BUFALIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H34O4
Molecular Weight	386.5244
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC[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=QEEBRPGZBVVINN-BMPKRDENSA-N

InChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C24H34O4
Molecular Weight	386.5244
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23317181 | https://www.ncbi.nlm.nih.gov/pubmed/22502710 | https://www.ncbi.nlm.nih.gov/pubmed/24390736 | https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=637352 | https://www.ncbi.nlm.nih.gov/pubmed/19701908

Bufalin is a traditional oriental medicines, originally isolated from the Chinese toad venom. Bufalin is a cardiotonic steroid that has the potential to induce differentiation and apoptosis of tumor cells. Research on bufalin has so far mainly involved leukemia, prostate cancer, gastric cancer and liver cancer, and has been confined to in vitro studies. The bufadienolides bufalin and cinobufagin have been shown to induce apoptosis in a wide spectrum of cancer cell. Bufalin has being shown to be a potent small-molecule inhibitor of the steroid receptor coactivators SRC-3 and SRC-1. Bufalin is a component of Huachansu, a Chinese medicine that comes from dried toad venom from the skin glands of Bufo bufo gargarizans Cantor or B.melanotictus Schneider, has been used in the treatment of various cancers in China.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Apoptosis 156 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23317181 \| https://www.ncbi.nlm.nih.gov/pubmed/22502710	Activator 1447
HERG 99 Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28755515	Blocker 555	24.83 µM [IC50]
Nuclear receptor coactivator 3 1 Target ID: CHEMBL1615382 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24390736	Inhibitor 8504
Nuclear receptor coactivator 1 1 Target ID: CHEMBL1615387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24390736	Inhibitor 8504
Sodium/potassium-transporting ATPase 34 Target ID: CHEMBL2095186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26615828	Inhibitor 8504	28.7 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://clinicaltrials.gov/ct2/show/NCT00837239 https://www.ncbi.nlm.nih.gov/pubmed/19701908 https://www.ncbi.nlm.nih.gov/pubmed/23317181	Primary		Phase II 1147	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
Ambeed	A206803	http://www.ambeed.com/search/Search.html?keyword=A206803
Biopurify Phytochemicals	BP0288	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0288&searchhtmp=simplesearch&t=1
Cayman Chemical	15725	http://www.caymanchem.com/app/template/Product.vm/catalog/15725
Chem Scene	CS-3694	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3694
eMolecules	58033479	https://orderbb.emolecules.com/search/#?query=58033479
eMolecules	95707355	https://orderbb.emolecules.com/search/#?query=95707355
mcule	MCULE-9135055662	https://mcule.com/MCULE-9135055662/
MedChem Express	HY-N0877	https://www.medchemexpress.com/search.html?q=HY-N0877&ft=&fa=&fp=
MolPort	MolPort-003-940-374	https://www.molport.com/shop/molecule-link/MolPort-003-940-374
Ryan Scientific	Chitosan	https://ryansci.com/products?q=Chitosan&list_q=&search_type=exact
Specs	AM-721/20741010	http://www.specs.net/enter.php?specsid=AM-721/20741010
TargetMol	-	https://www.targetmol.com/search?keyword=-
TargetMol	465-21-4	https://www.targetmol.com/search?keyword=465-21-4
TargetMol	T1719	https://www.targetmol.com/search?keyword=T1719
Toronto Research Chemicals	B689510	https://www.trc-canada.com/product-detail/?CatNum=B689510
Toronto Research Chemicals	P835245	https://www.trc-canada.com/product-detail/?CatNum=P835245

PubMed

Title	Date	PubMed
Bufalin inhibits migration and invasion in human hepatocellular carcinoma SK-Hep1 cells through the inhibitions of NF-kB and matrix metalloproteinase-2/-9-signaling pathways.	2015-01	23949904
A bufadienolide derived androgen receptor antagonist with inhibitory activities against prostate cancer cells.	2014-01-25	24211617
Bufalin-inhibited migration and invasion in human osteosarcoma U-2 OS cells is carried out by suppression of the matrix metalloproteinase-2, ERK, and JNK signaling pathways.	2014-01	21922632
Interaction of digitalis-like compounds with p-glycoprotein.	2013-02	23104431
Induction of cytochrome P450 3A by Shexiang Baoxin Pill and its main components.	2012-01-25	22178124
Critical role of heat shock protein 27 in bufalin-induced apoptosis in human osteosarcomas: a proteomic-based research.	2012	23091618
Selective inhibition of the cellular sodium pump by emicymarin and 14ß anhydroxy bufadienolides.	2010-12-12	20688094
Effects of bufalin on the proliferation of human lung cancer cells and its molecular mechanisms of action.	2010-12	20963488
Analysis of the bioactive constituents of ChanSu in rat plasma by high performance liquid chromatography with mass spectrometric detection.	2010-11-02	20570458
Retraction of "Effect of bufalin on proliferation and apoptosis of human non-small cell lung cancer A549 Cell. Zhongguo Fei Ai Za Zhi, 2010, 13(9): 841-845".	2010-11	21081045
[Bufalin induces apoptosis in osteosarcoma U-2OS and U-2OS methotrexate 300-resistant cell lines in vitro].	2010-10	21163061
Delisheng, a Chinese medicinal compound, exerts anti-proliferative and pro-apoptotic effects on HepG2 cells through extrinsic and intrinsic pathways.	2010-10	20012371
Wheat germ agglutinin-grafted lipid nanoparticles: preparation and in vitro evaluation of the association with Caco-2 monolayers.	2010-09-15	20599600
Cytotoxic profile of natural and some modified bufadienolides from toad Rhinella schneideri parotoid gland secretion.	2010-09-01	20381513
[Effect of Bufalin on proliferation and apoptosis of human non-small cell lung cancer A549 cell].	2010-09	20840810
Inhibition of P-glycoprotein at the blood-brain barrier by phytochemicals derived from traditional Chinese medicine.	2010-07-27	20656985
Circumvention of multi-drug resistance of cancer cells by Chinese herbal medicines.	2010-07-25	20653978
Preparative separation of four major bufadienolides from the Chinese traditional medicine, Chansu, using high-speed counter-current chromatography.	2010-07	20734934
Steroid-like compounds in Chinese medicines promote blood circulation via inhibition of Na+/K+ -ATPase.	2010-06	20523340
Pheromone-induced life-history shifts A novel approach to controlling invasive toads.	2010-05	20714402
Ouabain attenuates cardiotoxicity induced by other cardiac steroids.	2010-05	20423344
Preparative separation and purification of bufadienolides from Chinese traditional medicine of ChanSu using high-speed counter-current chromatography.	2010-05	20201046
Titanate-silica mesostructured nanocables: synthesis, structural analysis and biomedical applications.	2010-02-10	20061597
Na, K-ATPase: Ubiquitous Multifunctional Transmembrane Protein and its Relevance to Various Pathophysiological Conditions.	2010-02	22457695
An improved formulation screening and optimization method applied to the development of a self-microemulsifying drug delivery system.	2010-01	20045959
Human tumor cell sensitivity to oleandrin is dependent on relative expression of Na+, K+ -ATPase subunitst.	2010	21222360
Anti-hepatitis B virus activities of cinobufacini and its active components bufalin and cinobufagin in HepG2.2.15 cells.	2010	20930383
Cardiac glycosides induce cell death in human cells by inhibiting general protein synthesis.	2009-12-16	20016840
Pilot study of huachansu in patients with hepatocellular carcinoma, nonsmall-cell lung cancer, or pancreatic cancer.	2009-11-15	19701908
[Determination of plasma protein binding rate of bufalin].	2009-11	20209923
Preparation and evaluation of lyophilized liposome-encapsulated bufadienolides.	2009-09	19365782
Traditional Chinese Medicines in the treatment of hepatocellular cancers: a systematic review and meta-analysis.	2009-08-12	19674474
Sudden death associated with intravenous injection of toad extract.	2009-07-01	19303230
Bufalin inhibits CYP3A4 activity in vitro and in vivo.	2009-05	19417737
Increased nuclear expression and transactivation of vitamin D receptor by the cardiotonic steroid bufalin in human myeloid leukemia cells.	2009-04	19429444
FLIM and emission spectral analysis of caspase-3 activation inside single living cell during anticancer drug-induced cell death.	2009-04	19132366
Microarray and biochemical analysis of bufalin-induced apoptosis of HL-60 Cells.	2009-04	19039527
Simultaneous quantification of seven major bufadienolides in three traditional Chinese medicinal preparations of chansu by HPLC-DAD.	2009-02	19370919
[Effects of Bufalin on SYK and CBL family proteins in induction of HL-60 cell apoptosis].	2009-02	19236749
PI3K/Akt is involved in bufalin-induced apoptosis in gastric cancer cells.	2009-01	19343001
[The influence of bortezomib on HL-60 cell function induced by all-trans retinoic acid plus bufalin and its mechanism].	2008-12	19176038
Apoptotic signaling in bufalin- and cinobufagin-treated androgen-dependent and -independent human prostate cancer cells.	2008-12	19037992
Agents from amphibians with anticancer properties.	2008-11	18827558
Characterization of in vivo metabolites of toad venom using liquid chromatography-mass spectrometry.	2008-07	18647476
[Determination of apparent aqueous solubility and apparent oil-water partition coefficients of three bufadienolides composition].	2008-06	18831199
Gene expression in Pre-MBT embryos and activation of maternally-inherited program of apoptosis to be executed at around MBT as a fail-safe mechanism in Xenopus early embryogenesis.	2008-05-29	19787085
Bufalin induces growth inhibition, cell cycle arrest and apoptosis in human endometrial and ovarian cancer cells.	2008-05	18425357
Simultaneous determination of three bufadienolides in rat plasma after intravenous administration of bufadienolides extract by ultra performance liquid chromatography electrospray ionization tandem mass spectrometry.	2008-03-10	18291133
[Determination of three bufogenins in toad venom using reversed-phase high performance liquid chromatography].	2008-03	18581850
Effect of Chinese medicines Chan Su and Lu-Shen-Wan on serum digoxin measurement by Digoxin III, a new digoxin immunoassay.	2008-02	18223469

Patents

Sample Use Guides

In Vivo Use Guide

The typical dose of Huachansu used in China is 20-25 mL (approximatelty 15 mL/m2).

Route of Administration: Intravenous

In Vitro Use Guide

Under sub-lethal concentrations (from 25 up to 100 nM), bufalin significantly inhibits the invasion and migration nature of NCI-H460 cells that were measured by Matrigel Cell Migration Assay and Invasion System.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:04:38 GMT 2025` Edited by `admin` on `Mon Mar 31 22:04:38 GMT 2025`
Record UNII	U549S98QLW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUFALIN

Common Name

English

NSC-89595

Preferred Name

English

BUFALIN [MI]

Common Name

English

Bufalin [WHO-DD]

Common Name

English

BUFA-20,22-DIENOLIDE, 3,14-DIHYDROXY-, (3.BETA.,5.BETA.)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C471