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Sulfanegen Sodium

Names
IUPAC name disodium (2R,5S)-2,5-dihydroxy-1,4-dithiane-2,5-dicarboxylate
Other names Sulfanegen Sodium
Identifiers
3D model (JSmol)	Interactive image
InChI InChI=1S/C6H8O6S2.2Na/c7-3(8)5(11)1-13-6(12,2-14-5)4(9)10;;/h11-12H,1-2H2,(H,7,8)(H,9,10);;/q;2*+1/p-2/t5-,6+;;
SMILES {{C1[C@@](SC[C@](S1)(C(=O)[O-])O)(C(=O)[O-])O.[Na+].[Na+]}}
Properties
Chemical formula	C 6H 6Na 2O 6S 2
Molar mass	284.218 g/mol
Melting point	132-134°C
Solubility in water	.35M at 20 °C
Acidity (pKa)	2.14
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tracking categories (test):

• SizeSet

Sulfanegen Sodium

Sulfanegen sodium, also known as sulfanegen, is a 3-mercaptopyruvate prodrug currently being tested that shows potential as a future human antidote for cyanide poisening.

Structure

Sulfanegen sodium contains a six membered ring with 2 Sulfurs that are para to each other. For each sulfur there is a carboxylic acid and alcohol group in the ortho position. The two sulfur atoms play a key role in the reaction. The sulfur atoms are isolated out from Sulfanegen sodium compound such that they undergo a reaction with cyanide. The binding of Sulfur to the cyanide molecule inhibits cyanide's toxic effects as an anion.

Properties

Sulfanegen sodium is a drug that lessens the effect of cyanide poisoning. It is most commonly formulated with sodium salts. The sodium atoms are there to prevent the carboxylic acid functional groups from participating in the reaction. The molecular formula of of sulfanegen sodium is C6H6Na2O6S2, and the molecule has a molar mass of 284.218g/mol. It has a melting temperature between the range of 132-134 °C. Sulfanegen is highly water soluble. The solubility is 0.35M at 20°C and it has a pka at 2.14. It's IUPAC name is disodium (2R,5S)-2,5-dihydroxy-1,4-dithiane-2,5-dicarboxylate.

Applications and Occurrences

Cyanide Poisoning

Cyanide poisoning can occur in several different ways, such as through industrial use, through combustion products, and through the environment. The body produces limited amounts of an enzyme called 3-mercaptopyruvate sulfurtransferase (3-MST) in most organs that detoxifies cyanide. This enzyme cannot be produced at great enough quantities to combat acute levels of cyanide however which can lead to poisoning. The severity of cyanide poisoning depends on how cyanide enters the body, either orally, through the skin, or inhalation, and on the amount of cyanide that enters the body. When cyanide enters the body, it targets an enzyme called cytochrome c oxidase that is found in the mitochondria of all cells. This is extremely dangerous to cells because cytochrome c oxidase donates an electron to oxygen as the last component of the electron transport chain. Cyanide disrupts the electron transport chain so that there is a critical decrease in the amount of ATP created for the body. This causes seizures, dyspnea, and the irregularity of vital signs.

Antidotes

Sulfanegen sodium is a very successful antidote to cyanide poisoning. An experiment was done using juvenile pigs to show that Sulfanegen sodium is effective at reversing the effects of cyanide poisoning. Some of the pigs were injected with cyanide while some were untouched to use as comparison. Of the pigs that were injected, half of the pigs received a placebo drug and the other half received Sulfanegen sodium. The pigs that received the placebo had signs of deterioration in their vitals which eventually led to mortality. The pigs that were treated with Sulfanegen sodium survived the poisoning and returned to normal a few hours after the experiment. Sulfanegen sodium was successful at preventing further damage from the cyanide. Another experiment also studied sulfanegen sodium's ability to reverse cyanide poisoning/effects. In this study a total of 35 rabbits were observed. The results showed that when sulfanegen sodium was allocated intravenously or intramuscularly, the effects of cyanide on oxyhemoglobin and deoxyhemoglobin were reversed very rapidly in comparison to the control animals.

Testing

There are multiple ways to administer the prodrug, such as intramuscular, intravenous, oral, and intraosseous during testing. Sulfanegen sodium is most effective when administered via intramuscular injections or via intravenous injections. Sulfanegen sodium's water soluble properties allow for rapid administration of antidotes via intramuscular injections. Sulfanegen has shown a lot of promise as an effective cyanide poisening prevention drug due to its fast acting nature when compared to current alternatives. Further testing is being employed to explore other forms of administration that can be rapid and easily distributed. Sulfanegen sodium is currently not on the market for human use.

Reactions

Sulfanegen sodium is the prodrug that is used to reduce cyanide toxicity. It is a dimer that is converted to its monomers 3-MP nonenzymatically in systems where the pH is between 2 -7.4. The monomeric form is metabolized by an enzyme called 3-MST which releases a sulfane sulfur intermediate that ends up converting a cyanide anion to SCN. In the first picture we can see the reaction as to how we can get singlet sulfur that will react with the cyanide anion. Once the singlet sulfur binds the cyanide it creates a product that cannot go further reaction. This is how we can prevent cyanide poisoning.

The six-membered sulfanegen sodium ring opens up and now in the subsequent steps we can generate a carbonyl with a sulfur at the end. Eventually, we can isolate out a singlet sulfur such that it can react with the cyanide anion.