Imiquimod

Base Information

• Chemical Name: Imiquimod
• CAS No.: 99011-02-6
• Molecular Formula: C14H16N4
• Molecular Weight: 240.308
• Hs Code.: 29339900
• European Community (EC) Number: 618-567-3,619-387-8
• NSC Number: 759651,369100
• UNII: P1QW714R7M
• DSSTox Substance ID: DTXSID7041047
• Nikkaji Number: J501.447F
• Wikipedia: Imiquimod
• Wikidata: Q423417
• NCI Thesaurus Code: C1431
• RXCUI: 59943
• Pharos Ligand ID: THC972DPF6QR
• Metabolomics Workbench ID: 43030
• ChEMBL ID: CHEMBL1282
• Mol file: 99011-02-6.mol

Synonyms:1-isobutyl-1H-imidazo(4,5-c)quinolin-4-amine;Aldara;imiquimod;R 837;R-837;R837;S 26308;S-26308;Zyclara

Chemical Property of Imiquimod

Chemical Property:

• Appearance/Colour: White to off white crystalline powder
• Melting Point: 292-294 °C
• Boiling Point: 456.7 °C at 760 mmHg
• PKA: 6.28±0.30(Predicted)
• Flash Point: 230 °C
• PSA: 56.73000
• Density: 1.28 g/cm³
• LogP: 3.40390
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: soluble
• Water Solubility.: Soluble in dimethyl sulfoxide and dimethyl formamide. Slightly soluble in water. Insoluble in ethanol.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 240.137496527
• Heavy Atom Count: 18
• Complexity: 294

Purity/Quality:

99%min ^*data from raw suppliers

Imiquimod ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi
• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 26-45-36/37/39-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CN1C=NC2=C1C3=CC=CC=C3N=C2N
• Recent ClinicalTrials: Immunologic Profile of Chronically Photodamaged Skin
• Recent EU Clinical Trials: Gene and protein expression profiles after treatment of actinic keratosis
• Uses: It can be used for anti-genital warts and as immunomodulators raw material for Latamoxef, Cefminox, Ceftizoxime, Cefoxitin, Cefmetazole An immune response modifier. It stimulates the production of interferon-a 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.
• Description: 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.
• 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.

Technology Process of Imiquimod

There total 51 articles about Imiquimod which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-Hydrazino-1-(2-methylpropyl)-1H-imidazo [4,5-c]quinoline (201030-96-8) → imiqimod (99011-02-6)

Guidance literature:

With hydrogenchloride; sodium formate; palladium 10% on activated carbon; In water; for 84h; Product distribution / selectivity; Heating / reflux;

Reference yield: 98.0%

4-chloro-1H-imidazo[4,5-c]-quinoline (132206-92-9) → imiqimod (99011-02-6)

Guidance literature:

formamide; With potassium tert-butylate; In dimethyl sulfoxide; for 0.5h;

4-chloro-1H-imidazo[4,5-c]-quinoline; In dimethyl sulfoxide; at 105 ℃; for 2h;

With hydrogenchloride; In water; dimethyl sulfoxide; pH=8; Product distribution / selectivity;

Reference yield: 91.8%

N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-phthalimide → imiqimod (99011-02-6)

Guidance literature:

With ethylenediamine; In water; at 70 - 95 ℃; for 4h;

upstream raw materials:

1-Isobutyl-2-methylsulfanyl-1H-imidazo[4,5-c]quinolin-4-ylamine

1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5N-oxide

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

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

Downstream raw materials:

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

N-benzyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline fumarate

Refernces

• 1、 -. "IMIQUIMOD PRODUCTION PROCESS". Page/Page column 2-3. . Retrieved 2008/12/07.
• 2、 -. "Preparation of 1H-imidazo[4,5-c]quinolin-4-amines via 1H-imidazo[4, 5-c]quinolin-4-phtalimide intermediates". Page/Page column 5. . Retrieved 2008/06/13.