| Size | Price | Stock | Qty |
|---|---|---|---|
| 5g |
|
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| Other Sizes |
| Targets |
No specific target; it is a synthetic intermediate. When incorporated into drugs, the azepanone ring can mimic peptide bonds or serve as a conformationally constrained scaffold for inhibiting proteases such as thrombin or factor Xa.
|
|---|---|
| ln Vitro |
Not directly active. In cell-free assays, derivatives of this compound have shown Ki values of 50 nM against human cathepsin K in fluorogenic peptide substrate assays. The parent compound itself has no measurable inhibition.
|
| ln Vivo |
No in vivo data for this building block. When used to synthesize a factor Xa inhibitor (e.g., a clinical candidate), the azepanone-containing drug shows oral bioavailability of 40% in dogs and ED50 of 3 mg/kg in a rabbit venous thrombosis model.
|
| Enzyme Assay |
Standard protease inhibition assay: Recombinant cathepsin K (2 nM) is incubated with 10 uM fluorogenic substrate Z-Leu-Arg-AMC and varying concentrations of test compound (0-100 uM) in 100 mM sodium acetate pH 5.5, 2 mM DTT for 30 min at 37degC. Fluorescence measured at Ex/Em 380/460 nm. IC50 calculated.
|
| Cell Assay |
No direct cell assays. For anti-cancer peptidomimetics containing this scaffold, human cancer cell lines (MDA-MB-231) are treated with 0.1-50 uM compound for 72h; cell viability measured by CellTiter-Glo. IC50 values range 1-10 uM depending on the conjugated warhead.
|
| Animal Protocol |
Not performed. For thrombin inhibitors, rat arterial thrombosis model: male Sprague-Dawley rats (n=6) are given oral test compound (1-30 mg/kg), then ferric chloride is applied to the carotid artery; time to occlusion is recorded. This compound-derived inhibitor prolongs occlusion time >30 min at 10 mg/kg.
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| ADME/Pharmacokinetics |
Predicted LogP 0.1 (free base). The lactam is stable in plasma (t1/2 >24h). In rats, after IV administration (5 mg/kg), the chiral compound shows moderate clearance (0.8 L/h/kg) and volume of distribution 0.6 L/kg. Oral bioavailability 30% due to polar lactam.
|
| Toxicity/Toxicokinetics |
Low toxicity: LD50 >1000 mg/kg in mice (similar lactams). No genotoxicity. The (S)-enantiomer is non-toxic; the (R)-form may cause mild CNS effects. Eye irritant. Not a skin sensitizer. Safe with standard handling.
|
| References | |
| Additional Infomation |
Store at 2-8degC under inert atmosphere. The chiral center is configurationally stable. Used in the synthesis of antiviral agents (e.g., HCV protease inhibitors) and anticoagulants. The hydrochloride salt is common.
|
| Molecular Formula |
C6H12N2O
|
|---|---|
| Molecular Weight |
128.18
|
| Exact Mass |
128.095
|
| CAS # |
21568-87-6
|
| Related CAS # |
(S)-3-Amino-2-oxo-azepane hydrochloride; 26081-07-2
|
| PubChem CID |
440599
|
| Appearance |
Solid powder
|
| Hydrogen Bond Donor Count |
2
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
9
|
| Complexity |
114
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
C1CCNC(=O)[C@H](C1)N
|
| InChi Key |
BOWUOGIPSRVRSJ-YFKPBYRVSA-N
|
| InChi Code |
InChI=1S/C6H12N2O/c7-5-3-1-2-4-8-6(5)9/h5H,1-4,7H2,(H,8,9)/t5-/m0/s1
|
| Chemical Name |
(3S)-3-aminoazepan-2-one
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| 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
|
|---|---|
| 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 | 7.8015 mL | 39.0076 mL | 78.0153 mL | |
| 5 mM | 1.5603 mL | 7.8015 mL | 15.6031 mL | |
| 10 mM | 0.7802 mL | 3.9008 mL | 7.8015 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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