Chloropyramine hydrochloride (Alergosan, Nilfan, Sinopen, Allergan hydrochloride, Suprastin) is an antihistamine drug acting as a histamine receptor H1 antagonist. It has usefulness in the treatment of breast cancer.
Physicochemical Properties
| Molecular Formula | C16H20CLN3 |
| Molecular Weight | 289.8 |
| Exact Mass | 289.135 |
| Elemental Analysis | C, 66.31; H, 6.96; Cl, 12.23; N, 14.50 |
| CAS # | 59-32-5 |
| Related CAS # | Chloropyramine hydrochloride; 6170-42-9 |
| PubChem CID | 25295 |
| Appearance | Solid powder |
| Density | 1.158g/cm3 |
| Boiling Point | 413.5ºC at 760 mmHg |
| Melting Point | 25°C |
| Flash Point | 203.9ºC |
| Index of Refraction | 1.6 |
| LogP | 3.303 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 20 |
| Complexity | 264 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CN(CCN(C1=CC=CC=N1)CC1C=CC(Cl)=CC=1)C |
| InChi Key | ICKFFNBDFNZJSX-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C16H20ClN3/c1-19(2)11-12-20(16-5-3-4-10-18-16)13-14-6-8-15(17)9-7-14/h3-10H,11-13H2,1-2H3 |
| Chemical Name | N'-[(4-chlorophenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine |
| Synonyms | Avapena; Synopen; Suprastin; Anaphylline; Chlorneoantergan; Chloropyramine; Chlorpyramine; Halopyramine |
| 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
| Targets | H1 Receptor |
| ln Vitro | Chloropyramine (25, 50 μM; 24 h, 48 h) causes SASH1 expression and apoptosis in breast cancer cell lines[1]. |
| ln Vivo | Chloropyramine (i.p.; 10 mg/kg) abolishes hypothermia in rats[2]. |
| Cell Assay |
Cell Line: Breast cancer cell lines Concentration: 25 or 50 μM Incubation Time: 24 h Result: Increased SASH1 expression in breast cancer cell lines. |
| Animal Protocol |
Rats 10 mg/kg Intraperitoneal |
| References |
[1]. SASH1 mediates sensitivity of breast cancer cells to chloropyramine and is associated with prognosis in breast cancer. Oncotarget. 2016 Nov 8;7(45):72807-72818. |
| Additional Infomation |
N'-[(4-chlorophenyl)methyl]-N,N-dimethyl-N'-(2-pyridinyl)ethane-1,2-diamine is an aminopyridine. Chlorpyramine is a first generation antihistamine used in Eastern European countries to treat bronchial asthma as well as allergice rhinitis, allergic conjunctivitis, and other allergic reactions. It is also indicated for Quincke's edema, allergic reactions to insect bites, food and drug allergies, and anaphylactic shock. Drug Indication For the treatment of allergic conjunctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions. Mechanism of Action Chloropyramine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine. Pharmacodynamics Chlorpyramine is a competitive reversible H1 receptor antagonist. This inhibits vasodilation, increases in vascular permeability, and tissue edema associated with histamine release. In addition, chloropyramine has some anticholinergic properties. These effects, along with its ability to pass through the blood-brain barrier lead to side effects such as drowsiness, weakness, vertigo, fatigue, dryness in the mouth, constipation, and rarely - visual disturbances and increase of intraocular pressure. |
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 | 3.4507 mL | 17.2533 mL | 34.5066 mL | |
| 5 mM | 0.6901 mL | 3.4507 mL | 6.9013 mL | |
| 10 mM | 0.3451 mL | 1.7253 mL | 3.4507 mL |