Imiquimod
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MedKoo CAT#: 100472

CAS#: 99011-02-6

Description: 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

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Imiquimod
CAS# 99011-02-6

Theoretical Analysis

MedKoo Cat#: 100472
Name: Imiquimod
CAS#: 99011-02-6
Chemical Formula: C14H16N4
Exact Mass: 240.1375
Molecular Weight: 240.3
Elemental Analysis: C, 69.97; H, 6.71; N, 23.32

Price and Availability

Size Price Availability Quantity
500.0mg USD 150.0 Same day
1.0g USD 190.0 Same day
2.0g USD 250.0 Same day
5.0g USD 450.0 Same day
10.0g USD 750.0 Same day
20.0g USD 1250.0 Same day
50.0g USD 2350.0 Same day
Bulk inquiry

Synonym: S26308; S 26308 ; S26308; 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

InChi Key: DOUYETYNHWVLEO-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)

SMILES Code: NC1=NC2=CC=CC=C2C3=C1N=CN3CC(C)C

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, not in water

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

Preparing Stock Solutions

The following data is based on the product molecular weight 240.3 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

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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.  

Imiquimod

500.0mg / USD 150.0


Additional Information

Imiquimod  was approved by  FDA on February 27, 1997, FDA Application No. (NDA) 020723. Imiquimod is approved for the uses described below under Uses. Adverse side effects have been reported, in some cases serious and systemic, resulting in the revision of warning labels.
 
Imiquimod is a patient-applied cream used to treat certain diseases of the skin, including skin cancers (basal cell carcinoma, Bowen's disease,  superficial squamous cell carcinoma, some superficial malignant melanomas, and actinic keratosis) as well as genital warts (condylomata acuminata). It has also been tested for treatment of molluscum contagiosum, vulvar intraepithelial neoplasia, common warts that have proven difficult to treat,  and vaginal intraepithelial neoplasia. Outstanding cosmetic result has resulted from the treatment of both large superficial basal cell carcinoma and squamous cell carcinoma in-situ, but the morbidity and discomfort of the treatment can be severe, and can very occasionally result in some degree of permanent[citation needed] mild scarring. Focal recurrence of tumor has been seen after imiquimod treatment, but appear to be amenable to surgical excision. (source: http://en.wikipedia.org/wiki/Imiquimod).