Details of the Drug

General Information of Drug (ID: DMWE2N4)

Drug Name

Auranofin

Synonyms

Ridaura; Ridauran; Ridaura (TN); SK&F 39162; SK&F-39162; Gold, (1-thio-.beta.-D-glucopyranosato)(triethylphosphine)-, 2,3,4,6-tetraacetate; (1-Thio-.beta.-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate

Indication

Disease Entry	ICD 11	Status	REF
Inflammatory arthritis	FA2Z	Approved	[1], [2]

Therapeutic Class

Antirheumatic Agents

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski):
2

Molecular Weight

678.5

Topological Polar Surface Area

Not Available

Rotatable Bond Count

12

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

10

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [3]
Elimination: 60% of drug is excreted from urine in the unchanged form [3]

Chemical Identifiers

Formula: C20H34AuO9PS
IUPAC Name: gold(1+);3,4,5-triacetyloxy-6-(acetyloxymethyl)oxane-2-thiolate;triethylphosphane
Canonical SMILES: CCP(CC)CC.CC(=O)OCC1C(C(C(C(O1)[S-])OC(=O)C)OC(=O)C)OC(=O)C.[Au+]
InChI: 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

Cross-matching ID

PubChem CID: 24199313
CAS Number: 34031-32-8
DrugBank ID: DB00995
TTD ID: D0L2UN
VARIDT ID: DR01329
ACDINA ID: D00051

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Steroid hormone receptor ERR (ESRR)	TTP3UTW	ERR1_HUMAN; ERR2_HUMAN; ERR3_HUMAN	Modulator	[4]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[5]
Multidrug and toxin extrusion protein 1 (SLC47A1)	DTZGT0P	S47A1_HUMAN	Substrate	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Auranofin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of peripheral neuropathy by the combination of Auranofin and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[22]
Thalidomide	DM70BU5	Moderate	Increased risk of peripheral neuropathy by the combination of Auranofin and Thalidomide.	Multiple myeloma [2A83]	[23]
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Auranofin and Ocrelizumab.	Multiple sclerosis [8A40]	[24]
Omacetaxine mepesuccinate	DMPU2WX	Moderate	Additive myelosuppressive effects by the combination of Auranofin and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[25]
Ganciclovir	DM1MBYQ	Moderate	Increased risk of nephrotoxicity by the combination of Auranofin and Ganciclovir.	Virus infection [1A24-1D9Z]	[26]
Valganciclovir	DMS2IUH	Moderate	Additive myelosuppressive effects by the combination of Auranofin and Valganciclovir.	Virus infection [1A24-1D9Z]	[26]
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⏷ Show the Full List of 6 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
Cetylpyridinium chloride	E00330	31239	Antimicrobial preservative; Penetration agent; Solubilizing agent; Surfactant
D&C red no. 33	E00261	19116	Colorant
FD&C blue no. 1	E00263	19700	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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⏷ Show the Full List of 11 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Auranofin 3 mg capsule	3 mg	Oral Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6306).
2	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 018689.
3	BDDCS applied to over 900 drugs
4	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
5	Selection and characterization of a human ovarian cancer cell line resistant to auranofin. Oncotarget. 2017 Oct 9;8(56):96062-96078.
6	Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71.
7	Human multidrug and toxin extrusion 1 (MATE1/SLC47A1) transporter: functional characterization, interaction with OCT2 (SLC22A2), and single nucleotide polymorphisms. Am J Physiol Renal Physiol. 2010 Apr;298(4):F997-F1005.
8	Molecular mechanism of renal tubular secretion of the antimalarial drug chloroquine. Antimicrob Agents Chemother. 2011 Jul;55(7):3091-8.
9	Reduced renal clearance of a zwitterionic substrate cephalexin in MATE1-deficient mice. J Pharmacol Exp Ther. 2010 Aug;334(2):651-6.
10	Abemaciclib Inhibits Renal Tubular Secretion Without Changing Glomerular Filtration Rate. Clin Pharmacol Ther. 2019 May;105(5):1187-1195.
11	FDA Drug Development and Drug Interactions
12	Are organic cation transporters capable of transporting prostaglandins? Naunyn Schmiedebergs Arch Pharmacol. 2005 Aug;372(2):125-30.
13	Cisplatin and oxaliplatin, but not carboplatin and nedaplatin, are substrates for human organic cation transporters (SLC22A1-3 and multidrug and toxin extrusion family). J Pharmacol Exp Ther. 2006 Nov;319(2):879-86.
14	Pharmacologic markers and predictors of responses to imatinib therapy in patients with chronic myeloid leukemia. Leuk Lymphoma. 2008 Apr;49(4):639-42.
15	Organic cation transporters are determinants of oxaliplatin cytotoxicity. Cancer Res. 2006 Sep 1;66(17):8847-57.
16	Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
17	Implications of genetic polymorphisms in drug transporters for pharmacotherapy. Cancer Lett. 2006 Mar 8;234(1):4-33.
18	Upregulation of histone acetylation reverses organic anion transporter 2 repression and enhances 5-fluorouracil sensitivity in hepatocellular carcinoma
19	Comparison of type I and type II organic cation transport by organic cation transporters and organic anion-transporting polypeptides. J Pharmacol Exp Ther. 2001 Jul;298(1):110-5.
20	Organic cation transporters and their pharmacokinetic and pharmacodynamic consequences. Drug Metab Pharmacokinet. 2008;23(4):243-53.
21	Influx Transport of Cationic Drug at the Blood-Retinal Barrier: Impact on the Retinal Delivery of Neuroprotectants. Biol Pharm Bull. 2017;40(8):1139-1145.
22	Carrion C, Espinosa E, Herrero A, Garcia B "Possible vincristine-isoniazid interaction." Ann Pharmacother 29 (1995): 201. [PMID: 7756727]
23	Argov Z, Mastaglia FL "Drug-induced peripheral neuropathies." Br Med J 1 (1979): 663-6. [PMID: 219931]
24	Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
25	Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
26	Cerner Multum, Inc. "Australian Product Information.".