PROSCILLARIDIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H42O8
Molecular Weight	530.6497
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]6(O[C@H]1CC[C@@]2(C)C(CC[C@]3([H])[C@]2([H])CC[C@]4(C)[C@H](CC[C@]34O)C5=COC(=O)C=C5)=C1)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]6O

InChI

InChIKey=MYEJFUXQJGHEQK-ALRJYLEOSA-N

InChI=1S/C30H42O8/c1-16-24(32)25(33)26(34)27(37-16)38-19-8-11-28(2)18(14-19)5-6-22-21(28)9-12-29(3)20(10-13-30(22,29)35)17-4-7-23(31)36-15-17/h4,7,14-16,19-22,24-27,32-35H,5-6,8-13H2,1-3H3/t16-,19-,20+,21-,22+,24-,25+,26+,27-,28-,29+,30-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.google.si/patents/US20060135468
Curator's Comment: description was created based on several sources, including, http://www.ijppsjournal.com/Vol5Issue4/7570.pdf, http://www.ptfarm.pl/pub/File/Acta_Poloniae/2005/4/319.pdf

Proscillaridin is a substance that was used in Europe for the treatment of heart failure and atrial fibrillation. Proscillaridin belongs to glycosides and acts as a Na+/K+-ATPase inhibitor.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/potassium-transporting ATPase 39 Target ID: CHEMBL2095186 Sources: http://www.ptfarm.pl/pub/File/Acta_Poloniae/2005/4/319.pdf	Inhibitor 8297		0.17 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic cardiac insufficiency 1 Sources: http://www.ptfarm.pl/pub/File/Acta_Poloniae/2005/4/319.pdf	Primary		Approved 8429	TALUSIN Approved Use Unknown
Atrial fibrillation 131 Sources: http://www.ptfarm.pl/pub/File/Acta_Poloniae/2005/4/319.pdf	Primary		Approved 8429	TALUSIN Approved Use Unknown

PubMed

Title	Date	PubMed
Sanguinarine induces K+ outflow from yeast cells expressing mammalian sodium pumps.	2001 Feb	11218072
The T-cell suppressive effect of bufadienolides: structural requirements for their immunoregulatory activity.	2001 Jan	11367509
[An elderly case of idiopathic dilatation of the right atrium in which right-sided heart failure was exacerbated by drug-induced bradyarrhythmia].	2001 Jul	11523170
Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells.	2001 Jun	11395576
A novel endogenous digitalis, telocinobufagin, exhibits elevated plasma levels in patients with terminal renal failure.	2005 Jan	15607315
Inhibition of DNA topoisomerases I and II, and growth inhibition of breast cancer MCF-7 cells by ouabain, digoxin and proscillaridin A.	2006 Jul	16819197
Combinatorial computational approaches to identify tetracycline derivatives as flavivirus inhibitors.	2007 May 9	17502914
Apoptosis-mediated cytotoxicity of ouabain, digoxin and proscillaridin A in the estrogen independent MDA-MB-231 breast cancer cells.	2007 Oct	18038900
Antiproliferative activity of derivatives of ouabain, digoxin and proscillaridin A in human MCF-7 and MDA-MB-231 breast cancer cells.	2008 Jun	18520043
Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs.	2009 Nov	19894733
Identification of novel p53 pathway activating small-molecule compounds reveals unexpected similarities with known therapeutic agents.	2010 Sep 27	20885994

Patents

Sample Use Guides

In Vivo Use Guide

The typical dose for current indication (p.o.) is about 1.5 mg/day.

Route of Administration: Oral

In Vitro Use Guide

Aggregation of platelets, preincubated 20 min with 100 uM and 200 uM proscillaridin was studied in vitro. Proscillaridin induced, in adose and time dependent manner, aprocoagulant response in platelets. Maximal procoagulant response was observed at 100 uM.

Name

Type

Language

PROSCILLARIDIN

Official Name

English

PROSCILLARIDIN [MI]

Common Name

English

NSC-7521

Code

English

proscillaridin [INN]

Common Name

English

Proscillaridin [WHO-DD]

Common Name

English

PROSCILLARIDIN [MART.]

Common Name

English

PROSCILLARIDIN [USAN]

Common Name

English

TALUSIN

Brand Name

English

BUFA-4,20,22-TRIENOLIDE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-14-HYDROXY-, (3.BETA.)-

Common Name

English

A-32686

Code

English

PROSCILLARIDIN [JAN]

Common Name

English

Proscillaridin A

Common Name

English

((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-14-HYDROXYBUFA-4,20,22-TRIENOLIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78322