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Loxoribine

CAT: 0804-HY-108472-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-108472-01Size:5 mg
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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].
CAS Number
121288-39-9
Product Name Alternative
7-Allyl-8-oxoguanosine; RWJ 21757
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Influenza Virus; Toll-like Receptor (TLR)
Type
Reference compound
Related Pathways
Anti-infection; Immunology/Inflammation
Applications
Cancer-programmed cell death
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/loxoribine.html
Purity
99.94
Solubility
DMSO : 100 mg/mL (ultrasonic) |H2O : 40 mg/mL (ultrasonic)
Smiles
OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(N=C(N)NC3=O)=C3N(CC=C)C2=O)O1
Molecular Formula
C13H17N5O6
Molecular Weight
339.30
Precautions
H302, H315, H319, H335
References & Citations
[1]Heil F, et al. The Toll-like receptor 7 (TLR7) -specific stimulus loxoribine uncovers a strong relationship within the TLR7, 8 and 9 subfamily. Eur J Immunol. 2003 Nov;33 (11) :2987-97.|[2]Dzopalic T, et al. 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. Int Immunopharmacol. 2010 Nov;10 (11) :1428-33.|[3]Pope BL, et al. In vivo enhancement of murine natural killer cell activity by 7-allyl-8-oxoguanosine (loxoribine) . Int J Immunopharmacol. 1992 Nov;14 (8) :1375-82.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Phase 2
Isoform
TLR7

Chemical Information

Loxoribine

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.

CAS Number121288-39-9
PubChem CID135410906
IUPAC Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-enyl-1H-purine-6,8-dione
Molecular FormulaC13H17N5O6
Molecular Weight339.30
XLogP-2.7
Topological Polar Surface Area161
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Heavy Atom Count24
Formal Charge0
Complexity661
SMILES
C=CCN1C2=C(N=C(NC2=O)N)N(C1=O)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
InChI
InChI=1S/C13H17N5O6/c1-2-3-17-6-9(15-12(14)16-10(6)22)18(13(17)23)11-8(21)7(20)5(4-19)24-11/h2,5,7-8,11,19-21H,1,3-4H2,(H3,14,15,16,22)/t5-,7-,8-,11-/m1/s1
InChIKey
VDCRFBBZFHHYGT-IOSLPCCCSA-N
Chemical Structure
2D Structure
2D structure of Loxoribine
CAS: 121288-39-9
CID: 135410906
Formula: C13H17N5O6
MW: 339.30
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight339.30
XLogP3-2.7
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass339.11788328
Monoisotopic Mass339.11788328
Topological Polar Surface Area161 Ų
Heavy Atom Count24
Formal Charge0
Complexity661
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
461580Loxoribine
TBI3780-5MGLoxoribine, TLR7 agonist
TRC-A550000-10MG7-Allyl-7,8-dihydro-8-oxoguanosine(Loxoribine)

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