Imiquimod

Bezeichnung:Imiquimod

CAS-Nr99011-02-6

Englisch Name:Imiquimod

CBNumberCB2664655

SummenformelC14H16N4

Molgewicht240.3

MOL-Datei99011-02-6.mol

Imiquimod physikalisch-chemischer Eigenschaften

Schmelzpunkt	292-294°C
Siedepunkt	456.7±48.0 °C(Predicted)
Dichte	1.28±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
Löslichkeit	DMSO: soluble
pka	6.28±0.30(Predicted)
Aggregatzustand	White solid
Farbe	White
Wasserlöslichkeit	Soluble in dimethyl sulfoxide and dimethyl formamide. Slightly soluble in water. Insoluble in ethanol.
maximale Wellenlänge (λmax)	245nm(H2O/MeOH)(lit.)
Merck	14,4922
Stabilität	Incompatible with strong oxidizing agents.
InChIKey	DOUYETYNHWVLEO-UHFFFAOYSA-N
CAS Datenbank	99011-02-6(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	T,Xi
R-Sätze:	25-36/37/38
S-Sätze:	26-45-36/37/39-27
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	NJ5903450
HazardClass	6.1
PackingGroup	III
HS Code	29339900
Giftige Stoffe Daten	99011-02-6(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Imiquimod Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S27:Beschmutzte, getränkte Kleidung sofort ausziehen.
Beschreibung
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.
Chemische Eigenschaften
White to off white crystalline powder
Originator
3M Pharmaceuticals (US)
Verwenden
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.
Verwenden
An immune response modifier. It stimulates the production of interferon-a
Verwenden
raw material for Latamoxef, Cefminox, Ceftizoxime, Cefoxitin, Cefmetazole
Indications
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.
Definition
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.
Trademarks
Aldara (3M Pharmaceuticals).
Pharmazeutische Anwendungen
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.
Biologische Aktivität
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.
Mechanism of action
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.
Lager
+4°C
Einzelnachweise
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

Imiquimod Upstream-Materialien And Downstream Produkte

Imiquimod Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

99011-02-6, Imiquimod Verwandte Suche:

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