Gitoformate

Gitoformate
Clinical data
Trade names	Dynocard
Other names	Gitoxin 3',3'',3''',4''',16-pentaformate
ATC code	C01AA09 (WHO) ;
Identifiers
	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;
CAS Number	10176-39-3 ;
PubChem CID	65598;
ChemSpider	16736524 ;
UNII	B69U29O7J9;
KEGG	D07147 ;
ChEMBL	ChEMBL2103959 ;
CompTox Dashboard (EPA)	DTXSID80144173 ;
ECHA InfoCard	100.030.397
Chemical and physical data
Formula	C46H64O19
Molar mass	920.999 g·mol−1
3D model (JSmol)	Interactive image;
	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]

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gollark: It'll get mouse_move events from both, meaning that depending on how it's done you would end up with it working "correctly" but with multiple things selected, randomly flicker between them, or it might implode or something.

References

Rietbrock N, Woodcock BG, Hrazdil U (1984). "[Gitoformate and digitoxin as alternatives to kidney-dependent glycosides in the therapy of cardiac insufficiency]". Arzneimittel-Forschung. 34 (8): 915–7. PMID 6541927.
Dei Cas L, Affatato A, Buia E, Casciarri G, Faggiano P, Giunti G, et al. (1984). "[Plasma levels of gitoxin (by RIA and rubidium-86 uptake) and systolic time after treatment with a single dose of gitoformate]". Cardiologia. 29 (5–6): 291–300. PMID 6542412.
CID 91540 from PubChem
Foye WO, Lemke TL, Williams DA (2008). Foye's principles of medicinal chemistry. p. 699. ISBN 978-0-7817-6879-5.

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[1] Rietbrock N, Woodcock BG, Hrazdil U (1984). "[Gitoformate and digitoxin as alternatives to kidney-dependent glycosides in the therapy of cardiac insufficiency]". Arzneimittel-Forschung. 34 (8): 915–7. PMID 6541927.

[2] Dei Cas L, Affatato A, Buia E, Casciarri G, Faggiano P, Giunti G, et al. (1984). "[Plasma levels of gitoxin (by RIA and rubidium-86 uptake) and systolic time after treatment with a single dose of gitoformate]". Cardiologia. 29 (5–6): 291–300. PMID 6542412.

[3] CID 91540 from PubChem

[4] Foye WO, Lemke TL, Williams DA (2008). Foye's principles of medicinal chemistry. p. 699. ISBN 978-0-7817-6879-5.