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SML1269

Sigma-Aldrich

Cepharanthine

≥95% (HPLC)

Synonym(s):

(+)-Cepharanthine, 6′,12′-Dimethoxy-2,2′-dimethyl-6,7-(methylenebis(oxy))oxyacanthan, O-Methylcepharanoline, CEP, Cepharanthin, Cepharantin, NSC 623442, [14aS-(14aR*,26aS*)]-2,3,13,14,14a,15,26,26a-octahydro-22,30-dimethoxy-1,14-dimethyl- H-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

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About This Item

Empirical Formula (Hill Notation):
C37H38N2O6
CAS Number:
481-49-2
Molecular Weight:
606.71
MDL number:
MFCD00210482
UNSPSC Code:
12352200
PubChem Substance ID:
329825757
NACRES:
NA.77

biological source

(isolated from the tuber of Stephania Cepharantha Hayata (plant).)

assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

CN1CCC2=CC3=C(OCO3)C(O4)=C2[C@@H]1CC5=CC=C(OC6=C(OC)C=CC(C[C@@H]7C8=CC4=C(OC)C=C8CCN7C)=C6)C=C5

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

InChI key

YVPXVXANRNDGTA-WDYNHAJCSA-N

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Biochem/physiol Actions

Cepharanthine is an anti-inflammatory, antiallergic, immunomo- modulatory and antineoplastic alkaloid isolated from Stephania cepharantha Hayata. Cepharanthine is an inhibitor of efflux transporter ABCC10. Also, Cepharanthine binds to central portion of Hsp90 with Kd 15 nM. Recent studies suggest that Cepharanthine inhibits the entry of HIV-1 by reducing plasma membrane fluidity.
Cepharanthine is known to be the only biscoclaurine alkaloid containing a methylenedioxy group. It promotes leukocytosis, as a result, it might activate the reticular endothelial system, hematopoietic tissue and bone marrow hyperplasia. It is known to inhibit Ehrlich tumor proliferation. Cepharanthine can increase the sensitivity and efficacy of antitumor drugs.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rishil J Kathawala et al.
Chinese journal of cancer, 33(5), 223-230 (2013-10-10)
ABCC10, also known as multidrug-resistant protein 7 (MRP7), is the tenth member of the C subfamily of the ATP-binding cassette (ABC) superfamily. ABCC10 mediates multidrug resistance (MDR) in cancer cells by preventing the intracellular accumulation of certain antitumor drugs. The
Kouki Matsuda et al.
Bioorganic & medicinal chemistry letters, 24(9), 2115-2117 (2014-04-08)
The anti-HIV-1 activity of cepharanthine (CEP), a natural product derived from Stephania cepharantha Hayata, was evaluated. CEP stabilized plasma membrane fluidity and inhibited HIV-1 envelope-dependent cell-to-cell fusion of HIV-1-infected cells as well as cell-free infection. It is suggested that CEP
The Alkaloids, 223-223 (2014)
Natural Small Molecule Drugs from Plants, 499-499 (2018)
Jun Haginaka et al.
Analytical biochemistry, 434(1), 202-206 (2012-12-12)
Heat shock protein 90α (Hsp90α) immobilized on aminopropyl silica gels was prepared via the N- or C-terminal, which was termed Hsp90α-NT or Hsp90α-CT, respectively. Binding interactions of biscoclaurine alkaloids (cepharanthine (CEP), berbamine (BBM), isotetrandrine (ITD), and cycleanine (CCN)) with Hsp90α

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