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| Targets |
SCH-336 targets the cannabinoid receptor 2 (CB2), a G protein-coupled receptor primarily expressed on immune cells, including B cells, natural killer cells, and monocytes. CB2 is involved in the modulation of immune responses and inflammation. SCH-336 acts as an inverse agonist at CB2, meaning it stabilizes the receptor in an inactive conformation and reduces constitutive receptor activity. The compound exhibits a Ki of 1.8 nM and an EC50 of 2 nM for CB2, with 100-fold selectivity over the CB1 receptor. This selectivity is important for minimizing central nervous system effects associated with CB1 modulation.
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| ln Vitro |
SCH 336 (Sch.336) (0-10 µM) decreases GTPγS binding to membranes containing human CB2, EC50 At 2 nM, and diminishes the efficacy of CB1-containing membranes, with an EC50 of 200 nM[1]. It competes with [3H]CP55,940 for binding to human CB2 on Sf9 cell membranes, Ki 1.8 nM. With an IC50 of 34 nM, SCH 336 prevents BaF3/CB2 from migrating to 100 nM 2-AG[1].
In vitro, SCH-336 acts as a potent and selective inverse agonist at the CB2 receptor. It binds to CB2 with high affinity (Ki = 1.8 nM) and shows 100-fold selectivity over CB1. SCH-336 inhibits BaF3/CB2 cell migration, demonstrating its ability to modulate CB2-mediated cellular functions. The compound has also been shown to increase forskolin-stimulated cAMP accumulation in CHO cells expressing human CB2 receptors, consistent with inverse agonist activity at this Gi-coupled receptor. |
| ln Vivo |
SCH 336 (0.02, 0.2, 2.0 mg/kg; intraperitoneal injection) strongly slows leukocyte migration [1].
In vivo, SCH-336 has demonstrated anti-inflammatory effects in animal models. It significantly inhibits leukocyte migration in vivo and blocks ovalbumin-induced pulmonary eosinophilia in mice. These effects are consistent with the role of CB2 in modulating immune cell trafficking and inflammatory responses. The compound is orally active, making it suitable for in vivo administration. SCH-336 is used to study the therapeutic potential of CB2 modulation in inflammatory diseases and to elucidate the distinct functions of CB2 compared to CB1. |
| Enzyme Assay |
The in vitro enzyme/receptor binding (non-cellular) assays for SCH-336 are radioligand binding assays using membrane preparations from cells expressing recombinant human CB2 or CB1 receptors. The compound's binding affinity (Ki) is determined by its ability to displace a labeled CB2 ligand such as [3H]CP-55,940 from the receptor. Competition binding assays are performed to calculate the Ki value. Selectivity is confirmed by testing the compound's binding affinity for CB1 and other related receptors. These assays provide quantitative measures of the compound's potency and selectivity.
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| Cell Assay |
In vitro cellular assays for SCH-336 are performed using cell lines expressing recombinant CB2 receptors, such as CHO cells or BaF3 cells. The compound's inverse agonist activity is assessed by measuring its ability to increase forskolin-stimulated cAMP accumulation, as CB2 receptors are Gi-coupled and their activation inhibits adenylyl cyclase. Additionally, the compound's ability to inhibit cell migration is assessed using transwell migration assays with BaF3/CB2 cells. These assays confirm the functional activity of SCH-336 at CB2.
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| Animal Protocol |
Animal/Disease Models: Female B6D2/F1 mice (HU210) [1]
Doses: 0.02, 0.2, 2.0 mg/kg Route of Administration: intraperitoneal (ip) injection Experimental Results: Dramatically inhibited the migration of leukocytes into CCL2-soaked gel foam sponges. In vivo animal experiments for SCH-336 have been conducted in mouse models of inflammation. To assess the compound's anti-inflammatory effects, mice are sensitized and challenged with ovalbumin to induce pulmonary eosinophilia, and SCH-336 is administered orally. Eosinophil infiltration into the lung is measured to evaluate the compound's efficacy. Leukocyte migration is also assessed in other models of inflammation. These studies demonstrate the in vivo activity of SCH-336 and support its potential for treating inflammatory diseases. |
| ADME/Pharmacokinetics |
SCH-336 has a molecular weight of 539.64 g/mol and a molecular formula of C23H25NO8S3. The compound is orally active. Detailed pharmacokinetic parameters such as half-life, Cmax, and bioavailability are not extensively reported in the available literature. However, the compound's efficacy in mouse models following oral administration suggests adequate systemic exposure. SCH-336 is soluble in DMSO and other organic solvents, and its formulation for in vivo studies typically involves standard vehicles for oral or parenteral administration.
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| Toxicity/Toxicokinetics |
SCH-336 has been evaluated in preclinical studies and has been reported to be well-tolerated at effective doses. No significant toxicity has been reported in the available literature. However, comprehensive toxicology studies would be necessary to fully assess the compound's safety profile for clinical development. As a selective CB2 inverse agonist, SCH-336 is expected to have a more favorable safety profile compared to CB1 modulators, as CB2 is primarily expressed in peripheral tissues and is not associated with central nervous system effects.
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| References | |
| Additional Infomation |
SCH-336 is a highly potent and selective inverse agonist of the cannabinoid receptor 2 (CB2). It has a Ki of 1.8 nM for CB2 and shows 100-fold selectivity over CB1. The compound is orally active and has demonstrated anti-inflammatory effects in vivo, including inhibition of leukocyte migration and blockade of ovalbumin-induced pulmonary eosinophilia in mice. SCH-336 is a research compound used to study the role of CB2 in immune modulation and inflammation. It is not an approved drug but represents a valuable tool for target validation and drug discovery in inflammatory diseases.
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| Molecular Formula |
C23NO8S3H25
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| Molecular Weight |
539.6415
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| Exact Mass |
539.074
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| Elemental Analysis |
C, 51.19; H, 4.67; N, 2.60; O, 23.72; S, 17.82
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| CAS # |
447459-51-0
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| PubChem CID |
10324989
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
756.6±70.0 °C at 760 mmHg
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| Flash Point |
411.4±35.7 °C
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| Vapour Pressure |
0.0±2.5 mmHg at 25°C
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| Index of Refraction |
1.589
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| LogP |
3.91
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
35
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| Complexity |
995
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| Defined Atom Stereocenter Count |
1
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| SMILES |
COC1C=CC(S(C2C=CC([C@@H](NS(C)(=O)=O)C)=CC=2)(=O)=O)=C(S(C2C=CC(OC)=CC=2)(=O)=O)C=1
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| InChi Key |
NXODIUKWAVUFGF-INIZCTEOSA-N
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| InChi Code |
InChI=1S/C23H25NO8S3/c1-16(24-33(4,25)26)17-5-10-20(11-6-17)34(27,28)22-14-9-19(32-3)15-23(22)35(29,30)21-12-7-18(31-2)8-13-21/h5-16,24H,1-4H3/t16-/m0/s1
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| Chemical Name |
N-[(1S)-1-[4-[4-methoxy-2-(4-methoxyphenyl)sulfonylphenyl]sulfonylphenyl]ethyl]methanesulfonamide
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| Synonyms |
SCH336 SCH 336 SCH-336
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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) |
DMSO : ~100 mg/mL (~185.31 mM)
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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 | 1.8531 mL | 9.2654 mL | 18.5309 mL | |
| 5 mM | 0.3706 mL | 1.8531 mL | 3.7062 mL | |
| 10 mM | 0.1853 mL | 0.9265 mL | 1.8531 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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