Gitoformate: Difference between revisions

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 447907815

| IUPAC_name = [3-[5-(4,5-diformyloxy-6-methyloxan-2-yl)oxy-4-formyloxy-6-methyloxan-2-yl]oxy-6-{{bracket|[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

| image = Gitoformate skeletal.svg

| tradename = Dynocard

| synonyms = Gitoxin 3{{prime}},3{{prime}},3′′′,4′′′′,16-pentaformate

| CAS_number_Ref = {{cascite|correct|??}}

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2103959

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D07147

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 16736524

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = DOMHWKQEPDYUQX-UHFFFAOYSA-N

| 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

'''Gitoformate''' ([[International Nonproprietary Name|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).<ref>{{cite journal | vauthors = Rietbrock N, Woodcock BG, Hrazdil U | title = [Gitoformate and digitoxin as alternatives to kidney-dependent glycosides in the therapy of cardiac insufficiency] | journal = Arzneimittel-Forschung | volume = 34 | issue = 8 | pages = 915–917 | year = 1984 | pmid = 6541927 }}</ref> Produced by [[Madaus]], it is not available in the US, and does not seem to be available in Europe either.

==Chemistry==

{{stack|[[File:Gitoxigenin.svg|thumb|Gitoxigenin, the [[aglycon]]]]}}

Gitoformate is a derivative of the [[glycoside]] gitoxin, with five of the six free [[hydroxyl]] groups [[formyl]]ated, one on the [[aglycon]] and four on the sugar.<ref>{{cite journal | vauthors = Dei Cas L, Affatato A, Buia E, Casciarri G, Faggiano P, Giunti G, Metra M, Pelagatti T, Quinzanini M | display-authors = 6 | title = [Plasma levels of gitoxin (by RIA and rubidium-86 uptake) and systolic time after treatment with a single dose of gitoformate] | journal = Cardiologia | volume = 29 | issue = 5–6 | pages = 291–300 | year = 1984 | pmid = 6542412 }}</ref><ref>{{cite web | url = https://pubchem.ncbi.nlm.nih.gov/compound/91540 | work = PubChem | publisher = U.S. National Library of Medicine | title = Gitoxin }}</ref> 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.<ref>{{cite book| vauthors = Foye WO, Lemke TL, Williams DA |title=Foye's principles of medicinal chemistry |page=699 |isbn=978-0-7817-6879-5 |url=https://books.google.com/books?id=R0W1ErpsQpkC |year=2008 |publisher=Lippincott Williams & Wilkins }}</ref>

== References ==

{{reflist}}

{{Cardiac glycosides}}

[[Category:Formate esters]]

[[Category:Tertiary alcohols]]