Arenobufagin

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H32O6
Molecular Weight	416.5073
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CC[C@]3([H])[C@]([H])([C@H](O)C(=O)[C@]4(C)[C@H](CC[C@]34O)C5=COC(=O)C=C5)[C@@]1(C)CC[C@H](O)C2

InChI

InChIKey=JGDCRWYOMWSTFC-AZGSIFHYSA-N

InChI=1S/C24H32O6/c1-22-9-7-15(25)11-14(22)4-5-17-19(22)20(27)21(28)23(2)16(8-10-24(17,23)29)13-3-6-18(26)30-12-13/h3,6,12,14-17,19-20,25,27,29H,4-5,7-11H2,1-2H3/t14-,15+,16-,17-,19-,20+,22+,23+,24+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C24H32O6
Molecular Weight	416.5073
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26485758 | https://www.ncbi.nlm.nih.gov/pubmed/23393227 | https://www.ncbi.nlm.nih.gov/pubmed/27428326

Arenobufagin, a representative natural bufadienolide compound, is the major active component extracted from toad venom. Arenobufagin is a part of Chinese medicine Chan'su. It possesses significant antineoplastic activity in vitro. Antineoplastic activity of arenobufagin was tested using cell lines from different cancers: breast cancer, hepatocellular carcinoma, prostatic cancer, etc. Arenobufagin acts by intercalating with DNA and disrupting the cell cycle. Also it was shown to inhibit PI3K/Akt/mTOR pathway (in hepatocellular carcinoma cells) and inhibit Na, K-ATPase.

Approval Year

Targets

Primary Target	Pharmacology	Potency
mTOR signaling pathway 7 Target ID: map04150 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23393227	Inhibitor 8297
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26485758	Binding Agent 1064	4.12 µM [Kd]
Sodium/potassium-transporting ATPase 39 Target ID: CHEMBL2095186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27428326	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Cervical cancer 40 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27428326	Primary	Basic research	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26662961	Primary	Basic research	Unknown Approved Use Unknown
Hepatocellular carcinoma 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23393227	Primary	Basic research	Unknown Approved Use Unknown
Osteosarcoma 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26300346	Primary	Basic research	Unknown Approved Use Unknown
Neuroblastoma 25 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21800539	Primary	Basic research	Unknown Approved Use Unknown
Nasopharyngeal carcinoma 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21800539	Primary	Basic research	Unknown Approved Use Unknown
Colon adenocarcinoma 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21800539	Primary	Basic research	Unknown Approved Use Unknown
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21800539	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Analysis on competitive interaction between arenobufagin and verapamil hydrochloride with serum albumin].	2011 Jul	21749828
Qualitative and Quantitative Analysis of the Major Constituents in Shexiang Tongxin Dropping Pill by HPLC-Q-TOF-MS/MS and UPLC-QqQ-MS/MS.	2015 Oct 14	26473821
Arenobufagin intercalates with DNA leading to G2 cell cycle arrest via ATM/ATR pathway.	2015 Oct 27	26485758
Proteasome Inhibition Contributed to the Cytotoxicity of Arenobufagin after Its Binding with Na, K-ATPase in Human Cervical Carcinoma HeLa Cells.	2016	27428326
Bufadienolides from parotoid gland secretions of Cuban toad Peltophryne fustiger (Bufonidae): Inhibition of human kidney Na(+)/K(+)-ATPase activity.	2016 Feb	26615828

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Human hepatocellular carcinoma cell lines (HepG2 and HepG2/ADM) were treated with arenobufagin (10(-6)-10(-9) M). The growth of both cell lines was inhibited in a dose- and time-dependent manner with IC50 values of 20.24 nM and 7.46 nM after 72 h treatment, respectively.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:59:32 GMT 2023` Edited by `admin` on `Sat Dec 16 17:59:32 GMT 2023`
Record UNII	27R42QLM25
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Arenobufagin

Common Name

English

(3β,5β,11α)-3,11,14-Trihydroxy-12-oxobufa-20,22-dienolide

Common Name

English

5-((3S,5R,10S,11S,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-one

Systematic Name

English

Bufa-20,22-dienolide, 3,11,14-trihydroxy-12-oxo-, (3β,5β,11α)-

Common Name

English

5β-Bufa-20,22-dienolide, 3β,11α,14-trihydroxy-12-oxo-

Common Name

English

Code System Code Type Description

FDA UNII

27R42QLM25