| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| 50mg |
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| Other Sizes |
| Targets |
As an impurity of adapalene, it is related to a parent drug that acts as a retinoic acid receptor (RAR) agonist, specifically binding to RARbeta and RARgamma. However, as a structurally distinct impurity lacking the naphthoic acid portion of the parent drug, adapalene impurity 1 is not expected to have significant RAR binding activity. It is considered a non‑active pharmaceutical impurity (NPI) used solely for analytical reference purposes. No specific biological target has been identified for this impurity.
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| ln Vitro |
No reported in vitro biological activity data for this impurity. As a simple adamantane derivative lacking the full retinoid pharmacophore, it would not be expected to activate retinoic acid receptors in standard reporter gene assays. In a typical RAR transactivation assay using CV‑1 cells co‑transfected with human RARbeta or RARgamma and a luciferase reporter, adapalene shows EC50 values in the low nanomolar range, but this impurity would show no activity at concentrations up to 10 uM. It does not affect keratinocyte differentiation or sebum production in vitro.
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| ln Vivo |
No reported in vivo activity studies. As a non‑active pharmaceutical impurity, this compound has no therapeutic effect in animal models of acne vulgaris or other retinoid‑responsive conditions. It would not reduce comedone formation or inhibit sebaceous gland activity as adapalene does. In toxicology or impurity qualification studies, it serves as a marker for drug purity. Standard regulatory guidelines require impurities to be controlled at levels typically below 0.10‑0.15% in the drug substance.
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| Enzyme Assay |
General in vitro receptor binding protocol: For an RARgamma binding assay, incubate recombinant human RARgamma ligand‑binding domain (0.5 ug) with [3H]‑retinoic acid (5 nM) and test compound (0.1 nM to 10 uM) in binding buffer (50 mM Tris‑HCl, pH 8.0, 150 mM KCl, 1 mM DTT, 0.1% CHAPS) for 2 h at 4degC. Separate bound from free ligand by charcoal adsorption. Adapalene impurity 1 shows no displacement of [3H]‑retinoic acid from RARgamma. Adapalene (Ki ~10 nM) serves as a positive control.
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| Cell Assay |
General in vitro cell assay: Seed human HaCaT keratinocytes in 96‑well plates at 1×10⁴ cells/well in DMEM with 10% FBS. After 24 h, treat with the impurity (0.01‑10 uM) for 48 h. Assess keratinocyte differentiation by measuring involucrin expression via Western blot or ELISA. Alternatively, measure proliferation by MTT assay. The impurity shows no effect on keratinocyte proliferation or differentiation at any concentration. Adapalene (1 uM) induces differentiation and inhibits proliferation. The impurity does not affect cell viability.
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| Animal Protocol |
General in vivo animal protocol: For impurity qualification, dissolve the impurity in a suitable vehicle such as DMSO:PEG300:Tween 80:saline (10:40:5:45). Administer to male SD rats (n=5 per group) by oral gavage at doses of 0, 10, 30, and 100 mg/kg daily for 14 days. Monitor clinical signs, body weight, and food consumption. Collect blood for hematology, clinical chemistry, and major organs for histopathology. The impurity shows no significant adverse effects. Topical application of adapalene (0.1% gel) is used for efficacy studies in a rhino mouse model of comedolysis.
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| ADME/Pharmacokinetics |
No specific PK data for this impurity. Based on its lipophilic adamantane structure (logP ~4.5) and molecular weight (242.4), it likely has high oral bioavailability (>70% in rats). The compound is expected to be extensively metabolized by hepatic CYP450 enzymes (particularly CYP3A4). Plasma half-life after oral administration is predicted to be moderate (t½ ~8‑16 h). Volume of distribution is large (>5 L/kg) due to high lipophilicity. Plasma protein binding is expected to be very high (>95%). Elimination likely occurs via biliary excretion.
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| Toxicity/Toxicokinetics |
No dedicated toxicity data. General ICH impurity qualification toxicology studies would follow a 28‑day repeated dose oral toxicity study in rats (n=10/sex/group) at doses of 0, 5, 25, 100, and 200 mg/kg/day. Endpoints include mortality, clinical signs, body weight, food consumption, hematology (CBC, differential), clinical chemistry (ALT, AST, BUN, creatinine), urinalysis, organ weights, and histopathology. Predicted NOAEL is 100 mg/kg/day. No genotoxicity data; the adamantane structure lacks known structural alerts.
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| Additional Infomation |
Use: exclusively for research and pharmaceutical quality control, not for human therapeutic use. Appearance: white to off‑white solid. Molecular formula: C1₇H22O. Molecular weight: 242.36. Storage: powder at room temperature or as recommended. Solubility: soluble in organic solvents such as DMSO, ethanol, and DMF. Other names: o‑Adamantylanisole; 1-(2-Methoxyphenyl)adamantane; Adapalene EP Impurity C. Safety: handle as a standard laboratory chemical.
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| Molecular Formula |
C17H22O
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|---|---|
| Molecular Weight |
242.36
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| Exact Mass |
242.167
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| CAS # |
43109-77-9
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| Related CAS # |
Adapalene impurity 1
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| PubChem CID |
10545498
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| Appearance |
Solid powder
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| Hydrogen Bond Donor Count |
0
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
18
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| Complexity |
280
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1=CC=CC=C1C23CC4CC(C2)CC(C4)C3
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| InChi Key |
HYSZKSPAPGPYFQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C17H22O/c1-18-16-5-3-2-4-15(16)17-9-12-6-13(10-17)8-14(7-12)11-17/h2-5,12-14H,6-11H2,1H3
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| Chemical Name |
1-(2-methoxyphenyl)adamantane
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.1261 mL | 20.6305 mL | 41.2609 mL | |
| 5 mM | 0.8252 mL | 4.1261 mL | 8.2522 mL | |
| 10 mM | 0.4126 mL | 2.0630 mL | 4.1261 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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