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)-
CEPHARANTHIN · cepharantin · Cepharanthine, >=98% · (15S,31R)-36,54-Dimethoxy-16,32-dimethyl-15,16,17,18,31,32,33,34-octahydro-2,6-dioxa-1(4,5)-[1,3]dioxolo[4,5-g]isoquinolina-3(7,1)-isoquinolina-5(1,3),7(1,4)-dibenzenacyclooctaphane · NSC-623442 · Stephanotis · Stephanolin · CEPHARANTHINE
![Molekülstruktur von 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)-](/img/chemical/360849.png)
Identifikatoren & physikalische Daten
| CAS No. | 481-49-2 |
|---|---|
| Summenformel | C37H38N2O6 |
| Durchschnittliche Molmasse | 606,7 g/mol |
| Monoisotopische Masse | 606,27298694 g/mol |
| SMILES | COc1ccc2cc1Oc1ccc(cc1)CC1c3c(cc4c(c3Oc3cc5c(cc3OC)CCN(C)C5C2)OCO4)CCN1C |
| InChIKey | YVPXVXANRNDGTA-UHFFFAOYSA-N |
| PubChem CID | 360849 |
| ChEMBL | CHEMBL1473842 |
Chemische & physikalische Eigenschaften
| XLogP | 6,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 61,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 45 |
| Formalladung | 0 |
| Komplexität | 994 |
| Schmelzpunkt | 145-155° |
| Siedepunkt | 654.03°C (rough estimate) |
| Dichte | 1.1761 (rough estimate) |
| Brechungsindex | 1.5300 (estimate) |
| Lagerbedingungen | under inert gas (nitrogen or Argon) at 2-8°C |
| Löslichkeit | Soluble in DMSO (35 mg/mL) or ethanol (20 mg/mL) |
| Aggregatzustand | solid |
| pKa (Säurekonstante) | 7.61±0.20(Predicted) |
| Farbe | Pale yellow |
| Stabilität | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months. |
| Hauptanwendungen | metabolomicsvitamins, nutraceuticals, and natural products |
| 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 |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | WGK 1 |
|---|---|
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Beschreibung
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.
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 the silicosis symptoms in rat . In 1993, it was issued as anti-pneumoconiosis drug by CFDA and is used for delaying the progress of pneumoconiosis in clinic.
Verwenden
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.