AURANOFIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H34AuO9PS
Molecular Weight	678.484
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=IRPYFWIZKIOHQN-XTZHGVARSA-N

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;/t10-,11-,12+,13-,14+;;/m1../s1

HIDE SMILES / InChI

Molecular Formula	C20H35AuO9PS
Molecular Weight	679.492
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=05c34ddf-a0f7-4267-83f5-d02be3defc37

Auranofin (brand name Ridaura) is an organogold compound classified by the World Health Organization as an antirheumatic agent. Ridaura is indicated in the management of adults with active classical or definite rheumatoid arthritis (ARA criteria) who have had an insufficient therapeutic response to, or are intolerant of, an adequate trial of full doses of one or more nonsteroidal anti-inflammatory drugs. The mechanism of action of is not understood. In patients with adult rheumatoid arthritis, it may modify disease activity as manifested by synovitis and associated symptoms, and reflected by laboratory parameters such as ESR. There is no substantial evidence, however, that gold-containing compounds induce remission of rheumatoid arthritis. It may act as an inhibitor of kappab kinase and thioredoxin reductase, which would lead to a decreased immune response and decreased free radical production, respectively. In patients with inflammatory arthritis, such as adult and juvenile rheumatoid arthritis, gold salts can decrease the inflammation of the joint lining. This effect can prevent destruction of bone and cartilage. Ridaura should be added to a comprehensive baseline program, including non-drug therapies. Unlike anti-inflammatory drugs, RIDAURA does not produce an immediate response. Therapeutic effects may be seen after three to four months of treatment, although improvement has not been seen in some patients before six months.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Inhibitor of nuclear factor kappa B kinase beta subunit 16 Target ID: CHEMBL1991 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17034761	Inhibitor 8297
Peroxiredoxin-5, mitochondrial 1 Target ID: P30044\|\|\|Q9UJU4 Gene ID: 25824.0 Gene Symbol: PRDX5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16036347	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=05c34ddf-a0f7-4267-83f5-d02be3defc37	Palliative		Approved 8429	RIDAURA Approved Use RIDAURA (auranofin) is indicated in the management of adults with active classical or definite rheumatoid arthritis (ARA criteria) who have had an insufficient therapeutic response to, or are intolerant of, an adequate trial of full doses of one or more nonsteroidal anti-inflammatory drugs. RIDAURA should be added to a comprehensive baseline program, including non-drug therapies. Unlike anti-inflammatory drugs, RIDAURA does not produce an immediate response. Therapeutic effects may be seen after three to four months of treatment, although improvement has not been seen in some patients before six months. When cartilage and bone damage has already occurred, gold cannot reverse structural damage to joints caused by previous disease. The greatest potential benefit occurs in patients with active synovitis, particularly in its early stage. In controlled clinical trials comparing RIDAURA with injectable gold, RIDAURA was associated with fewer dropouts due to adverse reactions, while injectable gold was associated with fewer dropouts for inadequate or poor therapeutic effect. Physicians should consider these findings when deciding on the use of RIDAURA in patients who are candidates for chrysotherapy. Launch Date 1985

C_max

Value	Dose	Co-administered	Analyte	Population
0.312 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27821451	6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered:		AURANOFIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
5.05 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27821451	6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered:		AURANOFIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
844 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27821451	6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered:		AURANOFIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6416259 Page: p.1310	unhealthy, 22-76 n = 72 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 22-76 Sex: M+F Population Size: 72 Sources: https://pubmed.ncbi.nlm.nih.gov/6416259 Page: p.1310	Disc. AE: Stomatitis, Diarrhea... AEs leading to discontinuation/dose reduction: Stomatitis (1.4%) Diarrhea (1.4%) Eosinophilia (1.4%) Leukopenia (1.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/6416259 Page: p.1310
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27821451 Page: p.2	healthy, 27+/-5 n = 15 Health Status: healthy Age Group: 27+/-5 Sex: M+F Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/27821451 Page: p.2	Sources: https://pubmed.ncbi.nlm.nih.gov/27821451 Page: p.2
6 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2688083 Page: p.254	unhealthy, 45-63 n = 67 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 45-63 Sex: M+F Population Size: 67 Sources: https://pubmed.ncbi.nlm.nih.gov/2688083 Page: p.254	Disc. AE: Exanthema, Pruritus... AEs leading to discontinuation/dose reduction: Exanthema (7.5%) Pruritus (6%) Diarrhea (3%) Nausea (1.5%) Bowel obstruction (1.5%) Glomerulonephritis (1.5%) Nephropathies (1.5%) Polyneuropathy (1.5%) Sweating (1.5%) Dry mouth (1.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/2688083 Page: p.254
27 mg 1 times / day multiple, oral (total daily dose) Overdose Dose: 27 mg, 1 times / day Route: oral Route: multiple Dose: 27 mg, 1 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=05c34ddf-a0f7-4267-83f5-d02be3defc37&type=display	unhealthy, 50 n = 1 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 50 Sex: F Population Size: 1 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=05c34ddf-a0f7-4267-83f5-d02be3defc37&type=display	Disc. AE: Encephalopathy, Peripheral neuropathy... AEs leading to discontinuation/dose reduction: Encephalopathy Peripheral neuropathy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=05c34ddf-a0f7-4267-83f5-d02be3defc37&type=display
3 mg 2 times / day multiple, oral Recommended Dose: 3 mg, 2 times / day Route: oral Route: multiple Dose: 3 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1536666 Page: p.266	unhealthy, 51 n = 115 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 51 Sex: M+F Population Size: 115 Sources: https://pubmed.ncbi.nlm.nih.gov/1536666 Page: p.266	Disc. AE: Distress gastrointestinal, Diarrhea... AEs leading to discontinuation/dose reduction: Distress gastrointestinal (0.9%) Diarrhea (3.5%) Rash (3.5%) Mucosal ulceration (2.6%) Leukopenia (0.9%) Proteinuria (2.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/1536666 Page: p.266
3 mg 3 times / day multiple, oral Recommended Dose: 3 mg, 3 times / day Route: oral Route: multiple Dose: 3 mg, 3 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=05c34ddf-a0f7-4267-83f5-d02be3defc37&type=display	unhealthy Health Status: unhealthy Condition: Rheumatoid arthritis Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=05c34ddf-a0f7-4267-83f5-d02be3defc37&type=display	Disc. AE: Hemoglobin decreased, Leukopenia... AEs leading to discontinuation/dose reduction: Hemoglobin decreased Leukopenia Agranulocytosis Thrombocytopenia Proteinuria Hematuria Pruritus Rash Stomatitis Diarrhea Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=05c34ddf-a0f7-4267-83f5-d02be3defc37&type=display

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2922	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2922
ChemicalBook	CB5363410	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5363410
MolPort	MolPort-006-822-544	https://www.molport.com/shop/molecule-link/MolPort-006-822-544
eMolecules	29539707	https://www.emolecules.com/cgi-bin/more?vid=29539707
eMolecules	30513134	https://www.emolecules.com/cgi-bin/more?vid=30513134

PubMed

Title	Date	PubMed
Nitritoid reactions: case reports, review, and recommendations for management.	2001 Oct	11669157
Sublethal concentrations of diverse gold compounds inhibit mammalian cytosolic thioredoxin reductase (TrxR1).	2006 Sep	16510263
Treatment of human cancer cells with selenite or tellurite in combination with auranofin enhances cell death due to redox shift.	2009 Sep 15	19486940
The gold compound auranofin induces apoptosis of human multiple myeloma cells through both down-regulation of STAT3 and inhibition of NF-κB activity.	2011 Feb	20542334
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells.	2013 Oct	23942037

Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dosage is 6 mg daily, given either as 3 mg twice daily or 6 mg once daily. Initiation of therapy at dosages exceeding 6 mg daily is not recommended because it is associated with an increased incidence of diarrhea. If response is inadequate after six months, an increase to 9 mg (3 mg three times daily) may be tolerated.

Route of Administration: Oral

In Vitro Use Guide

Auranofin possesses potent antibacterial activity against all tested strains of S. aureus, including meticillin-resistant S. aureus (MRSA), vancomycin-intermediate S. aureus (VISA) and vancomycin-resistant S. aureus (VRSA), with minimum inhibitory concentrations (MICs) ranging from 0.0625μg/mL to 0.125μg/mL.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:34:10 GMT 2023` Edited by `admin` on `Fri Dec 15 15:34:10 GMT 2023`
Record UNII	3H04W2810V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AURANOFIN

Official Name

English

AURANOFIN [MART.]

Common Name

English

auranofin [INN]

Common Name

English

GOLD, (2,3,4,6-TETRA-O-ACETYL-1-THIO-.BETA.-D-GLUCOPYRANOSATO-S)(TRIETHYLPHOSPHINE)-

Common Name

English

Auranofin [WHO-DD]

Common Name

English

SK&F-39162

Code

English

RIDAURA

Brand Name

English

AURANOFIN [HSDB]

Common Name

English

NSC-321521

Code

English

SK&F 39162

Code

English

AURANOFIN [MI]

Common Name

English

AURANOFIN [ORANGE BOOK]

Common Name

English

SK-39162

Code

English

(1-THIO-.BETA.-D-GLUCOPYRANOSATO)(TRIETHYLPHOSPHINE)GOLD 2,3,4,6-TETRAACETATE.

Common Name

English

AURANOFIN [JAN]

Common Name

English

AURANOFIN [USAN]

Common Name

English

AURANOFIN [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-ATC

M01CB03