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Resibufogenin

Names

[ CAS No. ]:
465-39-4

[ Name ]:
Resibufogenin

[Synonym ]:
(3b,5b,15b)-14,15-Epoxy-3-hydroxy-5-bufa-20,22-dienolide
Respigon
bufogenin
Resi (VAN)
20,22,5BETA-BUFADIENOLID-14BETA,15BETA-EPOXY-3BETA-OL
Resi
3β-Hydroxy-14,15β-epoxy-5β-bufa-20,22-dienolide
Bufa-20,22-dienolide, 14,15-epoxy-3-hydroxy-, (3β,5β,15β)-
(3β,5β,15β)-3-Hydroxy-14,15-epoxybufa-20,22-dienolide
14,15β-Epoxy-3β-hydroxy-5β-bufa-20,22-dienolide
RBG
Resibufogenin
bufogenina
resibufagenin
Recibufogenin

Biological Activity

[Description]:

Resibufogenin, a component of huachansu, has been shown to exhibit the anti-proliferative effect against cancer cells, and this may be attributed to the degradation of cyclin D1 caused by the activation of GSK-3β.IC50 Value:Target:In vitro: The effects of Resibufogenin on the outward delayed rectifier potassium current (IK) and outward transient potassium current (IA) in rat hippocampal neurons was investigated, and it inhibited both IK and IA, at 1 μM concentration RBG could alter some channel kinetics and gating properties of IK, such as steady-state activation and inactivation curves, open probability and time constants [1].In vivo: Resibufogenin prevented evidence of oxidative stress in "preeclamptic" rats [2].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Cancer
Natural Products >> Steroids

[References]

[1]. Hao S, et al. Effects of Resibufogenin and Cinobufagin on voltage-gated potassium channels in primary cultures of rat hippocampal neurons. Toxicol In Vitro. 2011 Dec;25(8):1644-53.

[2]. Uddin MN, et al. Resibufogenin administration prevents oxidative stress in a rat model of human preeclampsia. Hypertens Pregnancy. 2012;31(1):70-8.

[3]. Ichikawa M, et al. Resibufogenin Induces G1-Phase Arrest through the Proteasomal Degradation of Cyclin D1 in Human Malignant Tumor Cells. PLoS One. 2015 Jun 29;10(6):e0129851.

[4]. Hao S, et al. Effects of resibufogenin on voltage-gated sodium channels in cultured rat hippocampal neurons. Neurosci Lett. 2011 Aug 26;501(2):112-6.

[5]. Zheng J, et al. Novel microbial transformation of resibufogenin by Absidia coerules. Nat Prod Commun. 2011 Nov;6(11):1581-4.

[6]. Xin XL, et al. Novel microbial transformation of resibufogenin by Fusarium solani. J Asian Nat Prod Res. 2011 Sep;13(9):831-7.


[Related Small Molecules]

Captisol | Cyclosporin A | H2DCFDA | 0MPTP hydrochloride | GW4869 | Etomoxir | TD139 | Mitoquinone mesylate | GSK2795039 | JC-1 | BAPTA-AM | AP 20187 | Setanaxib (GKT137831) | D-Luciferin | Crotaline

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
554.9±50.0 °C at 760 mmHg

[ Melting Point ]:
155ºC

[ Molecular Formula ]:
C24H32O4

[ Molecular Weight ]:
384.509

[ Flash Point ]:
190.7±23.6 °C

[ Exact Mass ]:
384.230072

[ PSA ]:
62.97000

[ LogP ]:
2.89

[ Vapour Pressure ]:
0.0±3.4 mmHg at 25°C

[ Index of Refraction ]:
1.603

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
EI2975000
CHEMICAL NAME :
5-beta-Bufa-20,22-dienolide, 14,15-beta-epoxy-3-beta-hydroxy-
CAS REGISTRY NUMBER :
465-39-4
LAST UPDATED :
198806
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C24-H32-O4
MOLECULAR WEIGHT :
384.56
WISWESSER LINE NOTATION :
T E6 B6653 1A R AX RO QHTTTT&J GQ J1 N1 O- ET6OVJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2200 ug/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: 6,899,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
21 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 12,837,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
59800 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 24,1239,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
14 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 24,1239,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
104 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 24,1239,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4250 ug/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: 6,899,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Amphibian - frog
DOSE/DURATION :
7830 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 12,837,1987 *** REVIEWS *** TOXICOLOGY REVIEW 85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,193,1963

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300 + H310 + H330

[ Precautionary Statements ]:
P260-P280-P301 + P310 + P330-P302 + P352 + P310-P304 + P340 + P310-P403 + P233

[ Safety Phrases ]:
24/25

[ RIDADR ]:
UN 3172

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)


Related Compounds