Physicochemical Properties
| Molecular Formula | C22H21CLN2O8 |
| Molecular Weight | 476.86 |
| Exact Mass | 476.099 |
| CAS # | 2013-58-3 |
| Related CAS # | Meclocycline Sulfosalicylate Salt;73816-42-9 |
| PubChem CID | 54676539 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.72g/cm3 |
| Boiling Point | 716.4ºC at 760mmHg |
| Flash Point | 387.1ºC |
| Vapour Pressure | 0mmHg at 25°C |
| LogP | 0.915 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 33 |
| Complexity | 1040 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | C=C1C2=C(Cl)C=CC(O)=C2C(C3=C(O)[C@@]4(O)[C@@H]([C@@H](O)[C@H]13)[C@H](N(C)C)C(O)=C(C(N)=O)C4=O)=O |
| InChi Key | RNIADBXQDMCFEN-IWVLMIASSA-N |
| InChi Code | InChI=1S/C22H21ClN2O8/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30/h4-5,10,14-15,17,26-28,31,33H,1H2,2-3H3,(H2,24,32)/t10-,14-,15+,17+,22+/m1/s1 |
| Chemical Name | (4S,4aR,5S,5aR,12aR)-7-chloro-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide |
| 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
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion Estimated oral bioavailability of ~66% and tmax of 4h based on that of demeclocycline due to structural similarity. Estimated urinary excretion of ~40% and fecal excretion of ~43% based on that of demeclocycline due to structural similarity. Estimated Vd of 121L based on that of demeclocycline due to structural similarity. Metabolism / Metabolites Most tetracyclines are not metabolized. It is unlikely that meclocycline would be metabolized. Biological Half-Life Half life estimated to be ~5.6h based on that of chlortetracycline due to structural similarity. |
| Toxicity/Toxicokinetics |
Protein Binding Estimated plasma protein binding of ~75-91% based on that of demeclocycline due to structural similarity. |
| References |
[1]. Cytotoxicity induced by tetracyclines via protein photooxidation. Advances in Toxicology, 2015, 2015. |
| Additional Infomation |
Meclocycline is a member of tetracyclines. Meclocycline is under investigation in clinical trial NCT00385515 (Efficacy of SNX-1012 in the Treatment of Oral Mucositis). Drug Indication Currently under investigation for the topical treatment of ulcerative oral mucositis Mechanism of Action As a tetracycline, meclocycline likely works by reversably associating with the 30s subint of the bacterial ribosome. A likely binding site for tetracyclines has been identified on protein S7 of this subunit. This association blocks the association of aminoacyl-tRNA with the ribosome, inhibiting protein synthesis. Ultimately this inhibits bacterial growth due to a lack of proteins necessary for reproduction. Pharmacodynamics Tetracyclines such as meclocycline are broad spectrum bacteriostatic agents. Meclocyclin likely inhibits the growth of bacterial species present in the damaged oral mucosa, allowing the immune system to more easily eliminate infections. |
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 | 2.0971 mL | 10.4853 mL | 20.9705 mL | |
| 5 mM | 0.4194 mL | 2.0971 mL | 4.1941 mL | |
| 10 mM | 0.2097 mL | 1.0485 mL | 2.0971 mL |