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Gitoformate

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Chemical compound Pharmaceutical compound
Gitoformate
Clinical data
Trade namesDynocard
Other namesGitoxin 3′,3′,3′′′,4′′′′,16-pentaformate
ATC code
Identifiers
IUPAC name
  • oxy-6-[phenanthren-3-yl]oxy]-2-methyloxan-4-yl]formate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.030.397 Edit this at Wikidata
Chemical and physical data
FormulaC46H64O19
Molar mass920.999 g·mol
3D model (JSmol)
SMILES
  • CC1C(C(CC(O1)OC2C(OC(CC2OC=O)OC3C(OC(CC3OC=O)OC4CCC5(C(C4)CCC6C5CCC7(C6(CC(C7C8=CC(=O)OC8)OC=O)O)C)C)C)C)OC=O)OC=O
InChI
  • InChI=1S/C46H64O19/c1-24-41(59-23-51)32(55-19-47)14-38(60-24)64-43-26(3)62-39(16-34(43)57-21-49)65-42-25(2)61-37(15-33(42)56-20-48)63-29-8-10-44(4)28(13-29)6-7-31-30(44)9-11-45(5)40(27-12-36(52)54-18-27)35(58-22-50)17-46(31,45)53/h12,19-26,28-35,37-43,53H,6-11,13-18H2,1-5H3
  • Key:DOMHWKQEPDYUQX-UHFFFAOYSA-N
  (what is this?)  (verify)

Gitoformate (INN, or pentaformylgitoxin, trade name Dynocard) is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia (irregular heartbeat). Produced by Madaus, it is not available in the US, and does not seem to be available in Europe either.

Chemistry

Gitoxigenin, the aglycon

Gitoformate is a derivative of the glycoside gitoxin, with five of the six free hydroxyl groups formylated, one on the aglycon and four on the sugar. Gitoxin, a cardiac glycoside from the woolly foxglove (Digitalis lanata), has an aglycon of the cardenolide type named gitoxigenin, which is also the aglycon of lanatoside B, another Digitalis lanata glycoside.

References

  1. Rietbrock N, Woodcock BG, Hrazdil U (1984). "". Arzneimittel-Forschung. 34 (8): 915–917. PMID 6541927.
  2. Dei Cas L, Affatato A, Buia E, Casciarri G, Faggiano P, Giunti G, et al. (1984). "". Cardiologia. 29 (5–6): 291–300. PMID 6542412.
  3. "Gitoxin". PubChem. U.S. National Library of Medicine.
  4. Foye WO, Lemke TL, Williams DA (2008). Foye's principles of medicinal chemistry. Lippincott Williams & Wilkins. p. 699. ISBN 978-0-7817-6879-5.
Cardiac glycosides (C01A)
Bufadienolides
Bufo
Scilla
Kalanchoe
Cardenolides
Digitalis
Strophanthus
Thevetia
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