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Substance Name: Digoxigenin
RN: 1672-46-4
UNII: NQ1SX9LNAU
InChIKey: SHIBSTMRCDJXLN-KCZCNTNESA-N

Note

  • 3 beta,12 beta,14-Trihydroxy-5 beta-card-20(22)-enolide. A cardenolide which is the aglycon of digoxin. Can be obtained by hydrolysis of digoxin or from Digitalis orientalis L. and Digitalis lanata Ehrh.

Molecular Formula

  • C23-H34-O5

Molecular Weight

  • 390.5166
 

Classification Code

  • Drug / Therapeutic Agent
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Names and Synonyms

Name of Substance

  • Digoxigenin

MeSH Heading

  • Digoxigenin

Synonyms

  • 3-beta,12,14-Trioxy-carden-(20:22)-olid
  • 3-beta,12,14-Trioxy-carden-(20:22)-olid [German]
  • 3-beta,12,14-Trioxy-digen-(20:22)-olid
  • 3-beta,12,14-Trioxy-digen-(20:22)-olid [German]
  • 3-beta,12-beta,14-Trihydroxy-card-20(22)-enolide
  • 5-18-04-00380 (Beilstein Handbook Reference)
  • BRN 0096479
  • Cardogenen-(20:22)-triol-(3-beta,12,14)
  • Cardogenen-(20:22)-triol-(3-beta,12,14) [German]
  • delta-sup(20:22)-3-beta,12-beta,14,21-Tetrahydroxynorcholenic acid lactone
  • Digoxigenin
  • Digoxigenine
  • EINECS 216-806-2
  • HSDB 7108
  • Lanadigenin
  • UNII-NQ1SX9LNAU

Systematic Names

  • (3beta,5beta,12beta)-3,12,14-Trihydroxycard-20(22)-enolide
  • 5-beta-Card-20(22)-enolide, 3-beta,12-beta,14-trihydroxy-
  • Card-20(22)-enolide, 3,12,14-trihydroxy-, (3-beta,5-beta,12-beta)- (9CI)

Registry Numbers

CAS Registry Number

  • 1672-46-4

FDA UNII

  • NQ1SX9LNAU

System Generated Number

  • 0001672464

Structure Descriptors

InChI

1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-18(21)11-19(25)22(2)16(6-8-23(17,22)27)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16-,17-,18+,19-,21+,22+,23+/m1/s1

InChIKey

SHIBSTMRCDJXLN-KCZCNTNESA-N

Smiles

C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]3[C@@H]2C[C@@H](O)[C@]4(C)[C@H](CC[C@]34O)C5=CC(=O)OC5

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 244ug/kg (0.244mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Journal of the American Pharmaceutical Association. Vol. 27, Pg. 189, 1938.
cat LDLo unreported 285ug/kg (0.285mg/kg)   "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963Vol. -, Pg. 55, 1963.
guinea pig LDLo intravenous 3545ug/kg (3.545mg/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.
pigeon LDLo parenteral 1620ug/kg (1.62mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 8, Pg. 18, 1960.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 222 deg C   EXP
log P (octanol-water) 1.1 (none)   EXP
Water Solubility 403 mg/L 25 EST
Vapor Pressure 6.69E-15 mm Hg 25 EST
Henry's Law Constant 2.29E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.51E-11 cm3/molecule-sec 25 EST

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