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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H32O4
Molecular Weight 384.5085
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUFOGENIN

SMILES

[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@H](C[C@H]5O[C@@]345)C6=COC(=O)C=C6)[C@@]1(C)CC[C@H](O)C2

InChI

InChIKey=ATLJNLYIJOCWJE-CWMZOUAVSA-N
InChI=1S/C24H32O4/c1-22-9-7-16(25)11-15(22)4-5-18-17(22)8-10-23(2)19(12-20-24(18,23)28-20)14-3-6-21(26)27-13-14/h3,6,13,15-20,25H,4-5,7-12H2,1-2H3/t15-,16+,17+,18-,19-,20-,22+,23-,24-/m1/s1

HIDE SMILES / InChI

Molecular Formula C24H32O4
Molecular Weight 384.5085
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/5319694 http://www.ncbi.nlm.nih.gov/pubmed/26121043 http://www.ncbi.nlm.nih.gov/pubmed/20167272 https://books.google.ru/books?id=aTTBPedwFfAC&pg=PT2382&lpg=PT2382&dq=bufogenin+Na%2B/K%2B-ATPase&source=bl&ots=I9PGA17mS_&sig=BWLJrCAMHyf-S_po3P0sQcmQ5Cs&hl=ru&sa=X&ved=0ahUKEwjKzPvAhqjPAhUGDywKHRTQD0UQ6AEIKjAC#v=onepage&q=bufogenin%20Na%2B%2FK%2B-ATPase&f=false

Bufogenin (Resibufogenin) possesses significant pharmacological and toxicological effects, including cardiotonic, anesthetic, antitumor, and cardiotoxic effects. The bufodienolides are a group of steroid compounds that are classified as cardiac glycosides. Resibufogenin (RB), one of the major active compounds of the traditional Chinese medicine Chansu, has displayed great potential as a chemotherapeutic agent in oncology. Resibufogenin has been shown to exhibit the anti-proliferative effect against cancer cells. Although the mechanism of action of bufogenin is still under investigation, this agent is a specific Na+/K+-ATPase inhibitor and has been shown to reduce blood pressure in a rat model of preeclampsia.

Approval Year

PubMed

PubMed

TitleDatePubMed
Some effects of resibufogenin: an aglycone of animal origin.
1969 Oct
Occurrence of bufogenin conjugates in the skin of Korean toad.
1987 Dec
Resibufogenin-induced delayed afterdepolarization in rabbit heart in situ.
1988 Jul
Resibufogenin corrects hypertension in a rat model of human preeclampsia.
2006 Feb
Effects of resibufogenin in experimental hypertension.
2008
Effects of resibufogenin on voltage-gated sodium channels in cultured rat hippocampal neurons.
2011 Aug 26
Effects of Resibufogenin and Cinobufagin on voltage-gated potassium channels in primary cultures of rat hippocampal neurons.
2011 Dec
Marinobufagenin predicts and resibufogenin prevents preeclampsia: a review of the evidence.
2012 Nov
Resibufogenin and cinobufagin activate central neurons through an ouabain-like action.
2014
Liver-targeting Resibufogenin-loaded poly(lactic-co-glycolic acid)-D-α-tocopheryl polyethylene glycol 1000 succinate nanoparticles for liver cancer therapy.
2016
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://www.jstage.jst.go.jp/article/tjem1920/86/2/86_2_93/_pdf
One hundred and sixteen surgical patients were subjected to the trial of Resibufogenin, including 56 men and 60 women. Resibufogenin was administered intravenously during the operations in a dose of 0.1 mg/kg, usually for 10-15 seconds.
Route of Administration: Intravenous
In Vitro Use Guide
Human colon cancer HT-29 cells were maintained in DMEM. The media were supplemented with 10% FBS, 4 mM L-glutamine, 50 U/ml penicillin, and 100 μg/ml streptomycin. These cells were incubated at 37°C in a humidified atmosphere of 5% CO2. After the incubation of the HT-29 cells for 1, 2, or 3 days with the indicated concentrations of resibufogenin, the number of viable cells and dead cells was measured by a flow cytometer. Resibufogenin at 2 μM or more for 2 and 3 days significantly (P < 0.01) inhibited the viable cell number.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:26:54 UTC 2023
Edited
by admin
on Fri Dec 15 15:26:54 UTC 2023
Record UNII
3K654P2M4J
Record Status Validated (UNII)
Record Version
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Name Type Language
BUFOGENIN
INN   JAN   WHO-DD  
INN  
Official Name English
bufogenin [INN]
Common Name English
BUFOGENIN [JAN]
Common Name English
Bufogenin [WHO-DD]
Common Name English
RESIBUFOGENIN [MI]
Common Name English
NSC-90783
Code English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID0046808
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
EVMPD
SUB05964MIG
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
INN
1960
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
DRUG CENTRAL
3523
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
MERCK INDEX
m9536
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL250172
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
CAS
465-39-4
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
NCI_THESAURUS
C77829
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
CHEBI
31319
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
NSC
90783
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
MESH
C005734
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
SMS_ID
100000088457
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
PUBCHEM
6917974
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
FDA UNII
3K654P2M4J
Created by admin on Fri Dec 15 15:26:54 UTC 2023 , Edited by admin on Fri Dec 15 15:26:54 UTC 2023
PRIMARY
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