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DIGOXIN

DIGOXIN Structure
CAS No.
20830-75-5
Chemical Name:
DIGOXIN
Synonyms
digitalis;DIGACIN;digoxine;LANOXIN;lanoxicaps;DIGOXIN, AP;Digoxin for peak identification CRS;dokim;Digon;dixina
CBNumber:
CB2407221
Molecular Formula:
C41H64O14
Molecular Weight:
780.95
MOL File:
20830-75-5.mol
Modify Date:
2024/3/14 15:18:26

DIGOXIN Properties

Melting point 248 °C
alpha 25Hg +13.4 to 13.8° (c = 10 in pyridine)
Boiling point 661.93°C (rough estimate)
Density 1.1110 (rough estimate)
refractive index 12 ° (C=10, Pyridine)
Flash point 9℃
storage temp. Refrigerator
solubility Soluble in dimethyl sulfoxide and methanol.
form powder
pka 13.50±0.70(Predicted)
color White to Almost white
Water Solubility 46.08mg/L(room temperature)
Merck 14,3167
BRN 77011
BCS Class 1 (LogP), 3 (CLogP)
LogP 1.260
CAS DataBase Reference 20830-75-5
IARC 2B (Vol. 108) 2016
EPA Substance Registry System Digoxin (20830-75-5)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06,GHS08
Signal word  Danger
Hazard statements  H300-H331-H373
Precautionary statements  P260-P264-P270-P301+P310-P304+P340+P311-P314
Hazard Codes  T,T+,F
Risk Statements  25-26/27/28-23/25-39/23/24/25-23/24/25-11-28-26
Safety Statements  22-36/37/39-45-36/37-16-28A
RIDADR  UN 3462 6.1/PG 2
WGK Germany  3
RTECS  IH6125000
3-10
TSCA  Yes
HazardClass  6.1
PackingGroup  II
HS Code  29389090
Toxicity cat,LD50,oral,200ug/kg (0.2mg/kg),Archives Internationales de Pharmacodynamie et de Therapie. Vol. 159, Pg. 1, 1966.
NFPA 704
0
3 0

DIGOXIN price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) D6003 Digoxin analytical standard 20830-75-5 100MG ₹2392.33 2022-06-14 Buy
Sigma-Aldrich(India) PHR1771 Digoxin Pharmaceutical Secondary Standard; Certified Reference Material 20830-75-5 300MG ₹24312.95 2022-06-14 Buy
Sigma-Aldrich(India) D6770 Digoxin analytical standard 20830-75-5 1VIAL ₹37671 2022-06-14 Buy
Sigma-Aldrich(India) D6003 Digoxin analytical standard 20830-75-5 1G ₹11539.45 2022-06-14 Buy
Sigma-Aldrich(India) D6003 Digoxin analytical standard 20830-75-5 5G ₹45096.95 2022-06-14 Buy
Product number Packaging Price Buy
D6003 100MG ₹2392.33 Buy
PHR1771 300MG ₹24312.95 Buy
D6770 1VIAL ₹37671 Buy
D6003 1G ₹11539.45 Buy
D6003 5G ₹45096.95 Buy

DIGOXIN Chemical Properties,Uses,Production

Description

Digoxin, 3β,14β-dihydroxy-5β-card-20(22)-enolide-3-rigitoxide, is also a glycoside isolated from various types of foxgloves. It differs from digitoxin in that it has an additional hydroxyl group at C16 of the steroid skeleton. It is extracted form the leaves of Digitalis lanta, Digitalis orientalis, or Scrophulariaceae.

Chemical Properties

White Crystalline Powder

Physical properties

Appearance: white crystals or crystalline powder, odorless. Solubility: easily dissolved in pyridine, slightly soluble in dilute alcohol, slightly soluble in chloroform, insoluble in water and ethyl ether. Specific optical rotation: +9.5 to +12.0°. Melting point: 248–250?°C.

Uses

Digoxin exhibits strong systolic action and slows heart rate. It is removed from the organism faster than digitoxin. It is used from chronic cardiac insufficiency in decompensated valvular disease of the heart, myocardium overload in arterial hypertension, tachycardia, ventricular fibrillation, and other analogous situations.

Indications

Digoxin is used for congestive heart failure (CHF), paroxysmal supraventricular tachycarelia, atrial fibrillation, and atrial flutter.

Definition

ChEBI: A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.

General Description

Digitalis (Crystodigin) is isolated fromD. lanata and D. purpurea among other Digitalis spp., and isthe chief active glycoside in digitalis leaf, with 1 mg digitoxinequal to 1 g of digitalis leaf therapy. In patients who missdoses, digitalis is very useful for maintenance therapy becauseof the longer half-life it provides. The longer durationand increased half-life are a result of the lack of the C-12hydroxy that is present in digoxin. In digoxin, this hydroxyplays two roles: (a) it serves as a site for metabolism, whichreduces the compound’s half-life; and (b) it gives more hydrophiliccharacter, which results in greater water solubilityand ease in renal elimination.

Health Hazard

Material is a digitalis glycoside. Ingestion can cause death. Material is considered super toxic; probable human oral lethal dose is less than 5 mg/kg, a taste (less than 7 drops) for a 70 kg (150 lb.) person. Persons at risk include those taking drugs for thyroid and renal diseases. Quinidine and diuretics taken concurrently with DIGOXIN can be hazardous. It should be used with extreme care during pregnancy and in nursing mothers.

Fire Hazard

Avoid light.

Safety Profile

A deadly poison by most routes. Human systemic effects by ingestion: anorexia, cardlac arrhythmias, nausea and vomiting, visual field changes, pulse rate decrease, fall in blood pressure. An experimental teratogen. When heated to decomposition it emits acrid and irritating fumes. See also DIGITALIS.

Environmental Fate

Molecular weight: Digitoxin, 764.96; Digoxin, 780.96. Cardiac glycosides have a characteristic chemical structure called an aglycone ring. This is coupled with one or more sugars. The aglycone portion of the glycoside includes a steroid nucleus and a lactone ring at the C17 position. Hydroxyl groups, oriented to the beta position, are present at the C3 and C14 positions. Increases in numbers of hydroxyl groups cause an increase in polarity and decrease in lipid solubility. Increases in numbers of sugars also increase polarity and reduce lipid solubility. Sugars are attached to the steroid nucleus through a hydroxyl group at the C3 position and influences solubility, absorption, toxicity, and other pharmacological parameters.

Purification Methods

Crystallise digoxin from aqueous EtOH, aqueous pyridine, EtOH/CHCl3, and dry it in a vacuum at 100o. The melting point depends on heating rate, but when placed in a bath at 260o and heated slowly it decomposes at 265o. In EtOH it has max at 220nm ( 12,800). [Smith J Chem Soc 508 1930, X-ray: Go et al. Cryst Struct Commun 8 149, 1031 1979, Beilstein 18/4 V 381.] HIGHLY TOXIC.

DIGOXIN Preparation Products And Raw materials

Raw materials

Preparation Products

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DIGOXIN LANACORDIN 4-[3-[5-[5-(4,5-DIHYDROXY-6-METHYL-TETRAHYDROPYRAN-2-YL)OXY-4-HYDROXY-6-METHYL-TETRAHYDROPYRAN-2-YL]OXY-4-HYDROXY-6-METHYL-TETRAHYDROPYRAN-2-YL]OXY-12,14-DIHYDROXY-10,13-DIMETHYL-2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17-HEXADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-17-YL]-5H-FURAN-2-ONE 20(22),5BETA-CARDENOLID-3BETA,12BETA,14BETA-TRIOL 3BETA-2,6-DIDEOXY-4-O-[2,6-DIDEOXY-4-O-(2,6-DIDEOXY-BETA-D-RIBOHEXOPYRANOSYL)-BETA-D-RIBOHEXOPYRANOSIDE] 12BETA-HYDROXYDIGITOXIN Card-20(22)-enolide, 3-[(O-2,6-dideoxy-- D-ribo-hexopyranosyl-(1< (3beta,5beta,12beta)-3-((o-2,6-dideoxy-beta-d-ribo-hexapyranosyl-(1-4)-2,6-dide -12,14-dihydroxycard-20(22)-enolide 14-dihydroxy-,(3beta,5beta,12beta)-xopyranosyl)oxy]-1 14-dihydroxy-,(3beta,5beta,12beta)-y)-1 -2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1.fwdarw.)-2,6-dideoxy-beta-d-ribo-he dixina dokim dynamos homolle’sdigitalin lanatilin lanicor lanocardin lenoxicaps lenoxin longdigox neodioxanin oxy-beta-d-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-d-ribo-hexopyranosyl)oxy) rougoxin saroxin sk-digoxin stillacor Purgoxin Toloxin Vanoxin hexopyranosyl)oxy]-12,14-dihydroxy-,(3β,5β,12β)- (3,5,12)-3-[(O-2,6-Dideoxy--D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy--D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy--D-ribo-hexopyranosyl)oxyl]-12,14-dihydroxycard-20(22)-enolide digitaline cristallise digitoxine (3beta,5beta,12beta)-3-((O-2,6-Dideoxy-beta-D-ribo-hexapyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxycard-20(22)-enolide 12β,14β-Dihydroxy-5β-carda-20(22)-enolide-3β-yl 4-O-[4-O-(2,6-dideoxy-β-D-altropyranosyl)-2,6-dideoxy-β-D-altropyranosyl]-2,6-dideoxy-β-D-altropyranoside 3β-[[4-O-[4-O-(2,6-Dideoxy-β-D-ribo-hexopyranosyl)-2,6-dideoxy-β-D-ribo-hexopyranosyl]-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy]-12β,14-dihydroxy-5β,14β-card-20(22)-enolide 3β-[4-O-[4-O-(2,6-Dideoxy-β-D-ribo-hexopyranosyl)-2,6-dideoxy-β-D-ribo-hexopyranosyl]-2,6-dideoxy-β-D-ribo-hexopyranosyloxy]-12β,14-dihydroxy-5β,14β-carda-20(22)-enolide Digohan 12β-Hydroxydigitoxin, Digoxin Digoxin,95% (3beta,5beta,12beta)-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)oxyl]-12,14-dihydroxycard-20(22)-enolide Digoxin (250 mg) Methanol (Test Digoxin, 1.0 mg/mL) Digoxin 96% Digoxin solution (3β,5β,12β)- 3-[(O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-card-20(22)-enolide Digoxin, >=98% acygoxin card-20(22)-enolide,3-((o-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1-4)-o-2,6-di card-20(22)-enolide,3-[(o-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1.fwdarw.)-o cardoxin chloroformicdigitalin cordioxil davoxin deoxy-beta-d-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-d-ribo-hexopyranosyl)ox 4-[(3S,5R,8R,9S,10S,12R,13S,14S)-3-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-4,5-Dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyl-oxan-2-yl]oxy-4-hydroxy-6-methyl-oxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-5H-furan-2-one Digoxin (FDA)