R-837
Imiquimod
CAS: 99011-02-6
Molecular Formula: C14H16N4
R-837 - Names and Identifiers
| Name | Imiquimod |
| Synonyms | R-837 S-26308 Imiquimod IMIQUIMOD 4-amino-1-isobutyl-1h-imidazo[4,5-c]quinoline 4-amino- 1-isobutyl-1h-imidazo[4,5-c]quinoline 1-(2-methylpropyl)-1H-imidazo(4,5-quinolin-4-amine) 1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLIN-4-AMINE 1-(2-methylpropyl)-1h-imidazo[4,5-c]quinolin-4-amine 1-(2-Methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine, R-837, S-26308, Aldara |
| CAS | 99011-02-6 |
| EINECS | 619-387-8 |
| InChI | InChI=1/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 |
R-837 - Physico-chemical Properties
| Molecular Formula | C14H16N4 |
| Molar Mass | 240.3 |
| Density | 1.28±0.1 g/cm3(Predicted) |
| Melting Point | 292-294°C |
| Boling Point | 456.7±48.0 °C(Predicted) |
| Water Solubility | Soluble in dimethyl sulfoxide and dimethyl formamide. Slightly soluble in water. Insoluble in ethanol. |
| Solubility | DMSO: soluble |
| Appearance | White solid |
| Color | White |
| Maximum wavelength(λmax) | ['245nm(H2O/MeOH)(lit.)'] |
| Merck | 14,4922 |
| pKa | 6.28±0.30(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Stability | Incompatible with strong oxidizing agents. |
| MDL | MFCD00866946 |
| Use | Anti-condyloma acuminatum, immunomodulator |
R-837 - Risk and Safety
| Risk Codes | R25 - Toxic if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S27 - Take off immediately all contaminated clothing. |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | NJ5903450 |
| HS Code | 29339900 |
| Hazard Class | 6.1 |
| Packing Group | III |
R-837 - Nature
Open Data Verified Data
white crystalline powder. The melting point was 292-294 °c.
Last Update：2025-06-10 22:55:16
R-837 - Preparation Method
Open Data Verified Data
4 a hydroxyl group 2 A (1H) a quinoline ketone and glacial acetic acid mixture, after cooling, drop plus fuming nitric acid. The reaction solution was poured into ice and stirred. Filter, filter cake water to near neutral, dry, n-dimethylformamide recrystallization, 3-nitro -4-hydroxy -2-(1H) quinolinone. It was mixed with phosphorus oxychloride, reacted with pyridine Dropwise, poured into ice, the mixture was extracted with chloroform, and the extract was washed with water and brine, dried, filtered, and concentrated until a solid precipitated. Filtration, drying, and recrystallization from chloroform gave 3-nitro -2,4-= chloroquinoline. It was dissolved in ethanol, triethylamine was added, and isobutylamine was added dropwise. After completion of the reaction, the reaction solution was poured into ice water and stirred for 2H. Filtration and drying gave 2-chloro-3-nitro-4-isobutylaminoquinine. This was dissolved in absolute ethanol and Raney nickel was added for hydrogenation. After filtration and recrystallization from ethanol, 2-chloro-3-amino-4-isobutylaminoquinoline was obtained. This material reacts with triethyl orthoformate to give 1-(2-methylpropyl) 4 chloro -1H-imidazo [4,5-f] quinoline. The mixture was mixed with methoxyethanol and ammonia water, and then closed in an autoclave for reaction, filtered, and the filter cake was washed with a solvent, dried, and recrystallized to obtain fequinimod.
Last Update：2025-06-10 22:55:16
R-837 - Introduction
Imiquimod is a new synthetic agent with immunoreaction modification activity.
Last Update：2022-10-16 17:30:33
R-837 - Application
Open Data Verified Data
developed by 3M Pharmaceuticals, Inc., USA, in November 1997, Imiquimod Cream was first launched in the United States, and then quickly launched in Europe, South America, Japan, Hong Kong, China and other places. Imiquimod is a new non-nucleoside isocyclic amine compounds, by inducing the body to produce cytokines and play its role in anti-virus, anti-tumor and immune regulation. The product does not have direct antiviral activity, nor does it cause direct, non-specific cell lysis and destruction. Animal studies have demonstrated that Imiquimod and its analogs may exert their therapeutic effects by regulating the local inflammatory response in the skin of experimental animals. Imiquimod belongs to Class II new drugs in China.
Last Update：2025-08-19 16:24:40
R-837 - Reference Information
| Genital wart treatment drug | Imiquimod is an imidazolinyl amine interleukin agonist developed and produced by 3M Pharmaceuticals, USA, it is a drug for the treatment of genital warts, which is used to cause cytoplasmic division in mouse skin, and can produce alpha interferon, tumor necrosis factor and a variety of interleukins. Clinical can be used for the treatment of adult genital and perianal condyloma acuminatum immunomodulator, the use of convenient, good tolerance and unique mechanism of action makes it become the first choice for the treatment of condyloma acuminatum. In addition, there are reports that Imiquimod can also be used for verruca vulgaris, flat warts, soft warts, herpes simplex and other viral skin diseases, basal cell carcinoma, Bowen's disease, bowenoid papulosis, actinic keratosis, skin T cell tumor, Kaposi's sarcoma and other skin tumors, may be effective for vitiligo, alopecia areata. condyloma acuminatum (CA) is an infectious disease of human herpes Virus (HPV) infection, which is a major public health threat. At present, acuteness wet wart infection in the United States is the most common viral infection of sexually transmitted diseases and one of the most common sexually transmitted diseases, infection occurs in sexually active people, in particular, it occurs in people aged 20 to 24 years and pregnant women, and it is easy to occur in the warm and moist mucous membrane of the body, if the use of immunosuppressants or infected with human immunodeficiency virus prone to more serious clinical symptoms of infection. |
| Clinical Study | In an unpublished report, a double-blind trial was conducted in 209 patients with genital or perianal warts, both the product and the vehicle were used 3 times a week for 16 weeks. Results 33 cases (72%) in 46 women, 21 cases (33%) in 63 men, total warts Recovery Rate was 50%, in contrast, only 11%(20% of women and 5% of men) of the tissues were in the vehicle. In patients who were cured after 4 weeks of treatment, the average healing time was 12 weeks for men and 8 weeks for women, and in the subsequent 12 weeks, 39 of 54 patients were cured and no longer relapsed. |
| mechanism of action | imiquimod itself had no direct effect on Virus, instead, it stimulates the body to produce cytokines that trigger an immune response to eliminate wart tissue and reduce erosion by Virus. In vitro and in vivo studies have shown that Imiquimod can induce the production of cytokines in mice, rats, rabbits, guinea pigs, monkeys and humans. Ethnic cross-cell culture experiments showed that the main response cells were monocytes/macrophages; Cultured human peripheral mononuclear cells (PBMC) produced several IFN-α subtypes, TNF-α, IL-1,6,6,10,12, MIP-1 and MCP-1; Pre-administered gamma-IFN treatment, human single cells THP-1 will respond, produce TNF-α, IL-1,6,8, but not produce IFN-α; the same treatment of fresh mouse PBMCs produced the same cytokines as human PBMCs; Senescent Macrophages and alveolar macrophages produced the same cytokines, the mouse RAW264.7 and J774 macrophage family produced TNF-α and IL-6 and did not produce IFN-α. The induction of IFN-α and TNF-α by imiquimod was confirmed by cell assay. when human fibroblasts and keratinocytes were incubated with imiquimod or polyinosine: polycytidine mixture for 24 hours, IL-6 and IL-8 (without TNF-α) of keratinocytes had increased mRNA, However, only an appropriate amount of IL-8 protein was detected, and the secretion of IL-8 of fibroblasts was similar to that of keratinocytes at high concentration. The cellular immune response induced by cytokine secretion induced by imiquimod was similar to that of DTH response; imiquimod can activate the anti-tumor activity and DTH response of tumor-bearing mice transfected with HPV E7 tumor gene. Human and animal experiments show that Imiquimod can increase the 2'5 '-oligomeric adenylate synthase, the enzyme can induce the production of interferon antiviral; Interferon and other cytokines can activate NK cells to kill tumor cells and virus infected cells, in vivo and in vitro experiments show that Imiquimod can up regulate NK cell activity, stimulate mouse spleen B cell proliferation and activation, this effect is a direct effect, not cytokine-mediated; Imiquimod does not directly enhance the activity of T-lymphocytes, but in vitro mitogenic response can increase the production and proliferation of T-cells IL-2, in vivo experiments show that can enhance the activity of T cells; Imiquimod can increase the production of HSV-infected guinea pigs IL-2, T cell proliferation and T cell activity potentiate cell-mediated immune responses. |
| dosage | treatment of adult external genital and perianal condyloma acuminatum. 3 times a week, before going to bed, apply a thin layer on the surface of the wart body, gently massage until the product is completely absorbed, do not pack and keep it for 6 to 10 hours, the drug is then washed away from the site of administration with neutral soap and water. Before and after treatment Hand Sanitization. 250mg cream can be applied to 20 cm2 of warts, avoid excessive use of the drug. Patients should continue medication until the warts are completely removed. The fastest 2~4 weeks to clear the wart, generally in 8~12 weeks to clear, medication is not more than 16 weeks. Patients with local mild erythema after medication should not be discontinued; If the patient feels general malaise or has obvious local skin reaction (edema, erosion, pain, etc.), the drug should be discontinued, the drug was continued after the reaction was relieved. |
| adverse reactions | , clinical adverse reactions may occur mostly mild to moderate local skin inflammation, such as local skin may appear erythema, edema, erosion, ulcers, scaling, burning, pain, itching and so on.|
| note | ① do not pack, wash off the drug 6-10 hours after administration, local damage should avoid the use of this product, has been used drugs or laser treatment of condyloma, and the damaged parts, should wait until the wound healing before medication. (2) should not be used for eyes, mouth, nose, urethra, vaginal, cervical and anal mucosal parts of the treatment of condyloma. ③ during the use of drugs to avoid sexual life, the use of condoms, should first rinse the topical imiquimod clean, because Imiquimod can make condoms become fragile. ④ for male patients with foreskin, during the medication period, the foreskin should be turned up every day, and the medication site should be cleaned. If there is erosion, ulcer and edema on the mucosal surface of the foreskin, if the foreskin is difficult to turn up, treatment should be stopped immediately. (5) pregnant and lactating women have not found medication contraindications, but should be used with caution. |
| Use | Anti-condyloma acuminatum, immunomodulator |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:15
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