A cardiac glycoside with cardiotonic and antiarrhythmic activities
Related Products
Isomer(s)
22266Digoxin
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Gitoxin

Item No. 38888

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,5β,16β)-3-[(O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-14,16-dihydroxy-card-20(22)-enolide
CAS Number
4562-36-1
Synonyms
  • NSC 95099
Molecular Formula
C41H64O14
Formula Weight
780.9
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly SolubleMethanol: Slightly Soluble
SMILES
O[C@@]12[C@@]3([H])[C@@](CC[C@@]1([C@@H](C(CO4)=CC4=O)[C@H](C2)O)C)([H])[C@@]5([C@](C[C@H](CC5)O[C@H]6C[C@@H]([C@@H]([C@H](O6)C)O[C@@H]7O[C@@H]([C@H]([C@H](C7)O)O[C@@H]8O[C@@H]([C@H]([C@H](C8)O)O)C)C)O)([H])CC3)C
InChi Code
InChI=1S/C41H64O14/c1-19-36(47)27(42)14-33(50-19)54-38-21(3)52-34(16-29(38)44)55-37-20(2)51-32(15-28(37)43)53-24-8-10-39(4)23(13-24)6-7-26-25(39)9-11-40(5)35(22-12-31(46)49-18-22)30(45)17-41(26,40)48/h12,19-21,23-30,32-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25+,26-,27+,28+,29+,30+,32+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
InChi Key
LKRDZKPBAOKJBT-CNPIRKNPSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $28

    Add

    5 mg

    $104

    Add

    10 mg

    $193

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Gitoxin is a cardiac glycoside originally found in Digitalis that has cardiotonic and antiarrhythmic activities.1,2,3 It inhibits Na+/K+-ATPase in an isoform-specific biphasic manner with IC50 values of 0.298 and 410 µM for the high- and low affinity human erythrocyte isoenzymes, respectively, and 1.18 and 28.5 µM for the high- and low affinity porcine cerebral cortex isoenzymes, respectively.2 Gitoxin increases contractility and rhythmicity in isolated guinea pig heart in a concentration-dependent manner.3 It is also a degradation product of the cardiac glycoside digoxin (Item No. 22266).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Windaus, A., and Schwarte, G. A chloroform-insoluble glucoside from digitalis leaves, gitoxin. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 58B, 1515-1519 (1925).

    2. Krstić, D., Krinulović, K., Spasojević-Tisma, V., et al. Effects of digoxin and gitoxin on the enzymatic activity and kinetic parameters of Na+/K+-ATPase. J. Enzyme Inhib. Med. Chem. 19(5), 409-415 (2004).

    3. Haustein, K.O., and Hauptmann, J. Studies on cardioactive steroids. II. Structure-activity relationships in the isolated guinea-pig heart. Pharmacology 11(3), 129-138 (1974).

    4. Desta, B., Kwong, E., and McErlane, K.M. Separation of digoxin, digitoxin and their potential metabolites, impurities or degradation products by high-performance liquid chromatography. J. Chromatogr. 240(1), 137-143 (1982).