Basic information
- Standard SMILES
CO[C@H]1[C@@H](O)C[C@H](O[C@H]2[C@@H](O)C[C@H](O[C@H]3[C@@H](O)C[C@H](O[C@H]4CC[C@@]5(C)[C@H](CC[C@@H]6[C@@H]5C[C@@H](O)[C@]5(C)[C@@H](C7=CC(=O)OC7)CC[C@]65O)C4)O[C@@H]3C)O[C@@H]2C)O[C@@H]1C- InChIKey
IYJMSDVSVHDVGT-PEQKVOOWSA-N- Molecular formula
- C42H66O14
- Average molar mass
- 795 g/mol
- Monoisotopic mass
- 794.44525679
Overview
Metildigoxin is a cardenolide glycoside.
Names & identifiers
- Preferred name
- Methyldigoxin
- IUPAC
- 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
- English name
- Metildigoxin
- Molecular formula
- C42H66O14
- Molecular weight
- 794.97
Names & synonyms
metildigoxinMethyldigoxin30685-43-9MetildigoxinaMetildigoxineMetildigoxinumDigoxin, 4'''-O-methyl-DTXSID0023294Methyldigoxin, betaI7GG1YUC5VDTXCID0032943-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Show more names
b-MethyldigoxinMetildigoxin RSβ-Methyl Digoxin-β-Methyl Digoxinbeta-Methyldigoxin4'''-Methyldigoxin4'''-b-Methyldigoxin
metildigossina3-((3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-((2R,4S,5S,6R)-4-hydroxy-5-((2S,4S,5S,6R)-4-hydroxy-5-((2S,4S,5S,6R)-4-hydroxy-5-methoxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-17-yl)-2H-furan-5-oneRefChem:8187634'''-BETA-METHYLDIGOXINC01AA08250-292-0MEDIGOXINLanitop
Database identifiers
- CAS
30685-43-9- PubChem CID
- 443946
- DTXSID
DTXSID0023294- ChEMBL
CHEMBL1697843- ChEBI
CHEBI:135885- UNII
- I7GG1YUC5V
- EC Number
- 250-292-0
- Nikkaji
- J4.091F
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 192 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 8
- Heavy atoms
- 56
- Formal charge
- 0
- Complexity
- 1,460
Experimental & physicochemical properties
LogP1.73
Physicochemical properties
- Melting point
- 200 · 200-202°C (dec.)
- Boiling point
- 668.38 °C · 668.38°C (rough estimate)
- Density
- 1.102 · 1.1020 (rough estimate)
- refractive index
- 1.613 · 1.6130 (estimate)
- storage temp.
- Hygroscopic, Refrigerator, Under Inert Atmosphere
- solubility
- DMSO (Sparingly), Methanol (Slightly)
- pka
- 13.5 · 13.50±0.70(Predicted)
- form
- Solid
- color
- White to Off-White
- Stability
- Hygroscopic
- FDA UNII
- 7 GG1YUC5V · I7GG1YUC5V
- ATC code
- 1 AA08 · C01AA08
- Symbol(GHS)
- 8 · GHS08,GHS06
- Signal word
- Danger
- Hazard statements
- 412 · H412-H319-H330-H300-H372
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313P-P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P260-P264-P270-P314-P501-P273-P501-P264-P270-P301+P310-P321-P330-P405-P501
- Toxicity
- 50 in · LD50 in rats, mice (mg/kg): 4.8, 4.9 i.v.; 6.2, 4.8 i.p.; 8.3, 7.8 orally (Czerwek)
Safety & regulation
GHS classification
GHS Classification
Danger
H300 (50%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (50%)
Safety data
- Toxicity
- LD50 in rats, mice (mg/kg): 4.8, 4.9 i.v.; 6.2, 4.8 i.p.; 8.3, 7.8 orally (Czerwek)
- Signal word
- Danger
- Symbol(GHS)
- GHS08,GHS06
- Hazard statements
- H412-H319-H330-H300-H372
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P260-P264-P270-P314-P501-P273-P501-P264-P270-P301+P310-P321-P330-P405-P501
Chemistry & industry
Pharmacology
ATC Code
C01AA08
C - Cardiovascular system
QC - Cardiovascular system
MeSH Pharmacological Classification
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Applications
UsesCardiotonic. Obtained by the O-methylation of Digoxin.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Metildigoxin is a cardenolide glycoside.
Related reactions
2 records
Linked notes
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