Adapalene
- CAS No.
- 106685-40-9
- Chemical Name:
- Adapalene
- Synonyms
- Adapalen;Differin;6-(3-(AdaMantan-1-yl)-4-Methoxyphenyl)-2-naphthoic acid;6-[3-(1-ADAMANTYL)-4-METHOXYPHENYL]-2-NAPHTHALENE CARBOXYLIC ACID;6-[3-(1-adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic acid;ADPL;CD-271;Differi;p75(NTR);Adaparin
- CBNumber:
- CB6771245
- Molecular Formula:
- C28H28O3
- Molecular Weight:
- 412.52
- MOL File:
- 106685-40-9.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/6/25 20:17:06
| Melting point | 319-3220C |
|---|---|
| Boiling point | 606.3±55.0 °C(Predicted) |
| Density | 1.233±0.06 g/cm3(Predicted) |
| RTECS | QJ1987000 |
| storage temp. | 2-8°C |
| solubility | DMSO: >10mg/mL |
| pka | 4.2(at 25℃) |
| form | White solid |
| color | white to off-white |
| Merck | 14,150 |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or DMF may be stored at -20°C for up to 3 months |
| InChIKey | LZCDAPDGXCYOEH-UHFFFAOYSA-N |
| SMILES | C1=C2C(C=C(C3=CC=C(OC)C(C45CC6CC(CC(C6)C4)C5)=C3)C=C2)=CC=C1C(O)=O |
| CAS DataBase Reference | 106685-40-9(CAS DataBase Reference) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS08 |
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|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H361d | |||||||||
| Precautionary statements | P201-P202-P280-P308+P313-P405-P501 | |||||||||
| WGK Germany | nwg | |||||||||
| HS Code | 2918992090 | |||||||||
| NFPA 704 |
|
Adapalene price More Price(6)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | A7486 | Adapalene ≥98% (HPLC) | 106685-40-9 | 10MG | ₹8746.6 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1388 | Adapalene Pharmaceutical Secondary Standard; Certified Reference Material | 106685-40-9 | 500MG | ₹10835.83 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A7486 | Adapalene ≥98% (HPLC) | 106685-40-9 | 50MG | ₹21790.73 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 114825-M | Adapalene - CAS 106685-40-9 - Calbiochem A cell-permeable naphthoic acid compound that exhibits selective affinity and agonistic potency toward RARβ and RARγ over RARα. | 106685-40-9 | 25MG | ₹6990 | 2022-06-14 | Buy |
| TCI Chemicals (India) | A2549 | Adapalene | 106685-40-9 | 200MG | ₹4000 | 2022-05-26 | Buy |
Adapalene Chemical Properties,Uses,Production
Description
Adapalene is a synthetic retinoid and an agonist of retinoic acid receptors (RARs; Kds = 1,100, 34, and 130 nM for RARα, RARβ, and RARγ, respectively). It inhibits growth and differentiation of sebocytes in a concentration-dependent manner in primary rat preputial cell culture. Adapalene (10 μM) completely inhibits the activity of soybean 15-lipoxygenase (15-LOX) in an enzyme assay and inhibits the 5- and 15-LOX pathways in human blood polymorphonuclear leukocytes (PMNs). It reduces the protein levels of toll-like receptor 2 (TLR2) and IL-10 in skin explants isolated from patients with acne and healthy controls in a concentration-dependent manner but increases the expression of the antigen-presenting protein CD1d in acne skin explants while decreasing it in control explants. It inhibits inflammation in rodent models of ear edema induced by arachidonic acid and carrageenan-induced paw edema. Adapalene (100 μM) also induces apoptosis and inhibits proliferation of CC-531, HT-29, and LoVo colon cancer cells and reduces tumor growth in a DLD-1 colon cancer nude mouse xenograft model in a dose-dependent manner. Formulations containing adapalene have been used in the treatment of acne vulgaris.
Chemical Properties
White Crystalline Solid
Uses
Adapalene has been used as a retinoic acid receptor (RAR) agonist to study its effects on inhibiting transcription of hepatitis B virus in covalently closed circular DNA (cccDNA). It has also been used as a component to culture mixed lymphocyte reactions (MLR) to study its effects on isolated macrophages.
Indications
Adapalene (Differin) is a polyaromatic retinoidlike compound that binds to specific retinoic acid nuclear receptors and is thought to normalize the differentiation of keratinocytes in the sebaceous acroinfundibulum. Adapelene is indicated for topical treatment of acne. Minor local irritation is a common, usually tolerable side effect. In contrast to other drugs of the retinoid group, adapalene has not been shown to be teratogenic in rodents. However, since adequate human studies are lacking, its use in pregnant women should be discouraged until further information is available.
Definition
ChEBI: A naphthoic acid that is CD437 in which the phenolic hydroxy group has been converted to its methyl ether.
General Description
Adapalene is a third-generation synthetic retinoid and a highly lipophilic compound derived from naphthoic acid. It is widely used in the treatment of acne.
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.
Adapalene Preparation Products And Raw materials
Raw materials
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| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| NILKANTH HEALTH CHEM (I) PRIVATE LIMITED | +91 8000452862 | Gujarat, India | 17 | 58 | Inquiry |
| SEUTIC | +91-8309787199 +91-8309787199 | Hyderabad, India | 124 | 58 | Inquiry |
| Zuhhad international | +91-8454840801 +91-8454840801 | Mumbai, India | 21 | 58 | Inquiry |
| Glenmark Pharmaceuticals Limited | +912240189999 | Maharashtra, India | 93 | 58 | Inquiry |
| Hem-Deep Organics Pvt. Ltd. (HOPL) | +91-9998689897 +91-9824114578 | Gujarat, India | 12 | 58 | Inquiry |
| Aarti Industries Limited (AIL) | +91-84596144931 +91-9920899935 | Maharashtra, India | 235 | 58 | Inquiry |
| Dayaram Pharma Chem | +91-9601766800 +91-9601766800 | Gujarat, India | 61 | 58 | Inquiry |
| Rivashaa Agrotech Biopharma Pvt. Ltd. | +91-26463395 +91-7926462688 | Gujarat, India | 1615 | 58 | Inquiry |
| Prachin Chemicals Saykha Private Limited | +91-9537763493 +91-9904988839 | Gujarat, India | 16 | 58 | Inquiry |
| Paradise Healthcare | +91-8454840801 +91-8690548458 | Gujarat, India | 14 | 58 | Inquiry |
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