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CAS NO.106685-40-9
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106685-40-9
| Adapalene Basic information |
| Product Name: | Adapalene |
| Synonyms: | ADAPALENE;6-[3-(1-ADAMANTYL)-4-METHOXYPHENYL]-2-NAPHTHALENE CARBOXYLIC ACID;6-[3-(1-ADAMANTYL)-4-METHOXYPHENYL]-2-NAPHTHOIC ACID;6-[3-(1-adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic acid;Adapalen;6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic Acid;CD-271;Differi |
| CAS: | 106685-40-9 |
| MF: | C28H28O3 |
| MW: | 412.52 |
| EINECS: | |
| Product Categories: | APIs;Adamantane derivatives;Antiacne;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Adapalen;ULTANE;Pharmaceutical raw materials |
| Mol File: | 106685-40-9.mol |
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| Adapalene Chemical Properties |
| mp | 319-3220C |
| storage temp. | Store at +4°C |
| CAS DataBase Reference | 106685-40-9(CAS DataBase Reference) |
| Safety Information |
| MSDS Information |
| Provider | Language |
|---|---|
| 6-[3-(1-Adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic acid | English |
| Adapalene Usage And Synthesis |
| Naphthoic acid derivative | Adapalene, a new class of drugs Naphthoic acid derivatives, was developed by France Galdeama Laboratories Company. It first entered into market in June 1996, under the trade name "Differin", mainly used for relieving inflammatory skin lesions, adjusting differentiation of hair follicles, gland epithelial cells, and also acne treatment. |
| Pharmacological effects |
Adapalene is a retinoid compounds, and is proven to have anti-inflammatory properties in both in vivo and in vitro models of inflammation. It has stable chemical structure, and is not easily to break down in the air and the light. It shares the same mode of action with retinoic acid, bounding to specific retinoic acid nuclear receptors except that adapalene doesn’t bound to the cytoplasmic protein binding receptor. It has been proven to treat acne and affect acne vulgaris and differentiation in skin drug tests established by mouse animal model. Its mechanism of action is reducing the formation of micro-acne through leading the normal differentiation of hair follicle cells. In the standard anti-inflammatory assay both in vivo and in vitro, adapalene has a better effect than retinoic acid. It can inhibit the chemotaxis reaction of human polymorphonuclear leukocytes and also inhibit the metabolism of polymorphonuclear cell through inhibition the formation of anti-inflammatory mediators via oxidation reaction of arachidonic acid, thus relieving inflammatory response by the cell-mediated response. It is useful in the treatment of routine skin with acne, pimples and pustules as the main performance. It can also be used for the treatment of the acne presented in face, chest and back. The above information is edited by the Chemicalbook of Dai Xiongfeng. |
| Pharmacokinetics |
The transdermal absorption rate of adapalene is very low. In clinical trials, the adapalene level of skin acne areas subject to long-term treatment is undetectable. Appling C14 labeled adapalene for rats (intravenous, intraperitoneal injection, oral and dermal medication), rabbits (intravenous oral and dermal administration), respectively, clarified the distribution of radioactivity among various tissues. Also, liver, spleen adrenal and ovarian have the highest level. Adapalene is mainly metabolized through demethylation, hydroxylation and binding reactions of oxygen 1 and metabolism in vivo and mainly excreted through bile. [Interaction] No interaction between the product and other skin drugs has been reported. But we should not use other retinoids or other drugs with similar mechanism of action. Adapalene has stable chemical structure, and is not easily to break down in the air and sunlight. A wide range of animal and human studies found no phototoxicity and photosensitivity. However, it is not clear whether it is safe to take it when animal and humans are subject to repeated exposure to sunlight or ultraviolet. Avoid excessive sunshine and UV radiation when use this product. Adapalene has a very low level of transdermal absorption, making it impossible to interact with the systematic medication drugs. No evidence was found that the effect of birth control pills, antibiotics and other oral medications are affected by the using Duff Man for treating skin disease. Duff Man may have a slight local stimulation. Being treated together with the peeling agent, agent or contraction irritating substances can cause additional irritation. Therefore, use other skin medication early in the morning such as erythromycin (concentrations ≤4%), clindamycin phosphate (1%) aqueous solution or benzoyl peroxide gel (concentration ≤10%); Use Duff Man gel at night so that you can avoid drug co-degradation or accumulation of stimulation effect. [Adverse reactions] During the first 2-4 weeks of treatment, the most common adverse reactions are erythema, dryness, scaling, itching, burning or tingling. The extent is mostly mild to moderate. Less frequent adverse reactions include: sunburn, skin irritation, burning and stinging skin discomfort. Rarely adverse reactions include: redness of acne, dermatitis and contact dermatitis, eye swelling, conjunctivitis, redness, itching, skin discoloration, rashes and eczema. Reduce the amount of drugs applied or totally withdrawal when serious adverse reactions happen. |
| Adapalene acid drug safety compared with other topical Vitamin A |
The effect of traditional topical Vitamin A acid drugs (RA) on the treatment of acne vulgaris is indeed very good, but the irritating side effects limit its use. RA causes local irritation because of its unstable structure and poor receptor selectivity caused by series of weak divalent bond chains in its molecular structure. Studies have shown that RA can be degraded by a number of factors: exposure to sunlight within 24 h, 60.0% ~ 80.0% of baseline concentration RA degradation, and if use an oxidizing agent such as benzoyl peroxide the same time when apply RA, 80% of RA would be degraded within 4 h, and all RA disappear within 24 h. In order to find a more stable molecule with similar effect as RA but much smaller side effect, people developed a naphthoic acid derivative - adapalene. Adapalene has small irritation effect due to: 1. Molecularly stable: The unstable divalent bond chains in RA are replaced by the aromatic ring of naphthoic acid, making it stable in the light and oxidants without degradation even in 72 h. 2. Highly selective receptor binding: after entering the cell, RA first bound to cytoplasmic vitamin A acid bound protein (CRABP), and has no selectivity when binds to nuclear receptor RARα, β, γ. Adapalene does not bind CRABP, but selectively binds to specific amino acids sequences of the binding site in nuclear receptor RAR-β and RAR-γ receptor, then binds to RXR, further binds to specific DNA sites, regulating transcription machinery, protein synthesis, and cell proliferation and differentiation. Therefore, it is highly specific and has a small side effect. 3. Low cellular toxicity: Study found that effects of different vitamin A acid on keratinocyte cell cytotoxicity are also different. Adapalene molecule is neutral, has low cytotoxicity to keratinocytes compared with the long-chain organic acids, Vitamin A acid. 4. Adapalene has a clear anti-inflammatory effect. However, this kind of effect for other Vitamin A acid is not still clear. In short, adapalene, a third generation vitamin A drugs, not only have a stronger effect on regulation of epidermal cell differentiation, inhibit proliferation of hair follicle keratinocytes and keratinocytes, inhibition sebaceous cell proliferation, dissolved angle plug acne, etc than all-trans vitamin A acid drugs, but also has a strong anti-inflammatory effect. Because of its unique stability, its efficacy and tolerability is much higher than other Vitamin A acid drugs. |
| Application | Retinoic acid analogs. Adapalene is an agonist of RARβ, and RARγ receptor. Adapalene inhibits cell proliferation and inducing apoptosis in colorectal cancer cells in vitro. Adapalene gel is an effective medication for treatment of acne. |
| Chemical Properties | White Crystalline Solid |
| Usage | Retinoid selective for retinoic acid receptor (RAR) subtypes and . Antiacne |
| Usage | Retinoid selective for retinoic acid receptor (RAR) subtypes β and γ. Antiacne. |
| Usage | anesthetic |
| Usage | inhibits serotonin and noradrenaline reuptake antidepressant antimigraine therapeutic |
| Usage | Acnetreatment |
| Biological Activity | Retinoic acid analog that is a RAR β and RAR γ agonist (AC 50 values are 2.2, 9.3, 22 and > 1000 nM for RAR β , RAR γ , RAR α and RXR α receptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cell in vitro . Displays comedolytic activity. |