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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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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
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/s1InChIKey
LTMHDMANZUZIPE-PUGKRICDSA-NSmiles
C[C@H]1O[C@H](C[C@H](O)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.