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セファランチン

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)-

HCID 360849
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
481-49-2
標準SMILES
COc1ccc2cc1Oc1ccc(cc1)CC1c3c(cc4c(c3Oc3cc5c(cc3OC)CCN(C)C5C2)OCO4)CCN1C
InChIKey
YVPXVXANRNDGTA-UHFFFAOYSA-N
分子式
C37H38N2O6
平均分子量
606.7 g/mol
単同位体質量
606.27298694

概要

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)- has been reported in Stephania delavayi, Stephania cephalantha, and other organisms with data available.

名称と識別子

優先名称
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)-
IUPAC
22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene
現地名
セファランチン
英語名
Cepharanthine
分子式
C37H38N2O6
分子量
606.71

名称と別名

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)-C37H38N2O6NCGC00095194-0122,33-Dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaeneCepharanthine [M+H]+CHEMBL1473842HMS3370G06HMS5082L16s4238NCGC00095194-02NCGC00095194-03NCGC00095194-04
名称をさらに表示
セファランチン(+)-セファランチンO-メチルセファラノリン6',12'-ジメトキシ-2,2'-ジメチル-6,7-[メチレンビス(オキシ)]オキシアカンタンセファランチン® (原末)セファランチン, 95%タマサキツヅラフジ抽出アルカロイドセファランチン (JAN)(14S,27R)-22,33-ジメトキシ-13,28-ジメチル-2,5,7,20-テトラオキサ-13,28-ジアザオクタシクロ[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]ノナトリアコンタ-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-ドデカエン6′,12′-ジメトキシ-2,2′-ジメチル-6,7-[メチレンビス(オキシ)]オキシアカンタンCEPHARANTHINcepharantinCepharanthine, >=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)-dibenzenacyclooctaphaneNSC-623442StephanotisStephanolinCEPHARANTHINECEPHARANTHINUMSinoInterme? CPHE
Oxyacanthan,12'-dimethoxy-2,2'-dimethyl-6,7- [methylenebis(oxy)]-6',12'-Dimethoxy-2,2'-dimethyl-6,7-[methylenebis-(oxy)]oxyacanthan(14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2^{16,19.1^{3,10.1^{21,25.0^{4,8.0^{31,35.0^{14,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene

データベース識別子

CAS
481-49-2
PubChem CID
360849
ChEMBL
CHEMBL1473842
Nikkaji
J3.216.172C

物性

構造計算による物性

XLogP
6.5
極性表面積
61.9 Ų
水素結合供与体数
0
水素結合受容体数
8
回転可能結合数
2
重原子数
45
形式電荷
0
複雑度
994

物理化学的性質

融点
145 · 145-155°
比旋光度
20 · D20 +277° (c = 2 in chloroform)
沸点
654.03 °C · 654.03°C (rough estimate)
比重(密度)
1.1761 · 1.1761 (rough estimate)
屈折率
1.53 · 1.5300 (estimate)
貯蔵温度
2 · under inert gas (nitrogen or Argon) at 2-8°C
溶解性
DMSO (35 mg/mL) またはエタノール (20 mg/mL) に可溶
外見
個体
酸解離定数(Pka)
7.61 · 7.61±0.20(Predicted)
色
ペールイエロー
安定性
2 · 購入日から2年間安定です。この DMSO 溶液は、-20°C で 2 か月間保存できます。
主な用途
メタボロミクスビタミン、栄養補助食品、天然製品
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

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

安全データ

wgk
WGK 1
Hazard Classifications
Acute Tox. 4 Oral
ストレージクラス
11 - Combustible Solids

化学と産業

応用分野 · 4 件

解説セファランチンは,ツヅラフジ科のタマサキツヅラフジ Stephania cepharanthaなどの根に含まれているアルカロイド。去痰作用がある。結核に特効とされたこともある。ブリタニカ国際大百科事典 小項目事典 ブリタニカ

説明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.

来歴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.

使用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.

上流・下流製品情報

上流原料

Lonicerae Japonicae Caulis

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補足説明 · 1 件

定義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.

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