Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C37H38N2O6 |
Molecular Weight | 606.7074 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC3=CC(OC4=CC=C(C[C@]5([H])N(C)CCC6=C5C(OC7=CC1=C(CCN2C)C=C7OC)=C8OCOC8=C6)C=C4)=C(OC)C=C3
InChI
InChIKey=YVPXVXANRNDGTA-WDYNHAJCSA-N
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
Molecular Formula | C37H38N2O6 |
Molecular Weight | 606.7074 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21602589Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25145413
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21602589
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25145413
Cepharanthine (CEP) is a naturally occurring alkaloid extracted from the plant Stephania cepharantha Hayata. It has been widely used in Japan for more than 40 years to treat a wide variety of acute and chronic diseases. CEP inhibits tumor necrosis factor (TNF)-α-mediated NFκB stimulation, plasma membrane lipid peroxidation and platelet aggregation and suppresses cytokine production. It has also been shown to scavenge free radicals and to have a protective effect against some of the responses mediated by pro-inflammatory cytokines such as TNF-α, interleukin (IL)-1β and IL6. CEP has successfully been used to treat a diverse range of medical conditions, including radiation-induced leukopenia, idiopathic thrombocytopenic purpura, alopecia areata, alopecia pityrodes, venomous snakebites, xerostomia, sarcoidosis, refractory anemia and various cancer-related conditions. No safety issues have been observed with CEP, and side effects are very rarely reported. Recently was described a transcriptomic approach confirmed that cepharanthine might have a potential innovative antiplasmodial mechanism of action. Cepharanthine could interfere with several important functions for Plasmodium survival and virulence as the mitochondrion, apicoplast, cytoadherence antigenic variation and Maurer’s clefts. Thus, cepharanthine might play an ongoing role in the progress on anti-malarial drug discovery efforts. Also using intravenous and oral administration of CEP was shown its protective effect for acute or late toxicity to the bladder/urethra and rectum. It was discovered, that acute urinary toxicity was significantly milder for the intravenous group than for the oral and non-administration groups. The protective efficacy of CEP was not approved for acute rectal toxicity, but late rectal toxicity was significantly milder for the intravenous group than for the oral group. Intravenous Cepharanthin administration may prevent acute or late toxicity by radiotherapy for prostate cancer.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: mitochondrion, apicoplast of Plasmodium Sources: https://www.ncbi.nlm.nih.gov/pubmed/25145413 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15272586
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/?term=2559129
https://www.ncbi.nlm.nih.gov/pubmed/3428778
depends on treatment:
preventing leukopenia: cepharanthin was given at a dose of 1 mg/kg to the administration group (Ceph. group) and changes in the peripheral leukocyte count were examined in both the Ceph. and non-Ceph. groups.
The locally administered cepharanthine solution (0.1 mg/ml), by perfusing the nasal cavity, inhibited the dye leakage and an increase in lysosomal enzyme activity due to antigen stimulation.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=20412118
Cepharanthine (CEP) inhibited growth of Cholangiocarcinoma (CCA) cell lines of KKU-M213 and KKU-M214 at concentrations ranging between 2.5 and 20 ug ⁄mL (4.12–32.96 uM), which are clinically achievable suggesting the clinical efficacy of CEP for CCA.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:09:13 GMT 2023
by
admin
on
Fri Dec 15 16:09:13 GMT 2023
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Record UNII |
7592YJ0J6T
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C257
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FDA ORPHAN DRUG |
766520
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FDA ORPHAN DRUG |
794320
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SUB13288MIG
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C83611
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5375
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100000076320
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Cepharanthine
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623442
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3546
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10206
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C006947
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7592YJ0J6T
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m3254
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DTXSID6045957
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CHEMBL449782
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481-49-2
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TARGET -> INHIBITOR |
BINDING
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