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Substance Name: Digoxin [USP:INN:BAN:JAN]
RN: 20830-75-5
UNII: 73K4184T59
InChIKey: LTMHDMANZUZIPE-PUGKRICDSA-N

Note

  • A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666)

Molecular Formula

  • C41-H64-O14

Molecular Weight

  • 780.9426
 

Classification Codes

Classification Codes

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

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 10/10000 lb

Names and Synonyms

Name of Substance

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

MeSH Heading

  • Digoxin

Synonyms

  • (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
  • 12beta-Hydroxydigitoxin
  • 3beta,12beta,14-Trihydroxy-5beta,14beta-card-20(22)-enolid-3-tridigitoxosid
  • 3beta-((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)-12beta,14-dihydroxy-5beta-card-20(22)-enolide
  • 5-18-04-00381 (Beilstein Handbook Reference)
  • Acygoxin
  • BRN 0077011
  • 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)-12,14-dihydroxy-, (3beta,5beta,12beta)-
  • Cardigox
  • Cardiogoxin
  • Cardioxin
  • Cardoxin
  • Chloroformic digitalin
  • Coragoxine
  • Cordioxil
  • Davoxin
  • Digacin
  • Digitek
  • Digoksyna
  • Digoksyna [Polish]
  • Digomal
  • Digon
  • Digonix
  • Digos
  • Digosin
  • Digossina
  • Digossina [DCIT]
  • Digoxigenin-tridigitoxosid
  • Digoxigenin-tridigitoxosid [German]
  • Digoxin
  • Digoxin Nativelle
  • Digoxin pediatric
  • Digoxin-Sandoz
  • Digoxin-Zori
  • Digoxina
  • Digoxina [INN-Spanish]
  • Digoxina-Sandoz
  • Digoxine
  • Digoxine Navtivelle
  • Digoxinum
  • Digoxinum [INN-Latin]
  • Dilanacin
  • Dimecip
  • Dixina
  • Dokim
  • Dynamos
  • EINECS 244-068-1
  • Eudigox
  • Fargoxin
  • Grexin
  • Hemigoxine Nativelle
  • Homolle's digitalin
  • HSDB 214
  • Lanacordin
  • Lanacrist
  • Lanatilin
  • Lanicor
  • Lanikor
  • Lanorale
  • Lanoxicaps
  • Lanoxin
  • Lanoxin pediatric
  • Lanoxin PG
  • Lenoxicaps
  • Lenoxin
  • Lifusin
  • Longdigox
  • Mapluxin
  • Natigoxin
  • Neo-Lanicor
  • NeoDioxanin
  • Novodigal
  • Novodigal [inj.]
  • NSC 95100
  • Purgoxin
  • Rougoxin
  • Saroxin
  • SK-Digoxin
  • Stillacor
  • UNII-73K4184T59
  • Vanoxin

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)-12,14-dihydroxy-, (3beta,5beta,12beta)-
  • 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)-12,14-dihydroxy-, (3beta,5beta,12beta)-
  • 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)-12,14-dihydroxy-, (3beta,5beta,12beta)-
  • Digoxin

Superlist Name

  • Digoxin

Registry Numbers

CAS Registry Number

  • 20830-75-5

FDA UNII

  • 73K4184T59

Other Registry Numbers

  • 11000-95-6
  • 36-35-1
  • 39366-41-1
  • 8001-36-3
  • 8001-37-4
  • 8001-52-3
  • 82476-60-6

System Generated Number

  • 0020830755

Structure Descriptors

InChI

1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1

InChIKey

LTMHDMANZUZIPE-PUGKRICDSA-N

Smiles

C[C@H]1O[C@H](C[C@H](O)[C@@H]1O)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@]7(C)[C@H](CC[C@]67O)C8=CC(=O)OC8)C4)O[C@@H]3C)O[C@@H]2C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 200ug/kg (0.2mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 159, Pg. 1, 1966.
cat LDLo intraduodenal 441ug/kg (0.441mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1765, 1970.
cat LDLo intravenous 159ug/kg (0.159mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 657, 1969.
cat LDLo parenteral 1470ug/kg (1.47mg/kg)   Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 34, Pg. 431, 1977.
child TDLo oral 54ug/kg (0.054mg/kg) CARDIAC: PULSE RATE American Journal of Emergency Medicine. Vol. 4, Pg. 364, 1986.
child TDLo oral 127ug/kg (0.127mg/kg) CARDIAC: PULSE RATE American Family Physician. Vol. 34(1), Pg. 137, 1986.
dog LDLo intravenous 200ug/kg (0.2mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 109, Pg. 279, 1932.
dog LDLo oral 300ug/kg (0.3mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 109, Pg. 279, 1932.
frog LD50 subcutaneous 2240ng/kg (0.00224mg/kg)   Russian Pharmacology and Toxicology Vol. 53, Pg. 171, 1990.
frog LDLo parenteral 1mg/kg (1mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 11, Pg. 613, 1963.
guinea pig LD50 intraduodenal 3200ug/kg (3.2mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION
Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 225, 1971.
guinea pig LD50 intramuscular 630ug/kg (0.63mg/kg)   Drugs in Japan Vol. 6, Pg. 316, 1982.
guinea pig LD50 intraperitoneal 800ug/kg (0.8mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 373, 1973.
guinea pig LD50 oral 3500ug/kg (3.5mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 159, Pg. 1, 1966.
guinea pig LD50 subcutaneous 600ug/kg (0.6mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Journal of Pharmacy and Pharmacology. Vol. 35, Pg. 580, 1983.
guinea pig LDLo intravenous 468ug/kg (0.468mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 153, Pg. 436, 1965.
infant LDLo intravenous 200ug/kg (0.2mg/kg) CARDIAC: PULSE RATE Pediatrics. Vol. 77, Pg. 848, 1986.
infant TDLo intravenous 50ug/kg (0.05mg/kg) CARDIAC: PULSE RATE American Family Physician. Vol. 34(1), Pg. 137, 1986.
man TDLo oral 75ug/kg (0.075mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
American Journal of Emergency Medicine. Vol. 6, Pg. 465, 1988.
man TDLo oral 333ug/kg (0.333mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

CARDIAC: PULSE RATE
British Medical Journal. Vol. 287, Pg. 392, 1983.
man TDLo unreported 13ug/kg/4D-I (0.013mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CHANGES IN PSYCHOPHYSIOLOGICAL TESTS

VASCULAR: OTHER CHANGES
American Heart Journal. Vol. 106, Pg. 419, 1983.
mouse LD50 intracrebral 124ug/kg (0.124mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Pharmacological Research Communications. Vol. 6, Pg. 417, 1974.
mouse LD50 intraperitoneal 3964ug/kg (3.964mg/kg)   Chemotherapy Vol. 16, Pg. 371, 1971.
mouse LD50 intravenous 7670ug/kg (7.67mg/kg)   Pharmacological Research Communications. Vol. 6, Pg. 417, 1974.
mouse LD50 oral 17780ug/kg (17.78mg/kg) CARDIAC: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 153, Pg. 436, 1965.
mouse LD50 subcutaneous 8150ng/kg (0.00815mg/kg)   Russian Pharmacology and Toxicology Vol. 53, Pg. 171, 1990.
mouse LDLo parenteral 2947ug/kg (2.947mg/kg)   Shang-hai I Hsueh. Vol. 4(2), Pg. 32, 1981.
pig LDLo intraduodenal 1580ug/kg (1.58mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 229, 1970.
pig LDLo intravenous 230ug/kg (0.23mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 229, 1970.
pigeon LDLo intravenous 337ug/kg (0.337mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

CARDIAC: CHANGE IN RATE

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 126, Pg. 412, 1960.
pigeon LDLo parenteral 450ug/kg (0.45mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 11, Pg. 613, 1963.
rabbit LD50 intravenous 3560ug/kg (3.56mg/kg)   Drugs in Japan Vol. 6, Pg. 316, 1982.
rat LD50 intraperitoneal 4mg/kg (4mg/kg)   Journal of Drug Research. Vol. 17, Pg. 247, 1987.
rat LD50 intravenous 25mg/kg (25mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 165, 1965.
rat LD50 oral 28270ug/kg (28.27mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 47, 1966.
rat LD50 subcutaneous 8900ng/kg (0.0089mg/kg)   Russian Pharmacology and Toxicology Vol. 53, Pg. 171, 1990.
rat LDLo rectal 5mg/kg (5mg/kg) CARDIAC: PULSE RATE Planta Medica. Vol. 25, Pg. 88, 1974.
women TDLo oral 100ug/kg (0.1mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

GASTROINTESTINAL: NAUSEA OR VOMITING

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
New Zealand Medical Journal. Vol. 84, Pg. 443, 1976.
women TDLo oral 165ug/kg/33D- (0.165mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
British Medical Journal. Vol. 296, Pg. 1262, 1988.
women TDLo oral 500ug/kg (0.5mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

GASTROINTESTINAL: NAUSEA OR VOMITING

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Clinical Toxicology. Vol. 15, Pg. 437, 1979.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 249 dec deg C   EXP
log P (octanol-water) 1.26 (none)   EXP
Water Solubility 64.8 mg/L 25 EXP
Vapor Pressure 3.30E-30 mm Hg 25 EST
Henry's Law Constant 4.66E-27 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.45E-10 cm3/molecule-sec 25 EST

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