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

• ChemBase编号: 605
• 分子式: C14H16N4
• 平均质量: 240.30364
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
• IUPAC传统名: imiquimod; 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
• 商标名: Aldara
• 别名: 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

登记号

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

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 2.4031684
• LogD (pH = 7.4): 2.6464384
• Log P: 2.6506696
• 摩尔折射率: 72.5446 cm^3
• 极化性: 29.782703 Å^3
• 极化表面积: 56.73 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.83
• LOG S: -2.99
• 溶解度: 2.47e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; DMSO: soluble4 mg/mL (warming to 60 °C for 15 minutes); H2O: <2 mg/mL; Poorly soluble
• 外观: Off-White Solid; solid
• 熔点: 292-294°C
• 疏水性(logP): 2.7

安全信息

• 保存条件: -20°C; -20°C Freezer
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 25-36/37/38
• 安全公开号: 26-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300-H315-H319-H335
• GHS警示性声明: P261-P264-P301 + P310-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 生物活性机理: Interferon inducer; Reported cell proliferation inducer

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• 应用领域: Cytostatic; Immunostimulant; Virucide
• Empirical Formula (Hill Notation): C14H16N4

详细说明

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.

参考文献

• 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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• Bernstein, D.I. et al., Antiviral Res., 1993, 20, 45, (pharmacol)
• Witt, P.L. et al., Cancer Res., 1993, 53, 5176, (clin trial)
• Testerman, T.L. et al., J. Leukocyte Biol., 1995, 58, 365, (pharmacol)
• Yoshioka, H. et al., Chem. Pharm. Bull., 1996, 44, 709, (synth, pmr)
• Perry, C.M. et al., Drugs, 1999, 58, 375-390, (rev)
• Richwald, G.A. et al., Drugs of Today (Barcelona), 1999, 35, 497-511, (rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 613