Physicochemical Properties
| Molecular Formula | C26H42N4O5S2 |
| Molecular Weight | 554.7655 |
| Exact Mass | 590.236 |
| CAS # | 148927-60-0 |
| Related CAS # | L-368,899 hydrochloride;160312-62-9 |
| PubChem CID | 9872389 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.31g/cm3 |
| Index of Refraction | 1.61 |
| LogP | 5.577 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 9 |
| Heavy Atom Count | 37 |
| Complexity | 1040 |
| Defined Atom Stereocenter Count | 4 |
| SMILES | S(C([H])([H])[C@]12C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[C@]1([H])N([H])C([C@]([H])(C([H])([H])C([H])([H])S(C([H])([H])[H])(=O)=O)N([H])[H])=O)C2(C([H])([H])[H])C([H])([H])[H])(N1C([H])([H])C([H])([H])N(C2=C([H])C([H])=C([H])C([H])=C2C([H])([H])[H])C([H])([H])C1([H])[H])(=O)=O |
| InChi Key | MWIASLNTAGRGGA-ZJPWWDJASA-N |
| InChi Code | InChI=1S/C26H42N4O5S2/c1-19-7-5-6-8-22(19)29-12-14-30(15-13-29)37(34,35)18-26-11-9-20(25(26,2)3)17-23(26)28-24(31)21(27)10-16-36(4,32)33/h5-8,20-21,23H,9-18,27H2,1-4H3,(H,28,31)/t20-,21+,23+,26-/m1/s1 |
| Chemical Name | (2S)-2-amino-N-[(1S,2S,4R)-7,7-dimethyl-1-[[4-(2-methylphenyl)piperazin-1-yl]sulfonylmethyl]-2-bicyclo[2.2.1]heptanyl]-4-methylsulfonylbutanamide |
| 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) |
Biological Activity
| ln Vivo | L-368,899 (0.1, 0.3, 1 mg/kg; intravenous injection; single dosage) revealed dose-related antagonism to OT-stimulated uterine contractions with an in vivo AD50 value of 0.35 mg/kg [1]. L-368,899 (3, 10, 30 mg/kg; id; single dosage) suppresses the contractile impact of OT (AD50= 7 mg/kg) and has a long duration of action in vivo (>4 hours) (AD50: L-368,899 has to be OT reaction reduced by 50%) [1]. L-368,899 (10 mg/kg, oral; single dosage) demonstrates a bioavailability (AUC 0-6 hours) of 35% [1]. L-368,899 (0.54, 1.8, 5.4 mg/kg; IV; single dose) decreases oxytocin-induced and endogenous increases in plasma PGFM concentrations [2]. |
| Animal Protocol |
Animal/Disease Models: Adult female SD (SD (Sprague-Dawley)) rat (250-350 g) [1]. Doses: 0.1, 0.3, 1 mg/kg Route of Administration: intravenous (iv) (iv)injection; single. Experimental Results: Inhibition of OT-stimulated uterine contractions, AD50 value was 0.35 mg/kg. Animal/Disease Models: Adult female SD (SD (Sprague-Dawley)) rat (250-350 g) [1]. Doses: 3, 10, 30 mg/kg Route of Administration: Intraduodenal; single. Experimental Results: It has an antagonistic effect on OT-stimulated uterine contraction, with an AD50 of 7 mg/kg and a duration of more than 4 hrs (hrs (hours)). Animal/Disease Models: Adult female SD (SD (Sprague-Dawley)) rat (250-350 g) [1]. Doses: 10 mg/kg Route of Administration: po (po (oral gavage)) single dose. Experimental Results: demonstrated oral activity with bioavailability (AUC 0-6 hrs (hrs (hours))) of 35%. Animal/Disease Models: Mature Dorset cross ewes (53-57 kg; ovariectomy) [2]. Doses: 0.54, 1.8, 5.4 mg/kg (3, 10 and 30 µg/kg/min for 3 hrs (hrs (hours)); dissolved in 0.9% saline). Route of Administration: intravenous (iv) (iv)infusion; single. Experimental Results: The resulting increase in PGFM plasma concentration was Dramatically diminished in frequency (from 2.2 to 1.0 |
| References |
[1]. L‐368,899, a potent orally active oxytocin antagonist for potential use in preterm labor. Drug development research, 1993, 30(3): 129-142. [2]. Attenuation of PGF2alpha release in ewes infused with the oxytocin antagonist L-368,899. Domest Anim Endocrinol. 2003 Oct;25(3):255-62. [3]. 1-((7,7-Dimethyl-2(S)-(2(S)-amino-4-(methylsulfonyl)butyramido)bicyclo [2.2.1]-heptan-1(S)-yl)methyl)sulfonyl)-4-(2-methylphenyl)piperaz ine (L-368,899): an orally bioavailable, non-peptide oxytocin antagonist with potential utility fo. |
Solubility Data
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8025 mL | 9.0127 mL | 18.0255 mL | |
| 5 mM | 0.3605 mL | 1.8025 mL | 3.6051 mL | |
| 10 mM | 0.1803 mL | 0.9013 mL | 1.8025 mL |