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
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100472
Name: Imiquimod
CAS#: 99011-02-6
Chemical Formula: C14H16N4
Exact Mass: 240.14
Molecular Weight: 240.300
Elemental Analysis: C, 69.97; H, 6.71; N, 23.32

Price and Availability

Size Price Availability Quantity
100mg USD 70 Ready to ship
1g USD 190 Ready to ship
2g USD 320 Ready to ship
5g USD 550 Ready to ship
10g USD 950 Ready to ship
20g USD 1650 Ready to ship
50g USD 3450 Ready to ship
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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

More Info: 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).      

Biological target: Imiquimod (R 837), an immune response modifier, is a selective toll like receptor 7 (TLR7) agonist.
In vitro activity: Expression of MMP-2 decreased following incubation with increasing concentrations of imiquimod in both cell lines (Fig. 3A, B). However, the expression of MMP-9 was different in the SK-MEL-2 and SK-MLE-24 cell lines. Inactive and active forms of MMP-9 were observed in SK-MEL-2 cell line (Fig. 3C), while only its inactive form was observed in SK-MEL-24 cells (Fig. 3D). SK-MEL-2 cells showed a concentration-dependent increase in MMP-9 expression following imiquimod incubation (Fig. 3C). However, expression of MMP-9 decreased with increasing imiquimod concentrations in SK-MEL-24 cell lines (Fig. 3D). Reference: Ann Dermatol. 2014 Jun; 26(3): 363–373. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4069648/
In vivo activity: Tissue ELISA revealed that imiquimod specifically reduced IL-1β and IL-6 secretion in the treated mouse paws (Panels F-G), whereas neutrophil infiltration (visualized by MPO quantification, Panel H) and TNF-α production (panel I) remained unaffected. RTqPCR and western blot analysis further documented the negative effect of imiquimod on the transcription of the Il-1β and Il-6 genes (Panels J-K) and IL-1β pro-form expression (Panel L). Reference: Theranostics. 2020; 10(5): 2158–2171. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7019178/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 1.8 7.49
DMF 1.0 4.16
Water 2.6 10.99

Preparing Stock Solutions

The following data is based on the product molecular weight 240.30 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. Zaki L, Ghaffarifar F, Sharifi Z, Horton J, Sadraei J. Effect of Imiquimod on Tachyzoites of Toxoplasma gondii and Infected Macrophages in vitro and in BALB/c Mice. Front Cell Infect Microbiol. 2020 Jul 31;10:387. doi: 10.3389/fcimb.2020.00387. PMID: 32850486; PMCID: PMC7412631. 2. Jung JY, Kim HS, Roh MR, Roh HJ, Lee SY, Chung KY. The effect of imiquimod on matrix metalloproteinases and tissue inhibitors of metalloproteinases in malignant melanoma cell invasion. Ann Dermatol. 2014 Jun;26(3):363-73. doi: 10.5021/ad.2014.26.3.363. Epub 2014 Jun 12. PMID: 24966637; PMCID: PMC4069648. 3. Mariotte A, De Cauwer A, Po C, Abou-Faycal C, Pichot A, Paul N, Aouadi I, Carapito R, Frisch B, Macquin C, Chatelus E, Sibilia J, Armspach JP, Bahram S, Georgel P. A mouse model of MSU-induced acute inflammation in vivo suggests imiquimod-dependent targeting of Il-1β as relevant therapy for gout patients. Theranostics. 2020 Jan 12;10(5):2158-2171. doi: 10.7150/thno.40650. PMID: 32104502; PMCID: PMC7019178. 4. Almomen A, Jarboe EA, Dodson MK, Peterson CM, Owen SC, Janát-Amsbury MM. Imiquimod Induces Apoptosis in Human Endometrial Cancer Cells In vitro and Prevents Tumor Progression In vivo. Pharm Res. 2016 Sep;33(9):2209-17. doi: 10.1007/s11095-016-1957-6. Epub 2016 May 31. PMID: 27245465; PMCID: PMC4967407.
In vitro protocol: 1. Zaki L, Ghaffarifar F, Sharifi Z, Horton J, Sadraei J. Effect of Imiquimod on Tachyzoites of Toxoplasma gondii and Infected Macrophages in vitro and in BALB/c Mice. Front Cell Infect Microbiol. 2020 Jul 31;10:387. doi: 10.3389/fcimb.2020.00387. PMID: 32850486; PMCID: PMC7412631. 2. Jung JY, Kim HS, Roh MR, Roh HJ, Lee SY, Chung KY. The effect of imiquimod on matrix metalloproteinases and tissue inhibitors of metalloproteinases in malignant melanoma cell invasion. Ann Dermatol. 2014 Jun;26(3):363-73. doi: 10.5021/ad.2014.26.3.363. Epub 2014 Jun 12. PMID: 24966637; PMCID: PMC4069648.
In vivo protocol: 1. Mariotte A, De Cauwer A, Po C, Abou-Faycal C, Pichot A, Paul N, Aouadi I, Carapito R, Frisch B, Macquin C, Chatelus E, Sibilia J, Armspach JP, Bahram S, Georgel P. A mouse model of MSU-induced acute inflammation in vivo suggests imiquimod-dependent targeting of Il-1β as relevant therapy for gout patients. Theranostics. 2020 Jan 12;10(5):2158-2171. doi: 10.7150/thno.40650. PMID: 32104502; PMCID: PMC7019178. 2. Almomen A, Jarboe EA, Dodson MK, Peterson CM, Owen SC, Janát-Amsbury MM. Imiquimod Induces Apoptosis in Human Endometrial Cancer Cells In vitro and Prevents Tumor Progression In vivo. Pharm Res. 2016 Sep;33(9):2209-17. doi: 10.1007/s11095-016-1957-6. Epub 2016 May 31. PMID: 27245465; PMCID: PMC4967407.

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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.