SUPROFEN

First approved in 1985

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H12O3S
Molecular Weight	260.308
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C(O)=O)C1=CC=C(C=C1)C(=O)C2=CC=CS2

InChI

InChIKey=MDKGKXOCJGEUJW-UHFFFAOYSA-N

InChI=1S/C14H12O3S/c1-9(14(16)17)10-4-6-11(7-5-10)13(15)12-3-2-8-18-12/h2-9H,1H3,(H,16,17)

HIDE SMILES / InChI

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=4891

Suprafen is a dual inhibitor of COX-1 and COX-2, which was used for the inhibition of intraoperative miosis. Suprafen was marketed under the name Profenal, however, it is no longer available in the USA.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin G/H synthase 1 30 Target ID: P23219\|\|\|Q5T7T7 Gene ID: 5742.0 Gene Symbol: PTGS1 Target Organism: Homo sapiens (Human) Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=4891	Inhibitor 8297		1.1 µM [IC50]
Prostaglandin G/H synthase 2 48 Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=4891	Inhibitor 8297		8.3 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Intraoperative miosis 2 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=4891	Preventing		Approved 8429	PROFENAL Approved Use Inhibition of miosis during intraocular surgery. Launch Date 1988

C_max

Value	Dose	Co-administered	Analyte	Population
8.43 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3243932	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		SUPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
18.95 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3243932	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		SUPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
21.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3243932	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		SUPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
26.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3243932	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		SUPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
400 mg single, oral Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6361789	unhealthy, > 18 years n = 41 Health Status: unhealthy Age Group: > 18 years Sex: M+F Population Size: 41 Sources: https://pubmed.ncbi.nlm.nih.gov/6361789	Sources: https://pubmed.ncbi.nlm.nih.gov/6361789
600 mg single, oral Highest studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	healthy, adult n = 12 Health Status: healthy Age Group: adult Sex: M Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	Sources: https://pubmed.ncbi.nlm.nih.gov/3741528
400 mg single, oral Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	healthy, adult n = 12 Health Status: healthy Age Group: adult Sex: M Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	Other AEs: Nausea, Vomiting... Other AEs: Nausea (2 patients) Vomiting (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/3741528

AEs

AE	Significance	Dose	Population
Nausea	2 patients	400 mg single, oral Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	healthy, adult n = 12 Health Status: healthy Age Group: adult Sex: M Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/3741528
Vomiting	2 patients	400 mg single, oral Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	healthy, adult n = 12 Health Status: healthy Age Group: adult Sex: M Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/3741528

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1037 inhibitor 1767

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT2B7 146

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
UGT2B7 157	inhibitor 3277 Sources: https://link.springer.com/protocol/10.1385/1-59259-800-5:185 Page: 15.0	likely
CYP2C9 1819	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2610245/	yes [Ki 6.7 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1037	substrate 3367 Sources: https://www.ingentaconnect.com/content/ben/cmc/2009/00000016/00000027/art00003 Page: 2.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9362	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9362
ChemicalBook	CB2496867	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2496867
MolPort	MolPort-001-791-811	https://www.molport.com/shop/molecule-link/MolPort-001-791-811
Selleck Chemicals	Suprofen(Profenal)	http://www.selleckchem.com/products/Suprofen(Profenal).html
eMolecules	743277	https://www.emolecules.com/cgi-bin/more?vid=743277

PubMed

Title	Date	PubMed
Nonsteroid anti-inflammatory agents: regulators of the phagocytic secretion of lysosomal enzymes from guinea-pig neutrophils.	1978 Nov	712644
Skin sensitizing properties of arylalcanoic acids and their analogues.	1979 Sep	509935
Suprofen and acute renal failure.	1986 Dec	3777736
Suprofen-induced acute renal failure.	1986 Nov	3780418
Suprofen, acute renal failure, and hematuria.	1986 Nov	3767163
Suprofen-induced transient flank pain and renal failure.	1987 Apr 16	3561450
Suprofen-induced acute renal failure.	1987 Dec	3424239
Suprofen-related nephrotoxicity. A distinct clinical syndrome.	1987 Feb	3800183
Suprofen and renal failure.	1987 May	3565984
Renal effects of nonsteroidal anti-inflammatory drugs.	1988	3142236
The epidemiology of the acute flank pain syndrome from suprofen.	1989 Dec	2598570
Immune hemolytic anemia associated with tolmetin and suprofen.	1989 Sep	2773031
Effects of suprofen on the isolated perfused rat kidney.	1992	1636026
Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs.	2002 Apr	12147041
Capillary electrochromatographic separation of non-steroidal anti-inflammatory drugs with a histidine bonded phase.	2002 Dec 27	12489886
Topically applied vitamin C and cysteine derivatives protect against UVA-induced photodegradation of suprofen in ex vivo pigskin.	2003 Apr	12733644
Topical nonsteroidal anti-inflammatory therapy in ophthalmology.	2003 Mar-Apr	12592044
Dextrans--potential polymeric drug carriers for suprofen.	2003 Nov	14664336
Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen.	2003 Nov	14570769
UV-induced drug release from photoactive REV sensitized by suprofen.	2004 Apr 16	15063031
In vitro effects of risperidone and 9-hydroxy-risperidone on human platelet function, plasma coagulation, and fibrinolysis.	2004 Aug	15476907
Process modeling of the lipase-catalyzed dynamic kinetic resolution of (R, S)-suprofen 2,2,2-trifluoroethyl thioester in a hollow-fiber membrane.	2004 Dec	15645310
Enantioseparation on mono(6A-n-allylamino-6A-deoxy)permethylated 3-cyclodextrin covalently bonded silica gel.	2004 Dec 3	15628124
Optimization of sample stacking for the simultaneous determination of nonsteroidal anti-inflammatory drugs with a wall-coated histidine capillary column.	2004 Feb	14981683
Synthesis of precursor of anti-inflammatory agents by using highly reactive zinc.	2004 May	15468892
Monolithic silica columns with chemically bonded tert-butylcarbamoylquinine chiral anion-exchanger selector as a stationary phase for enantiomer separations.	2004 May 21	15146914
Cationic vesicles as chiral selector for enantioseparations of nonsteroidal antiinflammatory drugs by micellar electrokinetic chromatography.	2004 Sep 3	15453427
Use of vancomycin chiral stationary phase for the enantiomeric resolution of basic and acidic compounds by nano-liquid chromatography.	2005 Jul 15	16013606
Intramolecular electron transfer between tyrosine and tryptophan photosensitized by a chiral pi,pi* aromatic ketone.	2005 May 20	15798972
Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti-inflammatory drugs in capillary liquid chromatography.	2006 Aug	16634133
Predicting the pharmacokinetics of acyl glucuronides and their parent compounds in disease states.	2006 Feb	16472105
Non-steroidal anti-inflammatory drugs for heavy bleeding or pain associated with intrauterine-device use.	2006 Oct 18	17054271
Enantiomeric separation of acidic compounds using single-isomer amino cyclodextrin derivatives in nonaqueous capillary electrophoresis.	2006 Sep	16892479
Differential suppression of menstrual fluid prostaglandin F2a, prostaglandin E2, 6-keto prostaglandin F1a and thromboxane B2 by suprofen in women with primary dysmenorrhea.	2007 Feb	17259081
Nonaqueous capillary electrophoretic behavior of 2-aryl propionic acids in the presence of an achiral ionic liquid. A chemometric approach.	2007 Jan 5	17113588
Analysis of pharmacology data and the prediction of adverse drug reactions and off-target effects from chemical structure.	2007 Jun	17477341
New NSAIDs-NO hybrid molecules with antiproliferative properties on human prostatic cancer cell lines.	2008 Aug 15	18667313
Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment.	2008 Feb	18224312
Topical ocular delivery of NSAIDs.	2008 Jun	18437583
Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development.	2009	19515014
Chemoenzymatic and microbial dynamic kinetic resolutions.	2009 Apr	18655180
Photodegradation mechanism of nonsteroidal anti-inflammatory drugs containing thiophene moieties: suprofen and tiaprofenic acid.	2009 Aug 13	19719267
Mechanism-based inactivation of cytochrome P450 2C9 by tienilic acid and (+/-)-suprofen: a comparison of kinetics and probe substrate selection.	2009 Jan	18838506
Binding of CYP2C9 with diverse drugs and its implications for metabolic mechanism.	2009 May	19442216
Enantiomeric separation of acidic compounds by nano-liquid chromatography with methylated-beta-cyclodextrin as a mobile phase additive.	2009 May	19370733
Enantiomeric separation of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs by HPLC with hydroxypropyl-beta-cyclodextrin as chiral mobile phase additive.	2010 Aug	20017213
Characterization of glutathione conjugates of duloxetine by mass spectrometry and evaluation of in silico approaches to rationalize the site of conjugation for thiophene containing drugs.	2010 Aug 16	20669986
Novel metabolic bioactivation mechanism for a series of anti-inflammatory agents (2,5-diaminothiophene derivatives) mediated by cytochrome p450 enzymes.	2010 Sep	20530221
Single dose dipyrone for acute postoperative pain.	2010 Sep 8	20824835
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.	2014 Jan	24085192

Patents

Sample Use Guides

In Vivo Use Guide

Administration of Profenal (1% solution of suprafen) begins the day before surgery: 2 drops every 4 hours. On the day of surgery two drops are placed in the eye 3, 2 and 1 hour before the procedure.

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

SUPROFEN

Official Name

English

SUPROFEN [USAN]

Common Name

English

R-25061

Code

English

PROFENAL

Brand Name

English

NSC-303611

Code

English

TN-762

Code

English

RACEMIC SUPROFEN

Common Name

English

P-2-THENOYLHYDRATROPIC ACID

Common Name

English

SUPROFEN [USP IMPURITY]

Common Name

English

.ALPHA.-METHYL-4-(2-THIENYLCARBONYL)BENZENEACETIC ACID

Systematic Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-THIENYLCARBONYL)-

Common Name

English

SUPROFEN [ORANGE BOOK]

Common Name

English

P-(2-THENOYL)HYDRATROPIC ACID

Common Name

English

TOPALGIC

Brand Name

English

SUPROFEN [USP-RS]

Common Name

English

SULPROLTIN

Brand Name

English

SUPROFEN [MI]

Common Name

English

(±)-SUPROFEN

Common Name

English

SRENDAM

Brand Name

English

R-25,061

Code

English

suprofen [INN]

Common Name

English

SUPROFEN [MART.]

Common Name

English

SUPROFEN [JAN]

Common Name

English

2-(4-(THIOPHENE-2-CARBONYL)PHENYL)PROPANOIC ACID

Systematic Name

English

SUPROFEN [VANDF]

Common Name

English

Suprofen [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QM01AE07