Cepharanthine

Names

[ CAS No. ]:
481-49-2

[ Name ]:
Cepharanthine

[Synonym ]:
O-Methylcepharanoline
(14S,27R)-22,33-Dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2.1.1.0.0.0]nonatriaconta-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-dod ecaene
6',12'-dimethoxy-2,2'-dimethyl-6,7-[methylenebis-(oxy)]oxyacanthan
CEPHARANTHINE (RG)
(+)-cepharanthine
[methylenebis(oxy)]
Cepharanthine
sepharanthine
Cepharantin
CEPHARANTHINUM
(14S,27R)-22,33-Dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2.1.1.0.0.0]nonatriaconta-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-dodecaene
6',12'-Dimethoxy-2,2'-dimethyl-6,7-[methylenebis(oxy)]oxyacanthan
6,7-methanediyldioxy-6',12'-dimethoxy-2,2'-dimethyl-oxyacanthane
Stephanotis
Cepharanthin

Biological Activity

[Description]:

Cepharanthine, an alkaloid derived from Stephania cepharantha Hayata, with possesses anti-inflammatory and antioxidative activities[1][2][3]. Cepharanthine attenuates muscle and kidney injuries induced by limb ischemia/reperfusion (I/R)[3]. Cepharanthine induces autophagy, apoptosis and cell cycle arrest in breast cancer cells[4]. Cepharanthine inhibits the HIV-1 entry process by reducing plasma membrane fluidity[5].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Inflammation/Immunology

[References]

[1]. Huang H, et al. Cepharanthine, an alkaloid from Stephania cepharantha Hayata, inhibits the inflammatory response in the RAW264.7 cell and mouse models. Inflammation. 2014 Feb;37(1):235-46.

[2]. Nagano M, et al. Cepharanthine, an anti-inflammatory drug, suppresses mitochondrial membrane permeability transition. Physiol Chem Phys Med NMR. 2003;35(2):131-43.

[3]. Kao MC, et al. Salutary Effects of Cepharanthine against Skeletal Muscle and Kidney Injuries following Limb Ischemia/Reperfusion. Evid Based Complement Alternat Med. 2015;2015:504061.

[4]. Gao S, et al. Cepharanthine Induces Autophagy, Apoptosis and Cell Cycle Arrest in Breast Cancer Cells. Cell Physiol Biochem. 2017;41(4):1633-1648.

[5]. Matsuda K, et al. Cepharanthine inhibited HIV-1 cell-cell transmission and cell-free infection via modification of cell membrane fluidity. Bioorg Med Chem Lett. 2014 May 1;24(9):2115-7.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Melting Point ]:
140 - 145ºC

[ Molecular Formula ]:
C₃₇H₃₈N₂O₆

[ Molecular Weight ]:
606.707

[ Exact Mass ]:
606.273010

[ PSA ]:
61.86000

[ LogP ]:
5.23

[ Index of Refraction ]:
1.608

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FK0527000

CHEMICAL NAME :: Cepharanthine

CAS REGISTRY NUMBER :: 481-49-2

BEILSTEIN REFERENCE NO. :: 0075231

LAST UPDATED :: 199807

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C37-H38-N2-O6

MOLECULAR WEIGHT :: 606.77

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - chronic pulmonary edema Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >155 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,648,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 57 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1900 mg/kg

TOXIC EFFECTS :: Skin and Appendages - hair

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 125 mg/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

REFERENCE :: CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 24,2413,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 43500 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - chronic pulmonary edema

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5400 mg/kg/30D-C

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes Liver - other changes Blood - changes in spleen

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3640 mg/kg/26W-C

TOXIC EFFECTS :: Liver - other changes Kidney, Ureter, Bladder - other changes Kidney, Ureter, Bladder - other changes

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1200 mg/kg/30D-C

TOXIC EFFECTS :: Cardiac - other changes Lungs, Thorax, or Respiration - other changes Endocrine - other changes

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 182 mg/kg

SEX/DURATION :: male 26 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 182 mg/kg

SEX/DURATION :: female 26 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1200 mg/kg

SEX/DURATION :: female 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,3855,1982

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
T+

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
FK0527000

Synthetic Route

Click to get detail synthetic route

Articles

Interaction of cepharanthine with immobilized heat shock protein 90α (Hsp90α) and screening of Hsp90α inhibitors.

Anal. Biochem. 434(1) , 202-6, (2013)

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 biscoclauri...

Cepharanthine inhibited HIV-1 cell-cell transmission and cell-free infection via modification of cell membrane fluidity.

Bioorg. Med. Chem. Lett. 24(9) , 2115-7, (2014)

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-depende...

Recent advances regarding the role of ABC subfamily C member 10 (ABCC10) in the efflux of antitumor drugs.

Chin. J. Cancer 33(5) , 223-30, (2014)

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 c...