121288-39-9

121288-39-9 structure

Name: Loxoribine
Chemical Name: 7-allyl-8-oxoguanosine
CAS Number: 121288-39-9
Molecular Formula: C₁₃H₁₇N₅O₆
Molecular Weight: 339.30400
Catalog: Biochemical Nucleoside drugs Nucleoside intermediate
Create Date: 2018-12-16 12:20:33
Modify Date: 2024-01-04 16:54:26
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].

Name	7-allyl-8-oxoguanosine
Synonyms	7-ALLYL-7 8-DIHYDRO-8-OXOGUANOSINE 95 7-allyl-8-oxo-G Loxoribine 7-Allyl-7,8-dihydro-8-oxoguanosine MFCD00867591

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].
Related Catalog	Signaling Pathways >> Immunology/Inflammation >> Toll-like Receptor (TLR) Research Areas >> Cancer Research Areas >> Infection
Target	TLR7[1]
In Vitro	Loxoribine induces maturation of human monocyte-derived dendritic cells DCs and stimulates their Th-1- and Th-17-polarizing capability[2]. Loxoribine (250 μM; 48 hours) stimulates maturation of MoDCs as shown by up-regulation of CD80, CD83, CD40, CD54 and CCR7[2]. loxoribine activates cells of the innate immune system selectively via the Toll-like receptor (TLR) 7/MyD88-dependent signaling pathway[1].
In Vivo	Loxoribine (2 mg; s.c.or i.v.) activates murine natural killer (NK) cells in vivo[3]. Animal Model: 8-12 weeks male CBA/J mice[3] Dosage: 2 mg Administration: Subcutaneous or intravenous injection Result: activates murine natural killer (NK) cells in vivo.
References	[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.

Density	1.92g/cm3
Boiling Point	591.8ºC at 760mmHg
Melting Point	227-230ºC(lit.)
Molecular Formula	C₁₃H₁₇N₅O₆
Molecular Weight	339.30400
Flash Point	311.7ºC
Exact Mass	339.11800
PSA	168.62000
Vapour Pressure	1.81E-16mmHg at 25°C
Index of Refraction	1.812
Storage condition	Desiccate at +4°C

WGK Germany	3

126138-81-6

~99%

121288-39-9

Literature: WO2013/67597 A1, ; Page/Page column 108 ;

4016-63-1

121288-39-9

Literature: Journal of Medicinal Chemistry, , vol. 37, # 21 p. 3561 - 3578

19029-70-0

106-95-6

121288-39-9

Literature: Nucleosides and Nucleotides, , vol. 13, # 1-3 p. 551 - 562

Precursor 4
126138-81-6 4016-63-1 19029-70-0 106-95-6
DownStream 0

1158522-08-7	2171854-31-0
1866814-81-4	940364-43-2
134104-43-1	131615-57-1
6906-52-1	930439-75-1
1018584-77-4	1375289-11-4