4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase ID: 1207
• Molecular Formular: C41H64O13
• Molecular Mass: 764.93906
• Monoisotopic Mass: 764.43469211
• SMILES: O[C@@]12[C@H]3[C@@H]([C@@]4([C@H](CC3)C[C@@H](O[C@@H]3O[C@@H]([C@@H](O[C@@H]5O[C@@H]([C@@H](O[C@@H]6O[C@@H]([C@@H](O)[C@@H](O)C6)C)[C@@H](O)C5)C)[C@@H](O)C3)C)CC4)C)CC[C@@]1([C@H](CC2)C1=CC(=O)OC1)C
• Canonical SMILES: O=C1OCC(=C1)[C@H]1CC[C@]2([C@]1(C)CC[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@@H](C2)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O)O
• InChI: InChI=1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
• InChIKey: WDJUZGPOPHTGOT-XUDUSOBPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one; 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]-2,5-dihydrofuran-2-one; 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• IUPAC Traditional name: digitoxin
• Brand Name: Digitaline; Crystodigin; Unidigin; Tardigal
• Synonyms: Digitoxin; 5β,20(22)-Cardenolide-3β,14-diol-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; Digitoxinum; Digitoxoside; Digitoksin; Digitalin; Digitoxin; 洋地黄毒苷

Database IDs

• CAS Number: 71-63-6
• EC Number: 200-760-5
• MDL Number: MFCD00003686
• Beilstein Number: 76678
• PubChem SID: 160964669; 46506035; 24893976
• PubChem CID: 441207
• CHEBI ID: 28544
• ATC CODE: C01AA04
• CHEMBL: 254219
• Chemspider ID: 389987
• DrugBank ID: DB01396
• KEGG ID: D00297
• Unique Ingredient Identifier: E90NZP2L9U
• Wikipedia Title: Digitoxin

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.182636
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): 3.5885735
• LogD (pH = 7.4): 3.175141
• Log P: 3.5974917
• Molar Refractivity: 191.7173 cm^3
• Polarizability: 78.34437 Å^3
• Polar Surface Area: 182.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.33
• LOG S: -4.42
• Solubility (Water): 2.89e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.0039 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; chloroform: soluble
• Apperance: powder
• Melting Point: 240 °C (dec.)(lit.); 256-257°C
• Optical Rotation: [α]20/D +17±1°, 7 hr, c = 2% in chloroform; [α]23/D +5.4°, c = 1.2 in dioxane
• Hydrophobicity(logP): 1.85 [SANGSTER (1993)]

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• RTECS: IH2275000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544; 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; I
• Australian Hazchem: 2X
• Risk Statements: 23/25-33; R:23/25-33
• Safety Statements: 45; S:45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 151
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H331-H373
• GHS Precautionary statements: P261-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1

Pharmacology Properties

• Bioavailability: 95% (Oral)
• Half Life: 5~7 days
• Metabolism: Liver

Product Information

• Purity: ≥92% (HPLC); ≥98.0% (HPLC); 97%
• Ignition Residue: ≤0.05%
• Empirical Formula (Hill Notation): C41H64O13

DETAILS

MP Biomedicals - 02190514

Crystalline

DrugBank - DB01396

• Drug Groups: approved
• Description: A cardiac glycoside sometimes used in place of digoxin. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665)
• Indication: For the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure.
• Pharmacology: Digitoxin is a cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). Unlike digoxin (which is eliminated from the body via the kidneys), it is eliminated via the liver, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current UK medical practice. While there have been several controlled trials which have shown digoxin to be effective in a proportion of patients treated for heart failure, there is not the same strong evidence base for digitoxin, although it is presumed to be similarly effective.
• Toxicity: Digitoxin exhibits similar toxic effects to the more-commonly used digoxin, namely: anorexia, nausea, vomiting, diarrhoea, confusion, visual disturbances, and cardiac arrhythmias.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• References: Belz GG, Breithaupt-Grogler K, Osowski U: Treatment of congestive heart failure--current status of use of digitoxin. Eur J Clin Invest. 2001;31 Suppl 2:10-7. [Pubmed] ; Kurowski V, Iven H, Djonlagic H: Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies. Intensive Care Med. 1992;18(7):439-42. [Pubmed] ; Johansson S, Lindholm P, Gullbo J, Larsson R, Bohlin L, Claeson P: Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. Anticancer Drugs. 2001 Jun;12(5):475-83. [Pubmed] ; Hippius M, Humaid B, Sicker T, Hoffmann A, Gottler M, Hasford J: Adverse drug reaction monitoring--digitoxin overdosage in the elderly. Int J Clin Pharmacol Ther. 2001 Aug;39(8):336-43. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - D5878

包装
1, 5, 10 g in glass bottle
250, 500 mg in glass bottle

REFERENCES

• Belz GG, Breithaupt-Grogler K, Osowski U: Treatment of congestive heart failure--current status of use of digitoxin. Eur J Clin Invest. 2001;31 Suppl 2:10-7. Pubmed
• Kurowski V, Iven H, Djonlagic H: Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies. Intensive Care Med. 1992;18(7):439-42. Pubmed
• Johansson S, Lindholm P, Gullbo J, Larsson R, Bohlin L, Claeson P: Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. Anticancer Drugs. 2001 Jun;12(5):475-83. Pubmed
• Hippius M, Humaid B, Sicker T, Hoffmann A, Gottler M, Hasford J: Adverse drug reaction monitoring--digitoxin overdosage in the elderly. Int J Clin Pharmacol Ther. 2001 Aug;39(8):336-43. Pubmed