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Imiquimod

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Category Herpes simplex Virus (HSV)
CAS 99011-02-6
Description An agonist of TLR7 with immune response modifying activity, Approved for basal cell carcinoma, In Phase III for VIN and CIN, Imiquimod's proapoptotic activity appears to be related to Bcl-2 overexpression in susceptible tumor cells.
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Product Information

Synonyms 1-(2-Methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine; R-837; S-26308; Aldara; TMX-101; 1H-Imidazo[4,5-c]quinolin-4-amine, 1-(2-methylpropyl)-; 1-Isobutyl-1H-imidazo[4,5-c]quinolin-4-amine; 1-Isobutyl-1H-imidazo[4,5-c]quinolin-4-ylamine; Aldara; Beselna; Keravort; R 837; R837; S 26308; TMX 101; Zartra; Zyclara
IUPAC Name 1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine
Molecular Weight 240.30
Molecular Formula C14H16N4
Canonical SMILES CC(C)CN1C=NC2=C1C3=CC=CC=C3N=C2N
InChI 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)
InChIKey DOUYETYNHWVLEO-UHFFFAOYSA-N
Boiling Point 456.7±48.0°C at 760 mmHg
Melting Point 292-294°C
Flash Point 230.0±29.6 °C
Purity >98%
Density 1.28±0.1 g/cm3
Solubility Soluble in Aqueous Acid (Slightly), DMSO (Very Slightly, Heated)
Appearance Off-White Solid
Application An immune response modifier. It stimulates the production of interferon-a
Shelf Life ≥98%
Storage Store at -20°C
Complexity 294
Exact Mass 240.137496527
Index Of Refraction 1.681
In Vivo In animal models, imiquimod stimulates the innate immune response by increasing NK cell activity, activating macrophages to secretecytokines and nitric oxide, and inducing proliferation and differentiation of B lymphocytes. Imiquimod stimulates the innate immune response through induction, synthesis, and release of cytokines, including interferon-a (IFN-α), interleukin (IL)-6, and tumour necrosis factor (TNF)-α.
PSA 56.73000
Target Toll-like Receptor (TLR); Autophagy; SARS-CoV; HSV
Vapor Pressure 0.0±1.1 mmHg at 25°C
XLogP3-AA 2.6

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