1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

• ChemBase ID: 605
• Molecular Formular: C14H16N4
• Molecular Mass: 240.30364
• Monoisotopic Mass: 240.13749653
• SMILES: n1(CC(C)C)c2c3c(nc(N)c2nc1)cccc3
• Canonical SMILES: CC(Cn1cnc2c1c1ccccc1nc2N)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
• IUPAC Traditional name: imiquimod; 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
• Brand Name: Aldara
• Synonyms: Imiquimod acetate; imiquimod; Imiquimod; 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine; 1-(2-Methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine, R-837, S-26308, Aldara; 1-(2-Methylpropyl)-1H-imidazole[4,5-c]quinoline-4-amine; Imiquimod; Aldara

Database IDs

• CAS Number: 99011-02-6
• MDL Number: MFCD00866946
• PubChem SID: 24724516; 160964068; 46505394
• PubChem CID: 57469

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.4031684
• LogD (pH = 7.4): 2.6464384
• Log P: 2.6506696
• Molar Refractivity: 72.5446 cm^3
• Polarizability: 29.782703 Å^3
• Polar Surface Area: 56.73 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.83
• LOG S: -2.99
• Solubility (Water): 2.47e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble4 mg/mL (warming to 60 °C for 15 minutes); H2O: <2 mg/mL; Poorly soluble
• Apperance: Off-White Solid; solid
• Melting Point: 292-294°C
• Hydrophobicity(logP): 2.7

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H315-H319-H335
• GHS Precautionary statements: P261-P264-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Mechanism of Action: Interferon inducer; Reported cell proliferation inducer

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Application(s): Cytostatic; Immunostimulant; Virucide
• Empirical Formula (Hill Notation): C14H16N4

DETAILS

DrugBank - DB00724

• Drug Groups: approved; investigational
• Description: Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist. Imiquimod is commonly used topically to treat warts on the skin of the genital and anal areas. Imiquimod does not cure warts, and new warts may appear during treatment. Imiquimod does not fight the viruses that cause warts directly, however, it does help to relieve and control wart production. miquimod is also used to treat a skin condition of the face and scalp called actinic keratoses and certain types of skin cancer called superficial basal cell carcinoma.
• Indication: For the topical treatment of clinically typical, nonhyperkeratotic, nonhypertrophic actinic keratoses on the face or scalp in immunocompetent adults. Also indicated for the treatment of external genital and perianal warts/condyloma acuminata in individuals 12 years old and above.
• Pharmacology: Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist. Imiquimod is commonly used topically to treat warts on the skin of the genital and anal areas. Imiquimod does not cure warts, and new warts may appear during treatment. Imiquimod does not fight the viruses that cause warts directly, however, it does help to relieve and control wart production. It is not used on warts inside the vagina, penis, or rectum. Imiquimod is also used to treat a skin condition of the face and scalp called actinic keratoses. Imiquimod can also be used to treat certain types of skin cancer called superficial basal cell carcinoma. Imiquimod is particularly useful on areas where surgery or other treatments may be difficult, complicated or otherwise undesirable, especially the face and lower legs.
• Toxicity: Symptoms of overdose include flu-like symptoms, such as fever, fatigue, headache, nausea, diarrhoea and muscle pain.
• Affected Organisms: Humans and other mammals
• Absorption: Well absorbed through skin (as a cream)
• Half Life: 20 hours (topical dose), 2 hours (subcutaneous dose)
• References: [Link] ; van Egmond S, Hoedemaker C, Sinclair R: Successful treatment of perianal Bowen's disease with imiquimod. Int J Dermatol. 2007 Mar;46(3):318-9. [Pubmed] ; Hemmi H, Kaisho T, Takeuchi O, Sato S, Sanjo H, Hoshino K, Horiuchi T, Tomizawa H, Takeda K, Akira S: Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway. Nat Immunol. 2002 Feb;3(2):196-200. Epub 2002 Jan 22. [Pubmed] ; Bilu D, Sauder DN: Imiquimod: modes of action. Br J Dermatol. 2003 Nov;149 Suppl 66:5-8. [Pubmed] ; Miller RL, Gerster JF, Owens ML, Slade HB, Tomai MA: Imiquimod applied topically: a novel immune response modifier and new class of drug. Int J Immunopharmacol. 1999 Jan;21(1):1-14. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1211

Research Area: Human papillomavirus infection
Biological Activity:
Imiquimod(Aldara) is a novel synthetic agent with immune response modifying activity. As an immune response modifier (IRM), imiquimod stimulates cytokine production, especially interferon production, and exhibits antitumor activity, particularly against cutaneous cancers. Imiquimod’s proapoptotic activity appears to be related to Bcl-2 overexpression in susceptible tumor cells. [1,2]

Sigma Aldrich - I5159

Biochem/physiol Actions
Imiquimod is a caspase 3 activator, which directly induces procaspase 3 cleavage to active caspase 3. Imiquimod induces apoptosis in vivo in basal cell carcinoma. Its anti-tumor activity is related to the induction of apoptosis. Imiquimod has anti-angiogenic, anti-inflammatory, anti-viral activities. Imiquimod also acts as an immune response modulator inducing the secretion of various cytokines and chemokines.

Toronto Research Chemicals - I475000

An immune response modifier. It stimulates the production of interferon-a.

REFERENCES

• van Egmond S, Hoedemaker C, Sinclair R: Successful treatment of perianal Bowen's disease with imiquimod. Int J Dermatol. 2007 Mar;46(3):318-9. Pubmed
• Hemmi H, Kaisho T, Takeuchi O, Sato S, Sanjo H, Hoshino K, Horiuchi T, Tomizawa H, Takeda K, Akira S: Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway. Nat Immunol. 2002 Feb;3(2):196-200. Epub 2002 Jan 22. Pubmed
• Miller RL, Gerster JF, Owens ML, Slade HB, Tomai MA: Imiquimod applied topically: a novel immune response modifier and new class of drug. Int J Immunopharmacol. 1999 Jan;21(1):1-14. Pubmed
• Link
• Bilu D, Sauder DN: Imiquimod: modes of action. Br J Dermatol. 2003 Nov;149 Suppl 66:5-8. Pubmed
• http://en.wikipedia.org/wiki/Imiquimod
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• Witt, P.L., et al.: Cancer Res., 53, 5176 (1995)
• Edwards, L., et al.: Arch. Dermatol., 134, 25 (1998)
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• Witt, P.L. et al., Cancer Res., 1993, 53, 5176, (clin trial)
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• Perry, C.M. et al., Drugs, 1999, 58, 375-390, (rev)
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• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 613