A Na+/K+-ATPase inhibitor and an active metabolite of digoxin
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Digoxigenin

Item No. 30817

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5β)-3β,12β,14-trihydroxy-card-20(22)-enolide
CAS Number
1672-46-4
Synonyms
  • DIG
  • Lanadigenin
  • Lanadigigenin
Molecular Formula
C23H34O5
Formula Weight
390.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥ 10 mg/mlEthanol: Sparingly soluble: 1-10 mg/ml
SMILES
O=C1OCC([C@@]2([H])CC[C@@]3([C@@]4(CC[C@@]5(C[C@H](CC[C@@]5([C@]4(C[C@H]([C@]23C)O)[H])C)O)[H])[H])O)=C1
InChi Code
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
InChi Key
SHIBSTMRCDJXLN-KCZCNTNESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Digoxigenin is a Na+/K+-ATPase inhibitor and an active metabolite of digoxin (Item No. 22266).1,2 It is formed from digoxin by cytochrome P450 (CYP) isoform 3A (CYP3A) via digoxigenin bisdigitoxoside (Item No. 35356) and digoxigenin monodigitoxoside (Item No. 21699) intermediates. Digoxigenin inhibits Na+/K+-ATPase isoforms α1β1 and α2β1 (Ki = 97 and 90 nM, respectively).1 It is also an antagonist of human-ether-a-go-go (hERG), also known as Kv11.1 (IC50 = 206.3 nM).3 Digoxigenin (100 µM) decreases intraocular pressure induced by 4-aminopyridine (Item No. 18511) in rabbits.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Katz, A., Tal, D.M., Heller, D., et al. Digoxin derivatives with enhanced selectivity for the α2 isoform of Na,K-ATPase: Effects on intraocular pressure in rabbits. The Journal of Biological Chemisty 289(30), 21153-21162 (2014).

    2. Salphati, L., and Benet, L.Z. Metabolism of digoxin and digoxigenin digitoxosides in rat liver microsomes: Involvement of cytochrome P4503A. Xenobiotica 29(2), 171-185 (1999).

    3. Wang, L., Wible, B.A., Wan, X., et al. Cardiac glycosides as novel inhibitors of human ether-a-go-go-related gene channel trafficking. J. Pharmacol. Exp. Ther. 320(2), 525-534 (2007).