Auranofin | Ridaura | SKF-39162 | CAS#34031-32-8 | Chrysotherapeutic Agent

MedKoo Cat#: 329314 | Name: Auranofin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Auranofin, also known as Ridaura and SKF-39162, is an oral chrysotherapeutic agent for the treatment of rheumatoid arthritis. Auranofin's exact mechanism of action is unknown, but it is believed to act via immunological mechanisms and alteration of lysosomal enzyme activity. Auranofin's efficacy is slightly less than that of injected gold salts, but it is better tolerated, and side effects which occur are potentially less serious.

Chemical Structure

Auranofin

CAS#34031-32-8

Theoretical Analysis

MedKoo Cat#: 329314

Name: Auranofin

CAS#: 34031-32-8

Chemical Formula: C20H34AuO9PS

Exact Mass: 678.1327

Molecular Weight: 678.48

Elemental Analysis: C, 35.41; H, 5.05; Au, 29.03; O, 21.22; P, 4.57; S, 4.73

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,950.00	2 Weeks

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Synonym

Auranofin; SKF-39162; SKF 39162; SKF39162; SKF-D-39162; SKF D 39162; SKFD-39162; SKFD39162; NSC 321521; NSC321521; NSC-321521; Ridauragold thiol; Ridaura;

IUPAC/Chemical Name

(1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate

InChi Key

AUJRCFUBUPVWSZ-XTZHGVARSA-M

InChi Code

InChI=1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1

SMILES Code

CC(OC[C@H]1O[C@@H](S[Au]=P(CC)(CC)CC)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O)=O

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Certificate of Analysis

View CoA: current batch, Lot#C20M08C20

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 678.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Yamashita M. Auranofin: Past to Present, and repurposing. Int Immunopharmacol. 2021 Dec;101(Pt B):108272. doi: 10.1016/j.intimp.2021.108272. Epub 2021 Oct 29. PMID: 34731781. 2: Sonzogni-Desautels K, Ndao M. Will Auranofin Become a Golden New Treatment Against COVID-19? Front Immunol. 2021 Sep 22;12:683694. doi: 10.3389/fimmu.2021.683694. PMID: 34630379; PMCID: PMC8492993. 3: Kean WF, Hart L, Buchanan WW. Auranofin. Br J Rheumatol. 1997 May;36(5):560-72. doi: 10.1093/rheumatology/36.5.560. PMID: 9189058. 4: Freire Boullosa L, Van Loenhout J, Flieswasser T, De Waele J, Hermans C, Lambrechts H, Cuypers B, Laukens K, Bartholomeus E, Siozopoulou V, De Vos WH, Peeters M, Smits ELJ, Deben C. Auranofin reveals therapeutic anticancer potential by triggering distinct molecular cell death mechanisms and innate immunity in mutant p53 non-small cell lung cancer. Redox Biol. 2021 Jun;42:101949. doi: 10.1016/j.redox.2021.101949. Epub 2021 Mar 19. PMID: 33812801; PMCID: PMC8113045. 5: Momose I, Onodera T, Kawada M. [Potential Anticancer Activity of Auranofin]. Yakugaku Zasshi. 2021;141(3):315-321. Japanese. doi: 10.1248/yakushi.20-00179-2. PMID: 33642497. 6: Lee SM, Koh DH, Jun DW, Roh YJ, Kang HT, Oh JH, Kim HS. Auranofin attenuates hepatic steatosis and fibrosis in nonalcoholic fatty liver disease via NRF2 and NF- κB signaling pathways. Clin Mol Hepatol. 2022 Oct;28(4):827-840. doi: 10.3350/cmh.2022.0068. Epub 2022 Jun 22. PMID: 35730208; PMCID: PMC9597229. 7: Onodera T, Momose I, Kawada M. Potential Anticancer Activity of Auranofin. Chem Pharm Bull (Tokyo). 2019;67(3):186-191. doi: 10.1248/cpb.c18-00767. PMID: 30827998. 8: Cox AR, Masschelin PM, Saha PK, Felix JB, Sharp R, Lian Z, Xia Y, Chernis N, Bader DA, Kim KH, Li X, Yoshino J, Li X, Li G, Sun Z, Wu H, Coarfa C, Moore DD, Klein S, Sun K, Hartig SM. The rheumatoid arthritis drug auranofin lowers leptin levels and exerts antidiabetic effects in obese mice. Cell Metab. 2022 Dec 6;34(12):1932-1946.e7. doi: 10.1016/j.cmet.2022.09.019. Epub 2022 Oct 14. PMID: 36243005; PMCID: PMC9742315. 9: Kim HR, Eom YB. Auranofin promotes antibacterial effect of doripenem against carbapenem-resistant Acinetobacter baumannii. J Appl Microbiol. 2022 Sep;133(3):1422-1433. doi: 10.1111/jam.15644. Epub 2022 Jun 13. PMID: 35633297. 10: Liu Y, Lu Y, Xu Z, Ma X, Chen X, Liu W. Repurposing of the gold drug auranofin and a review of its derivatives as antibacterial therapeutics. Drug Discov Today. 2022 Jul;27(7):1961-1973. doi: 10.1016/j.drudis.2022.02.010. Epub 2022 Feb 19. PMID: 35192926. 11: Ndugire W, Raviranga NGH, Lao J, Ramström O, Yan M. Gold Nanoclusters as Nanoantibiotic Auranofin Analogues. Adv Healthc Mater. 2022 May;11(9):e2101032. doi: 10.1002/adhm.202101032. Epub 2021 Aug 5. PMID: 34350709; PMCID: PMC8816973. 12: Szeliga M, Rola R. Menadione Potentiates Auranofin-Induced Glioblastoma Cell Death. Int J Mol Sci. 2022 Dec 11;23(24):15712. doi: 10.3390/ijms232415712. PMID: 36555352; PMCID: PMC9778806. 13: Ito K, Nishida Y, Hamada S, Shimizu K, Sakai T, Ohkawara B, Alman BA, Enomoto A, Ikuta K, Koike H, Zhang J, Ohno K, Imagama S. Efficacy of auranofin as an inhibitor of desmoid progression. Sci Rep. 2022 Jul 13;12(1):11918. doi: 10.1038/s41598-022-15756-9. PMID: 35831372; PMCID: PMC9279441. 14: Suarez-Almazor ME, Spooner CH, Belseck E, Shea B. Auranofin versus placebo in rheumatoid arthritis. Cochrane Database Syst Rev. 2000;2000(2):CD002048. doi: 10.1002/14651858.CD002048. PMID: 10796461; PMCID: PMC8436883. 15: Kato I, Kasukabe T, Kumakura S. Menin‑MLL inhibitors induce ferroptosis and enhance the anti‑proliferative activity of auranofin in several types of cancer cells. Int J Oncol. 2020 Oct;57(4):1057-1071. doi: 10.3892/ijo.2020.5116. Epub 2020 Aug 28. PMID: 32945449. 16: Lucignano R, Pratesi A, Imbimbo P, Monti DM, Picone D, Messori L, Ferraro G, Merlino A. Evaluation of Auranofin Loading within Ferritin Nanocages. Int J Mol Sci. 2022 Nov 16;23(22):14162. doi: 10.3390/ijms232214162. PMID: 36430642; PMCID: PMC9695178. 17: Gamberi T, Chiappetta G, Fiaschi T, Modesti A, Sorbi F, Magherini F. Upgrade of an old drug: Auranofin in innovative cancer therapies to overcome drug resistance and to increase drug effectiveness. Med Res Rev. 2022 May;42(3):1111-1146. doi: 10.1002/med.21872. Epub 2021 Dec 1. PMID: 34850406; PMCID: PMC9299597. 18: Abou-El-Naga IF, Mogahed NMFH. Repurposing auranofin for treatment of Experimental Cerebral Toxoplasmosis. Acta Parasitol. 2021 Sep;66(3):827-836. doi: 10.1007/s11686-021-00337-z. Epub 2021 Feb 8. PMID: 33555553. 19: Yam JKH, Tan LZW, Hong Z, Salido MMS, Woo BY, Yong AMH, Tan CAZ, Li SFY, Yang L, Givskov M, Chng SS. Auranofin inhibits virulence pathways in Pseudomonas aeruginosa. Bioorg Med Chem. 2023 Feb 1;79:117167. doi: 10.1016/j.bmc.2023.117167. Epub 2023 Jan 12. PMID: 36682225. 20: Hutton ML, Pehlivanoglu H, Vidor CJ, James ML, Thomson MJ, Lyras D. Repurposing auranofin as a Clostridioides difficile therapeutic. J Antimicrob Chemother. 2020 Feb 1;75(2):409-417. doi: 10.1093/jac/dkz430. PMID: 31642901.