MedKoo Cat#: 128641 | Name: Imiquimod maleate

Description:

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

Imiquimod is a prescription medication that acts as an immune response modifier. Imiquimod signals to the innate arm of the immune system through the toll-like receptor 7 (TLR7), commonly involved in pathogen recognition. Cells activated by imiquimod via TLR-7 secrete cytokines (primarily interferon-α (INF-α), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α)). Imiquimod, when applied to skin, can lead to the activation of Langerhans cells, which subsequently migrate to local lymph nodes to activate the adaptive immune system. Other cell types activated by imiquimod include natural killer cells, macrophages and B-lymphocytes.

Chemical Structure

Imiquimod maleate
Imiquimod maleate
CAS#896106-16-4 (maleate)

Theoretical Analysis

MedKoo Cat#: 128641

Name: Imiquimod maleate

CAS#: 896106-16-4 (maleate)

Chemical Formula: C18H20N4O4

Exact Mass: 356.1485

Molecular Weight: 356.38

Elemental Analysis: C, 60.66; H, 5.66; N, 15.72; O, 17.96

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Imiquimod maleate; R 837 maleate; S26308; S 26308; S-26308; R837; R837; R 837; TMX-101; TMX 101; TMX101; Imiquimod Brand name: Aldara; Zyclara; Vyloma; Beselna.
IUPAC/Chemical Name
1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine maleate
InChi Key
KYQFLNAOJRNEDV-BTJKTKAUSA-N
InChi Code
InChI=1S/C14H16N4.C4H4O4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15;5-3(6)1-2-4(7)8/h3-6,8-9H,7H2,1-2H3,(H2,15,17);1-2H,(H,5,6)(H,7,8)/b;2-1-
SMILES Code
NC1=NC2=CC=CC=C2C3=C1N=CN3CC(C)C.O=C(O)/C=C\C(O)=O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 356.38 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
1: Kohrt H. Breast Cancer Treatment with Imiquimod: Applying an Old Lotion to a New Disease. Clin Cancer Res. 2012 Dec 6. [Epub ahead of print] PubMed PMID: 23172886. 2: Kidner TB, Morton DL, Lee DJ, Hoban M, Foshag LJ, Turner RR, Faries MB. Combined Intralesional Bacille Calmette-Guérin (BCG) and Topical Imiquimod for In-transit Melanoma. J Immunother. 2012 Nov;35(9):716-20. doi: 10.1097/CJI.0b013e31827457bd. PubMed PMID: 23090081. 3: Tinelli M, Ozolins M, Bath-Hextall F, Williams HC. What determines patient preferences for treating low risk basal cell carcinoma when comparing surgery vs imiquimod? A discrete choice experiment survey from the SINS trial. BMC Dermatol. 2012 Oct 4;12(1):19. [Epub ahead of print] PubMed PMID: 23035730. 4: Tandon Y, Brodell RT. Local reactions to imiquimod in the treatment of basal cell carcinoma. Dermatol Online J. 2012 Sep 15;18(9):1. PubMed PMID: 23031368. 5: Casanova D, Martignoni G, Boccaletti V, Di Nuzzo S. Bowen's disease in a renal transplant recipient treated with a single application of topical imiquimod: severe adverse skin reaction with favourable clinical outcome. Acta Biomed. 2012 Apr;83(1):81-3. PubMed PMID: 22978064. 6: Grimm C, Polterauer S, Natter C, Rahhal J, Hefler L, Tempfer CB, Heinze G, Stary G, Reinthaller A, Speiser P. Treatment of cervical intraepithelial neoplasia with topical imiquimod: a randomized controlled trial. Obstet Gynecol. 2012 Jul;120(1):152-9. doi: 10.1097/AOG.0b013e31825bc6e8. PubMed PMID: 22914404. 7: Wang JY, Liu LF, Mao XH. Treatment of lymphangioma circumscriptum with topical imiquimod 5% cream. Dermatol Surg. 2012 Sep;38(9):1566-9. doi: 10.1111/j.1524-4725.2012.02528.x. Epub 2012 Jul 17. PubMed PMID: 22805499. 8: Arbiser JL, Bips M, Seidler A, Bonner MY, Kovach C. Combination therapy of imiquimod and gentian violet for cutaneous melanoma metastases. J Am Acad Dermatol. 2012 Aug;67(2):e81-3. doi: 10.1016/j.jaad.2011.10.028. PubMed PMID: 22794825. 9: Wong JG, Toole JW, Demers AA, Musto G, Wiseman MC. Topical 5% imiquimod in the treatment of lentigo maligna. J Cutan Med Surg. 2012 Jul-Aug;16(4):245-9. PubMed PMID: 22784516. 10: Adams S, Kozhaya L, Martiniuk F, Meng TC, Chiriboga L, Liebes L, Hochman T, Shuman N, Axelrod D, Speyer J, Novik Y, Tiersten A, Goldberg JD, Formenti SC, Bhardwaj N, Unutmaz D, Demaria S. Topical TLR7 Agonist Imiquimod Can Induce Immune-Mediated Rejection of Skin Metastases in Patients with Breast Cancer. Clin Cancer Res. 2012 Dec 6. [Epub ahead of print] PubMed PMID: 22767669.