Imiquimod

Imiquimod (CAS 99011-02-6)

Imiquimod | CAS 99011-02-6 is rated 5.0 out of 5 by 1.
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Synonym: 1-(2-Methylpropyl)-1H-imidazole[4,5-c]quinoline-4-amine
Application: A TLR7 activator and angiogenesis inhibitor
CAS Number: 99011-02-6
Purity: ≥98%
Molecular Weight: 240.30
Molecular Formula: C14H16N4
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
Submit a review for this product and receive 15 CruzCredits

Imiquimod is a derivative of imidazoquinolinamine that inhibits angiogenesis and is an immune response modifier. Studies have reported that Imiquimod has the ability to downregulate metastasis and induce alpha-interferon (IFN-α). Additionally, Imiquimod is a TLR7 (toll-like receptor 7) agonist which induces plasmacytoid dendritic cell (pDC) maturation. Imiquimod acts on dendritic cells expressing TLR7, and induces an immune response. Nuclear factor-B helps mediate the activity of Imiquimod, and is involved in increasing chemokine and cytokine levels. The antiangiogenic property of Imiquimod has been shown to be mediated by IL-18. Research shows that Imiquimod can induce apoptosis in cancer cells. Also suggested to be an activator of caspase-3 and NFκB.


References

1. Franconi, F., et al. 1992. Adv. Exp. Med. Biol. 315: 181-186. PMID: 1509937
2. Sidky, Y.A., et al. 1992. Cancer Res. 52: 3528-3533. PMID: 1377595
3. Gibson, S.J., et al. 2002. Cell. Immunol. 218: 74-86. PMID: 12470615
4. Schön, M., et al. 2003. J. Natl. Cancer Inst. 95: 1138-1149. PMID: 12902443
5. Majewski, S., et al. 2005. Int. J. Dermatol. 44: 14-19. PMID: 15663652
6. Li, V.W., et al. 2005. J Drugs Dermatol. 4: 708-717. PMID: 16302556

Physical State :
Solid
Solubility :
Soluble in DMSO (4 mg/ml ,warming to 60 °C for 15 minutes) DMF (1.5 mg/ml) at 37 °C, and water (slightly soluble) at 37 °C. Insoluble in ethanol.
Storage :
Store at -20° C
Melting Point :
292-294° C
Boiling Point :
~456.7° C at 760 mmHg (Predicted)
Density :
~1.3 g/cm3 (Predicted)
Refractive Index :
n20D 1.68 (Predicted)
IC50 :
LS174T: IC50 = 34.4 µM (human); A375: IC50 = 70.3 µM (human)
pK Values :
pKb: 6.28 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
NJ5903450
Transport :
UN 2811, Class 6.1, Packing group III
PubChem CID :
57469
Merck Index :
14: 4922
MDL Number :
MFCD00866946
EC Number :
619-387-8
SMILES :
CC(C)CN1C=NC2=C1C3=CC=CC=C3N=C2N

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Certificate of Analysis

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Imiquimod  Product Citations

See how others have used Imiquimod. Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 26462419  Wu, V. et al. 2016. Mucosal immunology. 9: 777-86.

PMID: # 25767074  Li, ZJ. et al. 2015. Biochem. Biophys. Res. Commun. 459: 673-8.

PMID: # 24743316  Sohn, KC. et al. 2014. PloS one. 9: e95337.

Citations 1 to 3 of 3 total

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. Imiquimod, sc-200385, is a white to off-white powder or solid.
Answered by: Chemical Support 4
Date published: 2017-04-05
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Rated 5 out of 5 by from Li et al Li et al. (PuMed ID 16302556) found that imiquimod inhibited angiogenesis by inducing cytokine activity, upregulated endogenous angiogenesis inhibtitors, downregulated pro-angionic factors and promoted cell apoptosis. -SCBT Publication Review
Date published: 2015-06-10
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