DESLANOSIDE

US Previously Marketed

First approved in 1956

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C47H74O19
Molecular Weight	943.0791
Optical Activity	UNSPECIFIED
Defined Stereocenters	26 / 26
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(C[C@H](O)[C@H](O[C@@]2([H])C[C@H](O)[C@H](O[C@@]3([H])C[C@H](O)[C@H](O[C@]4([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1)O[C@H]5CC[C@@]6(C)[C@]([H])(CC[C@]7([H])[C@]6([H])C[C@@H](O)[C@]8(C)[C@H](CC[C@]78O)C9=CC(=O)OC9)C5

InChI

InChIKey=OBATZBGFDSVCJD-LALPQLPRSA-N

InChI=1S/C47H74O19/c1-20-41(64-36-16-30(50)42(21(2)60-36)65-37-17-31(51)43(22(3)61-37)66-44-40(56)39(55)38(54)32(18-48)63-44)29(49)15-35(59-20)62-25-8-10-45(4)24(13-25)6-7-27-28(45)14-33(52)46(5)26(9-11-47(27,46)57)23-12-34(53)58-19-23/h12,20-22,24-33,35-44,48-52,54-57H,6-11,13-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27-,28+,29+,30+,31+,32-,33-,35+,36+,37+,38-,39+,40-,41-,42-,43-,44+,45+,46+,47+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C47H74O19
Molecular Weight	943.0791
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	26 / 26
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB01078
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68003892

Deslanoside is a cardiotonic glycoside from the leaves of Digitalis lanata. It is used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation. Deslanoside inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). It also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/potassium-transporting ATPase 39 Target ID: CHEMBL2095186 Sources: https://www.drugbank.ca/drugs/DB01078	Inhibitor 8297		41.3 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heart failure 103 Sources: https://www.drugbank.ca/drugs/DB01078	Primary		Approved 8429	CEDILANID-D Approved Use For the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure.
Cardiac arrhythmia 19 Sources: https://www.drugbank.ca/drugs/DB01078	Primary		Approved 8429	CEDILANID-D Approved Use For the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure.

T_1/2

Value	Dose	Co-administered	Analyte	Population
36 h REVIEW https://pubmed.ncbi.nlm.nih.gov/356122	1.6 mg unknown, intravenous dose: 1.6 mg route of administration: Intravenous experiment type: UNKNOWN co-administered:		DESLANOSIDE serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31468	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31468
ChemicalBook	CB6683081	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6683081
MolPort	MolPort-006-122-280	https://www.molport.com/shop/molecule-link/MolPort-006-122-280
ZINC	ZINC000253668332	http://zinc15.docking.org/substances/ZINC000253668332

PubMed

Title	Date	PubMed
Cortical control of neurally mediated arrhythmogenic properties of desacetyllanatoside C.	1981 Mar	7266787
Study on cardioactive effects of brazilein.	2006	16319518
Characteristics of deslanoside-induced modulation on jejunal contractility.	2012 Nov 7	23139604

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Intravenous

In Vitro Use Guide

Deslanoside produced significant stimulatory effects (45.3% ± 4.0% vs 87.0% ± 7.8%, P < 0.01) on the contractility of rat jejunal smooth muscle fragment (JSMF) in the low contractile states, and produced significant inhibitory effects (180.6% ± 17.8% vs 109.9% ± 10.8%, P < 0.01) on the contractility of rat JSMF in the high contractile states.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:06:42 GMT 2023` Edited by `admin` on `Fri Dec 15 15:06:42 GMT 2023`
Record UNII	YGY317RK75
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DESLANOSIDE

Official Name

English

CEDILANID-D

Brand Name

English

DESLANOSIDE [EP MONOGRAPH]

Common Name

English

DEACETYLANATOSIDE C

Common Name

English

DESLANOSIDE [VANDF]

Common Name

English

DESLANOSIDE [MI]

Common Name

English

CARD-20(22)-ENOLIDE, 3-((O-.BETA.-D-GLUCOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-12,14-DIHYDROXY-, (3.BETA.,5.BETA.,12.BETA.)-

Common Name

English

DESLANOSIDE [JAN]

Common Name

English

Deslanoside [WHO-DD]

Common Name

English

DESLANOSIDE [ORANGE BOOK]

Common Name

English

DESLANOSIDE [MART.]

Common Name

English

DESLANOSIDE [USP IMPURITY]

Common Name

English

deslanoside [INN]

Common Name

English

DESLANOSIDE [USP-RS]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QC01AA07