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Substance Name: Digitoxin [USP:INN:BAN:JAN]
RN: 71-63-6
UNII: E90NZP2L9U
InChIKey: WDJUZGPOPHTGOT-XUDUSOBPSA-N

Note

  • 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)

Molecular Formula

  • C41-H64-O13

Molecular Weight

  • 764.9436
 

Classification Codes

Classification Codes

  • Anti-Arrhythmia Agents
  • Cardiotonic
  • Cardiotonic Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Natural Product
  • Protective Agents
  • Reproductive Effect
  • Skin / Eye Irritant

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 100/10000 lb

Names and Synonyms

Name of Substance

  • Digitoxin
  • Digitoxin [USP:INN:BAN:JAN]

MeSH Heading

  • Digitoxin

Synonyms

  • 5-18-03-00354 (Beilstein Handbook Reference)
  • Acedoxin
  • Asthenthilo
  • BRN 0076678
  • Card-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, (3beta,5beta)-
  • Cardidigin
  • Cardigin
  • Carditalin
  • Carditoxin
  • Caswell No. 349
  • CCRIS 7116
  • Coramedan
  • Cristapurat
  • Crystalline digitalin
  • Crystodigin
  • De-Tone
  • Digicor
  • Digilong
  • Digimerck
  • Digipural
  • Digisidin
  • Digitalin, crystalline
  • Digitaline cristallisee
  • Digitaline nativelle
  • Digitalinum verum
  • Digitoksim
  • Digitoksin
  • Digitophyllin
  • Digitossina
  • Digitossina [DCIT]
  • Digitoxigenin tridigitoxoside
  • Digitoxigenin-tridigitoxosid
  • Digitoxigenin-tridigitoxosid [German]
  • Digitoxin
  • Digitoxina
  • Digitoxina [INN-Spanish]
  • Digitoxine
  • Digitoxine [INN-French]
  • Digitoxinum
  • Digitoxinum [INN-Latin]
  • Digitoxoside
  • Digitoxosidum
  • Digitrin
  • Ditaven
  • EINECS 200-760-5
  • EPA Pesticide Chemical Code 097002
  • Glucodigin
  • HSDB 215
  • Lanatoxin
  • Mono-digitoxid
  • Mono-digitoxid [German]
  • Mono-glycocard
  • Monodigitoxoside
  • Myodigin
  • Natigal
  • NSC 7529
  • Purodigin
  • Purodigin, crystalline
  • Purpurid
  • Tardigal
  • Tri-digitoxoside
  • Tri-digitoxoside [German]
  • Unidigin
  • UNII-E90NZP2L9U

Systematic Names

  • Card-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-, (3beta,5beta)-
  • Card-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-, (3beta,5beta)-
  • Card-20(22)-enolide, 3-((O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1.fwdarw.4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1.fwdarw.4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14-hydroxy-, (3beta,5beta)-
  • Digitoxin

Superlist Name

  • Digitoxin

Registry Numbers

CAS Registry Number

  • 71-63-6

FDA UNII

  • E90NZP2L9U

Other Registry Numbers

  • 1339-93-1
  • 1367-39-1
  • 1391-34-0
  • 82476-56-0

System Generated Number

  • 0000071636

Structure Descriptors

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

Smiles

C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2O)O[C@@H]3[C@H](O[C@H](C[C@@H]3O)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5CC[C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)C)C)C)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intraperitoneal 170ug/kg (0.17mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 165, 1965.
cat LD50 oral 180ug/kg (0.18mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 159, Pg. 1, 1966.
cat LDLo intraarterial 440ug/kg (0.44mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 141, Pg. 329, 1929.
cat LDLo intraduodenal 315ug/kg (0.315mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1765, 1970.
cat LDLo intravenous 180ug/kg (0.18mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 184, Pg. 181, 1937.
cat LDLo unreported 325mg/kg (325mg/kg)   "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963Vol. -, Pg. 33, 1963.
dog LDLo intravenous 500ug/kg (0.5mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1343, 1935.
frog LD50 intravenous 730ug/kg (0.73mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 61, Pg. 231, 1965.
frog LD50 oral 3050ug/kg (3.05mg/kg)   Japanese Journal of Pharmacology. Vol. 9, Pg. 91, 1960.
frog LD50 subcutaneous 1050ug/kg (1.05mg/kg)   Japanese Journal of Pharmacology. Vol. 9, Pg. 91, 1960.
frog LDLo parenteral 1mg/kg (1mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 11, Pg. 613, 1963.
guinea pig LD50 intraduodenal 3mg/kg (3mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 225, 1971.
guinea pig LD50 intraperitoneal 1800ug/kg (1.8mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 242, Pg. 35, 1979.
guinea pig LD50 oral 3700ug/kg (3.7mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958.
guinea pig LDLo intraduodenal 7250ug/kg (7.25mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 229, 1970.
guinea pig LDLo intravenous 310ug/kg (0.31mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 237, Pg. 222, 1959.
infant TDLo oral 150ug/kg (0.15mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

GASTROINTESTINAL: NAUSEA OR VOMITING
American Journal of Diseases of Children. Vol. 130, Pg. 425, 1976.
infant TDLo parenteral 270ug/kg/1D-I (0.27mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Indian Pediatrics. Vol. 30, Pg. 81, 1993.
man LDLo oral 286ug/kg (0.286mg/kg) BLOOD: THROMBOCYTOPENIA

PERIPHERAL NERVE AND SENSATION: PARESTHESIS

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Clinical Toxicology. Vol. 18, Pg. 679, 1981.
man LDLo unreported 44ug/kg (0.044mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo oral 71ug/kg (0.071mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
American Journal of Emergency Medicine. Vol. 2, Pg. 504, 1984.
mouse LD50 intracrebral 49ug/kg (0.049mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 908, 1961.
mouse LD50 intraperitoneal 3900ug/kg (3.9mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 165, 1965.
mouse LD50 intravenous 4100ug/kg (4.1mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958.
mouse LD50 oral 4950ug/kg (4.95mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958.
mouse LD50 subcutaneous 22180ug/kg (22.18mg/kg) CARDIAC: OTHER CHANGES

BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 153, Pg. 436, 1965.
pig LDLo intraduodenal 550ug/kg (0.55mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 229, 1970.
pig LDLo intravenous 400ug/kg (0.4mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 229, 1970.
pigeon LD50 intraperitoneal 320ug/kg (0.32mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 14, Pg. 96, 1962.
pigeon LDLo intravenous 443ug/kg (0.443mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 225, 1971.
pigeon LDLo parenteral 600ug/kg (0.6mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 11, Pg. 613, 1963.
rabbit LDLo intravenous 1mg/kg (1mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1343, 1935.
rat LD50 intravenous 3900ug/kg (3.9mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 848, 1961.
rat LD50 oral 23750ug/kg (23.75mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 47, 1966.
rat LD50 subcutaneous 16430ug/kg (16.43mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 47, 1966.
women TDLo oral 300ug/kg (0.3mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) American Journal of Emergency Medicine. Vol. 2, Pg. 504, 1984.
women TDLo oral 400ug/kg (0.4mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

GASTROINTESTINAL: NAUSEA OR VOMITING
Clinical Toxicology. Vol. 18, Pg. 679, 1981.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 255.5 deg C   EXP
log P (octanol-water) 1.85 (none)   EXP
Water Solubility 3.9 mg/L 25 EXP
Vapor Pressure 6.93E-29 mm Hg 25 EST
Henry's Law Constant 1.27E-25 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.36E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.