Gitoformate

Gitoformate

Systematic (IUPAC) name
[3-[5-(4,5-diformyloxy-6-methyloxan-2-yl)oxy-4-formyloxy-6-methyloxan-2-yl]oxy-6-[[16-formyloxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-2-methyloxan-4-yl]formate
Clinical data
Trade names	Dynocard
Identifiers
CAS Number	10176-39-3
ATC code	C01AA09 (WHO)
PubChem	CID 65598
ChemSpider	16736524
UNII	B69U29O7J9
KEGG	D07147
ChEMBL	CHEMBL2103959
Synonyms	Gitoxin 3',3'',3''',4''',16-pentaformate
Chemical data
Formula	C46H64O19
Molar mass	920.989 g/mol
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
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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).^[1] 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.^[2][3] 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.^[4]

References

1. Rietbrock, N.; Woodcock, B. G.; Hrazdil, U. (1984). "Gitoformate and digitoxin as alternatives to kidney-dependent glycosides in the therapy of cardiac insufficiency". Arzneimittel-Forschung 34 (8): 915–917. PMID 6541927.
2. Dei Cas, L.; Affatato, A.; Buia, E.; Casciarri, G.; Faggiano, P.; Giunti, G.; Metra, M.; Pelagatti, T.; Quinzanini, M. (1984). "Plasma levels of gitoxin (by RIA and rubidium-86 uptake) and systolic time after treatment with a single dose of gitoformate". Cardiologia (Rome, Italy) 29 (5–6): 291–300. PMID 6542412.
3. CID 91540 from PubChem
4. William O. Foye,Thomas L. Lemke, David A. Williams. Foye's principles of medicinal chemistry. p. 699. ISBN 978-0-7817-6879-5.