Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00051)
Name
Auranofin
Synonyms    Click to Show/Hide the Synonyms of This API
34031-32-8; AURANOFIN; (1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate; BCP08217; MMV688978; SKF 39162; AKOS026750078; FT-0662343; 1-Thio-; A-D-glucopyranosatotriethylphosphine gold-2,3,4,6-tetraacetate; 3,4,5-Triacetyloxy-6-(acetyloxymethyl) oxane-2-thiolate triethylphosphanium; gold(1+);3,4,5-triacetyloxy-6-(acetyloxymethyl)oxane-2-thiolate;triethylphosphane; SKF-39162; SKF-D-39162; SKF 39162; SKF D 39162; SKFD-39162; SKFD39162
Clinical Status
Approved
Disease Indication Rheumatoid arthritis ICD-11: FA20 [1]
PubChem CID
24199313
Formula
C20H34AuO9PS
Canonical SMILES
CCP(CC)CC.CC(=O)OCC1C(C(C(C(O1)[S-])OC(=O)C)OC(=O)C)OC(=O)C.[Au+]
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
InChIKey
AUJRCFUBUPVWSZ-UHFFFAOYSA-M
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=24199313"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 678.5 Topological Polar Surface Area 115
XlogP N.A. Complexity 532
Heavy Atom Count 32 Rotatable Bond Count 12
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 10
Full List of Drug Formulations (DFMs) Containing This API
          Auranofin 3 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose; Sodium lauryl sulfate; Fd&c red no. 40; Benzyl alcohol; D&c red no. 33; Fd&c blue no. 1; Fd&c yellow no. 6; Magnesium stearate; Cetylpyridinium chloride; Titanium dioxide; Povidone; Cellulose, microcrystalline; Gelatin; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Capsule
                   Company Prometheus Laboratories; Sebela Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
D&C red no. 33 DIG Info Solute carrier SLCO2B1 (Ki = 58.1 uM) [3]
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [4]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
Cetylpyridinium chloride DIG Info Dopamine D3 receptor (IC50 = 0.55 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
References
1 FDA label for approved auranofin from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
4 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
5 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
6 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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