Aurothioglucose

Last updated
Aurothioglucose
Authioglucose.png
Aurothioglucose-3D-vdW.png
Clinical data
Other namesGold thioglucose, Solganal, Auromyose
AHFS/Drugs.com Consumer Drug Information
Routes of
administration
Intramuscular injection
ATC code
Pharmacokinetic data
Bioavailability 0%
Identifiers
  • gold(I) (2S,3S,4R,5S)-3,4,5-trihydroxy-
    6-(hydroxymethyl)-oxane-2-thiolate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.032.138 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C6H11AuO5S
Molar mass 392.18 g·mol−1
3D model (JSmol)
  • O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1S[Au]
  • InChI=1S/C6H12O5S.Au/c7-1-2-3(8)4(9)5(10)6(12)11-2;/h2-10,12H,1H2;/q;+1/p-1/t2-,3-,4+,5-,6-;/m1./s1 Yes check.svgY
  • Key:XHVAWZZCDCWGBK-WYRLRVFGSA-M Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Aurothioglucose, also known as gold thioglucose, is a chemical compound with the formula AuSC6H11O5. This derivative of the sugar glucose was formerly used to treat rheumatoid arthritis.

Contents

History

Throughout history, gold was used to cure diseases, although the efficacy was not established. In 1935, gold drugs were reported to be effective for the treatment of rheumatoid arthritis. [1] Although many patients reacted positively to the drug, gold thioglucose was not uniformly effective.

Only one gold drug remains in active clinical use for this purpose in the United States: auranofin although sodium aurothiomalate (gold sodium thiomalate) and aurothioglucose were still used until recently. In the United Kingdom, only sodium aurothiomalate and auranofin were used recently.

In 2001, aurothioglucose was withdrawn from the Dutch market, where it had been the only injectable gold preparation available since 1943, forcing hospitals to change medication for a large number of patients to aurothiomalate. [2] The drug had been in use for more than 70 years, and four years later the reasons for its sudden disappearance remained unclear. [3]

It was recently discontinued from the US market along with sodium aurothiomalate leaving only Auranofin as the only gold salt on the US market

Medicinal chemistry

Gold thioglucose features gold in the oxidation state of +I, like other gold thiolates. It is a water-soluble, non-ionic species that is assumed to exist as a polymer. [1] Under physiological conditions, an oxidation-reduction reaction leads to the formation of metallic gold and sulfinic acid derivative of thioglucose.

2 AuSTg → 2 Au + TgSSTg
TgSSTg + H2O → TgSOH + TgSH
2 TgSOH → TgSO2H + TgSH
Overall: 2 H2O + 4 AuSTg → 4 Au + TgSO2H + 3 TgSH

(where AuSTg = gold thioglucose, TgSSTg = thioglucose disulfide, TgSO2H = sulfinic acid derivative of thioglucose)

Preparation

Gold thioglucose can be prepared by treating gold bromide with thioglucose solution saturated with sulfur dioxide. Gold thioglucose is precipitated with methanol and recrystallized with water and methanol.

Miscellaneous observations

In recent research, it was found that injection of gold thioglucose induces obesity in mice. [4] Aurothioglucose has an interaction with the antimalarial medication hydroxychloroquine.

See also

Related Research Articles

Arthritis Type of joint disorder

Arthritis is a term often used to mean any disorder that affects joints. Symptoms generally include joint pain and stiffness. Other symptoms may include redness, warmth, swelling, and decreased range of motion of the affected joints. In some types of arthritis, other organs are also affected. Onset can be gradual or sudden.

Infliximab Pharmaceutical drug

Infliximab, a chimeric monoclonal antibody, sold under the brand name Remicade among others, is a medication used to treat a number of autoimmune diseases. This includes Crohn's disease, ulcerative colitis, rheumatoid arthritis, ankylosing spondylitis, psoriasis, psoriatic arthritis, and Behçet's disease. It is given by slow injection into a vein, typically at six- to eight-week intervals.

Disease-modifying antirheumatic drug Category of drugs

Disease-modifying antirheumatic drugs (DMARDs) comprise a category of otherwise unrelated drugs defined by their use in rheumatoid arthritis to slow down disease progression. The term is often used in contrast to nonsteroidal anti-inflammatory drugs and steroids.

Naproxen Nonsteroidal anti-inflammatory drug (NSAID) used to treat pain

Naproxen, sold under the brand name Aleve or Apronax among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, inflammatory diseases such as rheumatoid arthritis, gout and fever. It is taken orally. It is available in immediate and delayed release formulations. Onset of effects is within an hour and lasts for up to twelve hours.

Rabeprazole Stomach acid suppressing medication

Rabeprazole, sold under the brand name Aciphex, among others, is a medication that decreases stomach acid. It is used to treat peptic ulcer disease, gastroesophageal reflux disease, and excess stomach acid production such as in Zollinger–Ellison syndrome. It may also be used in combination with other medications to treat Helicobacter pylori. Effectiveness is similar to other proton pump inhibitors (PPIs). It is taken by mouth.

Folinic acid Derivative of folic acid used in cancer treatment

Folinic acid, also known as leucovorin, is a medication used to decrease the toxic effects of methotrexate and pyrimethamine. It is also used in combination with 5-fluorouracil to treat colorectal cancer and pancreatic cancer, may be used to treat folate deficiency that results in anemia, and methanol poisoning. It is taken by mouth, injection into a muscle, or injection into a vein.

Indometacin Anti-inflammatory drug

Indometacin, also known as indomethacin, is a nonsteroidal anti-inflammatory drug (NSAID) commonly used as a prescription medication to reduce fever, pain, stiffness, and swelling from inflammation. It works by inhibiting the production of prostaglandins, endogenous signaling molecules known to cause these symptoms. It does this by inhibiting cyclooxygenase, an enzyme that catalyzes the production of prostaglandins.

Oxaprozin Chemical compound

Oxaprozin, also known as oxaprozinum, is a nonsteroidal anti-inflammatory drug (NSAID), used to relieve the inflammation, swelling, stiffness, and joint pain associated with osteoarthritis and rheumatoid arthritis. Chemically, it is a propionic acid derivative. Safety and efficacy has been established in children over 6 years with juvenile rheumatoid arthritis only, and there is an increased risk of adverse reactions in the elderly population.

Penicillamine

Penicillamine, sold under the brand name of Cuprimine among others, is a medication primarily used for the treatment of Wilson's disease. It is also used for people with kidney stones who have high urine cystine levels, rheumatoid arthritis, and various heavy metal poisonings. It is taken by mouth.

Gold salts Ionic chemical compounds of the element

Gold salts are ionic chemical compounds of gold. The term, "gold salts" is a misnomer, and is the term for the gold compounds used in medicine. "Chrysotherapy" and "aurotherapy" are the applications of gold compounds to medicine. Contemporary research on the effect of gold salts treatment began in 1935, primarily to reduce inflammation and to slow disease progression in patients with rheumatoid arthritis. The use of gold compounds has decreased since the 1980s because of numerous side effects and monitoring requirements, limited efficacy, and very slow onset of action. Most chemical compounds of gold, including some of the drugs discussed below, are not salts, but are examples of metal thiolate complexes.

Disodium aurothiomalate

Disodium aurothiomalate is a chemical compound with the formula AuSCH(CO2Na)CH2CO2Na. In conjunction with its monoprotonated derivative, this coordination complex or closely related species are used to treat rheumatoid arthritis, under the tradename Myochrysine. The thiomalate is racemic in most formulation.

Sulfinic acid

Sulfinic acids are oxoacids of sulfur with the structure RSO(OH). In these organosulfur compounds, sulfur is pyramidal.

Auranofin

Auranofin is a gold salt classified by the World Health Organization as an antirheumatic agent. It has the brand name Ridaura.

Sodium aurothiomalate Pharmaceutical drug

Sodium aurothiomalate is a gold compound that is used for its immunosuppressive anti-rheumatic effects. Along with an orally-administered gold salt, auranofin, it is one of only two gold compounds currently employed in modern medicine.

Copper aspirinate Chemical compound

Copper(II) aspirinate is an aspirin chelate of copper(II) cations (Cu2+). It is used to treat rheumatoid arthritis.

Tolmetin

Tolmetin is a nonsteroidal anti-inflammatory drug (NSAID) of the heterocyclic acetic acid derivative class. It is used primarily to reduce hormones that cause pain, swelling, tenderness, and stiffness in conditions such as osteoarthritis and rheumatoid arthritis, including juvenile rheumatoid arthritis. In the United States it is marketed as Tolectin and comes as a tablet or capsule.

Janus kinase inhibitors, also known as JAK inhibitors or jakinibs, are a type of medication that functions by inhibiting the activity of one or more of the Janus kinase family of enzymes, thereby interfering with the JAK-STAT signaling pathway.

Tofacitinib Medication

Tofacitinib, sold under the brand Xeljanz among others, is a medication used to treat rheumatoid arthritis, psoriatic arthritis, and ulcerative colitis.

Sarilumab, sold under the brand name Kevzara, is a human monoclonal antibody medication against the interleukin-6 receptor. Regeneron Pharmaceuticals and Sanofi developed the drug for the treatment of rheumatoid arthritis (RA), for which it received US FDA approval on 22 May 2017 and European Medicines Agency approval on 23 June 2017.

Upadacitinib Chemical compound (medication)

Upadacitinib, sold under the brand name Rinvoq, is a Janus kinase (JAK) inhibitor medication for the treatment of moderately to severely active rheumatoid arthritis and psoriatic arthritis in adults where methotrexate did not work well or could not be tolerated. It was approved for medical use in the United States and in the European Union in 2019, and was developed by the biotech company AbbVie.

References

  1. 1 2 Shaw, III C. F. (1999). "Gold-Based Therapeutic Agents". Chemical Reviews. 99 (9): 2589–600. doi:10.1021/cr980431o. PMID   11749494.
  2. Parenteral gold preparations. Efficacy and safety of therapy after switching from aurothioglucose to aurothiomalate (van Roon et al., J Rheumatol 2005)
  3. Klinkhoff, A (2005). "An editorial is a golden opportunity". The Journal of Rheumatology. 32 (6): 978–9. PMID   15940754.
  4. Naruta E, Buko V (2001). "Hypolipidemic effect of pantothenic acid derivatives in mice with hypothalamic obesity induced by aurothioglucose". Exp Toxicol Pathol. 53 (5): 393–8. doi:10.1078/0940-2993-00205. PMID   11817109.

Commons-logo.svg Media related to Aurothioglucose at Wikimedia Commons