Cepharanthine CAS 481-49-2
Introduction：Basic information about Cepharanthine CAS 481-49-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Cepharanthine Basic information
| Product Name: | Cepharanthine |
| Synonyms: | 1H-4,6:16,19-Dietheno-21,25-metheno-12H-[1,3]dioxolo[4,5-g]pyrido[2',3':17,18][1,10]dioxacycloeicosino[2,3,4-ij]isoquinoline, 2,3,13,14,14a,15,26,26a-octahydro-22,30-dimethoxy-1,14-dimethyl-, (14aS,26aR)-;Cepharanthine, >=98%;Cepharanthin, 98%, from Stephania japonica (Thunb.) Miers;Cepharanthine|||CEPHARANTHINE;CEPHARANTHIN;CEPHARANTHINE;OXYACANTHAN,6',12'-DIMETHOXY-2,2'-DIMETHYL-6,7-(METHYLLENEBIS (OXY))-;cepharantin |
| CAS: | 481-49-2 |
| MF: | C37H38N2O6 |
| MW: | 606.71 |
| EINECS: | 228-085-1 |
| Product Categories: | Inhibitors;Other APIs;standardized herbal extract;Alkaloids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM). |
| Mol File: | 481-49-2.mol |
Cepharanthine Chemical Properties
| Melting point | 145-155° |
| alpha | D20 +277° (c = 2 in chloroform) |
| Boiling point | 654.03°C (rough estimate) |
| density | 1.1761 (rough estimate) |
| refractive index | 1.5300 (estimate) |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| solubility | Soluble in DMSO (35 mg/mL) or ethanol (20 mg/mL) |
| form | solid |
| pka | 7.61±0.20(Predicted) |
| color | Pale yellow |
| Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months. |
| Major Application | metabolomics vitamins, nutraceuticals, and natural products |
| InChI | InChI=1S/C37H38N2O6/c1-38-13-11-24-18-31(41-4)33-20-27(24)28(38)16-23-7-10-30(40-3)32(17-23)44-26-8-5-22(6-9-26)15-29-35-25(12-14-39(29)2)19-34-36(37(35)45-33)43-21-42-34/h5-10,17-20,28-29H,11-16,21H2,1-4H3/t28-,29+/m1/s1 |
| InChIKey | YVPXVXANRNDGTA-WDYNHAJCSA-N |
| SMILES | C1CC2C=C3OCOC3=C3OC4C(OC)=CC5CCN(C)[C@]([H])(CC6=CC(=C(OC)C=C6)OC6C=CC(C[C@@]([H])(C=23)N1C)=CC=6)C=5C=4 |
Safety Information
| WGK Germany | WGK 1 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Description | Cepharanthine is diclofenac quinoline alkaloid isolated from rhizome of Stephania japonica, which was first recorded in “Bencao shiyi” and functions as clearing heat, promoting diuresis and detumescence in traditional Chinese medicine. Cepharanthine is a pure and natural extract of the Stephania cepharantha Hayata plant, a rare species that is native to Kotosho Island, southeast of Taiwan. In 1914, the renowned botanist, Bunzo Hayata reported the plant for the first time. Two decades later, Dr. Heisaburo Kondo purified its active ingredient and named it “Cepharanthine.” Stephania japonica was used to treat tuberculosis and other consumptive diseases which provided a clue for its development on lung disease. |
| Chemical Properties | Derived from the roots of Stephania japonica (Thunb.) Miers, family Anthemis. |
| Physical properties | Appearance: light yellow or yellow powder. Solubility: soluble in acidic aqueous solution and ether, acetone, and other organic solvents; insoluble in petroleum ether. Melting point: 148–150?°C. Specific optical rotation: +277°. |
| History | Promoting leukocytosis of cepharanthine in tuberculosis patients was first recorded in the proceeding Institute of Chemotherapy by the Japanese scholar Yamaguchi in 1946. In 1948, Chinese scholar Yuhuang Zhao also received this compound and published it in D.M.?Med. It is thought that cepharanthine may stimulate the reticuloendothelial system, then activate hematopoietic tissue, and promote myeloproliferation. Therefore, the number of white blood cells in the peripheral blood increased significantly. Due to its good safety, cepharanthine is currently widely used in cancer patients with granulocytopenia or leukopenia embolism after radiotherapy and chemotherapy and so on. In addition, Chinese scientists extracted five kinds of dibenzylisoquinoline alkaloids from Chinese herbal medicine in 1977, which could significantly improve thesilicosis symptoms in rat . In 1993, it was issued as anti-pneumoconiosis drug byCFDA and is used for delaying the progress of pneumoconiosis in clinic. |
| Uses | Cepharanthine is a biscoclaurine alkaloid that has antiinflammatory, antineoplastic, hepatoprotectant, radiopropective and other biological functions. It is used to treat many acute and chronic diseases, including pit viper bites, alopecia areata, and leucopenia in radiation therapy. |
| Definition | ChEBI: Cepharanthine is a bisbenzylisoquinoline alkaloid from tubers of Stephania; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation. It is a member of isoquinolines and a bisbenzylisoquinoline alkaloid. |
| benefits | When Cepharanthine is absorbed into the body, it acts through multiple biochemical and pharmacological mechanisms and generates a tremendous amount of beneficial effects on one's health. Regrow hair in a number of patients with different types of alopecia Inhibit various types of cancerous tumor growth Prevent cancer metastasis Stimulate white blood cell production Induce apoptosis (cell death) and autophagy in cancerous cells Restore the effectiveness of anticancer drugs for resistant tumors Boost the effectiveness of certain chemotherapies Inhibit the replication of HIV-1 virus Inhibit different types of Coronavirus Provide relief of allergies by inhibiting the release of histamine Possess anti-viral and anti-inflammatory effects Scavenge free radicals and prevent oxidation |
| Biological Activity | Cepharanthine, a biscoclaurine alkaloid isolated from a Chinese folklore plant Stephania cepharantha, inhibited HIV-1 replication by inhibiting kappa B, a potent inducer of HIV-1 gene expression and displayed potent activity against SARS coronavirus, HSV-1, and coxsackie B3 along with antitumor and immunomodulating activity. As cepharanthine had strong activity against both RNA and DNA viruses it may be a source of potential lead compounds for developing new antivirals. |
| Pharmacology | The pharmacological effects of cepharanthine are very broad, mainly for the promotion of leukocytosis, antitumor, anti-inflammation, improvement of the body immunity, and other aspects of efficacy. Improvement of leukocytosis is the most widelystudied among them, and the mechanism may be to stimulate the reticular endothelium system, activate hematopoietic tissue, and promote bone marrow hyperplasia . Cepharanthine is also a good antitumor drug sensitizer. It can significantlyimprove their efficacy and reduce their side effects when combined with other antitumor drugs, as manifested by increasing the concentration of FT-207 metabolite(5-Fu) in tumor tissue under cepharanthine and FT-207 combination therapy, whichwas significantly higher than that in blood , suggesting that cepharanthine has thepotential to improve the efficacy of antitumor drugs. |
| Clinical Use | The major clinical application of cepharanthine is to improve their immunity impaired by chemotherapy or radiotherapy in tumor patients. In addition, cepharanthine can increase the sensitivity to antitumor drugs, and itself also has a certain antitumor effect. Now, it is commonly used as adjuvant drug for anticancer treatment. |
| Side effects | Cepharanthine is an extraordinary medicine from Japan, where it has been widely used for the past seventy years to treat a variety of acute and chronic diseases, with little known side-effects. Common side effects are reported as below. loss of appetite, disc omfort in stomach, rash/eruption, itch , nausea, diarrhea, headache, dizziness, swelling in face/hands/feet, irregular menstruation, etc. |
| Synthesis | The production of cepharanthine currently relies mainly on natural extraction from the tuberous roots of plants in the genus Stephania (such as Stephania cepharantha Hayata). The process typically involves solvent extraction using ethanol or salt solutions, purification by adsorption with macroporous resins, and recrystallization to obtain a high-purity alkaloid product. Although Tomita et al. achieved its total synthesis as early as 1967, the complex bisbenzylisoquinoline macrocyclic structure of the molecule makes the chemical synthesis steps cumbersome and extremely costly, thus large-scale industrial synthesis and production have not yet been achieved. |
| References | [1] MOSHE ROGOSNITZKY Rachel D. Therapeutic potential of the biscoclaurine alkaloid, cepharanthine, for a range of clinical conditions[J]. Pharmacological Reports, 2011, 63 2: Pages 337-347. DOI:10.1016/s1734-1140(11)70500-x [2] HAILONG HUANG. Cepharanthine, an alkaloid from Stephania cepharantha Hayata, inhibits the inflammatory response in the RAW264.7 cell and mouse models.[J]. Inflammation, 2014, 37 1: 235-246. DOI:10.1007/s10753-013-9734-8 [3] YAO WANG. Cepharanthine hydrochloride induces mitophagy targeting GPR30 in hepatocellular carcinoma (HCC).[J]. Expert Opinion on Therapeutic Targets, 2020, 24 4: 389-402. DOI:10.1080/14728222.2020.1737013 [4] YANHAO ZHANG. Downregulation of MYO1C mediated by cepharanthine inhibits autophagosome-lysosome fusion through blockade of the F-actin network[J]. Journal of Experimental & Clinical Cancer Research, 2019, 75 1. DOI:10.1186/s13046-019-1449-8 [5] MOSHE ROGOSNITZKY Igor K Paul Okediji. Cepharanthine: a review of the antiviral potential of a Japanese-approved alopecia drug in COVID-19.[J]. Pharmacological reports : PR, 2020: 1509-1516. DOI:10.1007/s43440-020-00132-z |
Cepharanthine Preparation Products And Raw materials
| Raw materials | Lonicerae Japonicae Caulis |
