Synonym
SM-324405; SM324405; SM 324405;
IUPAC/Chemical Name
Methyl 3-[(6-amino-2-butoxy-7,8-dihydro-8-oxo-9H-purin-9-yl)methyl]benzeneacetate
InChi Key
MXILFZWMVNDOIZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H23N5O4/c1-3-4-8-28-18-22-16(20)15-17(23-18)24(19(26)21-15)11-13-7-5-6-12(9-13)10-14(25)27-2/h5-7,9H,3-4,8,10-11H2,1-2H3,(H,21,26)(H2,20,22,23)
SMILES Code
O=C(OC)CC1=CC=CC(CN2C(NC3=C(N)N=C(OCCCC)N=C23)=O)=C1
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
>2 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
2934.99.9001
Biological target:
SM-324405 is a TLR7 agonist (EC50 = 50.1 nM). It is selective for TLR7 over TLR8 (EC50 = >10 µM). SM-324405 induces proliferation of isolated mouse, rat, and dog splenocytes (EC50s = 3.98, 6.31, and 12.59 nM, respectively).
In vivo activity:
SM-324405 is a novel candidate for immunotherapy of allergic diseases. SM-324405 was a potent TLR7 agonist (EC(50) 50 nM) and rapidly metabolized by human plasma (T(1/2) 2.6 min) to the much less active carboxylic acid 16. Intratracheal administration of SM-324405 effectively inhibited allergen-induced airway inflammation without inducing cytokines systemically.
Reference: J Med Chem. 2010 Apr 8;53(7):2964-72. https://pubmed.ncbi.nlm.nih.gov/20232824/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
38.5 |
100.00 |
|
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
385.42
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.
| 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. Biffen M, Matsui H, Edwards S, Leishman AJ, Eiho K, Holness E, Satterthwaite G, Doyle I, Wada H, Fraser NJ, Hawkins SL, Aoki M, Tomizawa H, Benjamin AD, Takaku H, McInally T, Murray CM. Biological characterization of a novel class of toll-like receptor 7 agonists designed to have reduced systemic activity. Br J Pharmacol. 2012 May;166(2):573-86. doi: 10.1111/j.1476-5381.2011.01790.x. PMID: 22122192; PMCID: PMC3417490.
2. Kurimoto A, Hashimoto K, Nakamura T, Norimura K, Ogita H, Takaku H, Bonnert R, McInally T, Wada H, Isobe Y. Synthesis and biological evaluation of 8-oxoadenine derivatives as toll-like receptor 7 agonists introducing the antedrug concept. J Med Chem. 2010 Apr 8;53(7):2964-72. doi: 10.1021/jm100070n. PMID: 20232824.
In vivo protocol:
1. Biffen M, Matsui H, Edwards S, Leishman AJ, Eiho K, Holness E, Satterthwaite G, Doyle I, Wada H, Fraser NJ, Hawkins SL, Aoki M, Tomizawa H, Benjamin AD, Takaku H, McInally T, Murray CM. Biological characterization of a novel class of toll-like receptor 7 agonists designed to have reduced systemic activity. Br J Pharmacol. 2012 May;166(2):573-86. doi: 10.1111/j.1476-5381.2011.01790.x. PMID: 22122192; PMCID: PMC3417490.
2. Kurimoto A, Hashimoto K, Nakamura T, Norimura K, Ogita H, Takaku H, Bonnert R, McInally T, Wada H, Isobe Y. Synthesis and biological evaluation of 8-oxoadenine derivatives as toll-like receptor 7 agonists introducing the antedrug concept. J Med Chem. 2010 Apr 8;53(7):2964-72. doi: 10.1021/jm100070n. PMID: 20232824.
1: Biffen M, Matsui H, Edwards S, Leishman AJ, Eiho K, Holness E, Satterthwaite G, Doyle I, Wada H, Fraser NJ, Hawkins SL, Aoki M, Tomizawa H, Benjamin AD, Takaku H, McInally T, Murray CM. Biological characterization of a novel class of toll-like receptor 7 agonists designed to have reduced systemic activity. Br J Pharmacol. 2012 May;166(2):573-86. doi: 10.1111/j.1476-5381.2011.01790.x. PubMed PMID: 22122192; PubMed Central PMCID: PMC3417490.
2: Kurimoto A, Hashimoto K, Nakamura T, Norimura K, Ogita H, Takaku H, Bonnert R, McInally T, Wada H, Isobe Y. Synthesis and biological evaluation of 8-oxoadenine derivatives as toll-like receptor 7 agonists introducing the antedrug concept. J Med Chem. 2010 Apr 8;53(7):2964-72. doi: 10.1021/jm100070n. PubMed PMID: 20232824.
