosine,7,8-dihydro-8-oxo-7-(2-propen-1-yl)-;Guanosine,7,8-dihydro-8-oxo-7-(2-propenyl)-;7,8-Dihydro-8-oxo-7-(2-propen-1-yl)guanosine;Loxoribine;RWJ 21757;7-Allyl-8-oxoguanosine

  • Categories:

    Biochemical Engineering  >  Saccharides

Description

Loxoribine (7-Allyl-8-oxoguanosine) is a guanosine analog with anti-viral and anti-tumor activities. Loxoribine is an orally bioavailable and selective Toll-like receptor (TLR) 7 agonist[1][2][3].


Loxoribine is a guanine ribonucleotide derivative with immunostimulatory and immunomodulatory activity. Loxoribine undergoes facilitated transport across the plasma membrane into the cytoplasmic compartment of the cell and acts intracellularly, bypassing the biochemical steps involved in the membrane signal transduction pathway used by Ag or anti-IgM Abs to activate B cells. This agent activates the Toll-like receptor 7 (TLR7), a member of the TLR family of pathogen-associated molecular pattern recognition receptors thereby activating the innate immune system. This activation requires endosomal maturation and recognition is restricted to TLR7. As a result, loxoribine induces cycling B cells to proliferate and differentiate non-specifically and recruit antigen-reactive B cells to undergo differentiation to antibody production, markedly amplifying the underlying response in the process.

Loxoribine Basic Attributes

339.306

339.30

9CAS0V66OI

DTXSID3046748

C1470

Characteristics

168.62000

1.92g/cm3

227-230 °C(lit.)

591.8ºC at 760mmHg

311.7ºC

1.812

Desiccate at +4°C

Safety Information

3

Drug Information

7-allyl-8-oxoguanosine

Loxoribine Use and Manufacturing

Small-molecule immunostimulants

Computed Properties

Molecular Weight:339.30
XLogP3:-2.7
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:339.11788328
Monoisotopic Mass:339.11788328
Topological Polar Surface Area:161
Heavy Atom Count:24
Complexity:661
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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