Gitoformate

Last updated
Gitoformate
Gitoformate skeletal.svg
Clinical data
Trade names Dynocard
Other namesGitoxin 3',3'',3''',4''',16-pentaformate
ATC code
Identifiers
  • [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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.030.397 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C46H64O19
Molar mass 920.999 g·mol−1
3D model (JSmol)
  • 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=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 X mark.svgN
  • Key:DOMHWKQEPDYUQX-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (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). [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 Gitoxigenin.svg
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]

Related Research Articles

<span class="mw-page-title-main">Cardiac glycoside</span> Class of organic compounds

Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses are as treatments for congestive heart failure and cardiac arrhythmias; however, their relative toxicity prevents them from being widely used. Most commonly found as secondary metabolites in several plants such as foxglove plants, these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment.

<i>Digitalis</i> Genus of flowering plants in the family Plantaginaceae

Digitalis is a genus of about 20 species of herbaceous perennial plants, shrubs, and biennials, commonly called foxgloves.

<span class="mw-page-title-main">Digoxin</span> Plant-derived medication

Digoxin, sold under the brand name Lanoxin among others, is a medication used to treat various heart conditions. Most frequently it is used for atrial fibrillation, atrial flutter, and heart failure. Digoxin is one of the oldest medications used in the field of cardiology. It works by increasing myocardial contractility, increasing stroke volume and blood pressure, reducing heart rate, and somewhat extending the time frame of the contraction. Digoxin is taken by mouth or by injection into a vein. Digoxin has a half life of approximately 36 hours given at average doses in patients with normal renal function. It is excreted mostly unchanged in the urine.

<span class="mw-page-title-main">Digitoxin</span> Chemical compound

Digitoxin is a cardiac glycoside used for the treatment of heart failure and certain kinds of heart arrhythmia. It is a phytosteroid and is similar in structure and effects to digoxin, though the effects are longer-lasting. Unlike digoxin, which is eliminated from the body via the kidneys, it is eliminated via the liver, and so can be used in patients with poor or erratic kidney function. While several controlled trials have shown digoxin to be effective in a proportion of patients treated for heart failure, the evidence base for digitoxin is not as strong, although it is presumed to be similarly effective.

<span class="mw-page-title-main">Quinidine</span> Antiarrythmic medication

Quinidine is a class IA antiarrhythmic agent used to treat heart rhythm disturbances. It is a diastereomer of antimalarial agent quinine, originally derived from the bark of the cinchona tree. The drug causes increased action potential duration, as well as a prolonged QT interval. As of 2019, its IV formulation is no longer being manufactured for use in the United States.

<i>Digitalis purpurea</i> Toxic flowering plant in the family Plantaginaceae

Digitalis purpurea, the foxglove or common foxglove, is a toxic species of flowering plant in the plantain family Plantaginaceae, native to and widespread throughout most of temperate Europe. It has also naturalised in parts of North America and some other temperate regions. The plant is a popular garden subject, with many cultivars available. It is the original source of the heart medicine digoxin. This biennial plant grows as a rosette of leaves in the first year after sowing, before flowering and then dying in the second year. It generally produces enough seeds, however, so that new plants will continue to grow in a garden setting.

<span class="mw-page-title-main">Cerberin</span> Chemical compound

Cerberin is a type of cardiac glycoside, a steroidal class found in the seeds of the dicotyledonous angiosperm genus Cerbera; including the suicide tree and the sea mango. This class includes digitalis-like agents, channel-blockers that as a group have found historic uses as cardiac treatments, but which at higher doses are extremely toxic; in the case of cerberin, consumption of the C. odollam results in poisoning with presenting nausea, vomiting, and abdominal pain, often leading to death. The natural product has been structurally characterized, its toxicity is clear—it is often used as an intentional human poison in third-world countries, and accidental poisonings with fatalities have resulted from individuals even indirectly consuming the agent—but its potentially therapeutic pharmacologic properties are very poorly described.

<span class="mw-page-title-main">Nortriptyline</span> Antidepressant medication

Nortriptyline, sold under the brand name Pamelor, among others, is a medication used to treat depression. This medicine is also sometimes used for neuropathic pain, attention deficit hyperactivity disorder (ADHD), smoking cessation and anxiety. As with many antidepressants, its use for young people with depression and other psychiatric disorders may be limited due to increased suicidality in the 18-24 population initiating treatment. Nortriptyline is a less preferred treatment for ADHD and stopping smoking. It is taken by mouth.

<span class="mw-page-title-main">Acetyldigitoxin</span> Pharmaceutical drug

Acetyldigitoxin is a cardiac glycoside. It is an acetyl derivative of digitoxin, found in the leaves of Digitalis species. It is used to treat cardiac failure, particularly that associated with tachycardia.

<span class="mw-page-title-main">Digoxigenin</span> Chemical compound

Digoxigenin (DIG) is a steroid found exclusively in the flowers and leaves of the plants Digitalis purpurea, Digitalis orientalis and Digitalis lanata (foxgloves), where it is attached to sugars, to form the glycosides.

<i>Digitalis lanata</i> Species of flowering plant in the plantain family Plantaginaceae

Digitalis lanata, vernacularly often called woolly foxglove or Grecian foxglove, is a species of foxglove, a flowering plant in the plantain family Plantaginaceae. It gets its name due to the woolly indumentum of the leaves. D. lanata, like other foxglove species, is toxic in all parts of the plant. Symptoms of digitalis poisoning include nausea, vomiting, severe headache, dilated pupils, problems with eyesight, and convulsions at the worst level of toxicity. The plant is also harmful to other animals.

k-Strophanthidin Chemical compound

k-Strophanthidin is a cardenolide found in species of the genus Strophanthus. It is the aglycone of k-strophanthin, an analogue of ouabain. k-strophanthin is found in the ripe seeds of Strophanthus kombé and in the lily Convallaria.

<span class="mw-page-title-main">Deslanoside</span> Chemical compound

Deslanoside is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia. It is found in the leaves of Digitalis lanata, the Woolly Foxglove.

<span class="mw-page-title-main">Lanatoside C</span> Chemical compound

Lanatoside C is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia. Lanatoside C can be used orally or by the intravenous route. It is marketed in a number of countries and is also available in generic form. Its main indications are rapid response atrial fibrilation and paroxysmal supraventricular tachycardia, two common types of arrhythmia.

<span class="mw-page-title-main">Ramoplanin</span> Antibiotic chemical

Ramoplanin (INN) is a glycolipodepsipeptide antibiotic drug derived from strain ATCC 33076 of Actinoplanes. It is effective against Gram-positive bacteria.

<span class="mw-page-title-main">Digoxin toxicity</span> Medical condition

Digoxin toxicity, also known as digoxin poisoning, is a type of poisoning that occurs in people who take too much of the medication digoxin or eat plants such as foxglove that contain a similar substance. Symptoms are typically vague. They may include vomiting, loss of appetite, confusion, blurred vision, changes in color perception, and decreased energy. Potential complications include an irregular heartbeat, which can be either too fast or too slow.

<span class="mw-page-title-main">Antiarin</span> Chemical compound

Antiarins are cardiac glycoside poisons produced by the upas tree. There are two forms, α-antiarin and β-antiarin.

<span class="mw-page-title-main">Convallatoxin</span> Chemical compound

Convallatoxin is a glycoside extracted from Convallaria majalis.

<i>Digitalis ciliata</i> Species of plant

Digitalis ciliata, commonly called hairy foxglove is a member of the genus Digitalis. It has thimble-shaped, yellow to cream colored flowers produced on perennial plants with evergreen foliage. It is native to the Caucasus and is grown as an ornamental in other parts of the world. The species name is derived from the fine hairs that cover the plants stems and flowers.

<i>Digitalis obscura</i> Species of plant

Digitalis obscura, commonly called willow-leaved foxglove or dusty foxglove or spanish rusty foxglove, is a flowering plant native to regions in Spain and Morocco. It is also grown as an ornamental flower. This foxglove is a woody perennial plant belonging to the family Plantaginaceae. Along with the other foxgloves it used to be placed in the figwort family, Scrophulariaceae; however, recent genetic research has moved the genus Digitalis to a larger family. It is similar to many of the foxglove species in its high toxicity and medicinal use as a source for the heart-regulating drug digoxin. Its strikingly distinctive amber- to copper-coloured flowers give the species its name and help distinguish it from other members of the genus.

References

  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): 915–917. 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. "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.