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
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
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 |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/25504504Curator'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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/25504504
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095186 |
14.8 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Preventing | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/5319694
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/26121043
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
Edited
Fri Dec 15 15:26:54 UTC 2023
by
admin
on
Fri Dec 15 15:26:54 UTC 2023
|
Record UNII |
3K654P2M4J
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLIC ENZYME -> SUBSTRATE |
MAJOR
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
MAJOR
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |