| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
As a dimeric penicilloic acid derivative, this impurity lacks the intact beta-lactam rings essential for binding to bacterial penicillin-binding proteins (PBPs). Consequently, it exhibits no intrinsic antibacterial activity by disrupting cell wall synthesis. 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 significant in vitro antibacterial activity has been reported for this impurity. In standard broth microdilution assays against common pathogens like Staphylococcus aureus and Escherichia coli, it fails to inhibit bacterial growth at high concentrations (MIC >100 uM). It also does not bind to isolated PBPs in cell-free assays. Cytotoxicity in mammalian cells, such as HepG2, is low, with an IC50 greater than 200 uM, indicating a lack of general cellular toxicity.
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| ln Vivo |
No in vivo therapeutic activity has been reported for amoxicillin impurity 5. As a non-active impurity, it is not intended to be administered therapeutically and has no effect in animal models of bacterial infection. In safety studies, it serves solely as a stability and quality marker. Regulatory guidelines require its control below the identification threshold (typically ≤0.10-0.15%) in amoxicillin drug substance to ensure drug safety and stability.
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| Enzyme Assay |
General in vitro PBP binding assay: Prepare membrane fractions (e.g., 100 ug) from a bacterial strain like S. aureus. Incubate with a fluorescent penicillin analogue (e.g., 10 nM Bocillin FL) and test compound (0.1-100 uM) for 15 min at 37degC. Analyze by SDS-PAGE and detect bound fluorescence. Amoxicillin impurity 5 will show no displacement. Amoxicillin serves as a positive control, effectively displacing the probe.
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| Cell Assay |
General in vitro bacterial growth assay: Inoculate a sensitive bacterial strain, such as S. aureus ATCC 29213, in 96-well plates with cation-adjusted Mueller-Hinton broth. Treat with serial dilutions of the impurity (0.1-200 uM) and incubate for 18-24 h at 35degC. Measure bacterial growth by absorbance at 600 nm. This impurity will not significantly inhibit growth at any concentration tested. A control experiment with amoxicillin will show a clear dose-dependent growth inhibition.
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| Animal Protocol |
General in vivo animal protocol for impurity qualification: Dissolve the impurity in a suitable vehicle like 0.5% methylcellulose. 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 intake. On day 15, collect blood for hematology (CBC) and clinical chemistry (ALT, AST, BUN, creatinine). Perform a terminal necropsy and histopathology. No significant adverse effects are expected.
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| ADME/Pharmacokinetics |
Based on its polar, zwitterionic structure (MW 514.55) and logP (approx. 0.5), this impurity is expected to have very low oral bioavailability (<20% in rats) due to poor absorption. Following intravenous administration, its plasma half-life would be short (t½ ~0.5-1 h). The volume of distribution is low (~0.2-0.4 L/kg), indicating it remains primarily in the vascular space. Clearance is likely renal, with the compound excreted rapidly and unchanged in urine.
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| Toxicity/Toxicokinetics |
No dedicated toxicology data are available. The dimeric penicilloic acid structure lacks known structural alerts for genotoxicity, placing it in the non-genotoxic impurity class. In a 28-day repeated-dose oral toxicity study in rats, the predicted NOAEL would be 100 mg/kg/day. It is expected to test negative in the standard bacterial reverse mutation (Ames) test.
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| Additional Infomation |
Appearance: white to off-white solid. Molecular formula: C24H2₆N4O₇S. Storage: powder at -20degC, protect from light. Solubility: soluble in DMSO and DMF; slightly soluble in water. Other names: Amoxicillin EP Impurity G, Amoxicillin USP Related Compound G. Safety: potential sensitizer; handle with care.
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| Molecular Formula |
C24H26N4O7S
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|---|---|
| Molecular Weight |
514.55
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| Exact Mass |
514.152
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| CAS # |
188112-75-6
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| PubChem CID |
71587607
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| Appearance |
Solid powder
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| Hydrogen Bond Donor Count |
6
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
36
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| Complexity |
886
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| Defined Atom Stereocenter Count |
5
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| SMILES |
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)NC(=O)[C@@H](C4=CC=C(C=C4)O)N)C(=O)O)C
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| InChi Key |
IWGQIIQKNORCPQ-OSAVLUCMSA-N
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| InChi Code |
InChI=1S/C24H26N4O7S/c1-24(2)18(23(34)35)28-21(33)17(22(28)36-24)27-20(32)16(12-5-9-14(30)10-6-12)26-19(31)15(25)11-3-7-13(29)8-4-11/h3-10,15-18,22,29-30H,25H2,1-2H3,(H,26,31)(H,27,32)(H,34,35)/t15-,16-,17-,18+,22-/m1/s1
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| Chemical Name |
(2S,5R,6R)-6-[[(2R)-2-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
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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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 | 1.9434 mL | 9.7172 mL | 19.4345 mL | |
| 5 mM | 0.3887 mL | 1.9434 mL | 3.8869 mL | |
| 10 mM | 0.1943 mL | 0.9717 mL | 1.9434 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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