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| 融点 | 292-294°C | | 沸点 | 456.7±48.0 °C(Predicted) | | 比重(密度) | 1.28±0.1 g/cm3(Predicted) | | 貯蔵温度 | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | | 溶解性 | DMSO: soluble | | 酸解離定数(Pka) | 6.28±0.30(Predicted) | | 外見 | White solid | | 色 | White | | 水溶解度 | Soluble in dimethyl sulfoxide and dimethyl formamide. Slightly soluble in water. Insoluble in ethanol. | | 極大吸収波長 (λmax) | 245nm(H2O/MeOH)(lit.) | | Merck | 14,4922 | | 安定性： | Incompatible with strong oxidizing agents. | | InChIKey | DOUYETYNHWVLEO-UHFFFAOYSA-N | | CAS データベース | 99011-02-6(CAS DataBase Reference) |
| | イミキモド Usage And Synthesis |
| 外観 | 白色～ほとんど白色粉末～結晶 | | 効能 | 抗ウイルス薬, 免疫調節薬, Toll様受容体作動薬 | | 商品名 | ベセルナ (持田製薬) | | 説明 | Aldara was launched in the US for the topical treatment of genital warts
caused by human papillomavirus (HPV). It can be prepared in a six step approach
beginning with the nucleophilic substitution of 4-chloro-3-nitroquinolone with
isobutylamine or via a thermal electrocyclic ring closure of 1 - and 2-azahexatriene
systems. Aldara has antiviral and antitumor properties, with the former activity arising
from the induction of cytokines, in particular, INF-α. Aldara also induces TNF-γ, IL-1α, IL-1β, IL-1ra, IL-6, IL-8, IL-10, GM-CSF, G-CSF and MID-la formation 1-4 hr after
stimuli. The exact cells responsible for the response have not been determined,
however, it is not activating T lymphocytes, NK cells, B lymphocytes, or dendritic stem
cells but monocytes (CD14+, CD36+, HLA-DR+, HLA-DQ±, CD19-, CD16- and CD23-) are
partly responsible. The speculation is that Aldara may interact with a kinase
modulating the transduction pathway leading to cytokine genes. There is no direct
antiviral activity (induction of IFN does not follow true dose response) and it is not mutagenic. The hydroxylated metabolite also induces IFN-α. | | 化学的特性 | White to off white crystalline powder | | Originator | 3M Pharmaceuticals (US) | | 使用 | Imiquimod is a caspase 3 activator which acts as an immunomodulator and displays antiviral and anti-tumor activity. It is a patient-applied cream used for the treatment of genital warts and basal cell carcinoma. It is also used to cure actinic keratosis on the face and scalp. It belongs to a group of drugs called immune response modifiers, which work by activating the immune system to fight abnormal skin growth. | | 使用 | An immune response modifier. It stimulates the production of interferon-a | | 使用 | raw material for Latamoxef, Cefminox, Ceftizoxime, Cefoxitin, Cefmetazole | | 定義 | ChEBI: Imiquimod is an imidazoquinoline fused [4,5-c] carrying isobutyl and amino substituents at N-1 and C-4 respectively. A prescription medication, it acts as an immune response modifier and is used to treat genital warts, superficial basal cell carcinoma, and actinic keratosis. It has a role as an antineoplastic agent and an interferon inducer. | | 適応症 | Imiquimod (Aldara) is a topical immune response modifier
approved for the treatment of anogenital warts
(condylomata acuminata). The exact mechanism of action
is unknown; it has no direct antiviral activity in
vitro. It is thought to work in vivo by inducing the production
of tumor necrosis factor (TNF α ), interferons
(IFN)α and γ , and other cytokines with antiviral activity.
It may also be useful for treatment of other types of
warts, molluscum contagiosum, and certain forms of
skin cancer. Local irritant reactions related to the frequency
of application are common. | | brand name | Aldara (3M Pharmaceuticals). | | 応用例（製薬） | An imidazoquinoline used for the treatment of genital and
perianal warts. While the mechanism of action is not precisely
known, it is thought to induce interferon. It has no direct antiviral
activity. The 5% cream applied three times a week for
up to 16 weeks resulted in total wart clearance in 50% of
patients, with a better response in women than in men. Local
reactions are common and include erythema, erosion, excoriation
and edema. | | 生物活性 | Immunomodulator that displays antiviral and antitumor activity. Acts as a Toll-like receptor 7 (TLR-7) agonist; stimulates proinflammatory cytokine production and activates NF- κ B. | | 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. | | 作用機序 | Imiquimod (Aldara) is an imidazoquinolone amine that is an immune responsemodifier.
Its exact mechanism is unknown in the topical treatment of HPV and molluscum
contagiosum but may be related to the immunomodulating effect of the drug. It is also
effective in the treatment of actinic keratoses and superficial basal cell carcinoma.
It induces production of a variety of cytokines and can enhance cell-mediated
cytolytic antiviral activity. It is a rapid and potent inducer of interferon-α,
interleukin?1 α and β, interleukin 6, interleukin 8, tumor necrosis factor-α,
granulocyte-macrophage colony-stimulating factor, and granulocyte colonystimulating
factor. Systemic absorption is minimal. It is generally well tolerated.
Adverse local reactions include erythema, erosion, excoriation, flaking, and edema
of the treatment sites. | | Veterinary Drugs and Treatments | An immune response modifier, imiquimod may be useful in the treatment of a variety of topical conditions in animals. It is labeled for use
on humans as a treatment for genital or perianal warts, superficial basal cell carcinomas and actinic keratoses of the face and scalp. In dogs
and cats, imiquimod potentially may be of benefit in treating feline herpes virus dermatitis, actinic keratosis, squamous cell carcinoma
and Bowen’s disease, papillomas virus lesions, and localized solar dermatitis or solar carcinoma in situ. In horses, imiquimod has been
anecdotally used with success in treating sarcoids.
Imiquimod stimulates the patient’s own immune system to release a variety of cytokines including interferon-alpha and interleukin-
12. Imiquimod itself does not have in vitro activity against wart viruses, but stimulates monocytes and macrophages to release cytokines
that induce a regression in viral protein production. | | 貯蔵 | +4°C | | 参考文献 | 1) Hemmi?et al.?(2002),?Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway;?Nat. Immunol.?3?196
2) Stanley?et al.?(2002),?Imiquimod and the imidazoquinolones: mechanism of action and therapeutic potential;?Clin. Exp. Dermatol.?27?571
3) Schoen?et al.?(2006),?The small antitumoral immune response modifier imiquimod interacts with adenosine receptor signaling in a TLR7- and TLR8-independent fashion;?J.Invest.Dermatol.?126?1338
4) Kan?et al.?(2012),?Imiquimod Suppresses Propagation of Herpes Simplex Virus 1 by Upregulation of Cystatin A via the Adenosine Receptor A1?Pathway.; J. Virol.?86?10338
5) Urosevic?et al.?(2004),?Imiquimod Treatment Induces Expression of Opioid Growth Factor Receptor; Clin. Cancer Res.?10?4959
6) Zagon?et al.?(2008),?Imiquimod Upregulates the Opioid Growth Factor Receptor to Inhibit Cell Proliferation Independent of Immune Function.; Exp. Biol. Med.(Maywood)?233?968 |
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