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Cepharanthine

HCID 10206
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Basic information

CAS
481-49-2
Standard SMILES
COc1ccc2cc1Oc1ccc(cc1)C[C@H]1c3c(cc4c(c3Oc3cc5c(cc3OC)CCN(C)[C@@H]5C2)OCO4)CCN1C
InChIKey
YVPXVXANRNDGTA-WDYNHAJCSA-N
Molecular formula
C37H38N2O6
Average molar mass
606.7 g/mol
Monoisotopic mass
606.27298694

Overview

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 bisbenzylisoquinoline alkaloid and a member of isoquinolines.

Names & identifiers

Preferred name
Cepharanthine
IUPAC
(14S,27R)-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
English name
Cepharanthine
Molecular formula
C37H38N2O6
Molecular weight
606.71

Names & synonyms

CEPHARANTHINE481-49-2(+)-CepharanthineDTXSID6045957NSC-6234426',12'-Dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))oxyacanthanCHEBI:35467592YJ0J6T(14S,27R)-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-dodecaeneDTXCID4025957(14S,27R)-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-dodecaeneRefChem:124431
Show more names
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)-dibenzenacyclooctaphaneStephanotisStephanolinCEPHARANTHINUMSinoInterme? CPHE
683-114-9CepharanthinO-MethylcepharanolineCepharantinCepharanthine [JAN]MFCD00210482Ex Cepharantha tuberC37H38N2O6

Properties

Computed structural properties

XLogP
6.5
Topological polar surface area
61.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
8
Rotatable bonds
2
Heavy atoms
45
Formal charge
0
Complexity
994

Physicochemical properties

Melting point
145 · 145-155°
alpha
20 · D20 +277° (c = 2 in chloroform)
Boiling point
654.03 °C · 654.03°C (rough estimate)
Density
1.1761 · 1.1761 (rough estimate)
refractive index
1.53 · 1.5300 (estimate)
storage temp.
2 · 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 · 7.61±0.20(Predicted)
color
Pale yellow
Stability
2 years · 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
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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

wgk
WGK 1
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P264-P270-P301+P312-P330-P501

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 3 items

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.

Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military.

Applications · 3 items

DescriptionCepharanthine 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.

HistoryPromoting 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.

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Compound notes

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Database identifiers

CAS
481-49-2
PubChem CID
10206
DTXSID
DTXSID6045957
ChEMBL
CHEMBL2074948、CHEMBL449782
ChEBI
CHEBI:3546
UNII
7592YJ0J6T
EC Number
683-114-9
Nikkaji
J5.779G
EWG's Food Scores
1 · 1
FDA UNII
7592 YJ0J6T · 7592YJ0J6T
UNSPSC Code
12352205 · 12352205
NACRES
25 · NA.25
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P330-P501
WGK Germany
1 · WGK 1
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral

UsesCepharanthine 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.

Upstream & downstream products

Upstream raw materials

Lonicerae Japonicae Caulis
Additional notes · 1 item

DefinitionChEBI: 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.