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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

C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O)CC[C@]34C)[C@]15O[C@@H]5C[C@@H]2C6=COC(=O)C=C6

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.

CNS Activity

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 14.8 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Preventing
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
15.49%
EXPERIMENT
https://europepmc.org/article/med/23227551 | http://www.yxxb.com.cn:8081/aps/CN/abstract/abstract14301.shtml
BUFOGENIN plasma
Homo sapiens
PubMed

PubMed

TitleDatePubMed
Liver-targeting Resibufogenin-loaded poly(lactic-co-glycolic acid)-D-α-tocopheryl polyethylene glycol 1000 succinate nanoparticles for liver cancer therapy.
2016
Resibufogenin Induces G1-Phase Arrest through the Proteasomal Degradation of Cyclin D1 in Human Malignant Tumor Cells.
2015
Resibufogenin and cinobufagin activate central neurons through an ouabain-like action.
2014
Marinobufagenin predicts and resibufogenin prevents preeclampsia: a review of the evidence.
2012-11
Resibufogenin administration prevents oxidative stress in a rat model of human preeclampsia.
2012
Effects of Resibufogenin and Cinobufagin on voltage-gated potassium channels in primary cultures of rat hippocampal neurons.
2011-12
Effects of resibufogenin on voltage-gated sodium channels in cultured rat hippocampal neurons.
2011-08-26
Marinobufagenin, resibufogenin and preeclampsia.
2010-12
Resibufogenin prevents the manifestations of preeclampsia in an animal model of the syndrome.
2010-01
Effects of resibufogenin in experimental hypertension.
2008
Resibufogenin corrects hypertension in a rat model of human preeclampsia.
2006-02
Resibufogenin-induced delayed afterdepolarization in rabbit heart in situ.
1988-07
Occurrence of bufogenin conjugates in the skin of Korean toad.
1987-12
Some effects of resibufogenin: an aglycone of animal origin.
1969-10
Experimental and clinical studies of resibufogenin.
1965-07-25
Patents

Patents

JPH01180245A
1
JPH03122154A
1
JPH05228460A
1
JPS5826898A
2
JPS625972A
1
US7858604 B2
1

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 Mon Mar 31 17:58:05 GMT 2025
Edited
by admin
on Mon Mar 31 17:58:05 GMT 2025
Record UNII
3K654P2M4J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUFOGENIN
INN   JAN   WHO-DD  
INN  
Official Name English
NSC-90783
Preferred Name English
bufogenin [INN]
Common Name English
BUFOGENIN [JAN]
Common Name English
Bufogenin [WHO-DD]
Common Name English
RESIBUFOGENIN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID0046808
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
EVMPD
SUB05964MIG
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
INN
1960
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
DRUG CENTRAL
3523
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
MERCK INDEX
m9536
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL250172
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
CAS
465-39-4
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
NCI_THESAURUS
C77829
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
CHEBI
31319
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
NSC
90783
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
MESH
C005734
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
SMS_ID
100000088457
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
PUBCHEM
6917974
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
FDA UNII
3K654P2M4J
Created by admin on Mon Mar 31 17:58:05 GMT 2025 , Edited by admin on Mon Mar 31 17:58:05 GMT 2025
PRIMARY
Related Record Type Details
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
Structure of MARINOBUFAGENIN
METABOLITE -> PARENT
MAJOR
Related Record Type Details
Structure of BUFOGENIN
ACTIVE MOIETY
NIH
NCATS
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