| Targets |
As an impurity reference, this compound does not have a defined pharmacological target. Dapagliflozin, the parent drug, selectively inhibits SGLT2 (SLC5A2), a sodium‑glucose cotransporter expressed primarily in the proximal tubule of the kidney, thereby reducing glucose reabsorption and increasing urinary glucose excretion, leading to improved glycemic control and cardiovascular benefits in T2DM patients. This impurity may have structural similarity but is not intended to have SGLT2 inhibitory activity.
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|---|---|
| ln Vitro |
No specific in vitro activity data are available for this impurity. It serves as a reference standard to ensure the purity of dapagliflozin drug substance, rather than as a pharmacologically active compound. The iodine atom, chlorine atom, and the ketone group allow for further chemical transformations, but the compound is not tested in biological assays.
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| ln Vivo |
The compound is not used in vivo for therapeutic purposes. As a process‑related impurity, it may be present at trace levels in dapagliflozin drug substance and product, but it is not administered as an active agent. Its role is solely in pharmaceutical quality control.
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| Enzyme Assay |
Non‑cell‑based experiments for this compound are analytical. A typical HPLC method for impurity profiling uses a C18 reverse‑phase column (4.6 × 250 mm, 5 um) with a mobile phase of acetonitrile and 0.1% phosphoric acid in water (gradient elution 30→90% acetonitrile over 25 min) at 1.0 mL/min, with UV detection at 254 nm. LC‑MS in positive ESI mode shows an [M+H]+ ion at m/z 387.0 (with characteristic isotopic patterns for chlorine and iodine: for Cl, 3:1 ratio of m/z 387:389; for I, the m/z of 387 is the only abundant isotope, but iodine has an isotopic pattern of 127I (100%) and 129I (trace)). ¹H NMR (CDCl3 or DMSO‑d₆) shows characteristic signals for the aromatic protons and the ethoxy group (CH3, delta 1.4 ppm, t; CH2, delta 4.1 ppm, q). The compound is stored at room temperature, protected from light and moisture, in a sealed container. Purity is typically ≥95-97% from commercial suppliers.
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| Cell Assay |
Cell‑based assays are not applicable for this impurity. It is a reference material and is not intended for cellular evaluation. Any cell‑based studies would be performed on the parent drug dapagliflozin, not on its impurities. Dapagliflozin is tested for SGLT2 inhibition using transfected HEK‑293 cells expressing human SGLT2, measuring sodium‑dependent 14C‑methyl‑alpha‑D‑glucopyranoside uptake. This impurity is not tested.
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| Animal Protocol |
In vivo animal experiments are not conducted for this impurity. For the parent drug dapagliflozin, a standard protocol in the Zucker diabetic fatty (ZDF) rat model involves oral administration of dapagliflozin (0.1-10 mg/kg) once daily for 4 weeks. Blood glucose levels, urinary glucose excretion, body weight, and HbA1c are measured. This impurity is not administered in animals.
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| ADME/Pharmacokinetics |
Pharmacokinetic data are not applicable for this impurity. If present in a formulation, it would be at trace levels only. Based on its structure (molecular weight 386.61, estimated log P ~4.0-4.5), the compound is lipophilic. It is a solid at room temperature (melting point not reported) and is stored at room temperature, protected from light.
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| Toxicity/Toxicokinetics |
The toxicity profile of this compound has not been characterized. As a research chemical, standard safety precautions apply. The compound may be harmful if swallowed, inhaled, or absorbed through the skin. It may cause skin and eye irritation. The presence of the iodine atom may contribute to toxicity, but no direct data are available. It should be handled in a well‑ventilated area (fume hood) with appropriate PPE.
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| Additional Infomation |
Additional information: The compound has an MDL number and is also known as Dapagliflozin Impurity, (2‑chloro‑5‑iodophenyl)(4‑ethoxyphenyl)methanone. The product is for research and analytical use only, not for human or veterinary use. It is used as a reference standard for pharmaceutical impurity testing of dapagliflozin (Farxiga®). Synonyms include 2‑chloro‑5‑iodo‑4′‑ethoxybenzophenone.
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| Molecular Formula |
C15H12CLIO2
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|---|---|
| Molecular Weight |
386.61
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| Exact Mass |
385.957
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| CAS # |
1103738-26-6
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| PubChem CID |
57432783
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| Appearance |
Typically exists as solids at room temperature
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| Hydrogen Bond Donor Count |
0
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
19
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| Complexity |
303
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCOC1=CC=C(C=C1)C(=O)C2=C(C=CC(=C2)I)Cl
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| InChi Key |
BGRJXWMKCUZBIG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H12ClIO2/c1-2-19-12-6-3-10(4-7-12)15(18)13-9-11(17)5-8-14(13)16/h3-9H,2H2,1H3
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| Chemical Name |
(2-chloro-5-iodophenyl)-(4-ethoxyphenyl)methanone
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| Synonyms |
Dapagliflozin Impurity 43 (Standard); (2-Chloro-5-iodophenyl)(4-ethoxyphenyl)methanone (Standard)
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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 | 2.5866 mL | 12.9329 mL | 25.8659 mL | |
| 5 mM | 0.5173 mL | 2.5866 mL | 5.1732 mL | |
| 10 mM | 0.2587 mL | 1.2933 mL | 2.5866 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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