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MedKoo Cat#: 461580 | Name: Loxoribine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Loxoribine is a potent new immunostimulant with a relatively broad spectrum of immunobiological activities.

Chemical Structure

Loxoribine
Loxoribine
CAS#121288-39-9

Theoretical Analysis

MedKoo Cat#: 461580

Name: Loxoribine

CAS#: 121288-39-9

Chemical Formula: C13H17N5O6

Exact Mass: 339.1179

Molecular Weight: 339.31

Elemental Analysis: C, 46.02; H, 5.05; N, 20.64; O, 28.29

Price and Availability

Size Price Availability Quantity
25mg USD 285.00 2 weeks
50mg USD 450.00 2 weeks
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Related CAS #
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Synonym
Loxoribine; Loxoribina; Loxoribinum; RWJ-21757; RWJ 21757; RWJ21757;
IUPAC/Chemical Name
7-allyl-2-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7,9-dihydro-1H-purine-6,8-dione
InChi Key
VDCRFBBZFHHYGT-IOSLPCCCSA-N
InChi Code
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
SMILES Code
OC[C@@H]1[C@H]([C@H]([C@H](N2C(N(CC=C)C3=C2N=C(N)NC3=O)=O)O1)O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Loxoribine is an orally bioavailable and selective Toll-like receptor (TLR) 7 agonist.
In vitro activity:
Loxoribine up-regulated the expression of TLR7, CD40, CD54, CD80, CD83 and CCR7 and stimulated the production of IL-12, IL-23, IL-27 and IL-10 by MoDCs (human monocyte-derived myeloid dendritic cells), whereas the level of interferon (IFN)-β was not modulated. Allogeneic CD4(+)T cells in co-culture with loxoribine-treated MoDCs proliferated more strongly, at lower DC/CD4(+)T-cell ratio (1:80), and secreted significantly higher levels of IL-17 and IFN-γ compared to the cultures with control MoDCs. Reference: Int Immunopharmacol. 2010 Nov;10(11):1428-33. https://pubmed.ncbi.nlm.nih.gov/20817120/
In vivo activity:
Rats were treated with three weekly intraperitoneal injections of levamisole (2 mg per rat; n = 6), loxoribine (1 mg per rat; n = 6), or saline (control; n = 7) and killed 8 weeks after treatment. The loxoribine-treated group showed marked regression of both epithelial and stromal components. Loxoribine, a potent immunomodulatory drug, appeared to cause regression in both stromal and epithelium components in a rat model of endometriosis. Reference: Fertil Steril. 1999 Jul;72(1):135-41. https://pubmed.ncbi.nlm.nih.gov/10428162/
Solvent mg/mL mM
Solubility
DMF 30.0 88.42
DMSO 60.0 176.83
DMF:PBS (pH 7.2) (1:1) 0.5 1.47
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 339.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Dzopalic T, Dragicevic A, Vasilijic S, Vucevic D, Majstorovic I, Bozic B, Balint B, Colic M. 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. doi: 10.1016/j.intimp.2010.08.010. Epub 2010 Sep 15. PMID: 20817120. 2. Heil F, Ahmad-Nejad P, Hemmi H, Hochrein H, Ampenberger F, Gellert T, Dietrich H, Lipford G, Takeda K, Akira S, Wagner H, Bauer S. 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. doi: 10.1002/eji.200324238. PMID: 14579267. 3. Wang C, Zhou Q, Wang X, Wu X, Chen X, Li J, Zhu Z, Liu B, Su L. The TLR7 agonist induces tumor regression both by promoting CD4⁺T cells proliferation and by reversing T regulatory cell-mediated suppression via dendritic cells. Oncotarget. 2015 Jan 30;6(3):1779-89. doi: 10.18632/oncotarget.2757. PMID: 25593198; PMCID: PMC4359331. 4. Keenan JA, Williams-Boyce PK, Massey PJ, Chen TT, Caudle MR, Bukovsky A. Regression of endometrial explants in a rat model of endometriosis treated with the immune modulators loxoribine and levamisole. Fertil Steril. 1999 Jul;72(1):135-41. doi: 10.1016/s0015-0282(99)00157-0. PMID: 10428162.
In vitro protocol:
1. Dzopalic T, Dragicevic A, Vasilijic S, Vucevic D, Majstorovic I, Bozic B, Balint B, Colic M. 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. doi: 10.1016/j.intimp.2010.08.010. Epub 2010 Sep 15. PMID: 20817120. 2. Heil F, Ahmad-Nejad P, Hemmi H, Hochrein H, Ampenberger F, Gellert T, Dietrich H, Lipford G, Takeda K, Akira S, Wagner H, Bauer S. 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. doi: 10.1002/eji.200324238. PMID: 14579267.
In vivo protocol:
1. Wang C, Zhou Q, Wang X, Wu X, Chen X, Li J, Zhu Z, Liu B, Su L. The TLR7 agonist induces tumor regression both by promoting CD4⁺T cells proliferation and by reversing T regulatory cell-mediated suppression via dendritic cells. Oncotarget. 2015 Jan 30;6(3):1779-89. doi: 10.18632/oncotarget.2757. PMID: 25593198; PMCID: PMC4359331. 2. Keenan JA, Williams-Boyce PK, Massey PJ, Chen TT, Caudle MR, Bukovsky A. Regression of endometrial explants in a rat model of endometriosis treated with the immune modulators loxoribine and levamisole. Fertil Steril. 1999 Jul;72(1):135-41. doi: 10.1016/s0015-0282(99)00157-0. PMID: 10428162.
1: Swaggerty CL, He H, Genovese KJ, Duke SE, Kogut MH. Loxoribine pretreatment reduces Salmonella Enteritidis organ invasion in 1-day-old chickens. Poult Sci. 2012 Apr;91(4):1038-42. doi: 10.3382/ps.2011-01939. PubMed PMID: 22399745. 2: Dzopalic T, Dragicevic A, Vasilijic S, Vucevic D, Majstorovic I, Bozic B, Balint B, Colic M. 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. doi: 10.1016/j.intimp.2010.08.010. Epub 2010 Sep 15. PubMed PMID: 20817120. 3: Tosi P, Zinzani PL, Pellacani A, Ottaviani E, Magagnoli M, Tura S. Loxoribine affects fludarabine activity on freshly isolated B-chronic lymphocytic leukemia cells. Leuk Lymphoma. 1997 Jul;26(3-4):343-8. PubMed PMID: 9322897. 4: Pope BL, MacIntyre JP, Kimball E, Lee S, Zhou L, Taylor GR, Goodman MG. The immunostimulatory compound 7-allyl-8-oxoguanosine (loxoribine) induces a distinct subset of murine cytokines. Cell Immunol. 1995 May;162(2):333-9. PubMed PMID: 7743561. 5: Goodman MG. A new approach to vaccine adjuvants. Immunopotentiation by intracellular T-helper-like signals transmitted by loxoribine. Pharm Biotechnol. 1995;6:581-609. Review. PubMed PMID: 7551237. 6: Agarwala SS, Kirkwood JM, Bryant J. Phase 1, randomized, double-blind trial of 7-allyl-8-oxoguanosine (loxoribine) in advanced cancer. Cytokines Cell Mol Ther. 2000 Dec;6(4):171-6. PubMed PMID: 11565955. 7: Pellacani A, Tosi P, Zinzani PL, Ottaviani E, Albertini P, Magagnoli M, Tura S. Cytotoxic combination of loxoribine with fludarabine and mafosfamide on freshly isolated B-chronic lymphocytic leukemia cells. Leuk Lymphoma. 1999 Mar;33(1-2):147-53. PubMed PMID: 10194132. 8: Keenan JA, Williams-Boyce PK, Massey PJ, Chen TT, Caudle MR, Bukovsky A. Regression of endometrial explants in a rat model of endometriosis treated with the immune modulators loxoribine and levamisole. Fertil Steril. 1999 Jul;72(1):135-41. PubMed PMID: 10428162. 9: Pope BL, Chourmouzis E, Sigindere J, Capetola RJ, Lau CY. In vivo enhancement of murine natural killer cell activity by 7-allyl-8-oxoguanosine (loxoribine). Int J Immunopharmacol. 1992 Nov;14(8):1375-82. PubMed PMID: 1464469. 10: Heil F, Ahmad-Nejad P, Hemmi H, Hochrein H, Ampenberger F, Gellert T, Dietrich H, Lipford G, Takeda K, Akira S, Wagner H, Bauer S. 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. PubMed PMID: 14579267. 11: Makni-Maalej K, Marzaioli V, Boussetta T, Belambri SA, Gougerot-Pocidalo MA, Hurtado-Nedelec M, Dang PM, El-Benna J. TLR8, but not TLR7, induces the priming of the NADPH oxidase activation in human neutrophils. J Leukoc Biol. 2015 Jun;97(6):1081-7. doi: 10.1189/jlb.2A1214-623R. Epub 2015 Apr 15. PubMed PMID: 25877926. 12: Goodman MG, Goodman JH. Topology of the loxoribine binding site. Studies with inactive loxoribine analogues. J Immunol. 1994 Nov 1;153(9):4081-7. PubMed PMID: 7930614. 13: Goodman MG, Spinosa JC, Saven A, Piro LD, Wormsley S. New perspectives on the approach to chronic lymphocytic leukemia. Leuk Lymphoma. 1996 Jun;22(1-2):1-10. Review. PubMed PMID: 8724523. 14: Pope BL, Chourmouzis E, Sigindere J, MacIntyre JP, Capetola RJ, Lau CY. In vivo activation of natural killer cells and priming of IL-2 responsive cytolytic cells by loxoribine (7-allyl-8-oxoguanosine). Cell Immunol. 1993 Apr 1;147(2):302-12. PubMed PMID: 8453674. 15: Pope BL, Chourmouzis E, Victorino L, MacIntyre JP, Capetola RJ, Lau CY. Loxoribine (7-allyl-8-oxoguanosine) activates natural killer cells and primes cytolytic precursor cells for activation by IL-2. J Immunol. 1993 Sep 15;151(6):3007-17. PubMed PMID: 8376766. 16: Pope BL, Sigindere J, Chourmouzis E, MacIntyre P, Goodman MG. 7-Allyl-8-oxoguanosine (loxoribine) inhibits the metastasis of B16 melanoma cells and has adjuvant activity in mice immunized with a B16 tumor vaccine. Cancer Immunol Immunother. 1994 Feb;38(2):83-91. PubMed PMID: 8306370. 17: Goodman MG, Wormsley SB, Spinosa JC, Piro LD. Loxoribine induces chronic lymphocytic leukemia B cells to traverse the cell cycle. Blood. 1994 Nov 15;84(10):3457-64. PubMed PMID: 7949100. 18: Pope BL, Chourmouzis E, MacIntyre JP, Lee S, Goodman MG. Murine strain variation in the natural killer cell and proliferative responses to the immunostimulatory compound 7-allyl-8-oxoguanosine: role of cytokines. Cell Immunol. 1994 Dec;159(2):194-210. PubMed PMID: 7994754. 19: Steckner C, Weber A, Mausberg AK, Heininger M, Opdenhövel F, Kieseier BC, Hartung HP, Hofstetter HH. Alteration of the cytokine signature by various TLR ligands in different T cell populations in MOG37-50 and MOG35-55-induced EAE in C57BL/6 mice. Clin Immunol. 2016 Sep;170:22-30. doi: 10.1016/j.clim.2016.05.008. Epub 2016 May 24. PubMed PMID: 27233983. 20: Tao Y, Zhang X, Markovic-Plese S. Toll-like receptor (TLR)7 and TLR9 agonists enhance interferon (IFN) beta-1a's immunoregulatory effects on B cells in patients with relapsing-remitting multiple sclerosis (RRMS). J Neuroimmunol. 2016 Sep 15;298:181-8. doi: 10.1016/j.jneuroim.2016.07.019. Epub 2016 Jul 22. PubMed PMID: 27609294.