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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 of METILDIGOXIN

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

Molecular Formula C42H66O14
Molecular Weight 794.965
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 21 / 21
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The effects of digoxin and beta-methyldigoxin on the heart rate of decompensated patients with atrial fibrillation.
1977 Feb
[Serum digoxin in children treated with beta methyl digoxin].
1991 Nov-Dec
[Acute psychoses caused by digitalis poisoning].
1991 Nov-Dec
Meglumine antimoniate, amiodarone and torsades de pointes: a case report.
1999 Sep
[Disturbances of rhythm and atrio-ventricular conduction in digitalis overdose. Case reports].
2001
P-glycoprotein-mediated transport of digitoxin, alpha-methyldigoxin and beta-acetyldigoxin.
2001 Mar
Establishment of enzyme immunoassay for measuring beta-methyldigoxin levels in human serum by specific antiserum.
2002 Oct
Measurement of beta-methyldigoxin level in serum from patients by enzyme immunoassay using novel specific antiserum with a phenyl boric acid column.
2003 Aug
Pharmacokinetic study of beta-methyldigoxin by enzyme immunoassay using a novel specific antiserum in rats.
2003 Feb
[Application of HPLC/MS for evaluation of fatal poisoning with digoxin in the aspect of medico-legal evidence].
2003 Jan-Mar
Role of P-glycoprotein in pharmacokinetics and drug interactions of digoxin and beta-methyldigoxin in rats.
2003 Jul
Role of organic anion transporting polypeptide 2 in pharmacokinetics of digoxin and beta-methyldigoxin in rats.
2005 Jun
Selective inhibition of brain Na,K-ATPase by drugs.
2006
[Isolated non-compaction of the left ventricular myocardium in a neonate--a case report].
2006 Dec
Impact of ABCB1 (MDR1) gene polymorphism and P-glycoprotein inhibitors on digoxin serum concentration in congestive heart failure patients.
2007 Jan-Feb
Free and total digoxin in serum during treatment of acute digoxin poisoning with Fab fragments: case study.
2010 Jul
Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:48:26 GMT 2023
Edited
by admin
on Sat Dec 16 16:48:26 GMT 2023
Record UNII
I7GG1YUC5V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METILDIGOXIN
INN   MART.   WHO-DD  
INN  
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
MI  
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
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
WHO-ATC C01AA08
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C170170
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
DRUG BANK
DB13401
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
PUBCHEM
443946
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
INN
2876
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
RXCUI
6686
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY RxNorm
FDA UNII
I7GG1YUC5V
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
EVMPD
SUB08887MIG
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
SMS_ID
100000091460
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
CAS
30685-43-9
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
WIKIPEDIA
Metildigoxin
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
MESH
D008520
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
ECHA (EC/EINECS)
250-292-0
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
MERCK INDEX
m4456
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID0023294
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL1697843
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
DRUG CENTRAL
1761
Created by admin on Sat Dec 16 16:48:26 GMT 2023 , Edited by admin on Sat Dec 16 16:48:26 GMT 2023
PRIMARY
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