PERUVOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H44O9
Molecular Weight	548.665
Optical Activity	UNSPECIFIED
Defined Stereocenters	13 / 13
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@H](CC[C@]34O)C5=CC(=O)OC5)[C@]1(CC[C@@H](C2)O[C@]6([H])O[C@@H](C)[C@H](O)[C@@H](OC)[C@@H]6O)C=O

InChI

InChIKey=PMTSPAGBAFCORP-HBUONDEYSA-N

InChI=1S/C30H44O9/c1-16-24(33)26(36-3)25(34)27(38-16)39-19-6-10-29(15-31)18(13-19)4-5-22-21(29)7-9-28(2)20(8-11-30(22,28)35)17-12-23(32)37-14-17/h12,15-16,18-22,24-27,33-35H,4-11,13-14H2,1-3H3/t16-,18+,19-,20+,21-,22+,24-,25-,26+,27-,28+,29+,30-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4919553
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27110755 https://www.ncbi.nlm.nih.gov/pubmed/22396588

Peruvoside, main component of neriperside, a tevetoside extracted from Thevitia neriifolia Juss, cardiac glycoside, is used for the treatment of heart failure. It is Na+, K(+)-ATPase inhibitor. Peruvoside also demonstrates anti-cancer activities. Peruvoside inhibited cell growth in androgen-resistant LNCaP-abl prostate at 50 nM, lower than the concentrations required by both Digoxin and Strophanthidin (500 nM), suggesting that it may be a more potent anti-cancer candidate that other CGs. Peruvoside induced apoptotic cell death in human primitive AML KG1a cells and chronic myelogenous leukemia (CML) cell K562.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
K562 4 Target ID: CHEMBL385 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27110755	Inhibitor 8297	75.0 µM [IC50]
Sodium:potassium-exchanging ATPase activity 1 Target ID: Sodium:potassium-exchanging ATPase activity Sources: https://www.ncbi.nlm.nih.gov/pubmed/27780131 \| https://www.ncbi.nlm.nih.gov/pubmed/27110755	Inhibitor 8297	0.18 µM [IC50]
NCI-H460 5 Target ID: CHEMBL396 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27662422	Inhibitor 8297	45.0 nM [IC50]
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22396588	Inhibitor 8297	10.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Myeloid leukemia 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27110755	Primary	Basic research	Unknown Approved Use Unknown
Cardiac disorders 1 Sources: http://www.catalog.md/drugs/encordin.html http://www.ndrugs.com/?s=encordin https://www.ncbi.nlm.nih.gov/pubmed/4919553	Primary	Approved 8429	Encordin Approved Use Cardiac disorders
Lung cancer 69 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27662422	Primary	Basic research	Unknown Approved Use Unknown
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22396588	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Myasthenia-like syndrome induced by cardiovascular agents. Report of a case.	1987 Apr	3036745
Inhibition of the sodium potassium adenosine triphosphatase pump sensitizes cancer cells to anoikis and prevents distant tumor formation.	2009 Apr 1	19293189
Interaction of digitalis-like compounds with p-glycoprotein.	2013 Feb	23104431

Patents

Sample Use Guides

In Vivo Use Guide

Congattve Heart Failure :The average effective dose was 2.4 mg. (1.8 to 3.2 mg.) followed by a maintenance dose of 0.6 mg (0.3 to 0.9 mg.).

Route of Administration: Intra-arterial

In Vitro Use Guide

Peruvoside inhibited cell growth in androgen-resistant LNCaP-abl prostate at 50 nM

Name

Type

Language

PERUVOSIDE

Common Name

English

ENCORDIN

Brand Name

English

PERUVOSIDE [MI]

Common Name

English

CANNOGENIN .ALPHA.-L-THEVETOSIDE

Common Name

English

CARD-20(22)-ENOLIDE, 3-((6-DEOXY-3-O-METHYL-.ALPHA.-L-GLUCOPYRANOSYL)OXY)-14-HYDROXY-19-OXO-, (3.BETA.,5.BETA.)-

Systematic Name

English

CANNOGENIN THEVETOSIDE

Common Name

English

Peruvoside [WHO-DD]

Common Name

English

PERUVOSID

Common Name

English

Classification Tree Code System Code

WHO-ATC

C01AX02