Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C24H34O5 |
| Molecular Weight | 402.5238 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12C[C@@H](O)[C@H]3[C@@H](CC[C@@H]4C[C@@H](O)CC[C@]34C)[C@@]1(O)CC[C@@H]2C5=COC(=O)C=C5
InChI
InChIKey=FMTLOAVOGWSPEF-KJRPADTMSA-N
InChI=1S/C24H34O5/c1-22-9-7-16(25)11-15(22)4-5-18-21(22)19(26)12-23(2)17(8-10-24(18,23)28)14-3-6-20(27)29-13-14/h3,6,13,15-19,21,25-26,28H,4-5,7-12H2,1-2H3/t15-,16+,17-,18-,19-,21-,22+,23-,24+/m1/s1
DescriptionSources: Venomous Animals and Their Venoms: Venomous Vertebrates. Wolfgang Bücherl, Eleanor E. Buckley Elsevier, 2013. pp. 712 ISBN 148326288X, 9781483262888Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2872318 | https://www.ncbi.nlm.nih.gov/pubmed/19370919 | https://www.ncbi.nlm.nih.gov/pubmed/25175164 | https://www.ncbi.nlm.nih.gov/pubmed/23621895 | https://www.ncbi.nlm.nih.gov/pubmed/26657289 | https://www.ncbi.nlm.nih.gov/pubmed/26894970 | https://www.ncbi.nlm.nih.gov/pubmed/27384878
Sources: Venomous Animals and Their Venoms: Venomous Vertebrates. Wolfgang Bücherl, Eleanor E. Buckley Elsevier, 2013. pp. 712 ISBN 148326288X, 9781483262888
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2872318 | https://www.ncbi.nlm.nih.gov/pubmed/19370919 | https://www.ncbi.nlm.nih.gov/pubmed/25175164 | https://www.ncbi.nlm.nih.gov/pubmed/23621895 | https://www.ncbi.nlm.nih.gov/pubmed/26657289 | https://www.ncbi.nlm.nih.gov/pubmed/26894970 | https://www.ncbi.nlm.nih.gov/pubmed/27384878
Gamabufotalin belongs to bufadienolides was first isolated from B. formosus Boulenger and described by Kotake in 1928. Gamabufotalin is a component of traditional Chinese medicinal preparations containing ChanSu, also known as toad venom, a dried product of the skin and parotid venom glands from the Asiatic toad (Bufo gargarizans).
Gamabufotalin inhibits sodium/potassium-transporting ATPase activity and exhibited positive inotropic action in the papillary muscle preparations. Gamabufotalin demonstrates significant anti-tumor activity in vitro on cancer cells and in vivo on mouse tumor xenografts. Gamabufotalin, a major derivative of bufadienolide, inhibits VEGF-induced angiogenesis.
Originator
Sources: Kotake M. (1928) Ann. Chem. 465, 11; Kotake M. (1928) Sci. Papers Inst. Phys. Chem. Res. (Tokyo) 9, 233
Curator's Comment: references retrieved from Venomous Animals and Their Venoms: Venomous Vertebrates. Wolfgang Bücherl, Eleanor E. Buckley Elsevier, 2013. pp. 712 ISBN 148326288X, 9781483262888
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095165 |
|||
Target ID: CHEMBL1991 |
|||
Target ID: P05023|||Q9UJ20 Gene ID: 476.0 Gene Symbol: ATP1A1 Target Organism: Homo sapiens (Human) |
243.0 nM [Kd] | ||
Target ID: P50993 Gene ID: 477.0 Gene Symbol: ATP1A2 Target Organism: Homo sapiens (Human) |
247.0 nM [Kd] | ||
Target ID: P13637 Gene ID: 478.0 Gene Symbol: ATP1A3 Target Organism: Homo sapiens (Human) |
236.0 nM [Kd] | ||
Target ID: CHEMBL279 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Quantitative proteomics reveals molecular mechanism of gamabufotalin and its potential inhibition on Hsp90 in lung cancer. | 2016-11-22 |
|
| Gamabufotalin triggers c-Myc degradation via induction of WWP2 in multiple myeloma cells. | 2016-03-29 |
|
| Gamabufotalin, a major derivative of bufadienolide, inhibits VEGF-induced angiogenesis by suppressing VEGFR-2 signaling pathway. | 2016-01-19 |
|
| Gamabufotalin, a bufadienolide compound from toad venom, suppresses COX-2 expression through targeting IKKβ/NF-κB signaling pathway in lung cancer cells. | 2014-08-31 |
|
| Hellebrin and its aglycone form hellebrigenin display similar in vitro growth inhibitory effects in cancer cells and binding profiles to the alpha subunits of the Na+/K+-ATPase. | 2013-04-26 |
|
| Activities of novel polyhydroxylated cardiotonic steroids purified from nuchal glands of the snake, Rhabdophis tigrinus. | 1986-05 |
Patents
Sample Use Guides
After administration of Gamabufotalin at 5 and 20 mg/kg/day in the mice with A549-xenografts for 17 days, both the tumor volume and the tumor weights in the treated mice decreased significantly when compared with those in the control group.
Route of Administration:
Intraperitoneal
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SUBSTANCE RECORD
