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Digimed

HCID 3061
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Basic information

CAS
71-63-6
Standard SMILES
CC1OC(OC2C(O)CC(OC3C(O)CC(OC4CCC5(C)C(CCC6C5CCC5(C)C(C7=CC(=O)OC7)CCC65O)C4)OC3C)OC2C)CC(O)C1O
InChIKey
WDJUZGPOPHTGOT-UHFFFAOYSA-N
Molecular formula
C41H64O13
Average molar mass
764.9 g/mol
Monoisotopic mass
764.43469209

Overview

digitoxin has been reported in Digitalis cariensis, Digitalis lanata, and Adenium obesum with data available.

Names & identifiers

Preferred name
Digimed
IUPAC
3-[3-[5-[5-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-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
Digitoxin
Molecular formula
C41H64O13
Molecular weight
764.94

Names & synonyms

DigimedRefChem:9201853-(3-(5-(5-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-14-hydroxy-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-oneNatigalDe-TonePurodigin, crystallineAcedoxinCoramedanDigoxin EP Impurity ANSC 7529MFCD00003686NCGC00159428-02
Show more names
CRYSTODIGINDigitoxosideCardiginDIGITALINdigitoxinumDigitogenindigicorDitaven
CHEMBL267817WDJUZGPOPHTGOT-UHFFFAOYSA-NCard-20(22)-enolide, 3-[(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]-14-hydroxy-, (3.beta.,5.beta.)-NCGC00159428-03NCI60_041649DB-0555565.beta.-Card-20(22)-enolide,14-dihydroxy-, 3-[tris-(digitoxoside)]5.beta.-Card-20(22)-enolide, 3.beta.,14-dihydroxy-, 3-(tris-(digitoxoside))

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
183 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
13
Rotatable bonds
7
Heavy atoms
54
Formal charge
0
Complexity
1,410

Experimental & physicochemical properties

DrugsPharmaceuticals

Physicochemical properties

Melting point
240 °C · 240 °C (dec.)(lit.)
alpha
20 · D20 +4.8° (c = 1.2 in dioxane)
Boiling point
654.47 °C · 654.47°C (rough estimate)
Density
1.0971 · 1.0971 (rough estimate)
refractive index
17 ° · 17 ° (C=2, CHCl3)
Flash point
9 ℃ · 9℃
storage temp.
2 · 2-8°C
solubility
chloroform: soluble
form
powder
pka
13.5 · 13.50±0.70(Predicted)
color
White
Water Solubility
3.9 mg/L · 3.9mg/L(25 ºC)
Merck
14 · 14,3163
BRN
76678 · 76678

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
3-10
PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
IH2275000
ridadr
UN 2811 6.1/PG 1
hs_code
2938900000
Toxicity
LD50 in guinea pigs, cats (mg/kg): 60.0, 0.18 orally (Foerster)
risk_code
23/25-33-39/23/24/25-23/24/25-11
Signal word
Danger
Symbol(GHS)
GHS06,GHS08
hazard_code
T,F
safety_code
45-36/37-16
hazard_class
6.1(a)
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
II
Hazard statements
H300-H331-H373
Hazard Classifications
Acute Tox. 2 OralAcute Tox. 3 InhalationSTOT RE 2
Precautionary statements
P260-P264-P270-P301+P310-P304+P340+P311-P314
Hazardous Substances Data
71-63-6(Hazardous Substances Data)

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 3 items

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 · 5 items

DescriptionDigitoxin is the most powerful and reliable of the glucosides which have been extracted from digitalis leave. It is a cardiac glycoside (CG). It is a cardiotonic drug, which exhibits cardiac and anti-cancer properties. Digitoxin inhibits nuclear factor kappa B (NF-κB) signaling. It is used to treat congestive heart failure and cardiac arrhythmia. Digitoxin prevents microtubule formation.

DescriptionDigitoxin is a cardiac glycoside that has been found in Digitalis and has diverse biological activities. It inhibits human recombinant α1β1, α2β2, and α3β1 subunit-containing Na+/K+-ATPases with Ki values of 250, 63, and 136 nM, respectively. Digitoxin inhibits the human-ether-a-go-go (hERG) potassium channel, also known as Kv11.1, in HEK293 cells expressing hERG (IC50 = 11.1 nM). It enhances developed tension and contractile force in electrically stimulated isolated guinea pig left atrial muscle when used at concentrations of 0.2 and 0.4 μM, respectively. Dietary administration of digitoxin (~1 mg/kg per day) attenuates congestive heart failure and reduces myocardial hypertrophy in a rat model of myocardial infarction induced by coronary artery ligation. Digitoxin is also cytotoxic to a panel of 10 human cancer cell lines, including myeloma, lymphoma, and leukemia cancer cells, with IC50 values ranging from 12 to 76 nM. Formulations containing digitoxin have previously been used in the treatment of congestive heart failure and cardiac arrhythmias.

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Compound notes

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Database identifiers

CAS
71-63-6
PubChem CID
3061
ChEMBL
CHEMBL267817
Henry's Law Constant
7.6 · 7.6×1019 mol/(m3Pa) at 25℃, HSDB (2015)
Stability
Hygroscopic
InChIKey
WDJUZGPOPHTGOT-XUDUSOBPSA-N
EWG's Food Scores
1 · 1-4
FDA UNII
90 NZP2L9U · E90NZP2L9U
ATC code
1 AA04 · C01AA04
EPA Substance Registry System
Digitoxin (71-63-6)
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Symbol(GHS)
6 · GHS06,GHS08
Signal word
Danger
Hazard statements
300 · H300-H331-H373
Precautionary statements
260 · P260-P264-P270-P301+P310-P304+P340+P311-P314
PPE
2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes
T,F
Risk Statements
23 · 23/25-33-39/23/24/25-23/24/25-11
Safety Statements
45 · 45-36/37-16
RIDADR
2811 · UN 2811 6.1/PG 1
WGK Germany
3 · 3
RTECS
2275000 · IH2275000
F
3 · 3-10
TSCA
TSCA listed
HazardClass
6.1 · 6.1(a)
PackingGroup
II
HS Code
2938900000 · 2938900000
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
2 OralAcute · Acute Tox. 2 OralAcute Tox. 3 InhalationSTOT RE 2
Hazardous Substances Data
71 · 71-63-6(Hazardous Substances Data)
Toxicity
50 in · LD50 in guinea pigs, cats (mg/kg): 60.0, 0.18 orally (Foerster)

UsesDigitoxin is used for chronic cardiac insufficiency, tachyarrhythmia form of atrial fibrillation, paroxysmal ciliary arrhythmia, and paroxysmal supraventricular tachycaria.

UsesDigitoxin has been used as a labeled drugs for binding sites on human serum albumin (HSA). It has also been used to test its anti-transmissible gastroenteritis virus (TGEV) activity.

General DescriptionOdorless white or pale buff microcrystalline powder. Used as a cardiotonic drug.

Upstream & downstream products

Upstream raw materials

Dry acetonePENTYL ETHERLead acetateHydrogen SulfideD-ribo-Hex-1-enitol, 1,5-anhydro-2,6-dideoxy-4-O-[2,6-dideoxy-3,4-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-β-D-ribo-hexopyranosyl]-3-O-[(1,1-dimethylethyl)dimethylsilyl]-5-Hexyne-2,3-diol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, 2-benzoate, (2R,3R,4S)-D-ribo-Hex-1-enitol, 1,5-anhydro-2,6-dideoxy-3,4-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-
Additional notes · 1 item

DefinitionChEBI: Digitoxin is a cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain. It has a role as an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor. It is functionally related to a digitoxigenin. It is a conjugate acid of a digitoxin(1-).