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| Targets |
As an impurity of mometasone furoate, it is related to a parent drug that binds to the glucocorticoid receptor (GR), leading to anti-inflammatory effects. The oxidation at the 6-position is expected to significantly alter its binding conformation, likely resulting in a much lower affinity for the GR. Consequently, it would have a minimal or negligible anti-inflammatory effect. It is considered a non-active pharmaceutical impurity (NPI).
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| ln Vitro |
In a standard GR binding assay using [3H]-dexamethasone, mometasone furoate shows high affinity (Ki in the low nM range). Mometasone furoate impurity 1 would have a significantly reduced binding affinity (Ki > 100 nM). In a cell-based transactivation assay, this impurity would demonstrate a markedly reduced potency in activating GR-mediated gene transcription compared to the parent drug.
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| ln Vivo |
No specific in vivo activity data have been reported for this impurity. In an animal model of inflammation (e.g., croton oil-induced ear edema), the parent drug, mometasone furoate, is highly potent, while this impurity would show a much weaker or absent anti-inflammatory effect. In impurity qualification studies, it serves as a marker for drug purity and oxidative stability.
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| Enzyme Assay |
General in vitro GR binding assay: Incubate recombinant human GR ligand-binding domain with [3H]-dexamethasone (5 nM) and test compound (0.1 nM to 10 uM) for 2 h at 4degC. Separate bound from free using a charcoal adsorption method. This impurity would show minimal competition. Mometasone furoate would serve as a positive control.
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| Cell Assay |
General in vitro cell-based transactivation assay: Transfect A549 cells with a GR-responsive luciferase reporter plasmid, treat with the impurity (0.1 nM to 10 uM) for 24 h, and measure luciferase activity. The impurity would have minimal effect. Mometasone furoate would activate the reporter potently. Cytotoxicity can be assessed with an MTT assay.
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| Animal Protocol |
General in vivo animal protocol for impurity qualification: Apply a formulation containing the impurity (0.1-1%) topically to the ears of mice (n=8/group) once daily for 3 days. On day 3, apply croton oil to induce inflammation. Measure ear thickness as a marker of inflammation. The impurity would show little to no anti-inflammatory effect. The parent drug would serve as a positive control.
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| ADME/Pharmacokinetics |
Based on its molecular weight (535.41 g/mol) and high lipophilicity (logP > 4), this impurity is expected to be well-absorbed through the skin or from the gut, though its systemic absorption is not desired. If absorbed, it would be highly protein bound (>95%), have a large volume of distribution, and be eliminated slowly via hepatic metabolism. Its half-life would be similar to mometasone furoate.
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| Toxicity/Toxicokinetics |
No dedicated toxicology data are available for this impurity. The oxidation product of a corticosteroid, it lacks structural alerts for genotoxicity. It would likely be negative in the Ames test. In a 28-day dermal toxicity study in rats, a high concentration of this impurity would show no significant systemic or local toxicity other than potential skin irritation, with a predicted NOAEL of >1% in a typical formulation.
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| Additional Infomation |
Appearance: yellow solid. Molecular formula: C2₇H2₈Cl2O₇. Storage: powder at -20degC, protect from light. Solubility: soluble in DMSO and DMF. Other names: Mometasone Furoate EP Impurity F, 6-Oxo Mometasone Furoate. Safety: treat as a hazardous material.
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| Molecular Formula |
C27H28CL2O7
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|---|---|
| Molecular Weight |
535.41
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| Exact Mass |
534.121
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| CAS # |
1305334-30-8
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| PubChem CID |
129011919
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| Appearance |
Typically exists as solids at room temperature
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| Hydrogen Bond Donor Count |
1
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
36
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| Complexity |
1100
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| Defined Atom Stereocenter Count |
8
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| SMILES |
C[C@@H]1C[C@H]2[C@@H]3CC(=O)C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CCl)OC(=O)C5=CC=CO5)C)O)Cl)C
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| InChi Key |
XXMUYUVNHWPWLS-KORTYEGJSA-N
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| InChi Code |
InChI=1S/C27H28Cl2O7/c1-14-9-16-17-11-19(31)18-10-15(30)6-7-24(18,2)26(17,29)21(32)12-25(16,3)27(14,22(33)13-28)36-23(34)20-5-4-8-35-20/h4-8,10,14,16-17,21,32H,9,11-13H2,1-3H3/t14-,16+,17+,21+,24+,25+,26+,27+/m1/s1
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| Chemical Name |
[(8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-17-(2-chloroacetyl)-11-hydroxy-10,13,16-trimethyl-3,6-dioxo-8,11,12,14,15,16-hexahydro-7H-cyclopenta[a]phenanthren-17-yl] furan-2-carboxylate
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| Synonyms |
Mometasone Furoate EP Impurity F
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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 | 1.8677 mL | 9.3386 mL | 18.6773 mL | |
| 5 mM | 0.3735 mL | 1.8677 mL | 3.7355 mL | |
| 10 mM | 0.1868 mL | 0.9339 mL | 1.8677 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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