bufotalin profile

bufotalin: from toads; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	12302120
CHEMBL ID	463064
CHEBI ID	80799
SCHEMBL ID	865713
MeSH ID	M0045715

Synonym
471-95-4
bufotalin
5beta-bufa-20,22-dienolide, 3beta,14,16beta-trihydroxy-, 16-acetate
5-beta-bufa-20,22-dienolide, 3-beta,14,16-beta-trihydroxy-, 16-acetate
3beta-14,16beta-trihydroxy-5beta-bufa-20,22-dienolide
bufa-20,22-dienolide, 16-(acetyloxy)-3,14-dihydroxy-, (3beta,5beta,16beta)-
nsc 89596
3beta,14,16beta-trihydroxy-5beta-bufa-20,22-dienolide 16-acetate
C16923
CHEMBL463064
chebi:80799 ,
egl9670i6p ,
unii-egl9670i6p
SCHEMBL865713
VOZHMAYHYHEWBW-NVOOAVKYSA-N
(3s,5r,8r,9s,10s,13r,14s,16s,17r)-3,14-dihydroxy-10,13-dimethyl-17-(2-oxo-2h-pyran-5-yl)hexadecahydro-1h-cyclopenta[a]phenanthren-16-yl acetate
3.beta.,14,16.beta.-trihydroxy-5.beta.-bufa-20,22-dienolide 16-acetate
bufotalin [mi]
CS-3695
closantelsodium
AC-34086
Q-100499
HY-N0878
AKOS030526151
NCGC00485932-01
DTXSID60894008
Q5760807
mfcd00210248
[(3s,5r,8r,9s,10s,13r,14s,16s,17r)-3,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
AS-77232

Excerpt	Reference	Relevance
" However, there is insufficient information on the biopharmaceutical properties of bufotalin based on pharmacokinetic studies."	( Plasma pharmacokinetics and tissue distribution of bufotalin in mice following single-bolus injection and constant-rate infusion of bufotalin solution. Hou, HM; Yu, CL, 2011)	0.37

Excerpt	Reference	Relevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51

Class	Description
steroid lactone
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (23)

Assay ID	Title	Year	Journal	Article
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347160	Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159	Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID357628	Cytotoxicity against human KB cells after 72 hrs by MTT assay	2001	Journal of natural products, Sep, Volume: 64, Issue:9	Isolation and structure of five new cancer cell growth inhibitory bufadienolides from the Chinese traditional drug Ch'an Su.
AID773793	Cytotoxicity against KM mouse splenic lymphocytes assessed as cell viability at 5 uM	2013	Journal of natural products, Oct-25, Volume: 76, Issue:10	C23 steroids from the venom of Bufo bufo gargarizans.
AID333789	Growth inhibition of IL6-dependent mouse MH60 cells after 72 hrs by MTT assay in presence of human recombinant IL6	2004	Journal of natural products, Dec, Volume: 67, Issue:12	Inhibitory effects of bufadienolides on interleukin-6 in MH-60 cells.
AID155910	Inhibitory activity against the primary liver carcinoma (PLC) cell line PLC/PRF/5	2002	Journal of medicinal chemistry, Dec-05, Volume: 45, Issue:25	QSAR evaluation of the Ch'an Su and related bufadienolides against the colchicine-resistant primary liver carcinoma cell line PLC/PRF/5(1).
AID750878	Cytotoxicity against human PC3 cells after 3 days by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells.
AID155909	Inhibitory activity against colchicine resistant parent primary liver carcinoma (PLC) cell line PLC/PRF/5	2002	Journal of medicinal chemistry, Dec-05, Volume: 45, Issue:25	QSAR evaluation of the Ch'an Su and related bufadienolides against the colchicine-resistant primary liver carcinoma cell line PLC/PRF/5(1).
AID357629	Cytotoxicity against human HL60 cells after 72 hrs by MTT assay	2001	Journal of natural products, Sep, Volume: 64, Issue:9	Isolation and structure of five new cancer cell growth inhibitory bufadienolides from the Chinese traditional drug Ch'an Su.
AID773795	Cytotoxicity against human A549 cells after 24 hrs by MTT assay	2013	Journal of natural products, Oct-25, Volume: 76, Issue:10	C23 steroids from the venom of Bufo bufo gargarizans.
AID333788	Growth inhibition of IL-6-independent mouse MH60 cells after 72 hrs by MTT assay	2004	Journal of natural products, Dec, Volume: 67, Issue:12	Inhibitory effects of bufadienolides on interleukin-6 in MH-60 cells.
AID357630	Cytotoxicity against mouse MH60 cells after 72 hrs by MTT assay	2001	Journal of natural products, Sep, Volume: 64, Issue:9	Isolation and structure of five new cancer cell growth inhibitory bufadienolides from the Chinese traditional drug Ch'an Su.
AID750876	Cytotoxicity against human U373 cells after 3 days by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells.
AID750873	Cytotoxicity against mouse B16F10 cells after 3 days by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells.
AID750880	Cytotoxicity against human Hs683 cells after 3 days by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells.
AID750879	Cytotoxicity against human MCF7 cells after 3 days by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells.
AID750877	Cytotoxicity against human A549 cells after 3 days by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells.
AID750874	Cytotoxicity against mouse CT26.WT cells after 3 days by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells.
AID773796	Cytotoxicity against human HepG2 cells after 24 hrs by MTT assay	2013	Journal of natural products, Oct-25, Volume: 76, Issue:10	C23 steroids from the venom of Bufo bufo gargarizans.
AID750875	Cytotoxicity against human SK-MEL-28 cells after 3 days by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (3.85)	18.7374
1990's	1 (3.85)	18.2507
2000's	5 (19.23)	29.6817
2010's	11 (42.31)	24.3611
2020's	8 (30.77)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (3.70%)	6.00%
Case Studies	2 (7.41%)	4.05%
Observational	0 (0.00%)	0.25%
Other	24 (88.89%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
histamine [no description available]	2.6	1	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
periplogenin periplogenin: structure	2.01	1
hellebrigenin hellebrigenin: structure	2.44	2
cinobufotalin cinobufotalin: RN given refers to (3beta,5beta,15beta,16beta)-isomer; RN for cpd without isomeric designation not avail 4/90	2.73	3
Gamabufogenin gamabufotalin: antiangiogenic, main active compound isolated from Chinese medicine Chansu; structure in first source	2.41	2	steroid lactone
telocinobufagin telocinobufagin: structure	2.96	4	steroid lactone
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	2.49	2	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	2.1	1	one-carbon compound; thioureas; ureas	antioxidant; chromophore
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	2.42	2	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	7.6	1
digitoxigenin Digitoxigenin: 3 beta,14-Dihydroxy-5 beta-card-20(22)enolide. A cardenolide which is the aglycon of digitoxin. Synonyms: Cerberigenin; Echujetin; Evonogenin; Thevetigenin.. digitoxigenin : A 5beta-cardenolide that is 5beta-cardanolide with hydroxy substituents at the 3beta- and 14beta-positions and double bond unsaturation at C(20)-C(22).	2.01	1	14beta-hydroxy steroid; 3beta-hydroxy steroid
salubrinal salubrinal: prevents dephosphorylation of eIF2alpha; structure in first source. salubrinal : A member of the class of quinolines that is a mixed aminal resulting from the formal condensation oftrichloroacetaldehyde with the amide nitrogen of trans-cinnamamide and the primary amino group of 1-quinolin-8-ylthiourea. It is a selective inhibitor of cellular complexes that dephosphorylate eukaryotic translation initiation factor 2 subunit alpha (eIF2alpha).	2.1	1	aminal; organochlorine compound; quinolines; secondary carboxamide; thioureas
bufogenin bufogenin: respiratory stimulant; from toad; structure. bufogenin : A steroid lactone of Chan su (toad venom), a Chinese medicine obtained from the skin venom gland of toads. A specific Na/K-ATPase protein inhibitor, it is used as a cardiotonic and central nervous system (CNS) respiratory agent, an analgesic and anesthetic, and as a remedy for ulcers.	2.94	4	epoxy steroid; steroid lactone	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
bufalin bufalin: cardiotonic; powerful anesthetic & one of the active constituents of the Chinese drug ch'an su(senso); in Japan prepared from skin of Bufo bufo garfarizans; RN given refers to (3beta,5beta)-isomer. bufalin : A 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo.	3.14	5	14beta-hydroxy steroid; 3beta-hydroxy steroid	animal metabolite; anti-inflammatory agent; antineoplastic agent; cardiotonic drug
hellebrin hellebrin: from Helleborus purpurascens (Ranunculaceae)	2.08	1	alpha-L-rhamnoside; disaccharide derivative
desacetylcinobufagin desacetylcinobufagin: structure in first source	2.41	2
cinobufagin cinobufagin: isolated from Chinese medicinal preparation ch'an su; derived from toad venom	3.31	6	steroid lactone
bufadienolide bufadienolide: isolated from liushen pills; RN given for (14beta)-isomer. bufadienolide : The simplest member of the class of bufadienolides that is bufanolide with unsaturation at positions 20 and 22.	2.31	1	bufadienolides

Condition	Relationship Strength	Studies
Granulocytic Leukemia [description not available]	2	1
Cancer of Nasopharynx [description not available]	2	1
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	2	1
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	2	1
Cancer of Liver [description not available]	2.73	3
Liver Neoplasms Tumors or cancer of the LIVER.	2.73	3
Congenital Zika Syndrome [description not available]	2.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.67	6
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.25	1
Carcinoma, Non-Small Cell Lung [description not available]	2.58	2
Cancer of Lung [description not available]	2.58	2
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.58	2
Lung Neoplasms Tumors or cancer of the LUNG.	2.58	2
Allergic Rhinitis [description not available]	3.52	4
Sneezing The sudden, forceful, involuntary expulsion of air from the NOSE and MOUTH caused by irritation to the MUCOUS MEMBRANES of the upper RESPIRATORY TRACT.	3.52	4
Rhinitis, Allergic An inflammation of the NASAL MUCOSA triggered by ALLERGENS.	3.52	4
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.6	1
Local Neoplasm Recurrence [description not available]	2.6	1
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	2.6	1
Sicca Syndrome [description not available]	2.25	1
Sjogren's Syndrome Chronic inflammatory and autoimmune disease in which the salivary and lacrimal glands undergo progressive destruction by lymphocytes and plasma cells resulting in decreased production of saliva and tears. The primary form, often called sicca syndrome, involves both KERATOCONJUNCTIVITIS SICCA and XEROSTOMIA. The secondary form includes, in addition, the presence of a connective tissue disease, usually rheumatoid arthritis.	7.25	1
Dysplastic Nevus Syndrome, Hereditary [description not available]	2.21	1
Malignant Melanoma [description not available]	7.21	1
Cancer of Skin [description not available]	2.21	1
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	7.21	1
Skin Neoplasms Tumors or cancer of the SKIN.	2.21	1
Giant Osteoid Osteoma [description not available]	2.1	1
Bone Cancer [description not available]	2.1	1
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.1	1
Hepatocellular Carcinoma [description not available]	2.46	2
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.46	2
Benign Neoplasms [description not available]	2.99	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.99	1
Arrhythmia [description not available]	1.98	1
Drop Attack [description not available]	1.98	1
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	1.98	1
Syncope A transient loss of consciousness and postural tone caused by diminished blood flow to the brain (i.e., BRAIN ISCHEMIA). Presyncope refers to the sensation of lightheadedness and loss of strength that precedes a syncopal event or accompanies an incomplete syncope. (From Adams et al., Principles of Neurology, 6th ed, pp367-9)	1.98	1

bufotalin

Description

Cross-References

Synonyms (30)

Research Excerpts

Pharmacokinetics

Bioavailability

Drug Classes (1)

Bioassays (23)

Research

Studies (26)

Study Types

bufotalin

Description

Cross-References

Synonyms (30)

Research Excerpts

Pharmacokinetics

Bioavailability

Drug Classes (1)

Bioassays (23)

Research

Studies (26)

Study Types

Related Drugs (18)

Related Conditions (37)