METILDIGOXIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C42H66O14
Molecular Weight	794.965
Optical Activity	UNSPECIFIED
Defined Stereocenters	21 / 21
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](OC)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1)O[C@H]4CC[C@@]5(C)[C@]([H])(CC[C@]6([H])[C@]5([H])C[C@@H](O)[C@]7(C)[C@H](CC[C@]67O)C8=CC(=O)OC8)C4

InChI

InChIKey=IYJMSDVSVHDVGT-PEQKVOOWSA-N

InChI=1S/C42H66O14/c1-20-37(49-6)29(43)16-35(51-20)55-39-22(3)53-36(18-31(39)45)56-38-21(2)52-34(17-30(38)44)54-25-9-11-40(4)24(14-25)7-8-27-28(40)15-32(46)41(5)26(10-12-42(27,41)48)23-13-33(47)50-19-23/h13,20-22,24-32,34-39,43-46,48H,7-12,14-19H2,1-6H3/t20-,21-,22-,24-,25+,26-,27-,28+,29+,30+,31+,32-,34+,35+,36+,37-,38-,39-,40+,41+,42+/m1/s1

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/2693372

Beta-methyl digoxin (beta-methyl digoxin; Metildigoxin (INN, or medigoxin BAN, or methyldigoxin) is a methyl derivative (methyl group in position 4 of the digitoxose residue) of digoxin is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia (irregular heartbeat). The substance is closely related to digoxin; it differs from the latter only by an O-methyl group on the terminal monosaccharide.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Congestive heart failure 54 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6849743	Primary		Preclinical	Unknown Approved Use Unknown
Cardiac arrhythmia 19 Sources: http://www.ndrugs.com/?s=metildigoxin	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The effects of digoxin and beta-methyldigoxin on the heart rate of decompensated patients with atrial fibrillation.	1977 Feb	402273
[Serum digoxin in children treated with beta methyl digoxin].	1991 Nov-Dec	1845639
[Acute psychoses caused by digitalis poisoning].	1991 Nov-Dec	1669614
Meglumine antimoniate, amiodarone and torsades de pointes: a case report.	1999 Sep	10524732
[Disturbances of rhythm and atrio-ventricular conduction in digitalis overdose. Case reports].	2001	11450159
P-glycoprotein-mediated transport of digitoxin, alpha-methyldigoxin and beta-acetyldigoxin.	2001 Mar	11284449
Establishment of enzyme immunoassay for measuring beta-methyldigoxin levels in human serum by specific antiserum.	2002 Oct	12392073
Measurement of beta-methyldigoxin level in serum from patients by enzyme immunoassay using novel specific antiserum with a phenyl boric acid column.	2003 Aug	12883228
Pharmacokinetic study of beta-methyldigoxin by enzyme immunoassay using a novel specific antiserum in rats.	2003 Feb	12576688
[Application of HPLC/MS for evaluation of fatal poisoning with digoxin in the aspect of medico-legal evidence].	2003 Jan-Mar	14669547
Role of P-glycoprotein in pharmacokinetics and drug interactions of digoxin and beta-methyldigoxin in rats.	2003 Jul	12820149
Role of organic anion transporting polypeptide 2 in pharmacokinetics of digoxin and beta-methyldigoxin in rats.	2005 Jun	15858844
Selective inhibition of brain Na,K-ATPase by drugs.	2006	16083303
[Isolated non-compaction of the left ventricular myocardium in a neonate--a case report].	2006 Dec	17206542
Impact of ABCB1 (MDR1) gene polymorphism and P-glycoprotein inhibitors on digoxin serum concentration in congestive heart failure patients.	2007 Jan-Feb	17377214
Inhibition of methyldigoxin-induced arrhythmias by pentadecapeptide BPC 157: a relation with NO-system.	2009 Aug 7	19465062
Free and total digoxin in serum during treatment of acute digoxin poisoning with Fab fragments: case study.	2010 Jul	19875723

Patents

Sample Use Guides

In Vivo Use Guide

Methyldigoxin, 11.0 ug/kg was infused over a 5 min period into the right atrium using one of the two infusion routes available in the side walls of the double-lumen pulmonary artery catheter.

Route of Administration: Other

In Vitro Use Guide

After pretreatment of isolated porcine coronary arteries with therapeutic (2.5 X 10(-9) M) was well as with toxic (10(-6) M) doses of beta-methyldigoxin the serotonin-induced contractions were significantly amplified. Since serotonin released from destroyed thrombocytes may be one of the triggering factors eliciting coronary spasms, caution must be taken in the use of digitalis in coronary disease of spastic origin.

Name

Type

Language

METILDIGOXIN

Official Name

English

METILDIGOXIN [JAN]

Common Name

English

DIGOXIN, 4'''-O-METHYL-

Common Name

English

LANITOP

Common Name

English

METHYLDIGOXIN, BETA

Common Name

English

METILDIGOXIN [MART.]

Common Name

English

metildigoxin [INN]

Common Name

English

.BETA.-METHYLDIGOXIN [MI]

Common Name

English

4'''-O-METHYLDIGOXIN

Common Name

English

.BETA.-METHYLDIGOXIN

Common Name

English

CARD-20(22)-ENOLIDE, 3-((O-2,6-DIDEOXY-4-O-METHYL-.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.)-

Systematic Name

English

MEDIGOXIN

Common Name

English

Metildigoxin [WHO-DD]

Common Name

English

LANIRAPID

Common Name

English

4'''-.BETA.-METHYLDIGOXIN

Common Name

English

Classification Tree Code System Code

WHO-VATC

QC01AA08